Isoflavonoids (13) PDF

Summary

This document provides a detailed overview of isoflavonoids, covering their structural differences, biological activities (including estrogenic activity and their role in preventing certain cancers), and chemical composition. Isoflavonoids are a class of plant compounds, particularly important in the leguminous family (Fabaceae).

Full Transcript

ISOFLAVONOIDS ISOFLAVONOIDS D fference between flavono ds and soflayono ds Structurally R ng B s moved from pos t on 2 to 3 ❑ 1,2-diphenylpropane skeleton ❑ All molecules in this group can be related to the skeleton...

ISOFLAVONOIDS ISOFLAVONOIDS D fference between flavono ds and soflayono ds Structurally R ng B s moved from pos t on 2 to 3 ❑ 1,2-diphenylpropane skeleton ❑ All molecules in this group can be related to the skeleton of 3-phenylchromane Chromone do ❑ Generally found in Fabaceae Olab l r Legume fam ly Baklag ller 1 O thenvo monde 6 to 3 funI O Br ng ISOFLAVONOIDS Types of Isoflavonoids s ns t ▪ Isoflavones Phytoestrogens they show weedact v ty unl ke ▪ Isoflavanones estrad ol tself ▪ Isoflavans ▪ Isoflavens ▪ Pterocarpans (additional ring) ▪ Coumaranochromones ▪ Coumestans OI O O 2 OMe O 3 O O O Isoflavone Rotenoid O nsent ate O O O Isoflavanone O HO O O O Coumestan O O O OH HO 2 O Isoflavene Jun HO HO I add t onal 3 phenylcoumar n cycl zat on 3 phenyl r yl coumar n Pterocarpan Chief types of isoflavonoids O and interconversions ISOFLAVONOIDS Biological activity ❑ Rotenoids are insectiside (Derris spec.) natural safe nsect c ble agents ❑ Many of them are phytoalexins (substances Fendary metabol tes when plant s mpacted byyatff. s produced by the plant in response to anatensemetalsm infection by a pathogenic agent, most often fungi) ❑ Natural defense products for plants ISOFLAVONOIDS Biological activity ❑ Estrogenic activity: - Genistein, daidzein, methoxydaidzein and biochanin A - Excess consumption of clover induced infertility in sheeps love clover sheep - Compete with estradiol at estrogen receptors ❑ Preventive effect on hormone-dependent mammary, prostate and colon cancers ❑ Isoflavones and soybean decrease the symptoms of menopause E ean me most amount of phytoestrogens ❑ They also reduce the risk of osteoporosis Prevalence of breast cancer s found lower n As an women ISOFLAVONOIDS ROTENOID-CONTAINING DRUGS Derris Derris elliptica (Fabaceae) Roots Southeast Asia ISOFLAVONOIDS ROTENOID-CONTAINING DRUG Derris Derris elliptica (Fabaceae) Chemical composition ❖ Rotenoids (3-10%) - Enriched and titrated to contain 30% rotenone of Derris extract is on the market Pharmacological activity and uses ❖ Rotenone is responsible for the insecticidal property ❖ Inhibits mitochondrial respiration ❖ Powders and extracts are used for the treatment of house plants and ectoparasites of domestic animals ISOFLAVONOIDS ISOFLAVONOID-CONTAINING DRUGS Red clover, Kırmızı yonca m Trifolium pratense (Fabaceae) Flowering tops ISOFLAVONOIDS / Trifolium pratense Chemical composition - Isoflavonoids; HO O FEE Diadzein Dav dze n Biochanin A, genistein OH O OH Formononetin Metabolisation - Flavonoids; * Isorhamnetin HO O 1 TEETH * Kaempferol 3 * Quercetin glycosides - Coumarins ISAAC OH Equol - Saponins elm.tt Eet ne s Educed ISOFLAVONOIDS / Trifolium pratense Red clover, Kırmızı yonca Trifolium pratense (Fabaceae) Flowering tops Therapeutic indications ❖ For alleviating menopausal symptoms; - Hot flushes - Profuse sweating - Sleep disorders - Nervousness ❖ Cancer chemopreventive Breastancer FLAVONOIDS OH OH OH OH OH OH OH 4'4'4' 1' B 1' 1' HO HO HO 777 99 O O O 22 A C 10 10 OH OH 555 4444 O Flavone Flavonol Flavanonol Flavanone OH OH OH O O O anf.ua ❖ Possess 2-phenylchromone skeleton aKo g ❖ Universal plant pigments ❖ Structural diversity  ffrentn gtfMEse th s. nt ma n t es ❖ Exhibit a wide range of biological activities FLAVONOIDS & ISOFLAVONOIDS ❑ Glycyrrhiza L. (Fabaceae) ❖ Perennial herbs ❖  30 species worldwide ❖ Most used species; - G. glabralet (European licorice) taste due to sapon n IGlycyrrh z n - G. uralensis and G. inflata (Chinese licorice) Tegan ❖ Antiulcer, antiviral, hepatoprotector, antimicrobial l cor ceroot meyancok antiinflammatory and cytotoxic activities ❖ Widely used for its sweet taste Gafner et al., 2011. J. Nat. Prod. 74, 2514. Omura et al., 2002. Pure Appl.Chem, 74, 1199. ❑ Glycyrrhiza L. (Fabaceae) Chemical composition ❖ Triterpene saponins ❖ Flavonoids (flavanone and chalcone) ❖ Isoflavonoids (less common); * Isoflavans * Isoflavens * Pterocarpans * 3-arylcoumarins * Coumestans Montoro et al., 2011. J. Pharm. Biomed. Anal. 54, 535. Zheng et al., 2010. Planta Med., 76, 1457. ISOFLAVONOIDS HO HO HOHO HO 7 O OO O O 77 7 O A C 3333 555 1' 1'1' B 5 OH OH OO OH OH O OH OH HO OH OH isoflavene isoflavan isoflavanone isoflavone OH 3-Arylcoumarin Coumestan ❖ Possess 3-phenylchromone skeleton ❖ 11 subclasses ❖ Mainly in Fabaceae family ❖ Structural diversity  ISOFLAVONOIDS NEOFLAVONOIDS neothawno ds s on very small group ❑ C15 compounds of the Ar-C3-Ar type ❑ Structurally related to flavonoids and isoflavonoids ❑ Constructed on a 1,1-diphenylpropane skeleton ❑ Isolated from Fabaceae and Rubiaceae compared to the or g nal coumar n structure Dalbergin EEEIE.EEE ANTHOCYANINS ANTHOCYANINS ▪ ANTHOS (= Flower) + KUANOS (= Blue) ▪ Initially attributed to the substance responsible for the color of the cornflower ▪ Water-soluble pigments responsible for the red, pink, mauve, purple, blue, or violet color of most flowers and fruits H fall D fferentmeals su sst f. nt ▪ These pigments occur as glycosides (= anthocyanins) ▪ Their aglycones (= anthocyanidins) are derived from the 2-phenylbenzopyrylium cation (= flavylium cation) ▪ Present in almost all Angiosperms ANTHOCYANINS Roles in Plants; F rstytythean ng was extracted from ✓ Their colors attract insects and birds ✓ Play a role in pollination and seed dispersal b Structure and Biosynthesis Hs ng n Inf nthganta ns Anthocyan ol ns are water soluble p gments thus used R1 as well for color ng teas 3' OH 1 HO 7 O R1 R2 5' R2 + Pelargonidin H H 3 Cyanidin OH H OH 5 Peonidin OMe H OH Delphinidin OH OH Malvinidin OCH3 OCH3 ANTHOCYANINS Structure and Biosynthesis ✓ Occur in acidic medium as cations ✓ Always hydroxylated in the 3-position ✓ Most often penta-(3,5,7, 3’,4’) or hexasubstituted (3,5,7, 3’,4’,5’) by –OH groups; * Free * OMe * O-glyc. ✓ C-3(OH) group is always linked to a sugar (very often glucose) ANTHOCYANINS Structure and Biosynthesis ✓ Most common anthocyanins are 3-monoglycosides or 3,5-diglycosides ✓ The sugar residue can be mono-, di-, or triglycosides ✓ Many anthocyanins are acylated from their sugar units by; * Phenylpropanoic acids (caffeic, ferulic, p- coumaric acids) * Dicarboxylic acids (malonic, malic, oxalic and succinic acids) ANTHOCYANINS OH O HO O HO OH OH O O HO O O O + OH HO OH OH O O COOH O HO OH prett er OH O propant OH pheny Complexity of anthocyanins ANTHOCYANINS Physico-Chemical Properties ❑ Solutions in H2O; rae atE EEotcje nt. n e * 2-phenylbenzopyrylium cation possess a weak diacid and a good electrophilic reagent ❑ In strong acidic medium (pH

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