Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris

Krishnan, Premanand and Lee, Fong Kai and Chong, Kam Weng and Mai, Chun Wai and Muhamad, Azira and Lim, Siew Huah and Low, Yun Yee and Ting, Kang Nee and Lim, Kuan Hon (2018) Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris. Organic Letters, 20 (24). pp. 8014-8018. ISSN 1523-7060

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Official URL: https://doi.org/10.1021/acs.orglett.8b03592

Abstract

Two new monoterpenoid indole alkaloids, alstoscholactine (1) and alstolaxepine (2), were isolated from Alstonia scholaris. Compound 1 represents a rearranged stemmadenine alkaloid with an unprecedented C-6-C-19 connectivity, whereas compound 2 represents a 6,7-seco-angustilobine B-type alkaloid incorporating a rare γ-lactone-bridged oxepane ring system. Their structures and absolute configurations were determined by spectroscopic analyses. Compound 1 was successfully semisynthesized from 19E-vallesamine. Compound 2 induced marked vasorelaxation in rat isolated aortic rings precontracted with phenylephrine.

Item Type: Article
Uncontrolled Keywords: Alstonia; Alkaloids; Monoterpenoid indole
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
R Medicine
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 09 Jul 2019 04:46
Last Modified: 09 Jul 2019 04:46
URI: http://eprints.um.edu.my/id/eprint/21582

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