Planta Med 2014; 80 - PD143
DOI: 10.1055/s-0034-1382564

Absolute configuration of iboga-type alklaoids from Ervatamia officinalis

XQ Zhang 1, 2, BQ Tang 1, S Ou-yang 2, 3, WC Ye 1, CT Che 2
  • 1Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, P.R. China
  • 2Department of Medicinal Chemistry and Pharmacognosy, and WHO Collaborating Center for Traditional Medicine, University of Illinois at Chicago, Chicago, IL 60612, USA
  • 3College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, P.R. China

Four new iboga-type alkaloids, ervaoffines A–D (1–4), were isolated from the twigs and leaves of Ervatamia officinalis. The chemical structures and absolute configuration were elucidated by interpretation of the spectroscopic data, as well as X-ray diffraction and circular dichroism analyses. Compounds 1 and 2 are the first members of iboga-type pseudoindoxyl alkaloids bearing a C-2 spiro-carbon with opposite configuration to that of known structures such as iboluteine. The relationship between the absolute configuration of the spiro-carbon and the Cotton effect for iboga-type pseudoindoxyl and oxindole alkaloids was established.

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