Studies on monoterpene glucosides and related natural products. LV. Iridane skeleton formation from acyclic monoterpenes in the biosynthesis of iridoid glucosides in Gardenia jasminoides f. grandiflora cell suspension cultures.
- 1 January 1985
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 33 (10) , 4228-4234
- https://doi.org/10.1248/cpb.33.4228
Abstract
Administration of 3H- or 13C-labeled acyclic monoterpenes to Gardenia jasminoides f. grandiflora cell suspension cultures showed that tarennoside (20) and gardenoside (21) were biosynthesized in the cell cultures via the cyclization of 10-oxogeranial (5a)/10-oxoneral (5b) to iridodial cation (14). followed by extensive randomization of the carbon atoms 3 and 11. Furthermore, the intermediacy of (R)-(+)-and (S)-(-)-10-hydroxycitronellol (24a, 24b) and (R)-(+)-and (S)-(-)-9, 10-dihydroxycitronellol (28a, 28b) was disproved.Keywords
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