没药的呋喃倍半萜类化合物。

Furanosesquiterpenoids of Commiphora myrrha.

作者信息

Zhu N, Kikuzaki H, Sheng S, Sang S, Rafi M M, Wang M, Nakatani N, DiPaola R S, Rosen R T, Ho C T

机构信息

Department of Food Science, Rutgers University, New Brunswick, New Jersey 08901, USA.

出版信息

J Nat Prod. 2001 Nov;64(11):1460-2. doi: 10.1021/np010072j.

DOI:10.1021/np010072j

PMID:11720534

Abstract

An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one (3), rel-2R-methoxy-4R-furanogermacr-1(10)E-en-6-one (4), furanogermacra-1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5beta-isopropenyl-3,6beta-dimethyl-6-vinylbenzofuran-4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.

摘要

对没药树（Commiphora myrrha）树胶渗出物的研究导致分离出六种倍半萜类化合物。根据光谱数据解释，它们被确定为两种新的呋喃倍半萜类化合物，rel-1S,2S-环氧-4R-呋喃吉马烯-10(15)-烯-6-酮（1）和rel-2R-甲基-5S-乙酰氧基-4R-呋喃吉马烯-1(10)Z-烯-6-酮（2），以及四种已知的呋喃倍半萜类化合物，rel-3R-甲氧基-4S-呋喃吉马烯-1E,10(15)-二烯-6-酮（3）、rel-2R-甲氧基-4R-呋喃吉马烯-1(10)E-烯-6-酮（4）、呋喃吉马烯-1(10)Z,4Z-二烯-6-酮和莪术烯酮[6,7-二氢-5β-异丙烯基-3,6β-二甲基-6-乙烯基苯并呋喃-4(5H)-酮]。这是已知化合物3和4相对立体化学的首次报道。化合物1在克隆形成试验中对MCF-7乳腺癌细胞系表现出微弱的细胞毒性活性，而其他五种化合物在该试验中无活性。