Flavonolignan
Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.
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 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.[ 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]
Research
A 2022 research has concluded that flavonolignans "reduce the virulence of antibiotic-resistant bacterial strains ".[ 14]
References
^ Tůmová L, Řimáková J, Tůma J, Dušek J (2006). "Silybum marianum in vitro -flavonolignan production" (PDF) . Plant, Soil and Environment . 52 (10): 454–8. doi :10.17221/3466-PSE . Archived from the original (PDF) on 2011-07-18.
^ 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 .
^ Sarris, Jerome; Seaton, Kylie (2007). "Silyamandin: A New Flavonolignan" . Australian Journal of Medical Herbalism . 19 (4): 187.
^ 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 .
^ 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 .
^ 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 .
^ 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. doi :10.1248/yakushi1947.111.8_424 . PMID 1665511 .
^ CID 6438705 from PubChem
^ 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 .
^ 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 .
^ 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 . S2CID 19700016 .
^ 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 : 21–29. doi :10.1007/BF00579955 . S2CID 7656479 .
^ 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 .
^ Chemistry, University of; Prague, Technology. "Flavonolignans reduce the virulence of antibiotic-resistant bacterial strains" . phys.org . Retrieved 2022-11-03 .
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