Prenylflavonoid

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Chemical structure of 8-prenylnaringenin, a prenylated flavanone found in hops 8-Prenylnaringenin.svg
Chemical structure of 8-prenylnaringenin, a prenylated flavanone found in hops

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant [1] properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid. [2]

Contents

Monoprenyl isoflavone epoxidase is a key enzyme in fungal Botrytis cinerea metabolism of prenylated flavonoids. [3]

Many prenylflavonoids appear to have anticancer activity in vitro. [4]

Prenylchalcones, prenylflavones, prenylflavonols and prenylflavanones are classes of prenylflavonoids.

Examples

6-Prenylnaringenin, 6-geranylnaringenin, 8-prenylnaringenin and isoxanthohumol can be found in hops and beer. [5] [6] Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoestrogen known.

Australone A can be found in Morus australis . [7]

6,8-Diprenyleriodictyol, dorsmanin C and dorsmanin F can be found in Dorstenia mannii . [1]

Epimedium wushanense contains a number of flavanoids. 37 compounds were characterized from the underground and aerial parts of the plant. Among them, 28 compounds were prenylflavonoids. The predominant prenylated flavonoid, epimedin C, [8] ranged from 1.4 to 5.1% in aerial parts and 1.0 to 2.8% in underground parts. [9]

Artocarpus nobilis contains prenylated flavonoids in its root bark. [10]

8-Prenylkaempferol can be found in Sophora flavescens . [11]

Cannflavins are prenylflavonoids found in Cannabis sativa . [12]

Prenylated isoflavonoids

A number of bio-active chemicals have been reported from Millettia pachycarpa including several prenylflavonoids. [13] [14] Several chemical analyses have yielded a number of novel prenylated isoflavones including erysenegalensein E, euchrenone b10, isoerysenegalensein E, 6,8-diprenylorobol, furowanin A and B, millewanins-F, G and H, warangalone, and auriculasin from the leaves. [15] [16]

7-O-Methylluteone is a prenylated isoflavone. It can be found in the bark of Erythrina burttii .

Luteone is another prenylated isoflavone found in the pods of Laburnum anagyroides .

Wighteone (6-prenylgenistein), isowighteone (3′-prenylgenistein), and lupiwighteone (8-prenylgenistein) are genistein prenylated derivatives. [2]

Related Research Articles

<i>Humulus</i> Genus of flowering plants belonging to the hemp and hackberry family

Humulus, hop, is a small genus of flowering plants in the family Cannabaceae. The hop is native to temperate regions of the Northern Hemisphere. Hops are the female flowers of the hop species H. lupulus; as a main flavor and aroma ingredient in many beer styles, H. lupulus is widely cultivated for use by the brewing industry.

<i>Epimedium</i> Genus of flowering plants belonging to the barberry family

Epimedium, also known as barrenwort, bishop's hat, fairy wings, horny goat weed, or yin yang huo, is a genus of flowering plants in the family Berberidaceae. The majority of the species are endemic to China, with smaller numbers elsewhere in Asia, and a few in the Mediterranean region.

Daidzein Chemical compound

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease.

Eriodictyol Chemical compound

Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa, a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin.

In enzymology, an isoflavone 7-O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a monoprenyl isoflavone epoxidase (EC 1.14.99.34) is an enzyme that catalyzes the chemical reaction

<i>Sophora flavescens</i> Species of legume

Sophora flavescens, the shrubby sophora, is a species of plant in the genus Sophora of the family Fabaceae. This genus contains about 52 species, nineteen varieties, and seven forms that are widely distributed in Asia, Oceania, and the Pacific islands. About fifteen of these species have a long history of use in traditional Chinese medicines.

Icariin Chemical compound

Icariin is a chemical compound classified as a prenylated flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-O-diglucoside. The compound has been isolated from several species of plant belonging to the genus Epimedium which are commonly known as horny goat weed, Yin Yang Huo, and Herba epimedii. Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function. However, clinical trial data are lacking to support these claims.

The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.

Retusin (isoflavone) Chemical compound

Retusin is an O-methylated isoflavone, a type of flavonoid. It can be found in Fabaceae species like Dipteryx odorata, in Dalbergia retusa and in Millettia nitida. It can also be found in Maackia amurensis cell cultures.

Luteone (isoflavone) Chemical compound

Luteone is a prenylated isoflavone, a type of flavonoid. It can be found in the pods of Laburnum anagyroides and can be synthetized.

Xanthohumol Chemical compound

Xanthohumol is a natural product found in the female inflorescences of Humulus lupulus, also known as hops. This compound is also found in beer and belongs to a class of compounds that contribute to the bitterness and flavor of hops. Xanthohumol is a prenylated chalconoid, biosynthesized by a type III polyketide synthase (PKS) and subsequent modifying enzymes.

<i>Millettia pachycarpa</i> Species of legume

Millettia pachycarpa is a perennial climbing shrub belonging to the genus Millettia. It is one of the most well known among ~150 species of Millettia, as it is widely used in traditional practices, such as for poisoning fish, agricultural pesticide, blood tonic, and treatments of cancer and infertility. The bark fiber is used for making strong ropes.

Barbigerone Chemical compound

Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.

Pterocarpan

Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes which can be formed by coupling of the B ring to the 4-one position.

<i>Erythrina burttii</i> Species of legume

Erythrina burttii is a flowering plant species in the genus of Erythrina found in Kenya and Ethiopia.

8-Prenylnaringenin Chemical compound

8-Prenylnaringenin is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known. The compound is equipotent at the two forms of estrogen receptors, ERα and ERβ, and it acts as a full agonist of ERα. Its effects are similar to those of estradiol, but it is considerably less potent in comparison.

<i>Epimedium wushanense</i> Species of flowering plant

Epimedium wushanense, the Wushan fairy wings, is a flowering plant species in the genus Epimedium.

Isoxanthohumol Chemical compound

Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. It is abbreviated as IX or IXN.

Cannflavin Chemical compound

Cannflavins are a group of chemical compounds found in Cannabis sativa. Chemically, they are prenylflavonoids and are unrelated to THC and other cannabinoids. Cannflavins A and B were first identified in the 1980s and cannflavin C was identified in 2008.

References

  1. 1 2 Dufall, K.G.; Ngadjui, B.T.; Simeon, K.F.; Abegaz, B.M.; Croft, K.D. (2003). "Antioxidant activity of prenylated flavonoids from the West African medicinal plant Dorstenia mannii". Journal of Ethnopharmacology. 87 (1): 67–72. doi:10.1016/S0378-8741(03)00108-9. PMID   12787956.
  2. 1 2 Shen; Huhman, D.; Lei, Z.; Snyder, J.; Sumner, L. W.; Dixon, R. A.; et al. (March 2012). "Characterization of an Isoflavonoid-Specific Prenyltransferase from Lupinus albus" (PDF). Plant Physiology. 159 (1): 70–80. doi:10.1104/pp.112.195271. PMC   3375986 . PMID   22430842.
  3. ↑ Tanaka, Mitsuharu; Tahara, Satoshi (1997). "Fad-dependent epoxidase as a key enzyme in fungal metabolism of prenylated flavonoids". Phytochemistry. 46 (3): 433–9. doi:10.1016/S0031-9422(97)00322-1.
  4. ↑ Miranda, C.L.; Stevens, J.F.; Helmrich, A.; Henderson, M.C.; Rodriguez, R.J.; Yang, Y.-H.; Deinzer, M.L.; Barnes, D.W.; Buhler, D.R. (1999). "Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines". Food and Chemical Toxicology. 37 (4): 271–85. doi:10.1016/S0278-6915(99)00019-8. PMID   10418944.
  5. ↑ Stevens, Jan F; Page, Jonathan E (2004). "Xanthohumol and related prenylflavonoids from hops and beer: To your good health!". Phytochemistry. 65 (10): 1317–30. doi:10.1016/j.phytochem.2004.04.025. PMID   15231405.
  6. ↑ Dhooghe, Liene; Naessens, Tania; Heyerick, Arne; De Keukeleire, Denis; Vlietinck, Arnold J.; Pieters, Luc; Apers, Sandra (2010). "Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards". Talanta. 83 (2): 448–56. doi:10.1016/j.talanta.2010.09.041. PMID   21111159.
  7. ↑ Ko, Horng-Huey; Yu, Sheu-Meei; Ko, Feng-Nien; Teng, Che-Ming; Lin, Chun-Nan (1997). "Bioactive Constituents ofMorus australisandBroussonetia papyrifera". Journal of Natural Products. 60 (10): 1008–11. doi:10.1021/np970186o. PMID   9358644.
  8. ↑ epimedin C Archived 2011-09-10 at the Wayback Machine
  9. ↑ Li, Hui-Fang; Guan, Xiang-yu; Ye, Min; Xiang, Cheng; Lin, Chang-hu; Sun, Chao; Guo, De-an (2011). "Qualitative and quantitative analyses of Epimedium wushanense by high-performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry". Journal of Separation Science. 34 (12): 1437–46. doi:10.1002/jssc.201000899. PMID   21560245.
  10. ↑ Jayasinghe, U.L.B.; Samarakoon, T.B.; Kumarihamy, B.M.M.; Hara, N.; Fujimoto, Y. (2008). "Four new prenylated flavonoids and xanthones from the root bark of Artocarpus nobilis". Fitoterapia. 79 (1): 37–41. doi:10.1016/j.fitote.2007.07.014. PMID   17855020.
  11. ↑ Chiou, Wen-Fei; Chen, Chen-Chih; Wei, Bai-Luh (2011). "8-Prenylkaempferol Suppresses Influenza a Virus-Induced RANTES Production in A549 Cells via Blocking PI3K-Mediated Transcriptional Activation of NF-κB and IRF3". Evidence-Based Complementary and Alternative Medicine. 2011: 1–10. doi:10.1093/ecam/nep066. PMC   3137797 . PMID   19592477.
  12. ↑ Barrett, M. L.; Scutt, A. M.; Evans, F. J. (1986). "Cannflavin A and B, prenylated flavones from Cannabis sativa L". Experientia. 42 (4): 452–453. doi:10.1007/BF02118655. PMID   3754224.
  13. ↑ Singhal, Ashok K.; Sharma, Ram P.; Thyagarajan, Gopalakrishna; Herz, Werner; Govindan, Serengolam V. (1980). "New prenylated isoflavones and a prenylated dihydroflavonol from Millettia pachycarpa". Phytochemistry. 19 (5): 929–34. doi:10.1016/0031-9422(80)85140-5.
  14. ↑ Ye, Haoyu; Chen, Lijuan; Li, Yanfang; Peng, Aihua; Fu, Afu; Song, Hang; Tang, Minghai; Luo, Houding; Luo, Youfu; Xu, Yongbin; Shi, Jianyou; Wei, Yuquan (2008). "Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography". Journal of Chromatography A. 1178 (1–2): 101–7. doi:10.1016/j.chroma.2007.11.060. PMID   18082754.
  15. ↑ Okamoto, Yoshinori; Suzuki, Atsushi; Ueda, Koji; Ito, Chihiro; Itoigawa, Masataka; Furukawa, Hiroshi; Nishihara, Tsutomu; Kojima, Nakao (2006). "Anti-Estrogenic Activity of Prenylated Isoflavones from Millettia pachycarpa: Implications for Pharmacophores and Unique Mechanisms". Journal of Health Science. 52 (2): 186–91. doi: 10.1248/jhs.52.186 .
  16. ↑ Ito, Chihiro; Itoigawa, Masataka; Kumagaya, Minako; Okamoto, Yoshinori; Ueda, Koji; Nishihara, Tsutomu; Kojima, Nakao; Furukawa, Hiroshi (2006). "Isoflavonoids with Antiestrogenic Activity fromMillettiapachycarpa1". Journal of Natural Products. 69 (1): 138–41. doi:10.1021/np050341w. PMID   16441086.
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