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Dehydro-leucodin: a guaiane-type sesquiterpene lactone.

ABSTRACT: Dehydro-leucodin [systematic name: (1S,6S,2R)-9,13-dimeth-yl-5-methyl-ene-3-oxatricyclo-[8.3.0.0(2,6)]trideca-9,12-diene-4,11-dione], C(15)H(16)O(3), is a guanolide isolated from Artemisia douglasiana. The fused-ring system contains a seven-membered ring that adopts a chair conformation, a fused planar cyclo-pentenone ring and a five-membered lactone ring fused in envelope conformation. The absolute structure determined by X-ray analysis agrees with that previously assigned to this compound by NMR studies [Bohlmann & Zdero (1972 ▶). Tetra-hedron Lett.13, 621-624] and also with that of leucodine, a closely related guaianolide [Martinez et al. (1988 ▶). J. Nat. Prod.51, 221-228].

SUBMITTER: Priestap HA

PROVIDER: S-EPMC3239097 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Dehydro-leucodin: a guaiane-type sesquiterpene lactone.

Priestap Horacio A HA Abboud Khalil A KA Velandia Alvaro E AE Lopez Luis A LA Barbieri Manuel A MA

Acta crystallographica. Section E, Structure reports online 20111130 Pt 12

Dehydro-leucodin [systematic name: (1S,6S,2R)-9,13-dimeth-yl-5-methyl-ene-3-oxatricyclo-[8.3.0.0(2,6)]trideca-9,12-diene-4,11-dione], C(15)H(16)O(3), is a guanolide isolated from Artemisia douglasiana. The fused-ring system contains a seven-membered ring that adopts a chair conformation, a fused planar cyclo-pentenone ring and a five-membered lactone ring fused in envelope conformation. The absolute structure determined by X-ray analysis agrees with that previously assigned to this compound by N ...[more]

PMID: 22199945

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