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. 2005 Dec 8;7(25):5709-12.
doi: 10.1021/ol052498l.

A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra

Chen Li  1 , Dongho Lee, Tyler N Graf, Sharnelle S Phifer, Yuka Nakanishi, Jason P Burgess, Soedarsono Riswan, Fransisca M Setyowati, Achmad M Saribi, Djaja D Soejarto, Norman R Farnsworth, Joseph O Falkinham 3rd, David J Kroll, A Douglas Kinghorn, Mansukh C Wani, Nicholas H Oberlies
Affiliations

A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra

Chen Li et al. Org Lett. .

Abstract

[chemical reaction: see text]. Three new ent-trachylobane diterpenoids (1-3) were isolated and structures elucidated from Mitrephora glabra Scheff. (Annonaceae). Mitrephorone A (1) possesses a hexacyclic ring system with adjacent ketone moieties and an oxetane ring, both of which are unprecedented among trachylobanes. All compounds were evaluated for cytotoxicity against a panel of cancer cells, where 1 displayed the most potent and broadest activity, and against a battery of antimicrobial assays, where all compounds were approximately equipotent.

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Figures

Figure 1
Figure 1
Partial structures of compound 1 illustrating key COSY (—) and HMBC (→) correlations.
Figure 2
Figure 2
Energy minimized model of 1 illustrating the major ROESY correlations used to define the relative stereochemistry.
See this image and copyright information in PMC

References

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