Flavonolignan Explained

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

Examples

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.[1] Silibinin is found in the roots of S. marianum[2] while silyamandin[3] can be found in the fruit.[4]

Hydnocarpin can be found naturally in Onopordon corymbosum[5] and can be synthesised.[6]

Scutellaprostin A, B, C, D, E and F can be isolated from Scutellaria prostrata and can also be synthesized.[7]

Hydnowightin can be isolated from Hydnocarpus wightianus seeds.

Three flavonolignans derived from the flavone tricin have been isolated from the herb Avena sativa.[8]

Palstatin has been isolated from the Amazon tree Hymeneae palustris.[9]

Salcolin A and salcolin B can be found in Salsola collina.[10]

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.[11]

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.[12]

Research

A 2022 research has concluded that flavonolignans "reduce the virulence of antibiotic-resistant bacterial strains".[13]

Notes and References

  1. Tůmová L, Řimáková J, Tůma J, Dušek J . 2006 . Silybum marianum in vitro-flavonolignan production . Plant, Soil and Environment . 52 . 10 . 454–8 . 10.17221/3466-PSE . dead . https://web.archive.org/web/20110718170226/http://www.cazv.cz/userfiles/File/PSE%2052_454-458.pdf . 2011-07-18 . free .
  2. Alikaridis F, Papadakis D, Pantelia K, Kephalas T . Flavonolignan production from Silybum marianum transformed and untransformed root cultures . Fitoterapia . 71 . 4 . 379–84 . August 2000 . 10925007 . 10.1016/S0367-326X(00)00134-9.
  3. Jerome . Sarris . Kylie . Seaton . 2007 . Silyamandin: A New Flavonolignan . Australian Journal of Medical Herbalism . 19 . 4 . 187 .
  4. MacKinnon SL, Hodder M, Craft C, Simmons-Boyce J . Silyamandin, a new flavonolignan isolated from milk thistle tinctures . Planta Medica . 73 . 11 . 1214–6 . September 2007 . 17823870 . 10.1055/s-2007-981595.
  5. 10.1016/0031-9422(90)85131-X . Flavonoids, flavonolignans and a phenylpropanoid from Onopordon corymbosum . 1990 . Cardona . M . Garcia . B . Pedro . J . Sinisterra . J . Phytochemistry . 29 . 629 . 2.
  6. Guz NR, Stermitz FR . Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans . Journal of Natural Products . 63 . 8 . 1140–5 . August 2000 . 10978213 . 10.1021/np000166d.
  7. Kikuchi Y, Miyaichi Y, Tomimori T . [Total synthesis of flavonolignans, scutellaprostins A, B, C, D, E and F] . ja . Yakugaku Zasshi . 111 . 8 . 424–35 . August 1991 . 10.1248/yakushi1947.111.8_424 . 1665511. free .
  8. 10.1021/np049636k . Flavonolignans fromAvenasativa . 2005 . Wenzig . Eva . Kunert . Olaf . Ferreira . Daneel . Schmid . Martin . Schühly . Wolfgang . Bauer . Rudolf . Hiermann . Alois . Journal of Natural Products . 68 . 289–92 . 15730266 . 2.
  9. 10.1021/np020231e . Isolation and Structure of Palstatin from the Amazon TreeHymeneaepalustris1 . 2003 . Pettit . George R. . Meng . Yanhui . Stevenson . Clare A. . Doubek . Dennis L. . Knight . John C. . Cichacz . Zbigniew . Pettit . Robin K. . Chapuis . Jean-Charles . Schmidt . Jean M. . Journal of Natural Products . 66 . 259–62 . 12608861 . 2 .
  10. 10.1007/BF00630164 . Flavonolignans of Salsola collina . 1992 . Syrchina . A. I. . Gorshkov . A. G. . Shcherbakov . V. V. . Zinchenko . S. V. . Vereshchagin . A. L. . Zaikov . K. L. . Semenov . A. A. . Chemistry of Natural Compounds . 28 . 155 . 2. 19700016 .
  11. 10.1007/BF00579955 . The flavonoids of the rhizomes ofRhodiola rosea. II. A flavonolignan and glycosides of herbacetin . 1983 . Zapesochnaya . G. G. . Kurkin . V. A. . Chemistry of Natural Compounds . 19 . 21–29. 7656479 .
  12. Bouaziz M, Veitch NC, Grayer RJ, Simmonds MS, Damak M . Flavonolignans from Hyparrhenia hirta . Phytochemistry . 60 . 5 . 515–20 . July 2002 . 12052518 . 10.1016/S0031-9422(02)00145-0.
  13. Web site: Chemistry . University of . Prague . Technology . Flavonolignans reduce the virulence of antibiotic-resistant bacterial strains . 2022-11-03 . phys.org . en.

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