Flavonolignan

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

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 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]

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.
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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