Dihydrostilbenoid

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

Chemical structure of dihydro-resveratrol

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]