prenylflavonoid
File:8-Prenylnaringenin.svg, 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{{cite journal |doi=10.1016/S0378-8741(03)00108-9 |title=Antioxidant activity of prenylated flavonoids from the West African medicinal plant Dorstenia mannii |year=2003 |last1=Dufall |first1=K.G. |last2=Ngadjui |first2=B.T. |last3=Simeon |first3=K.F. |last4=Abegaz |first4=B.M. |last5=Croft |first5=K.D. |journal=Journal of Ethnopharmacology |volume=87 |pages=67–72 |pmid=12787956 |issue=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.{{Cite journal|url=http://www.plantphysiol.org/content/159/1/70.full.pdf|title=Characterization of an Isoflavonoid-Specific Prenyltransferase from Lupinus albus|author=Shen|volume=159|issue=1|pages= 70–80|date=March 2012 |doi=10.1104/pp.112.195271|first2=D.|last3=Lei|first3=Z.|last4=Snyder|first4=J.|last5=Sumner|first5=L. W.|last6=Dixon|first6=R. A.|journal=Plant Physiology|pmid=22430842|pmc=3375986|last2=Huhman|display-authors=etal}}
Monoprenyl isoflavone epoxidase is a key enzyme in fungal Botrytis cinerea metabolism of prenylated flavonoids.{{cite journal |doi=10.1016/S0031-9422(97)00322-1 |title=Fad-dependent epoxidase as a key enzyme in fungal metabolism of prenylated flavonoids |year=1997 |last1=Tanaka |first1=Mitsuharu |last2=Tahara |first2=Satoshi |journal=Phytochemistry |volume=46 |issue=3 |pages=433–9}}
Many prenylflavonoids appear to have anticancer activity in vitro.{{cite journal |doi=10.1016/S0278-6915(99)00019-8 |title=Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines |year=1999 |last1=Miranda |first1=C.L. |last2=Stevens |first2=J.F. |last3=Helmrich |first3=A. |last4=Henderson |first4=M.C. |last5=Rodriguez |first5=R.J. |last6=Yang |first6=Y.-H. |last7=Deinzer |first7=M.L. |last8=Barnes |first8=D.W. |last9=Buhler |first9=D.R. |journal=Food and Chemical Toxicology |volume=37 |issue=4 |pages=271–85 |pmid=10418944 }}
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.{{cite journal |doi=10.1016/j.phytochem.2004.04.025 |title=Xanthohumol and related prenylflavonoids from hops and beer: To your good health! |year=2004 |last1=Stevens |first1=Jan F |last2=Page |first2=Jonathan E |journal=Phytochemistry |volume=65 |issue=10 |pages=1317–30 |pmid=15231405}}{{cite journal |doi=10.1016/j.talanta.2010.09.041 |title=Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards |year=2010 |last1=Dhooghe |first1=Liene |last2=Naessens |first2=Tania |last3=Heyerick |first3=Arne |last4=De Keukeleire |first4=Denis |last5=Vlietinck |first5=Arnold J. |last6=Pieters |first6=Luc |last7=Apers |first7=Sandra |journal=Talanta |volume=83 |issue=2 |pages=448–56 |pmid=21111159}} Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoestrogen known.
Australone A can be found in Morus australis.{{cite journal |doi=10.1021/np970186o |title=Bioactive Constituents ofMorus australisandBroussonetia papyrifera |year=1997 |last1=Ko |first1=Horng-Huey |last2=Yu |first2=Sheu-Meei |last3=Ko |first3=Feng-Nien |last4=Teng |first4=Che-Ming |last5=Lin |first5=Chun-Nan |journal=Journal of Natural Products |volume=60 |issue=10 |pages=1008–11 |pmid=9358644}}
6,8-Diprenyleriodictyol, dorsmanin C and dorsmanin F can be found in Dorstenia mannii.
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,[http://www.biopurify.com/details.asp?id=205 epimedin C] {{webarchive|url=https://web.archive.org/web/20110910161747/http://www.biopurify.com/details.asp?id=205 |date=2011-09-10 }} ranged from 1.4 to 5.1% in aerial parts and 1.0 to 2.8% in underground parts.{{cite journal |doi=10.1002/jssc.201000899 |title=Qualitative and quantitative analyses of Epimedium wushanense by high-performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry |year=2011 |last1=Li |first1=Hui-Fang |last2=Guan |first2=Xiang-yu |last3=Ye |first3=Min |last4=Xiang |first4=Cheng |last5=Lin |first5=Chang-hu |last6=Sun |first6=Chao |last7=Guo |first7=De-an |journal=Journal of Separation Science |volume=34 |issue=12 |pages=1437–46 |pmid=21560245}}
Artocarpus nobilis contains prenylated flavonoids in its root bark.{{cite journal |doi=10.1016/j.fitote.2007.07.014 |title=Four new prenylated flavonoids and xanthones from the root bark of Artocarpus nobilis |year=2008 |last1=Jayasinghe |first1=U.L.B. |last2=Samarakoon |first2=T.B. |last3=Kumarihamy |first3=B.M.M. |last4=Hara |first4=N. |last5=Fujimoto |first5=Y. |journal=Fitoterapia |volume=79 |pages=37–41 |pmid=17855020 |issue=1}}
8-Prenylkaempferol can be found in Sophora flavescens.{{cite journal |doi=10.1093/ecam/nep066 |title=8-Prenylkaempferol Suppresses Influenza a Virus-Induced RANTES Production in A549 Cells via Blocking PI3K-Mediated Transcriptional Activation of NF-κB and IRF3 |year=2011 |last1=Chiou |first1=Wen-Fei |last2=Chen |first2=Chen-Chih |last3=Wei |first3=Bai-Luh |journal=Evidence-Based Complementary and Alternative Medicine |volume=2011 |pages=1–10 |pmid=19592477 |pmc=3137797}}
Cannflavins are prenylflavonoids found in Cannabis sativa.{{cite journal | doi = 10.1007/BF02118655 | pmid = 3754224 | title = Cannflavin A and B, prenylated flavones from Cannabis sativa L | journal = Experientia | volume = 42 | issue = 4 | pages = 452–453 | year = 1986 | last1 = Barrett | first1 = M. L. | last2 = Scutt | first2 = A. M. | last3 = Evans | first3 = F. J. | s2cid = 19652191 }}
Prenylated isoflavonoids
A number of bio-active chemicals have been reported from Millettia pachycarpa including several prenylflavonoids.{{cite journal |doi=10.1016/0031-9422(80)85140-5 |title=New prenylated isoflavones and a prenylated dihydroflavonol from Millettia pachycarpa |year=1980 |last1=Singhal |first1=Ashok K. |last2=Sharma |first2=Ram P. |last3=Thyagarajan |first3=Gopalakrishna |last4=Herz |first4=Werner |last5=Govindan |first5=Serengolam V. |journal=Phytochemistry |volume=19 |issue=5 |pages=929–34}}{{cite journal |doi=10.1016/j.chroma.2007.11.060 |title=Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography |year=2008 |last1=Ye |first1=Haoyu |last2=Chen |first2=Lijuan |last3=Li |first3=Yanfang |last4=Peng |first4=Aihua |last5=Fu |first5=Afu |last6=Song |first6=Hang |last7=Tang |first7=Minghai |last8=Luo |first8=Houding |last9=Luo |first9=Youfu |journal=Journal of Chromatography A |volume=1178 |pages=101–7 |pmid=18082754 |issue=1–2 |last10=Xu |first10=Yongbin |last11=Shi |first11=Jianyou |last12=Wei |first12=Yuquan}} 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.{{cite journal |doi=10.1248/jhs.52.186 |title=Anti-Estrogenic Activity of Prenylated Isoflavones from Millettia pachycarpa: Implications for Pharmacophores and Unique Mechanisms |year=2006 |last1=Okamoto |first1=Yoshinori |last2=Suzuki |first2=Atsushi |last3=Ueda |first3=Koji |last4=Ito |first4=Chihiro |last5=Itoigawa |first5=Masataka |last6=Furukawa |first6=Hiroshi |last7=Nishihara |first7=Tsutomu |last8=Kojima |first8=Nakao |journal=Journal of Health Science |volume=52 |issue=2 |pages=186–91|doi-access=free }}{{cite journal |doi=10.1021/np050341w |title=Isoflavonoids with Antiestrogenic Activity fromMillettiapachycarpa1 |year=2006 |last1=Ito |first1=Chihiro |last2=Itoigawa |first2=Masataka |last3=Kumagaya |first3=Minako |last4=Okamoto |first4=Yoshinori |last5=Ueda |first5=Koji |last6=Nishihara |first6=Tsutomu |last7=Kojima |first7=Nakao |last8=Furukawa |first8=Hiroshi |journal=Journal of Natural Products |volume=69 |pages=138–41 |pmid=16441086 |issue=1}}
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.
References
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