MACROCYCLIC DITERPENES - ALPHA- AND BETA-4,8,13-DUVATRIENE-1,3-DIOLS FROM TOBACCO
MACROCYCLIC DITERPENES - ALPHA- AND BETA-4,8,13-DUVATRIENE-1,3-DIOLS FROM TOBACCO
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DOI：
10.1021/jo01058a056
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发表时间：
1962-01-01
影响因子：
3.6
通讯作者：
ROWLAND, RL
中科院分区：
文献类型：
--
作者：
ROBERTS, DL;ROWLAND, RL
从烟草（Nicotiana tabacum）中分离的两种大环二萜，α-和β-4，8，13-杜瓦三烯-1，3-二醇，通过化学和物理化学发现显示为12-异丙基-1，5，9-三甲基-4，8，13-环十四碳三烯-1，3-二醇（I）的非对映异构体。这里所代表的十四元环以前从未遇到过。从天然来源中分离出的各种萜类化合物呈现出一系列令人印象深刻的、广泛不同的和独特的结构。具有九元、十元和十一元环系的大环萜类化合物是一组有趣的化合物。我们现在要报道两个新的大环萜类化合物的分离和表征，它们具有十四碳环系统。用己烷萃取陈化白肋烟（Nicotiana tabacum），经层析分离出两种异构醇，分别命名为n-4，8，13-杜伐三烯-1，3-二醇和6-4，8，13-杜伐三烯-1，3-二醇b。n-和6-杜伐三烯二醇占干白肋烟的0.01%和0.005%，也存在于烤烟、土耳其和未陈化的白肋烟中。
Two macrocyclic diterpenes, a- and# 3-4, 8, 13-duvatriene-l, 3-diols, isolatedfrom tobacco (Nicotiana tabacum), are shown through chemical and physicochemical findings to be diastereoisomers of 12-isopropyl-l, 5, 9-trimethyl-4, 8, 13-cyclotetradecatriene-l, 3-diol (I). The fourteen-membered ring here represented has not been encountered previously.The various terpenoids which havebeen isolated from natural sources present an imposing array of widely different and unique structures. An interesting group of compounds which have been characterized are the macrocyclic terpenes possess-ing nine-, ten-, and eleven-membered ring systems. 2 We now wish to report the isolation and characterization of two new macrocyclic terpenes for which a fourteen-carbon ring systemis indicated. Hexane extraction of aged burley tobacco (Nicotiana tabacum) andchromatography of the extract resulted in the isolation of two isomeric alcohols, to which the names«-4, 8, 13-duvatriene-1, 3-diol, and 6-4, 8, 13-duvatriene-l, 3-diollb have been assigned. The «-and 6-duvatrienediolsconstitute 0.01% and 0.005% of the dry burleyleaf and also are found in flue-cured, Turkish, and unaged burley tobaccos.