Flavonolignan

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

Contents

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". Plant, Soil and Environment 52 (10): 454–8. http://www.cazv.cz/userfiles/File/PSE%2052_454-458.pdf. 
  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. http://search.informit.com.au/documentSummary%3Bdn=002024714890175%3Bres=IELHEA. 
  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]" (in Japanese). Yakugaku Zasshi 111 (8): 424–35. PMID 1665511. 
  8. ^ PubChem 6438705
  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 et al. (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. 

External links

Types of Flavonoids
Flavonoids
Isoflavonoids
Neoflavonoids
Aurones
Other categories
Types of flavonolignans
Flavonolignans
Cinchonain-Ib | Dehydrosilybin | Deoxysilycistin | Deoxysilydianin | Hydnocarpin | Hydnowightin | Neosilyhermin | Palstatin | Rhodiolin | Salcolin A | Salcolin B | Scutellaprostin A, B, C, D, E and F | Silandrin | Silyamandin | Silibinin | Silybinome | Silicristin | Silydianin | Silyhermin | Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether | Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether