:Flavonolignan

Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.

Examples

File:Silibinin skeletal.svg]]

Flavonolignans identified in Silybum marianum (milk thistle) silymarin complex include silibinin, silychristin, silydianin, dehydrosilybin, deoxysilycistin, deoxysilydianin, silandrin, silybinome, silyhermin and neosilyhermin and can be produced in vitro.{{cite journal |vauthors=Tůmová L, Řimáková J, Tůma J, Dušek J |year=2006 |title=Silybum marianum in vitro-flavonolignan production |journal=Plant, Soil and Environment |volume=52 |issue=10 |pages=454–8 |doi=10.17221/3466-PSE |url=http://www.cazv.cz/userfiles/File/PSE%2052_454-458.pdf |url-status=dead |archive-url=https://web.archive.org/web/20110718170226/http://www.cazv.cz/userfiles/File/PSE%2052_454-458.pdf |archive-date=2011-07-18 |doi-access=free }} Silibinin is found in the roots of S. marianum{{cite journal |vauthors=Alikaridis F, Papadakis D, Pantelia K, Kephalas T |title=Flavonolignan production from Silybum marianum transformed and untransformed root cultures |journal=Fitoterapia |volume=71 |issue=4 |pages=379–84 |date=August 2000 |pmid=10925007 |doi=10.1016/S0367-326X(00)00134-9}} while silyamandin{{cite journal |first1=Jerome |last1=Sarris |first2=Kylie |last2=Seaton |year=2007 |title=Silyamandin: A New Flavonolignan |journal=Australian Journal of Medical Herbalism |volume=19 |issue=4 |pages=187 |url=http://search.informit.com.au/documentSummary%3Bdn=002024714890175%3Bres=IELHEA }} can be found in the fruit.{{cite journal |vauthors=MacKinnon SL, Hodder M, Craft C, Simmons-Boyce J |title=Silyamandin, a new flavonolignan isolated from milk thistle tinctures |journal=Planta Medica |volume=73 |issue=11 |pages=1214–6 |date=September 2007 |pmid=17823870 |doi=10.1055/s-2007-981595}}

Hydnocarpin can be found naturally in Onopordon corymbosum{{cite journal |doi=10.1016/0031-9422(90)85131-X |title=Flavonoids, flavonolignans and a phenylpropanoid from Onopordon corymbosum |year=1990 |last1=Cardona |first1=M |last2=Garcia |first2=B |last3=Pedro |first3=J |last4=Sinisterra |first4=J |journal=Phytochemistry |volume=29 |pages=629 |issue=2}} and can be synthesised.{{cite journal |vauthors=Guz NR, Stermitz FR |title=Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans |journal=Journal of Natural Products |volume=63 |issue=8 |pages=1140–5 |date=August 2000 |pmid=10978213 |doi=10.1021/np000166d}}

Scutellaprostin A, B, C, D, E and F can be isolated from Scutellaria prostrata and can also be synthesized.{{cite journal |vauthors=Kikuchi Y, Miyaichi Y, Tomimori T |title=[Total synthesis of flavonolignans, scutellaprostins A, B, C, D, E and F] |language=ja |journal=Yakugaku Zasshi |volume=111 |issue=8 |pages=424–35 |date=August 1991 |doi=10.1248/yakushi1947.111.8_424 |pmid=1665511|doi-access=free }}

Hydnowightin can be isolated from Hydnocarpus wightianus seeds.{{PubChem|6438705}}

Three flavonolignans derived from the flavone tricin have been isolated from the herb Avena sativa.{{cite journal |doi=10.1021/np049636k |title=Flavonolignans fromAvenasativa |year=2005 |last1=Wenzig |first1=Eva |last2=Kunert |first2=Olaf |last3=Ferreira |first3=Daneel |last4=Schmid |first4=Martin |last5=Schühly |first5=Wolfgang |last6=Bauer |first6=Rudolf |last7=Hiermann |first7=Alois |journal=Journal of Natural Products |volume=68 |pages=289–92 |pmid=15730266 |issue=2}}

Palstatin has been isolated from the Amazon tree Hymeneae palustris.{{cite journal |doi=10.1021/np020231e |title=Isolation and Structure of Palstatin from the Amazon TreeHymeneaepalustris1 |year=2003 |last1=Pettit |first1=George R. |last2=Meng |first2=Yanhui |last3=Stevenson |first3=Clare A. |last4=Doubek |first4=Dennis L. |last5=Knight |first5=John C. |last6=Cichacz |first6=Zbigniew |last7=Pettit |first7=Robin K. |last8=Chapuis |first8=Jean-Charles |last9=Schmidt |first9=Jean M. |journal=Journal of Natural Products |volume=66 |pages=259–62 |pmid=12608861 |issue=2 }}

Salcolin A and salcolin B can be found in Salsola collina.{{cite journal |doi=10.1007/BF00630164 |title=Flavonolignans of Salsola collina |year=1992 |last1=Syrchina |first1=A. I. |last2=Gorshkov |first2=A. G. |last3=Shcherbakov |first3=V. V. |last4=Zinchenko |first4=S. V. |last5=Vereshchagin |first5=A. L. |last6=Zaikov |first6=K. L. |last7=Semenov |first7=A. A. |journal=Chemistry of Natural Compounds |volume=28 |pages=155 |issue=2|s2cid=19700016 }}

Rhodiolin, the product of the oxidative coupling of coniferyl alcohol with the 7,8-dihydroxy grouping of the flavonol herbacetin, can be found in the rhizome of Rhodiola rosea.{{cite journal |doi=10.1007/BF00579955 |title=The flavonoids of the rhizomes ofRhodiola rosea. II. A flavonolignan and glycosides of herbacetin |year=1983 |last1=Zapesochnaya |first1=G. G. |last2=Kurkin |first2=V. A. |journal=Chemistry of Natural Compounds |volume=19 |pages=21–29|s2cid=7656479 }}

Glycosides

The flavonolignans tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether and tricin 4'-O-(threo-beta-guaiacylglyceryl) ether can be isolated together with their 7-O-glucosides in the leaves of Hyparrhenia hirta.{{cite journal |vauthors=Bouaziz M, Veitch NC, Grayer RJ, Simmonds MS, Damak M |title=Flavonolignans from Hyparrhenia hirta |journal=Phytochemistry |volume=60 |issue=5 |pages=515–20 |date=July 2002 |pmid=12052518 |doi=10.1016/S0031-9422(02)00145-0}}

Research

A 2022 research has concluded that flavonolignans "reduce the virulence of antibiotic-resistant bacterial strains".{{Cite web |last=Chemistry |first=University of |last2=Prague |first2=Technology |title=Flavonolignans reduce the virulence of antibiotic-resistant bacterial strains |url=https://phys.org/news/2022-11-flavonolignans-virulence-antibiotic-resistant-bacterial-strains.html |access-date=2022-11-03 |website=phys.org |language=en}}

References

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