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具刺孪叶豆中二萜类化合物的结构与绝对构型

Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa.

作者信息

Monteiro Afif F, Batista João M, Machado Michelle A, Severino Richele P, Blanch Ewan W, Bolzani Vanderlan S, Vieira Paulo C, Severino Vanessa G P

机构信息

†Unidade Acadêmica Especial de Física e Química, Universidade Federal de Goiás, Avenida Dr. Lamartine Pinto de Avelar, 1120, 75704-020, Catalão, GO, Brazil.

‡Departamento de Química Orgânica, Universidade Estadual Paulista "Júlio de Mesquita Filho", Rua Prof. Francisco Degni, 55, 14800-060, Araraquara, SP, Brazil.

出版信息

J Nat Prod. 2015 Jun 26;78(6):1451-5. doi: 10.1021/acs.jnatprod.5b00166. Epub 2015 Jun 3.

DOI:10.1021/acs.jnatprod.5b00166
PMID:26039872
Abstract

Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2-6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete (1)H and (13)C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.

摘要

对孪叶豆(Hymenaea stigonocarpa Mart. ex Hayne)花和叶的乙醇提取物进行化学研究,得到了一种新的对映-海松烷二萜,18-羟基-对映-海松-1(10),13-(E)-二烯-15-酸(1),以及五种已知化合物(2 - 6)。通过核磁共振(COSY、HSQC、HMBC和NOESY)和质谱分析进行结构解析。还报道了唇形-13-烯-8β-醇-15-酸(2)和唇形-7,13-二烯-15-酸(3)完整的¹H和¹³C核磁共振数据归属。通过比较实验和计算的拉曼光学活性光谱确定了1和2的绝对构型。

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