1.
Flavones
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Flavones, are a class of flavonoids based on the backbone of 2-phenylchromen-4-one shown on the right. Natural flavones include apigenin, luteolin, tangeritin, chrysin, 6-hydroxyflavone, baicalein, scutellarein, synthetic flavones include diosmin, flavoxate, and 7, 8-dihydroxyflavone. Flavone also refers to the flavone compound 2-phenyl-4H-chromen-4-one, flavones are mainly found in cereals and herbs. In the West, the daily intake of flavones is in the range 20–50 mg per day. In recent years, scientific and public interest in flavones has grown, as interpreted by the Linus Pauling Institute, dietary flavones, and more generally polyphenols, have little or no direct antioxidant food value following digestion. Flavones have effects on CYP activity which are enzymes that metabolize most drugs in the body, the Wessely–Moser rearrangement has been an important tool in structure elucidation of flavonoids. It involves the conversion of 5,7, 8-trimethoxyflavone into 5,6, flavones at the US National Library of Medicine Medical Subject Headings
2.
Plant
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Plants are mainly multicellular, predominantly photosynthetic eukaryotes of the kingdom Plantae. The term is generally limited to the green plants, which form an unranked clade Viridiplantae. This includes the plants, conifers and other gymnosperms, ferns, clubmosses, hornworts, liverworts, mosses and the green algae. Green plants have cell walls containing cellulose and obtain most of their energy from sunlight via photosynthesis by primary chloroplasts and their chloroplasts contain chlorophylls a and b, which gives them their green color. Some plants are parasitic and have lost the ability to produce amounts of chlorophyll or to photosynthesize. Plants are characterized by sexual reproduction and alternation of generations, although reproduction is also common. There are about 300–315 thousand species of plants, of which the great majority, green plants provide most of the worlds molecular oxygen and are the basis of most of Earths ecologies, especially on land. Plants that produce grains, fruits and vegetables form humankinds basic foodstuffs, Plants play many roles in culture. They are used as ornaments and, until recently and in variety, they have served as the source of most medicines. The scientific study of plants is known as botany, a branch of biology, Plants are one of the two groups into which all living things were traditionally divided, the other is animals. The division goes back at least as far as Aristotle, who distinguished between plants, which generally do not move, and animals, which often are mobile to catch their food. Much later, when Linnaeus created the basis of the system of scientific classification. Since then, it has become clear that the plant kingdom as originally defined included several unrelated groups, however, these organisms are still often considered plants, particularly in popular contexts. When the name Plantae or plant is applied to a group of organisms or taxon. The evolutionary history of plants is not yet settled. Those which have been called plants are in bold, the way in which the groups of green algae are combined and named varies considerably between authors. Algae comprise several different groups of organisms which produce energy through photosynthesis, most conspicuous among the algae are the seaweeds, multicellular algae that may roughly resemble land plants, but are classified among the brown, red and green algae. Each of these groups also includes various microscopic and single-celled organisms
3.
Fungus
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A fungus is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from the other eukaryotic life kingdoms of plants, a characteristic that places fungi in a different kingdom from plants, bacteria and some protists, is chitin in their cell walls. Similar to animals, fungi are heterotrophs, they acquire their food by absorbing dissolved molecules, growth is their means of mobility, except for spores, which may travel through the air or water. Fungi are the principal decomposers in ecological systems and this fungal group is distinct from the structurally similar myxomycetes and oomycetes. The discipline of biology devoted to the study of fungi is known as mycology, in the past, mycology was regarded as a branch of botany, although it is now known fungi are genetically more closely related to animals than to plants. Abundant worldwide, most fungi are inconspicuous because of the size of their structures. Fungi include symbionts of plants, animals, or other fungi and they may become noticeable when fruiting, either as mushrooms or as molds. Fungi perform a role in the decomposition of organic matter and have fundamental roles in nutrient cycling. Since the 1940s, fungi have been used for the production of antibiotics, Fungi are also used as biological pesticides to control weeds, plant diseases and insect pests. Many species produce bioactive compounds called mycotoxins, such as alkaloids and polyketides, the fruiting structures of a few species contain psychotropic compounds and are consumed recreationally or in traditional spiritual ceremonies. Fungi can break down manufactured materials and buildings, and become significant pathogens of humans, losses of crops due to fungal diseases or food spoilage can have a large impact on human food supplies and local economies. The fungus kingdom encompasses a diversity of taxa with varied ecologies, life cycle strategies. However, little is known of the biodiversity of Kingdom Fungi. Advances in molecular genetics have opened the way for DNA analysis to be incorporated into taxonomy, phylogenetic studies published in the last decade have helped reshape the classification within Kingdom Fungi, which is divided into one subkingdom, seven phyla, and ten subphyla. The English word fungus is directly adopted from the Latin fungus, used in the writings of Horace, a group of all the fungi present in a particular area or geographic region is known as mycobiota, e. g. the mycobiota of Ireland. Like plants, fungi grow in soil and, in the case of mushrooms, form conspicuous fruit bodies. The fungi are now considered a kingdom, distinct from both plants and animals, from which they appear to have diverged around one billion years ago. Fungi have membrane-bound cytoplasmic organelles such as mitochondria, sterol-containing membranes and they have a characteristic range of soluble carbohydrates and storage compounds, including sugar alcohols, disaccharides, and polysaccharides
4.
Phenyl group
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In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C6H5. Phenyl groups are related to benzene and can be viewed as a benzene ring, minus a hydrogen. Phenyl groups have six carbon atoms bonded together in a planar ring, five of which are bonded to individual hydrogen atoms. Phenyl groups are commonplace in organic chemistry, although often depicted with alternating double and single bonds, phenyl groups are chemically aromatic and show nearly equal bond lengths between carbon atoms in the ring. Usually, a group is synonymous to C6H5– and is represented by the symbol Ph or, archaically. Benzene is sometimes denoted as PhH, Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane has three groups attached to the same carbon center. Many or even most phenyl compounds are not described with the term phenyl, for example, the chloro derivative C6H5Cl is normally called chlorobenzene, although it could be called phenyl chloride. For example, O2NC6H4 is nitrophenyl and F5C6 is pentafluorophenyl, monosubstituted phenyl groups are associated with electrophilic aromatic substitution reactions and the products follow the arene substitution pattern. So, a substituted phenyl compound has three isomers, ortho, meta and para. A disubstituted phenyl compound may be, for example,1,3, 5-trisubstituted, or 1,2, higher degrees of substitution, of which the pentafluorophenyl group is an example, exist, and are named according to IUPAC nomenclature. Phenyl compounds are derived from benzene, at least conceptually and often in terms of their production, in terms of its electronic properties, the phenyl group is related to a vinyl group. Phenyl groups tend to resist oxidation and reduction, Phenyl groups have enhanced stability in comparison to equivalent bonding in aliphatic groups. This increased stability is due to the properties of aromatic molecular orbitals. The bond lengths between carbon atoms in a group are approximately 1.4 Å. In 1H-NMR spectroscopy, protons of a group typically have chemical shifts around 7.27 ppm. These chemical shifts are influenced by aromatic ring current and may change depending on substituents, Phenyl groups are usually introduced using reagents that behave as sources of the phenyl anion or the phenyl cation. Representative reagents include phenyllithium and phenylmagnesium bromide, electrophiles attack benzene to give phenyl derivatives, C6H6 + E+ → C6H5E + H+ where E+ = Cl+, NO2+, SO3
5.
IUPAC
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The International Union of Pure and Applied Chemistry /ˈaɪjuːpæk/ or /ˈjuːpæk/ is an international federation of National Adhering Organizations that represents chemists in individual countries. It is a member of the International Council for Science, IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the IUPAC Secretariat, is in Research Triangle Park, North Carolina, United States. This administrative office is headed by IUPACs executive director, currently Lynn Soby, IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, there are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPACs Inter-divisional Committee on Nomenclature and Symbols is the world authority in developing standards for the naming of the chemical elements. Since its creation, IUPAC has been run by different committees with different responsibilities. These committees run different projects which include standardizing nomenclature, finding ways to bring chemistry to the world, IUPAC is best known for its works standardizing nomenclature in chemistry and other fields of science, but IUPAC has publications in many fields including chemistry, biology and physics. IUPAC is also known for standardizing the atomic weights of the elements through one of its oldest standing committees, the need for an international standard for chemistry was first addressed in 1860 by a committee headed by German scientist Friedrich August Kekulé von Stradonitz. This committee was the first international conference to create an international naming system for organic compounds, the ideas that were formulated in that conference evolved into the official IUPAC nomenclature of organic chemistry. IUPAC stands as a legacy of this meeting, making it one of the most important historical international collaborations of chemistry societies, since this time, IUPAC has been the official organization held with the responsibility of updating and maintaining official organic nomenclature. IUPAC as such was established in 1919, one notable country excluded from this early IUPAC is Germany. Germanys exclusion was a result of prejudice towards Germans by the Allied powers after World War I, Germany was finally admitted into IUPAC during 1929. However, Nazi Germany was removed from IUPAC during World War II, during World War II, IUPAC was affiliated with the Allied powers, but had little involvement during the war effort itself. After the war, East and West Germany were eventually readmitted to IUPAC, since World War II, IUPAC has been focused on standardizing nomenclature and methods in science without interruption. In 2016, IUPAC denounced the use of chlorine as a chemical weapon, the letter stated, Our organizations deplore the use of chlorine in this manner. According to the CWC, the use, stockpiling, distribution, IUPAC is governed by several committees that all have different responsibilities. Each committee is made up of members of different National Adhering Organizations from different countries, the steering committee hierarchy for IUPAC is as follows, All committees have an allotted budget to which they must adhere. Any committee may start a project, if a projects spending becomes too much for a committee to continue funding, it must take the issue to the Project Committee
6.
Isoflavonoid
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Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estrogen receptor, medically, isoflavonoids and related compounds have been used in many dietary supplements, but the medical and scientific community is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, including biliatresone which may cause biliary atresia when infants are exposed to the plant product, while flavonoids have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone with no hydroxyl group substitution at position 2 or the 3-phenylchroman backbone
7.
Chromone
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Chromone is a derivative of benzopyran with a substituted keto group on the pyran ring. It is an isomer of coumarin, derivatives of chromone are collectively known as chromones. Most, though not all, chromones are also phenylpropanoids,6, 7-dimethoxy-2, 3-dihydrochromone has been isolated from Sarcolobus globosus. Eucryphin, a chromone rhamnoside, can be isolated from the bark of Eucryphia cordifolia, cromolyn was found to inhibit antigen challenge as well as stress induced symptoms. Cromoglicate is used as a mast cell stabilizer in allergic rhinitis, asthma, nedocromil sodium was found to have a somewhat longer half-life than cromolyn, however, production was discontinued in the US in 2008. Furanochromones Coumarin - a structural isomer CID from PubChem - 4-chromone Chromones at the US National Library of Medicine Medical Subject Headings Synthesis at organic-chemistry. org
8.
Neoflavonoid
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Neoflavonoids are a class of polyphenolic compounds. While flavonoids have the 2-phenylchromen-4-one backbone, neoflavonoids have the 4-phenylchromen backbone with no hydroxyl group substitution at position 2, neoflavonoids include 4-arylcoumarins, 4-arylchromanes, dalbergiones and dalbergiquinols. Neoflavones are derived from the 4-phenylcoumarin backbone, the first neoflavone isolated from natural sources was calophyllolide from Calophyllum inophyllum seeds. It is also known to found in bark and timber of Sri Lankan endemic plant Mesua thwaitesii
9.
Coumarin
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Coumarin is a fragrant organic chemical compound in the benzopyrone chemical class, which is a colorless crystalline substance in its standard state. It is a substance found in many plants. The name comes from a French term for the bean, coumarou. It has an odor, readily recognised as the scent of newly-mown hay. Sweet woodruff, meadowsweet, sweet grass and sweet-clover in particular are named for their sweet smell, Coumarin is used in certain perfumes and fabric conditioners. Coumarin was first synthesized in 1868, 4-hydroxycoumarins are a type of vitamin K antagonist. Pharmaceutical coumarins were all developed from the study of sweet clover disease, however, unmodified coumarin itself, as it occurs in plants, has no effect on the vitamin K coagulation system, or on the action of warfarin-type drugs. Coumarin has clinical medical value by itself, as an edema modifier, other biological activities that may lead to other medical uses have been suggested, with varying degrees of evidence. Coumarin is also used as a medium in some dye lasers. The word tonka for tonka beans is taken from the Galibi tongue spoken by natives of French Guiana, it appears in Old Tupi, another language of the same region. The old genus name, Coumarouna, was formed from another Tupi name for tree, the French word for the tonka bean, coumarou, is from this name. Coumarin, named for coumarou was first isolated from Tonka beans and sweet clover in 1820 by A. Vogel of Munich, also in 1820, Nicholas Jean Baptiste Gaston Guibourt of France independently isolated coumarin, but he realized that it was not benzoic acid. In a subsequent essay he presented to the section of the Académie Royale de Médecine. In 1835, the French pharmacist A. Guillemette proved that Vogel, Coumarin was first synthesized in 1868 by the English chemist William Henry Perkin. Coumarin can be prepared by a number of reactions with the Perkin reaction between salicylaldehyde and acetic anhydride being a popular example. The Pechmann condensation provides another route to coumarin and its derivatives, Coumarin is also found in extracts of Justicia pectoralis. Related compounds are found in some but not all specimens of licorice, the biosynthesis of coumarin in plants is via hydroxylation, glycolysis, and cyclization of cinnamic acid. The enzyme encoded by the gene UGT1A8 has glucuronidase activity with many substrates including coumarins, Coumarin has appetite-suppressing properties, which may discourage animals from eating plants which contain it
10.
Ketone
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In chemistry, a ketone /ˈkiːtoʊn/ is an organic compound with the structure RCR, where R and R can be a variety of carbon-containing substituents. Ketones and aldehydes are simple compounds that contain a carbonyl group and they are considered simple because they do not have reactive groups like −OH or −Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing −COOH. Many ketones are known and many are of importance in industry. Examples include many sugars and the industrial solvent acetone, which is the smallest ketone, the word ketone is derived from Aketon, an old German word for acetone. According to the rules of IUPAC nomenclature, ketones are named by changing the suffix -ane of the parent alkane to -anone, the position of the carbonyl group is usually denoted by a number. For the most important ketones, however, traditional names are still generally used. The common names of ketones are obtained by writing separately the names of the two alkyl groups attached to the group, followed by ketone as a separate word. The names of the groups are written alphabetically. When the two groups are the same, the prefix di- is added before the name of alkyl group. The positions of other groups are indicated by Greek letters, the α-carbon being the adjacent to carbonyl group. If both alkyl groups in a ketone are the same then the ketone is said to be symmetrical, although used infrequently, oxo is the IUPAC nomenclature for a ketone functional group. Other prefixes, however, are also used, for some common chemicals, keto or oxo refer to the ketone functional group. The term oxo is used widely through chemistry, for example, it also refers to an oxygen atom bonded to a transition metal. The ketone carbon is often described as sp2 hybridized, a description that includes both their electronic and molecular structure, ketones are trigonal planar around the ketonic carbon, with C−C−O and C−C−C bond angles of approximately 120°. Ketones differ from aldehydes in that the group is bonded to two carbons within a carbon skeleton. In aldehydes, the carbonyl is bonded to one carbon and one hydrogen and are located at the ends of carbon chains, ketones are also distinct from other carbonyl-containing functional groups, such as carboxylic acids, esters and amides. The carbonyl group is polar because the electronegativity of the oxygen is greater than that for carbon, thus, ketones are nucleophilic at oxygen and electrophilic at carbon. Because the carbonyl group interacts with water by bonding, ketones are typically more soluble in water than the related methylene compounds
11.
Anthoxanthin
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Anthoxanthins are a type of flavonoid pigments in plants. Anthoxanthins are water-soluble pigments which range in color from white or colorless to a creamy to yellow and these pigments are generally whiter in an acid medium and yellowed in an alkaline medium. They are very susceptible to changes with minerals and metal ions. As with all flavonoids, they exhibit antioxidant properties, and are important in nutrition, darkening with iron is particularly prominent in food products. They are considered to have more variety than anthocyanins
12.
Flavonols
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Flavonols are a class of flavonoids that have the 3-hydroxyflavone backbone. Their diversity stems from the different positions the phenolic -OH groups and they are distinct from flavanols such as catechin, another class of flavonoids. Flavonols are present in a variety of fruits and vegetables. In Western populations, estimated daily intake is in the range of 20–50 mg per day for flavonols, individual intake varies depending on the type of diet consumed. The phenomenon of fluorescence is induced by tautomerism of flavonols and could contribute to plant UV protection. Coli bacteria in the urinary tract so as to reduce the ability of those bacteria to stay put. Flavonol aglycones in plants are potent antioxidants that serve to protect the plant from reactive oxygen species, flavonoids have effects on CYP activity. Flavonols are inhibitor of CYP2C9 and CYP3A4, which are enzymes that metabolize most drugs in the body, phenolic compounds in wine Algar-Flynn-Oyamada reaction
13.
Phloroglucinol
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Phloroglucinol is an organic compound that is used in the synthesis of pharmaceuticals and explosives. It is a derivative with antispasmodic properties that is used primarily as a laboratory reagent. Austrian chemist Heinrich Hlasiwetz is remembered for his analysis of phloroglucinol. Phloroglucinol is also found in the flavonoid ring A substitution pattern. Phloroglucinol is a benzenetriol, found along with two isomers, hydroxyquinol and pyrogallol, Phloroglucinol, and its benzenetriol isomers, are still defined as phenols according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols by the cosmetic and parapharmaceutical industries and this molecule has a unique symmetric arene substitution pattern of a trisubstituted benzene. It is a type of enol and exists in two forms, or tautomers,1,3, 5-trihydroxybenzene, which has character, and 1,3, 5-cyclohexanetrione. These two tautomers are in equilibrium, Phloroglucinol is a useful intermediate because it is polyfunctional. From water, phloroglucinol crystallizes as the dihydrate, which has a point of 116–117 °C. It does not boil intact, but it does sublime, Phloroglucinol was originally isolated from phloretin, a compound found in fruit trees, using potassium hydroxide. Additionally, the compound can be prepared from glucosides, plant extracts and resins such as quercetin, catechin. It is synthesized via a number of processes, but representative is the route from trinitrobenzene. It is a selective trinitration where benzene is symmetrically trinitrated to 1,3,5 trinitrobenzene to produce a precursor for the synthesis of phloroglucinol, the synthesis is noteworthy because ordinary aniline derivatives are unreactive toward hydroxide. Because the triaminobenzene also exists as its imine tautomer, it is susceptible to hydrolysis, the compound behaves like a ketone in its reaction with hydroxylamine, forming the tris. But it behaves also like a benzenetriol, as the three groups can be methylated to give 1,3, 5-trimethoxybenzene. The Hoesch reaction allows the synthesis of 1-ethanone from phloroglucinol, leptospermone can be synthesized from phloroglucinol by a reaction with isovaleroylnitrile in the presence of a zinc chloride catalyst. Pentacarbon dioxide, described in 1988 by Günter Maier and others, can be obtained by pyrolysis of 1,3, methylation of Phloroglucinol results in 1,3, 5-trimethoxybenzene, which in-turn finds an application in the synthesis of fraxinol. Phloroglucinol readily forms 5-aminoresorcinol in aqueous ammonia at low temperatures, phloroglucinols are secondary metabolites that occur naturally in certain plant species
14.
Flavonoid biosynthesis
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Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins, methods of analysis should take this element into account especially regarding bioactivity or enzyme stereospecificity. The biosynthesis of flavonoids involves several enzymes
15.
Biological pigment
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Biological pigments, also known simply as pigments or biochromes, are substances produced by living organisms that have a color resulting from selective color absorption. Biological pigments include plant pigments and flower pigments, many biological structures, such as skin, eyes, feathers, fur and hair contain pigments such as melanin in specialized cells called chromatophores. For example, butterfly wings typically contain structural color, although many butterflies have cells that contain pigment as well, see conjugated systems for electron bond chemistry that causes these molecules to have pigment. Other functions of pigments in plants include attracting insects to flowers to encourage pollination, plant pigments include a variety of different kinds of molecule, including porphyrins, carotenoids, anthocyanins and betalains. All biological pigments selectively absorb certain wavelengths of light while reflecting others, the principal pigments responsible are, Chlorophyll is the primary pigment in plants, it is a chlorin that absorbs yellow and blue wavelengths of light while reflecting green. It is the presence and relative abundance of chlorophyll that gives plants their green color, all land plants and green algae possess two forms of this pigment, chlorophyll a and chlorophyll b. Kelps, diatoms, and other photosynthetic heterokonts contain chlorophyll c instead of b, all chlorophylls serve as the primary means plants use to intercept light in order to fuel photosynthesis. Carotenoids are red, orange, or yellow tetraterpenoids, during the process of photosynthesis, they have functions in light-harvesting, in photoprotection, and also serve as protein structural elements. In higher plants, they serve as precursors to the plant hormone abscisic acid. Plants, in general, contain six ubiquitous carotenoids, neoxanthin, violaxanthin, antheraxanthin, zeaxanthin, lutein, lutein is a yellow pigment found in fruits and vegetables and is the most abundant carotenoid in plants. Lycopene is the red pigment responsible for the color of tomatoes, other less common carotenoids in plants include lutein epoxide, lactucaxanthin, and alpha carotene. In cyanobacteria, many other carotenoids exist such as canthaxanthin, myxoxanthophyll, synechoxanthin, algal phototrophs such as dinoflagellates use peridinin as a light harvesting pigment. Anthocyanins are water-soluble flavonoid pigments that appear red to blue, according to pH and they occur in all tissues of higher plants, providing color in leaves, plant stem, roots, flowers, and fruits, though not always in sufficient quantities to be noticeable. Anthocyanins are most visible in the petals of flowers of many species, betalains are red or yellow pigments. Like anthocyanins they are water-soluble, but unlike anthocyanins they are synthesized from tyrosine and this class of pigments is found only in the Caryophyllales, and never co-occur in plants with anthocyanins. Betalains are responsible for the red color of beets. Chlorophylls degrade into colorless tetrapyrroles known as nonfluorescent chlorophyll catabolites, as the predominant chlorophylls degrade, the hidden pigments of yellow xanthophylls and orange beta-carotene are revealed. These pigments are present throughout the year, but the red pigments, pigmentation is used by many animals for protection, by means of camouflage, mimicry, or warning coloration
16.
Pollinator
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A pollinator is an animal that moves pollen from the male anther of a flower to the female stigma of a flower. This helps to bring about fertilization of the ovules in the flower by the gametes from the pollen grains. Insect pollinators include bees, pollen wasps, ants, flies including bee flies and hoverflies, lepidopterans, vertebrates, mainly bats and birds, but also some non-bat mammals and some lizards pollinate certain plants. Among the pollinating birds are hummingbirds, honeyeaters and sunbirds with long beaks, cycads, which are not flowering plants, are also pollinated by insects. A pollinator is different from a pollenizer, a plant that is a source of pollen for the pollination process, plants fall into pollination syndromes that reflect the type of pollinator being attracted. These are characteristics such as, overall size, the depth and width of the corolla, the color. When these characteristics are experimentally modified, pollinator visitation may decline and it has recently been discovered that cycads, which are not flowering plants, are also pollinated by insects. The most recognized pollinators are the species of bees, which are plainly adapted to pollination. Bees typically are fuzzy and carry an electrostatic charge, Honey bees, bumblebees, and their relatives do not have a scopa, but the hind leg is modified into a structure called the corbicula. Most bees gather nectar, an energy source, and pollen, which is high protein food, to nurture their young. Euglossine bees pollinate orchids, but these are male bees collecting floral scents rather than females gathering nectar or pollen, female orchid bees act as pollinators, but of flowers other than orchids. Eusocial bees such as honey bees need an abundant and steady pollen source to multiply, Honey bees travel from flower to flower, collecting nectar, and pollen grains. The bee collects the pollen by rubbing against the anthers, the pollen collects on the hind legs, in a structure referred to as a pollen basket. As the bee flies from flower to flower, some of the grains are transferred onto the stigma of other flowers. Nectar provides the energy for bee nutrition, pollen provides the protein, when bees are rearing large quantities of brood, bees deliberately gather pollen to meet the nutritional needs of the brood. Good pollination management seeks to have bees in a state during the bloom period of the crop, thus requiring them to gather pollen. Thus, the management techniques of a beekeeper providing pollination services are different from, and to some extent in tension with, many insects other than bees accomplish pollination by visiting flowers for nectar or pollen, or commonly both. Many do so adventitiously, but the most important pollinators are specialists for at least parts of their lifecycles for at least certain functions
17.
Rhizobia
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Rhizobia are soil bacteria that fix nitrogen after becoming established inside root nodules of legumes. In order to express genes for nitrogen fixation, rhizobia require a plant host, in general, they are Gram-negative, motile, non-sporulating rods. The first known species of rhizobia, Rhizobium leguminosarum, was identified in 1889, however, more advanced methods of analysis have revised this classification, and now there are many in other genera. Most research has been done on crop and forage legumes such as clover, alfalfa, beans, peas, the word rhizobia comes from the Ancient Greek ῥίζα, rhíza, meaning root and βίος, bios, meaning life. The word rhizobium is still used as the singular form of rhizobia Rhizobia are a paraphyletic group that fall into two classes of the proteobacteria—the alpha- and beta-proteobacteria. As shown below, most belong to the order Rhizobiales, and these groups include a variety of non-symbiotic bacteria. For instance, the plant pathogen Agrobacterium is a relative of Rhizobium than the Bradyrhizobium that nodulate soybean. The genes responsible for the symbiosis with plants, however, may be closely related than the organisms themselves. Evidence suggests that symbiosis islands exist and share similarities to pathogenicity islands, although much of the nitrogen is removed when protein-rich grain or hay is harvested, significant amounts can remain in the soil for future crops. This is especially important when nitrogen fertilizer is not used, as in organic rotation schemes or some less-industrialized countries, Nitrogen is the most commonly deficient nutrient in many soils around the world and it is the most commonly supplied plant nutrient. Supply of nitrogen through fertilizers has severe environmental concerns, Rhizobia is “the group of soil bacteria that infect the roots of legumes to form root nodules”. Rhizobia are found in the soil and after infection, produce nodules in the legume where they fix nitrogen gas from the atmosphere turning it into a more useful form of nitrogen. From here, the nitrogen is exported from the nodules and used for growth in the legume, once the legume dies, the nodule breaks down and releases the rhizobia back into the soil where they can live individually or reinfect a new legume host. Specific strains of rhizobia are required to make functional nodules on the roots able to fix the N2, having this specific rhizobia present is beneficial to the legume, as the N2 fixation can increase crop yield. Inoculation with rhizobia tends to increase yield, Legume inoculation has been an agriculture practice for many years and has continuously improved over time. 12-20 million hectares of soybeans are inoculated annually, the technology to produce these inoculants are microbial fermenters. Once this ideal inoculant in produced it is most likely in a liquid or powder form where it is applied directly to the seed before planting, many poor countries have trouble with the introduction of new crops and reaching attainable yield. As they introduce new crops into their soils, these inoculants may foster legume growth and success in the area, using these inoculants provide many other benefits as well such as not having to use nitrogen fertilizers
18.
Symbiosis
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Symbiosis is any type of a close and long-term biological interaction between two different species, be it mutualistic, commensalistic, or parasitic. In 1879, Heinrich Anton de Bary defined it as the living together of unlike organisms, Symbiosis can be obligatory, which means that one or both of the symbionts entirely depend on each other for survival, or facultative when they can generally live independently. When one organism lives on another such as mistletoe, it is called ectosymbiosis, or endosymbiosis when one partner lives inside the tissues of another, as in Symbiodinium in corals. In 1877, Albert Bernhard Frank used the term symbiosis which previously had used to depict people living together in community to describe the mutualistic relationship in lichens. In 1879, the German mycologist Heinrich Anton de Bary defined it as the living together of unlike organisms, symbiotic relationships can be obligate, meaning that one or both of the symbionts entirely depend on each other for survival. For example, in lichens, which consist of fungal and photosynthetic symbionts, the algal or cyanobacterial symbionts in lichens, such as Trentepohlia, can generally live independently, and their symbiosis is, therefore, facultative. Endosymbiosis is any relationship in which one symbiont lives within the tissues of the other, either within the cells or extracellularly. Mutualism or interspecies reciprocal altruism is a relationship between individuals of different species where both individuals benefit, in general, only lifelong interactions involving close physical and biochemical contact can properly be considered symbiotic. Mutualistic relationships may be either obligate for both species, obligate for one but facultative for the other, or facultative for both, a large percentage of herbivores have mutualistic gut flora to help them digest plant matter, which is more difficult to digest than animal prey. This gut flora is made up of cellulose-digesting protozoans or bacteria living in the herbivores intestines, coral reefs are the result of mutualisms between coral organisms and various types of algae which live inside them. Most land plants and land ecosystems rely on mutualisms between the plants, which fix carbon from the air, and mycorrhyzal fungi, which help in extracting water, an example of mutual symbiosis is the relationship between the ocellaris clownfish that dwell among the tentacles of Ritteri sea anemones. The territorial fish protects the anemone from anemone-eating fish, and in turn the stinging tentacles of the anemone protect the clownfish from its predators, a special mucus on the clownfish protects it from the stinging tentacles. A further example is the fish, which sometimes lives together with a shrimp. The shrimp digs and cleans up a burrow in the sand in which both the shrimp and the fish live. The shrimp is almost blind, leaving it vulnerable to predators when outside its burrow, in case of danger the goby fish touches the shrimp with its tail to warn it. When that happens both the shrimp and goby fish quickly retreat into the burrow, different species of gobies also exhibit mutualistic behavior through cleaning up ectoparasites in other fish. Another non-obligate symbiosis is known from encrusting bryozoans and hermit crabs, the bryozoan colony develops a cirumrotatory growth and offers the crab a helicospiral-tubular extension of its living chamber that initially was situated within a gastropod shell. A spectacular examples of mutualism is between the siboglinid tube worms and symbiotic bacteria that live at hydrothermal vents and cold seeps
19.
Nod factor
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Nodulation factors are signaling molecules produced by bacteria known as rhizobia during the initiation of nodules on the root of legumes. A symbiosis is formed when legumes take up the bacteria, the rhizobia produce nitrogen for the plant, and the legumes produce leghemoglobin to carry away any oxygen that would inhibit nitrogenase activity. Nod factors structurally are lipochitooligosaccharides that consist of an acylated chitin oligomeric backbone with various functional group substitutions at the terminal or non-terminal residues, the number of N-acetylglucosamine molecules vary among Nod factors, however, generally the length of a chitin backbone is from 3 to 5. The exact chemical structure of the Nod factor that is recognised by the plant varies between species and is the basis for host–symbiont specificity. Nod factors are recognized by a class of receptor kinases that have so-called LysM domains in their extracellular domains. The two LysM receptor kinases that appear to make up the Nod factor receptor were first isolated in the model legume Lotus japonicus in 2003 and they now have been isolated also from soybean and the model legume Medicago truncatula. NFR5 lacks the classical activation loop in the kinase domain, Nod gene expression is induced by the presence of certain flavonoids in the soil, which are secreted by the plant to attract the bacteria. These chemicals induce the formation of NodD, which in turn activates other genes involved in the expression of nod factors, Nod factors induce root-hair curling such that it envelops the bacterium. This is followed by the breakdown of the cell wall. The end result is the nodule, the structure in which nitrogen is fixed, Nod factors act by inducing changes in gene expression in the legume, most notable the nodulin genes, which are needed for nodule organogenesis. At least three plant genes which are stimulated by Nod factors are involved in the arbuscular mycorrhizal symbiosis. The addition of certain Nod factors enhances arbuscular mycorrhizal colonization, indicating that the two very different symbioses may share some common mechanisms
20.
Root nodule
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Root nodules occur on the roots of plants that associate with symbiotic nitrogen-fixing bacteria. Under nitrogen-limiting conditions, capable plants form a relationship with a host-specific strain of bacteria known as rhizobia. This process has evolved multiple times within the Fabaceae, as well as in species found within the Rosid clade. The Fabaceae include legume crops such as beans and peas and their ability to fix gaseous nitrogen makes legumes an ideal agricultural organism as their requirement for nitrogen fertilizer is reduced. Indeed high nitrogen content blocks nodule development as there is no benefit for the plant of forming the symbiosis, the energy for splitting the nitrogen gas in the nodule comes from sugar that is translocated from the leaf. Malate as a product of sucrose is the direct carbon source for the bacteroid. Nitrogen fixation in the nodule is very oxygen sensitive, Legume nodules harbor an iron containing protein called leghaemoglobin, closely related to animal myoglobin, to facilitate the conversion of nitrogen gas to ammonia. Plants that contribute to nitrogen fixation include the legume family – Fabaceae – with taxa such as kudzu, clovers, soybeans, alfalfa, lupines, peanuts, and rooibos. They contain symbiotic bacteria called rhizobia within the nodules, producing compounds that help the plant to grow. When the plant dies, the nitrogen is released, making it available to other plants. The great majority of legumes have this association, but a few genera do not, Inga alley farming relies on the leguminous genus Inga, a small tropical, tough-leaved, nitrogen-fixing tree. These plants belong to 25 genera distributed among 8 plant families, the ability to fix nitrogen is far from universally present in these families. For instance, of 122 genera in the Rosaceae, only 4 genera are capable of fixing nitrogen, all these families belong to the orders Cucurbitales, Fagales, and Rosales, which together with the Fabales form a clade of eurosids. Determinate nodules are found on certain tribes of tropical legume such as those of the genera Glycine, Phaseolus and these determinate nodules lose meristematic activity shortly after initiation, thus growth is due to cell expansion resulting in mature nodules which are spherical in shape. Another types of determinate nodule is found in a range of herbs, shrubs and trees. These are always associated with the axils of lateral or adventitious roots and are formed following infection via cracks where these roots emerge and their internal structure is quite different from those of the soybean type of nodule. Indeterminate nodules are found in the majority of legumes from all three sub-families, whether in temperate regions or in the tropics and this results in the nodule having a generally cylindrical shape, which may be extensively branched. Because they are growing, indeterminate nodules manifest zones which demarcate different stages of development/symbiosis
21.
Luteolin
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Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance. Luteolin is most often found in leaves, but it is seen in rinds, barks, clover blossom. It has also been isolated from the flowering plant, Salvia tomentosa in the mint family. Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges and it can also be found in the seeds of the palm Aiphanes aculeata
22.
Apigenin
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Apigenin, found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a crystalline solid that has been used to dye wool. In in vitro experiments and animal studies, a variety of biological activities of apigenin have been identified. Apigenin induces autophagy in leukemia cells, which may support a possible chemopreventive role, induced autophagy interfers with the action of the chemotherapy drug vincristine. Apigenin is a potent inhibitor of CYP2C9, a responsible for the metabolism of many pharmaceutical drugs in the body. Apigenin dimers can reverse the highest level of resistance found in cancer stem cells. Apigenin has been shown to prevent renal damage caused by ciclosporin in rats, ciclosporin enhances the expression of transforming growth factor-β in the rat kidney, which signifies accelerated apoptosis. Therefore, transforming growth factor-β and apoptotic index may be used to assess apigenin, apigenin acts as a monoamine transporter activator, one of the few chemicals demonstrated to possess this property. Apigenin is a ligand for central benzodiazepine receptors that competitively inhibited the binding of flunitrazepam with a Ki of 4 μM, exerting anxiolytic, apigenin shows second-order positive modulatory activity at GABAA receptors. It has also effects on adenosine receptors and blocks NMDA receptors, in addition, like various other flavonoids, apigenin has been found to possess nanomolar affinity for the opioid receptors, acting as a non-selective antagonist of all three opioid receptors. In vitro studies have shown that apigenin may be toxic to red blood cells, while potentially promising, the study used rats and its effects have yet to be demonstrated in humans. Apigenin readily crosses the barrier and has not demonstrated toxicity at high doses. It could thus prevent amyloid beta deposition and tau phosphorylation due to neuroinflammation, apigenin is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources. Apigenin is particularly abundant in the flowers of plants, constituting 68% of total flavonoids
23.
Tangeretin
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Tangeritin is an O-polymethoxylated flavone that is found in tangerine and other citrus peels. Tangeritin strengthens the wall and acts as a plants defensive mechanism against disease-causing pathogens. It has also used as a marker compound to detect contamination in citrus juices. Although few randomized, double-blind human studies have been done, animal shows the potential of tangeritin as a cholesterol lowering agent. A study on rats demonstrated potential protective effects against Parkinsons disease, tangeritin also shows enormous potential as an anti cancer agent. In in vitro studies, tangeritin appears to some of the adaptations of cancer cells. Tangeritin induced apoptosis in leukemia cells while sparing normal cells, once tangeritin was removed from the tumor cells, their cell cycle progression returned to normal. Tangeritin also counteracts tumor suppression of gap junction intercellular signaling, in summary, in vitro studies show antimutagenic, antiinvasive and antiproliferative effects. One caveat is that tangeritin appears to counteract the anticancer drug tamoxifen, tangeritin is commercially available as a dietary supplement
24.
Quercetin
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Quercetin /ˈkwɜːrsᵻtᵻn/ is a flavonol found in many fruits, vegetables, leaves, and grains. It can be used as an ingredient in supplements, beverages, while quercetin supplements have been promoted for prevention and treatment of cancer, there is no reliable clinical evidence that quercetin can prevent or treat cancer in humans. Also, there is no evidence that consuming foods rich in quercetin reduces the risk of cancer or any other disease, Quercetin supplements have also been promoted for the treatment of a wide spectrum of other diseases. Quercetin is contraindicated with some antibiotics, it may interact with fluoroquinolones, whether this inhibits or enhances the effect of fluoroquinolones is not certain. As paclitaxel is metabolized primarily by CYP2C8, its bioavailability may be increased unpredictably by quercetin, Quercetin is a flavonoid widely distributed in nature. The name has been used since 1857, and is derived from quercetum and it is a naturally occurring polar auxin transport inhibitor. Quercetin is one of the most abundant dietary flavonoids with a daily consumption of 25–50 mgs. In red onions, higher concentrations of quercetin occur in the outermost rings and in the part closest to the root, one study found that organically grown tomatoes had 79% more quercetin than non-organically grown fruit. Quercetin is present in various kinds of honey from different plant sources, one molecule of 4-coumaroyl-CoA is added to three molecules of malonyl-CoA to form tetrahydroxychalcone using 7, 2′-dihydroxy-4′-methoxyisoflavanol synthase. Tetrahydroxychalcone is then converted into naringenin using chalcone isomerase, naringenin is converted into eriodictyol using flavanoid 3′-hydroxylase. Eriodictyol is then converted into dihydroquercetin with flavanone 3-hydroxylase, which is converted into quercetin using flavonol synthase. Quercetin is the form of a number of other flavonoid glycosides, such as rutin and quercitrin, found in citrus fruit, buckwheat. Quercetin forms the glycosides quercitrin and rutin together with rhamnose and rutinose, likewise guaijaverin is the 3-O-arabinoside, hyperoside is the 3-O-galactoside, isoquercitin is the 3-O-glucoside and spiraeoside is the 4′-O-glucoside. CTN-986 is a quercetin derivative found in cottonseeds and cottonseed oil, the enzyme quercitrinase can be found in Aspergillus flavus. This enzyme hydrolyzes the glycoside quercitrin to release quercetin and L-rhamnose and it is an enzyme in the rutin catabolic pathway The oral bioavailability of quercetin in humans is low and highly variable and is rapidly cleared. Following dietary ingestion, quercetin undergoes rapid and extensive metabolism that makes the biological effects presumed from in vitro studies unlikely to apply in vivo, in rats, quercetin did not undergo any significant phase I metabolism. In contrast, quercetin did undergo extensive phase II to produce metabolites that are more polar than the parent substance and hence are more rapidly excreted from the body, the meta-hydroxyl group of catechol is methylated by catechol-O-methyltransferase. Four of the five groups of quercetin are glucuronidated by UDP-glucuronosyltransferase
25.
Kaempferol
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Kaempferol is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods. Kaempferol is a crystalline solid with a melting point of 276–278 °C. It is slightly soluble in water and highly soluble in hot ethanol, ethers, kaempferol acts as an antioxidant by reducing oxidative stress. Many studies suggest that consuming kaempferol may reduce the risk of various cancers, kaempferol is a secondary metabolite found in many plants, plant-derived foods, and traditional medicines. Kaempferol is common in Pteridophyta, Pinophyta and Angiospermae, within Pteridophyta and Pinophyta, kaempferol has been found in diverse families. Kaempferol has also identified in both Dicotyledons and Monocotyledons of Angiosperms. The total average intake of flavonols and flavones in a diet is estimated as 23 mg/day. This pathway is located in the plant plastid, and is the entry to the biosynthesis of phenylpropanoids, the phenylpropanoid pathway is the pathway that converts phenylalanine into tetrahydroxychalcone. Flavonols, including kaempferol, are products of this pathway, kaempferol is ingested as a glycoside, absorbed in the small intestine, usually by passive diffusion due to kaempferol’s lipophilicity, and metabolized in various areas of the body. In the small intestine, kaempferol is metabolized to glucuronides and sulfoconjugates by intestinal enzymes and it can also be metabolized by colon microflora which can hydrolyze the glycosides to aglycones or form simple phenolic compounds. These compounds can be absorbed or excreted, kaempferol is also extensively metabolized in the liver to form glucurono-conjugated and sulfo-conjugated forms. These forms of kaempferol, and kaempferol itself, can then be excreted in urine, about 2. 5% of kaempferol ingested is excreted as urine. Much of the rest of ingested kaempferol is present in the plasma, in vitro studies along with some animal testing has demonstrated the wide range of potential anti-cancer properties of kaempferol. It has been shown in malignant cancer cells to interrupt cell growth, limit angiogenesis, induce apoptosis, kaempferol has also been shown to reduce MMP-3 protein activity inferring potential ability to reduce metastasis. Estrogen receptors are important in maintaining a normal mammary gland, and in the development of primary and secondary breast cancer. Kaempferol has been shown to interact with the estrogen receptor pathway and this compound exhibits ability to lower levels of Aromatase. Kaempferol has also found to induce apoptosis in breast cancer cells through extracellular signal-regulated kinase ½ activation and up-regulation of p53. Available evidence has shown that kaempferol can “inhibit VEGF production and suppress cancer cell metastasis in vitro”
26.
Myricetin
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Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties. It is commonly derived from vegetables, fruits, nuts, berries, tea, myricetin is structurally similar to fisetin, luteolin, and quercetin and is reported to have many of the same functions as these other members of the flavonol class of flavonoids. Reported average intake of myricetin per day depending on diet. Dihydromyricetin is frequently sold as a supplement and has function as a partial GABAA receptor potentiator. Myricetin can alternatively be produced directly from kaempferol, which is another flavonol, antioxidants are molecules present in fruits and vegetables that have been demonstrated to protect against some forms of cancer and cardiovascular disease. Biomolecules and cell structures can experience oxidative stress due to the presence, ROS like •OH, •O2−, and H2O2 are produced during cellular metabolism processes. ROS can cause damage to lipids, DNA, and proteins, flavonoids including myricetin are able to scavenge for ROS and can chelate intracellular transition metal ions that ultimately produce ROS. Myricetin also enhances the effects of other antioxidants, myricetin can induce the enzyme glutathione S-transferase. GST has been suggested to protect cells against oxidative stress by protecting cells against free-radicals, in vitro studies have shown that myricetin significantly increased GST activity. Multiple studies have demonstrated that myricetin also has the potential to act as a pro-oxidant due to its tendency to undergo autoxidation depending upon its environment. It has been seen that when in the presence of cyanide, autoxidation is favored, resulting in superoxide, however, sodium azide, superoxide dismutase, and catalase have been seen to inhibit the autoxidation of myricetin. Myricetin may also act as a pro-oxidant in its ability to increase the production of hydroxy radicals through reactions with Fe2+ or Fe3+−EDTA, myricetin is also effective in protecting cells from carcinogenic mutation. Myricetin reduces the risk of skin tumorigenicity that is caused by aromatic hydrocarbons like benzopyrene. Myricetin provided protection against the formation of tumors in mice models after tumor initiating. On a more level, it was shown that topical application of myricetin to mice inhibited the binding of benzopyrenes to DNA. Myricetin also has shown to inhibit the act of genetic mutation as exhibited by the Ames test. This data shows that myricetin is not unilaterally able to reduce the activity of all polycyclic aromatic hydrocarbons or even the more specific subclass of benzopyrenes. It is to be noted that myricetin’s exact biochemical activity is not fully understood
27.
Fisetin
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Fisetin is a flavonol, a structurally distinct chemical substance that belongs to the flavonoid group of polyphenols. It can be found in plants, where it serves as a colouring agent. It is also found in fruits and vegetables, such as strawberries, apples, persimmons, onions. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891, the biological activity of fisetin has been studied in many laboratory assays, like other polyphenols it has many activities. Fisetin can be found in a variety of plants. Along with myricetin, fisetin provides the color of the yellow dye young fustic. Many fruits and vegetables also contain fisetin, including strawberries apples, fisetin can be extracted from fruit and herbal sources in juices, wines, and infusions such as teas. It is also found in Monocotyledons such as onions and it is also present in Pinophyta species such as the yellow cypress. Fisetin is a polyphenol, which is a flavonoid subgroup, flavonoid synthesis begins with the phenylpropanoid pathway, in which phenylalanine, an amino acid, is transformed into 4-coumaroyl-CoA. This is the compound that enters the flavonoid biosynthesis pathway, chalcone synthase, the first enzyme of this pathway, produces chalcone from 4-coumaroyl-CoA. All flavonoids are derived from this chalcone backbone, the activity of different enzymes, including isomerases and hydroxylases, alter the backbone depending on the subclass of the flavonoid being produced. Transferases help control changes in the solubility and reactivity by catalyzing the addition of things such as methyl groups. This allows for controlled fluctuations in physiological activities, flavonoid biosynthesis gene regulation occurs through the interaction of different transcription factors. Depending on the combination of transcription factor interactions, the genes involved in flavonoid biosynthesis are expressed in specific locations of the plant. These transcription factors continue to be studied in plant model organisms such as maize, the environment of the plant has also been shown to affect the flavonoid biosynthesis pathway. Shorter wavelengths of light, ranging from blue to UV light and these wavelengths activate enzymes that are involved in the phenylpropanoid and flavonoid biosynthesis pathways, stimulating the production of flavonoids. The level of stimulation can vary between individual fruits, fisetin, like other polyphenols such as resveratrol, is a sirtuin-activating compound and has been shown in laboratory studies to extend the life of simple organisms like yeast, worms, and flies. Fisetin has shown activity in studies on cells and model animals conducted in laboratories
28.
Galangin
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Galangin is a flavonol, a type of flavonoid. It is found in high concentrations in Alpinia officinarum and Helichrysum aureonitens and it is also found in the galangal rhizome and in propolis. Galangin has been shown to have in vitro antibacterial and antiviral activity, the flavonol also inhibits the growth of breast tumor cells in vitro. List of compounds with carbon number 15 Galangin on Chemblink. com
29.
Rhamnazin
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Rhamnazin is an O-methylated flavonol, a type of chemical compound. It can be found in Rhamnus petiolaris, a plant endemic to Sri Lanka. The enzyme 3-methylquercetin 7-O-methyltransferase uses S-adenosyl methionine and isorhamnetin to produce S-adenosylhomocysteine, the enzyme 3, 7-dimethylquercetin 4-O-methyltransferase uses S-adenosyl methionine and rhamnazin to produce S-adenosylhomocysteine and ayanin
30.
Hesperetin
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Hesperetin is the 4-methoxy derivative of eriodictyol, a flavanone. Hesperetins 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons, hesperetin are not found to a significant extent in Citrus spp. A variety of glycosides of hesperetin are known, including, Hesperidin is a water－insoluble flavonoid glycoside whose solubility is below 5 μg/ml in water, Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin. Neohesperidin is the 7-O-neohesperidoside of hesperetin, hesperetin-7-O-α-L-Rhamnopyranoside is found in the roots of clammy cherry. Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and it is found in the hyphomycetes species Stilbella fimetaria
31.
Naringenin
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Naringenin is a flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, naringenin can be found in grapefruit, oranges, tomatoes and in water mint. This bioflavonoid is difficult to absorb on oral ingestion, in the best-case scenario, only 15% of ingested naringenin will get absorbed in the human gastrointestinal tract. The naringenin-7-glucoside form seems less bioavailable than the aglycol form, grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice. Also found in grapefruit is the related compound kaempferol, which has a hydroxyl group next to the ketone group, naringenin can be absorbed from cooked tomato paste. The National Research Institute of Chinese Medicine in Taiwan conducted experiments on the effects of the grapefruit flavanones naringin and naringenin on CYP450 enzyme expression, naringenin proved to be a potent inhibitor of the benzopyrene metabolizing enzyme benzopyrene hydroxylase in experiments in mice. Naringenin has also shown to reduce oxidative damage to DNA in vitro. Naringenin has also shown to reduce hepatitis C virus production by infected hepatocytes in cell culture. This seems to be secondary to naringenins ability to inhibit the secretion of very-low-density lipoprotein by the cells, the antiviral effects of naringenin are currently under clinical investigation. Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet, naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet. It also produces BDNF-dependent antidepressant-like effects in mice, in 2006 it was shown to increase the mRNA expression levels of two DNA repair enzymes, DNA pol beta and OGG1, specifically in prostate cancer cells. Like many other flavonoids, naringenin has been found to possess activity at the opioid receptors. It specifically acts as a non-selective antagonist of all three opioid receptors, albeit with weak affinity, the enzyme naringenin 8-dimethylallyltransferase uses dimethylallyl diphosphate and --naringenin to produce diphosphate and 8-prenylnaringenin. Cunninghamella elegans, a model organism of the mammalian metabolism
32.
Homoeriodictyol
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Homoeriodictyol is a bitter-masking flavanone extracted from Yerba Santa a plant growing in America. Homoeriodictyol is one of the 4 flavanones identified by Symrise in this plant eliciting taste-modifying property, homoeriodictyol sodium salt, eriodictyol, homoeriodictyol Sodium salt elicited the most potent bitter-masking activity by reducing from 10 to 40% the bitterness of salicin, amarogentin, paracetamol and quinine. However no bitter-masking activity was detected with bitter linoleic acid emulsions, according to Symrises scientists homoeriodictyol sodium salt seems to be a taste-modifier with large potential in food applications and pharmaceuticals. Structural relatives investigation based on eriodictyol and homoeriodictyol, found 2, at 0. 1g/L, this vanillin derivative, was able to reduce the bitterness of a 0. 5g/L caffeine solution by about 30%
33.
Taxifolin
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Taxifolin is a flavan-on-ol, a type of flavonoid. It can be found in conifers like the Siberian larch, Larix sibirica, in Russia, in Pinus roxburghii, in Cedrus deodara and in the Chinese yew and it is also found in the silymarin extract from the milk thistle seeds. Taxifolin is present in vinegars aged in cherry wood, taxifolin is not mutagenic and less toxic than the related compound quercetin. It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism, taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner. There is also a correlation between the antiproliferative effects of dihydroquercetin derivatives on murine skin fibroblasts and human breast cancer cells. The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine, also taxifolin inhibited the cellular melanogenesis as effectively as arbutin, one of the most widely used hypopigmenting agents in cosmetics. However, arbutin acts as quercetin extremely mutagenic, carcinogenic and toxic, taxifolin, as well as many other flavonoids, has been found to act as a non-selective antagonist of the opioid receptors, albeit with somewhat weak affinity. Taxifolin has been found to act as an agonist of the adiponectin receptor 2, the enzyme taxifolin 8-monooxygenase uses taxifolin, NADH, NADPH, H+, and O2 to produce 2, 3-dihydrogossypetin, NAD+, NADP+, and H2O. The enzyme leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, taxifolin, succinate, CO2, astilbin is the 3-O-rhamnoside of taxifolin. Taxifolin deoxyhexose can be found in açai fruits, taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa. --Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa, -Taxifolin-3-O-β-D-pyranoglucoside has been isolated from the rhizome of Smilax glabra. Minor amount of taxifolin 4′-O-β-glucopyranoiside can be found in red onions, -Taxifolin 3-O-arabinoside and -taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides. -Leucocyanidin can be synthesized from taxifolin by sodium borohydride reduction
34.
Flavan-3-ol
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Flavan-3-ols are derivatives of flavans that use the 2-phenyl-3, 4-dihydro-2H-chromen-3-ol skeleton. These compounds include catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, flavanols are not to be confused with flavonols, a class of flavonoids containing a ketone group. The single-molecule catechin, or isomer epicatechin, adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers, flavanols possess two chiral carbons, meaning four diastereoisomers occur for each of them. Catechins are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, early use of the term bioflavonoid was imprecisely applied to include the flavanols, which are distinguished by absence of ketone. Catechin monomers, dimers, and trimers are colorless, higher order polymers, anthocyanidins, exhibit deepening reds and become tannins. The catechins are abundant in teas derived from the tea plant Camellia sinensis, as well as in some cocoas, catechins are also present in the human diet in fruits, vegetables and wine, and are found in many other plant species, as well as cocoa. Catechin and epicatechin are epimers, with -epicatechin and -catechin being the most common optical isomers found in nature, catechin was first isolated from the plant extract catechu, from which it derives its name. Heating catechin past its point of decomposition releases pyrocatechol, which explains the origin of the names of these compounds. Catechin gallates are gallic acid esters of the catechins, an example is epigallocatechin gallate, the flavonoids are products from a cinnamoyl-CoA starter unit, with chain extension using three molecules of malonyl-CoA. Reactions are catalyzed by a type III PKS enzyme and these enzyme do not use ACPSs, but instead employ coenzyme A esters and have a single active site to perform the necessary series of reactions, e. g. chain extension, condensation, and cyclization. Chain extension of 4-hydroxycinnamoyl-CoA with three molecules of malonyl-CoA gives initially a polyketide, which can be folded and these allow Claisen-like reactions to occur, generating aromatic rings. HSCoA, Coenzyme A. L-Tyr, L-tyrosine, L-Phe, L-phenylalanine, the supposed health benefits of catechins have been studied extensively in humans and animal models, but there are no proven effects that apply to human health. Until 2013, neither the Food and Drug Administration nor the European Food Safety Authority had approved any health claim for catechins or approved any as pharmaceutical drugs, moreover, several companies have been cautioned by the FDA over misleading health claims. Additionally, such a product is high in fat, sugar and Calories, fluorescence-lifetime imaging microscopy can be used to detect flavanols in plant cells Recent study tested catechins employed to coat nanoparticles of iron oxides in the blood. These particles allow visualization of vessels - and especially cancer tumors in mice - in an MRI exam, the nanoparticles would clump together without the catechin coating
35.
Flavan-4-ol
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The flavan-4-ols are flavone-derived alcohols and a family of flavonoids. Flavan-4-ols are colorless precursor compounds that polymerize to form red phlobaphene pigments and they can be found in the sorghum. Glycosides can be isolated from an extract of the rhizomes of Abacopteris penangiana. Apiforol Luteoforol Flavanone 4-reductase is an enzyme that uses -flavan-4-ol and NADP+ to produce -flavanone, NADPH and these compounds have absorption maxima of 564 nm
36.
Leucoanthocyanidin
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Leucoanthocyanidin are colorless chemical compounds related to anthocyanidins and anthocyanins. Leucoanthocyanins can be found in Anadenanthera peregrina and in species of Nepenthes including N. burbidgeae, N. muluensis, N. rajah, N. tentaculata. Bate-smith recommended in 1954 the use of the Forestal solvent for the isolation of leuco-anthocyanins, leucoanthocyanidin dioxygenase uses flavan-3, 4-diols to produce 3-hydroxyanthocyanidins. The gene encoding the enzyme has been identified in peach and expression has been studied in Vitis vinifera
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Catechin
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Catechin /ˈkætᵻtʃɪn/ is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite and it belongs to the group of flavan-3-ols, part of the chemical family of flavonoids. The name of the chemical family derives from catechu, which is the tannic juice or boiled extract of Mimosa catechu. Catechin possesses two benzene rings and a dihydropyran heterocycle with a group on carbon 3. The A ring is similar to a resorcinol moiety while the B ring is similar to a catechol moiety, there are two chiral centers on the molecule on carbons 2 and 3. Two of the isomers are in trans configuration and are called catechin, the most common catechin isomer is the -catechin. The other stereoisomer is -catechin or ent-catechin, the most common epicatechin isomer is -epicatechin. The different epimers can be distinguished using chiral column chromatography, making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called -catechin or DL-catechin and -epicatechin or DL-epicatechin, catechin and epicatechin are the building blocks of the proanthocyanidins, a type of condensed tannin. Diastereoisomers gallery Moreover, the flexibility of the C-ring allows for two isomers, putting the B ring either in a pseudoequatorial position or in a pseudoaxial position. Studies confirmed that -catechin adopts a mixture of A- and E-conformers in aqueous solution, as flavonoids, catechins can act as antioxidants when in high concentration in vitro, but compared with other flavonoids, their antioxidant potential is low. Electrochemical experiments show that -catechin oxidation mechanism proceeds in steps, related with the catechol and resorcinol groups. The oxidation of the catechol 3′, 4′-dihydroxyl electron-donating groups occurs first, at very low positive potentials, the hydroxyl groups of the resorcinol moiety oxidised afterwards were shown to undergo an irreversible oxidation reaction. The laccase/ABTS system oxidizes -catechin to oligomeric products of which proanthocyanidin A2 is a dimer, the two isomers are mostly found as cacao and tea constituents. -Epicatechin can be found in beans and was first called kakaool or cacao-ol. It was isolated from green tea by Michiyo Tsujimura in 1929, maximilian Nierenstein was among those who proved the presence of catechin in cocoa beans in 1931. Catechin is also found as glycoside and the form has also antioxidant properties in vitro. The main dietary sources of catechins in Europe and the United States are tea, catechins and epicatechins are found in cocoa, which, according to one database, has the highest content of catechins among foods analyzed, followed by prune juice and broad bean pod
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Epicatechin gallate
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Epicatechin gallate is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape, the tea component epicatechin gallate is being researched because in vitro experiments showed it can reverse methicillin resistance in bacteria like Staphylococcus aureus. If confirmed, this means the intake of a tea extract containing this component might also enhance the effectiveness of methicillin treatment against some resistant bacteria in vivo. Epicatechin, as well as other flavonoids, has been found to act as a non-selective antagonist of the opioid receptors. List of phytochemicals in food Green tea extract
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. PMID 20087468.
