Flavonolignan

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

Examples
Silibinin

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 synthetised.[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 wightiana seeds.[8]

Three flavonolignans derived from the flavone tricin have been isolated from the herb Avena sativa.[9]

Palstatin has been isolated from the Amazon tree Hymeneae palustris.[10]

Salcolin A and salcolin B can be found in Salsola collina.[11]

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.[12]

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.[13]

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References
  1. Tůmová L, Řimáková J, Tůma J, Dušek J (2006). "Silybum marianum in vitro-flavonolignan production" (PDF). Plant, Soil and Environment. 52 (10): 454–8. Archived from the original (PDF) on 2011-07-18.
  2. Alikaridis F, Papadakis D, Pantelia K, Kephalas T (August 2000). "Flavonolignan production from Silybum marianum transformed and untransformed root cultures". Fitoterapia. 71 (4): 379–84. doi:10.1016/S0367-326X(00)00134-9. PMID 10925007.
  3. Sarris, Jerome; Seaton, Kylie (2007). "Silyamandin: A New Flavonolignan". Australian Journal of Medical Herbalism. 19 (4): 187.
  4. MacKinnon SL, Hodder M, Craft C, Simmons-Boyce J (September 2007). "Silyamandin, a new flavonolignan isolated from milk thistle tinctures". Planta Medica. 73 (11): 1214–6. doi:10.1055/s-2007-981595. PMID 17823870.
  5. Cardona, M; Garcia, B; Pedro, J; Sinisterra, J (1990). "Flavonoids, flavonolignans and a phenylpropanoid from Onopordon corymbosum". Phytochemistry. 29 (2): 629. doi:10.1016/0031-9422(90)85131-X.
  6. Guz NR, Stermitz FR (August 2000). "Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans". Journal of Natural Products. 63 (8): 1140–5. doi:10.1021/np000166d. PMID 10978213.
  7. Kikuchi Y, Miyaichi Y, Tomimori T (August 1991). "[Total synthesis of flavonolignans, scutellaprostins A, B, C, D, E and F]". Yakugaku Zasshi (in Japanese). 111 (8): 424–35. PMID 1665511.
  8. CID 6438705 from PubChem
  9. Wenzig, Eva; Kunert, Olaf; Ferreira, Daneel; Schmid, Martin; Schühly, Wolfgang; Bauer, Rudolf; Hiermann, Alois (2005). "Flavonolignans fromAvenasativa". Journal of Natural Products. 68 (2): 289–92. doi:10.1021/np049636k. PMID 15730266.
  10. 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. (2003). "Isolation and Structure of Palstatin from the Amazon TreeHymeneaepalustris1". Journal of Natural Products. 66 (2): 259–62. doi:10.1021/np020231e. PMID 12608861.
  11. Syrchina, A. I.; Gorshkov, A. G.; Shcherbakov, V. V.; Zinchenko, S. V.; Vereshchagin, A. L.; Zaikov, K. L.; Semenov, A. A. (1992). "Flavonolignans of Salsola collina". Chemistry of Natural Compounds. 28 (2): 155. doi:10.1007/BF00630164.
  12. Zapesochnaya, G. G.; Kurkin, V. A. (1983). "The flavonoids of the rhizomes ofRhodiola rosea. II. A flavonolignan and glycosides of herbacetin". Chemistry of Natural Compounds. 19: 21. doi:10.1007/BF00579955.
  13. Bouaziz M, Veitch NC, Grayer RJ, Simmonds MS, Damak M (July 2002). "Flavonolignans from Hyparrhenia hirta". Phytochemistry. 60 (5): 515–20. doi:10.1016/S0031-9422(02)00145-0. PMID 12052518.


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