- 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
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Administration of (3)H- or (13)C-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 - iridoid glucoside; biosynthesis; iridane skeleton formation; 10-oxocitral; iridodial cation; tarennoside; Gardenia jasminoides; cell culture
- Kobayashi, Koji,Uesato, Shinichi,Ueda, Shinichi,Inouye, Hiroyuki
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p. 4228 - 4234
(2007/10/02)
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- Iridoids of Apocynaceae. III. Minor Iridoids from Allamanda neriifolia
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New iridoids, including isoallamandicin, allamcin, allamancin, 3-O-methyl derivatives of allamcin and allamancin, allamcidin, allamcidin glucoside, 13-O-acetylplumieride, plumiepoxide, and protoplumericin B, were isolated in addition to ten known iridoids from the stem and leaves of Allamanda neriifolia HOOK.Their structures were determined on the basis of spectral and chemical evidence.Gardenoside and 10-dehydrogardenoside, two ordinal-type iridoids, were also obtained.Keywords -iridoid; plumericin; plumieride; protoplumericin; plumericin monohydrate; plumericin dihydrate; epoxyplumieride; dihydroplumieride; 13-O-acylplumieride; Allamanda neriifolia, Apocynaceae.
- Abe, Fumiko,Mori, Tomojiro,Yamauchi, Tatsuo
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p. 2947 - 2956
(2007/10/02)
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