Stilbenoid biosynthesis Sample Clauses

Stilbenoid biosynthesis. Cannabis stilbenoids have been detected and isolated from stem (Xxxxxxx and Xxxxxxx, 1982), leaves (Kettenes-van den Bosch and Xxxxxxxx, 1978) and resin (El-Feraly et al., 1986). HOOC NH2 Phenylalanine COSCoA Dihydro-p-coumaroyl-CoA Malonyl-CoA OH COS Co A Dihydro-caffeoyl-CoA COSCoA OMe OH Dihydro-feruoyl-CoA Malonyl-CoA 3X BBS? MeO OH OH OMe Isoprenyl Me O OH Dihydro-m-coumaroyl-CoA Dihydroresveratrol OH OH A B Isoprenyl OMe OMT O Cannabispiradienone Me Me O OH OH OH OH Cannabistilbene IIa OH OMe O 3,4’-dihydroxy-5-methoxybibenzyl Canniprene Cannabispirenone-A MeO MeO Cannabistilbene IIb XX XX OMe Cannabispirone MeO OH OH OH MeO Cannithrene 1 OH Acetyl cannabispirol Cannithrene 2 C α H OAc -cannabispiranol Figure 9. Proposed pathway for the biosynthesis of stilbenoids in C. sativa. A) 3,3’-dihydroxy-5,4’- dimethoxybibenzyl; B) 3,4’-dihydroxy-5,3’-dimethoxy-5’-isoprenylbibenzyl;C) 7-hydroxy-5-methoxyindan-1- spiro-cyclohexane; D) Dienone-phenol in vitro rearrangement (heat, acidic pH). It has been suggested (Xxxxxxx and Xxxxxxx, 1982; Xxxxxxx and Xxxxxxxx, 1978) that their biosynthesis could have a common origin (Figure 9). The first step could be the formation of bibenzyl compounds from the condensation of one molecule of dihydro-p-coumaroyl-CoA and 3 molecules of malonyl-CoA to dihydroresveratrol. It was shown that in cannabis both dihydroresveratrol and canniprene are synthesized from dihydro-p-coumaric acid (Kindl, 1985). In orchids, the induced synthesis by fungal infection of bibenzyl compounds by a PKS, called Bibenzyl synthase (BBS), was shown to condense dihydro-m- coumaroyl-CoA and malonyl-CoA to 3,3’,5-trihydroxybibenzyl (Xxxxxxxx and Xxxxx, 1994a). It was also found that this enzyme can accept dihydro-p- coumaroyl-CoA and dihydrocinnamoyl-CoA as substrates, although to a lesser degree. Dihydropinosylvin synthase is an enzyme from Pinus sylvestris (Xxxxxxxxx et al., 1992) that accepts dihydrocinnamoyl-CoA as substrate to form bibenzyl dihydropinosylvin. Xxxxxxx and Xxxxx (1991) found a relationship between induced formation by wounding of 3,3’-dihydroxy-5,4’- dimethoxybibenzyl and the enzyme BBS in orchids. This result also suggests that in cannabis the 3,3’-dihydroxy-5,4’-dimethoxybibenzyl compound could have the 3,3’,5-trihydroxybibenzyl formed from dihydro-m-coumaroyl-CoA or dihydro-caffeoyl-CoA as intermediate. In orchids, however, the incorporation of phenylalanine into dihydro-m-coumaric acid, dihydrostilbene and dihydrophenanthrenes was ...
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Related to Stilbenoid biosynthesis

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