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Paper | Regular issue | Vol 41, No. 8, 1995, pp.1785-1796
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7117
■ Absolute Stereochemistries of Sylvaticin and 12,15-cis-Sylvaticin, Bioactive C-20,23-cis Non-adjacent Bistetrahydrofuran Annonaceous Acetogenins, from Rollinia mucosa

Guoen Shi, Lu Zeng, Zhe-ming Gu, John M. MacDougal, and Jerry L. McLaughlin

*Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, U.S.A.

Abstract

A new acetogenin, 12,15-cis-sylvaticin (2), and its stereoisomer, sylvaticin (1), a known acetogenin whose stereochemical structure has remained unsolved until now, were isolated, using activity-directed fractionation, from the leaf extracts of Rollinia mucosa (Jacq.) Baill. (Annonaceae). 1 is cis at C-20, 23 and trans at C-12, 15; 2 is cis at C-20, 23 and C-12, 15. A key step in solving their absolute stereochemistries was the determination of the relative configurations (cis or trans) of their 1,4-diols; this was achieved by a new procedure using the pattern recognition of the NOSEY spectra of their 1,4-diol formaldehyde acetal derivatives (1b and 2b). Both 1 and 2 showed potent and selective cytotoxicities, against the A-549 lung cancer and the PACA-2 pancreatic cancer, in a panel of six human solid tumor cell lines.