Chemical Artifacts from the Family Labiatae
Chemical Artifacts from the Family Labiatae
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唇形科化学制品
DOI：
10.1021/jo01020a012
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发表时间：
1965
影响因子：
3.6
通讯作者：
J. McChesney
中科院分区：
文献类型：
--
作者：
E. Wenkert;A. Fuchs;J. McChesney
已经观察到迷迭香碱是鼠尾草酸的氧化产物（7 b），似乎合理地假设鼠尾草酚也可能是其人工产生的衍生物。由于在迷迭香叶的乙酰化提取物的产物中仅少量存在迷迭香的二乙酸酯，并且鼠尾草提取物的溶液中不断再生迷迭香，因此对其天然产品地位产生严重怀疑。[11]将鼠尾草酸的甲醇溶液暴露于空气中几周，鼠尾草酸转化为鼠尾草酚，这证实了上述推测。对迷迭香油精的研究[12]旨在进一步分离萜类成分，其特征为二甲醚，在其他产物中产生羟基内酯5a及其醚5d。根据它们的7位含氧取代基对C-5 H和C-14 H化学位移的影响，对这些物质的C-7立体化学进行了归属。
Having observed rosmaricine to be an oxidation product of carnosic acid (7b), it seemed reasonable to assume that carnosol might also be an artificially produced derivative thereof. Serious doubt regarding its natural product status derived from the observa-tions of the presence of its diacetate in only a small extent among the products of acetylated extracts of rosemary leaves and its constant regeneration from solutions of extracts of sage. 11 The conversion of carnosic acid into carnosol by exposure of a methanolic solution of the acid to air for several weeks now con-firmed this conjecture.An investigation of rosemary oleoresin12 designed to isolate further terpenic constituents, characterized as dimethyl ethers, ledto the hydroxy lactone 5a and its ether 5d among other products. The C-7 stereo-chemistry of these substances was assigned on the basis of interpretation of the effect of their 7-oxygenated substituents on the chemical shifts of C-5 H and C-14 H.