Dihydrostilbenoid

Chemical structure of dihydro-resveratrol.

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 caffrum, 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]

References

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