Dihydrostilbenoid Explained

Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.

Examples

Dihydro-resveratrol is a natural phenol with a bibenzyl structure found in wine.^[1] It is also a metabolite of trans-resveratrol formed in the intestine by the hydrogenation of the double bond by microflora.^[2]

Combretastatin and combretastatin B-1 are two dihydrostilbenoids found in Combretum afrum, an African tree.

Isonotholaenic acid is another dihydrostilbenoid found in the Andean fern Argyrochosma nivea.^[3]

Bibenzyls (3,4'-dihydroxy-5,5'-dimethoxybibenzyl, 3,3'-dihydroxy-5-methoxybibenzyl (batatasin III)) can be found in the orchid Bulbophyllum vaginatum.^[4]

Bis(bibenzyls)^[5] and macrocyclic bis(benzyls)^[6] can be found in bryophytes, such as the compounds plagiochin E, 13,13'-O-isoproylidenericcardin D, riccardin H, marchantin E, neomarchantin A, marchantin A and marchantin B in the Chinese liverwort Marchantia polymorpha.^[7] Prenylated bibenzyls can be isolated from the New Zealand liverwort Marsupidium epiphytum^[8] or from Radula kojana.^[9]

One unique class of stilbenoid derivative was first isolated from Scorzonera humilis. They were named the tyrolobibenzyls after Tyrol in the eastern Alps, where the plant was collected.^[10]

Notes and References

1. 10.1016/j.bmcl.2010.08.002. 20813524. Dihydro-resveratrol—A potent dietary polyphenol. 2010. Gakh. Andrei A.. Anisimova. Natalia Yu. Kiselevsky. Mikhail V.. Sadovnikov. Sergey V.. Stankov. Ivan N.. Yudin. Mikhail V.. Rufanov. Konstantin A.. Krasavin. Mikhail Yu. Sosnov. Andrey V.. Bioorganic & Medicinal Chemistry Letters. 20. 20. 6149–51.
2. 10.1021/jf100836j. Determination of Dihydroresveratrol in Rat Plasma by HPLC. 2010. Juan. M. Emília. Alfaras. Irene. Planas. Joana M.. Journal of Agricultural and Food Chemistry. 58. 12. 7472–5. 20509689.
3. 10.1016/S0960-894X(03)00509-2. The imidazo\2,1-a]isoindole system. A new skeletal basis for antiplasmodial compounds. 2003. Del Olmo. Esther. Armas. Marlon Garcı́a. Ybarra. Mª Inés. López. Josè Luis. Oporto. Patricia. Giménez. Alberto. Deharo. Eric. San Feliciano. Arturo. Bioorganic & Medicinal Chemistry Letters. 13. 16. 2769–2772. 12873511 .
4. 10.1016/S0031-9422(96)00387-1. Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid bulbophyllum vaginatum. 1997. Yuan-Wah Leong. Chiang-Cheong Kang. Harrison. Leslie J.. Powell. Andrew D.. Phytochemistry. 44. 1 . 157–165. 1997PChem..44..157L .
5. 17348087. 2007. Guo. H. Xing. J. Xie. C. Qu. J. Gao. Y. Lou. H. Study of bis(bibenzyls) in bryophytes using electron ionization time-of-flight and electrospray ionization triple-quadrupole mass spectrometry. 21. 8. 1367–74. 10.1002/rcm.2972. Rapid Communications in Mass Spectrometry. 2007RCMS...21.1367G . free.
6. 10.1039/NP9951200069. The chemistry of macrocyclic bis(bibenzyls). 1995. Keserű . G. M.. Nógrádi. M.. Natural Product Reports. 12. 69–75.
7. 17193213. 2006. Niu. C. Qu. JB. Lou. HX. Antifungal bisbibenzyls from the Chinese liverwort Marchantia polymorpha L. 3. 1. 34–40. 10.1002/cbdv.200690004. Chemistry & Biodiversity. 46301279 .
8. 10.1248/cpb.59.480. Novel Prenyl Bibenzyls from the New Zealand Liverwort Marsupidium epiphytum. 2011. Toyota. Masao. Omatsu. Ikuko. Braggins. John. John E. Braggins. Asakawa. Yoshinori. Chemical & Pharmaceutical Bulletin. 59. 4. 480–3. 21467678. free.
9. 10.1016/0031-9422(91)84129-G. Prenyl bibenzyls from the liverwort Radula kojana. 1991. Asakawa. Yoshinori. Kondo. Keiko. Takikawa. Née K.. Tori. Motoo. Hashimoto. Toshihiro. Ogawa. Shunichi. Phytochemistry. 30. 1 . 219–234. 1991PChem..30..219A .
10. 2000 . Zidorn, C. . Tyrolobibenzyls ‒ Novel secondary metabolites from Scorzonera humilis . 83 . 2920–25 . 0018-019X . Helvetica Chimica Acta . 11 . 10.1002/1522-2675(20001108)83:11<2920::AID-HLCA2920>3.0.CO;2-5 . etal.