Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum.
نویسندگان
چکیده
[reaction: see text] Two new neoclerodane diterpenes, salvinicins A (4) and B (5), were isolated from the dried leaves of Salvia divinorum. The structures of these compounds were elucidated by spectroscopic techniques, including (1)H and (13)C NMR, NOESY, HMQC, and HMBC. The absolute stereochemistry of these compounds was assigned on the basis of single-crystal X-ray crystallographic analysis of salvinicin A (4) and a 3,4-dichlorobenzoate derivative of salvinorin B.
منابع مشابه
Synthetic studies of neoclerodane diterpenes from Salvia divinorum: semisynthesis of salvinicins A and B and other chemical transformations of salvinorin A.
Salvinorin A (1) is a hallucinogenic neoclerodane diterpene isolated from the widely available psychoactive plant Salvia divinorum and is the first example of a non-nitrogenous opioid receptor ligand. At present, there is little information available as to why this compound is selective for kappa opioid receptors. One approach to better understanding the mode of binding of 1 at kappa receptors ...
متن کاملSalvinorins D-F, new neoclerodane diterpenoids from Salvia divinorum, and an improved method for the isolation of salvinorin A.
Three new neoclerodane diterpenoids, salvinorins D-F (4-6), have been isolated from the leaves of Salvia divinorum. The structures were elucidated by chemical and spectroscopic methods, particularly 1D and 2D NMR. A simplified isolation method using chromatography on activated carbon also gave improved yields of the controlled substance salvinorin A (1) and of salvinorin C (3).
متن کاملDivinatorins A-C, new neoclerodane diterpenoids from the controlled sage Salvia divinorum.
Three new neoclerodane diterpenoids, divinatorins A-C (7-9), have been isolated from the leaves of Salvia divinorum. The compounds were identified by spectroscopic methods as derivatives of the antibiotic (-)-hardwickiic acid (10), which was also isolated, along with four other known terpenoids. Neither the crude extract nor 7-9 displayed antimicrobial activity.
متن کاملSalvinorins J from Salvia divinorum: mutarotation in the neoclerodane system.
A search for biosynthetic precursors of salvinorin A (1) led to the isolation of a new neoclerodane diterpenoid hemiacetal mixture, salvinorins J (2), from the chloroform extract of Salvia divinorum. A leaf surface extraction method was used on S. divinorum, affording a chlorophyll-free extract containing predominantly neoclerodane diterpenoids, including the new salvinorins J (2) and 14 known ...
متن کاملSynthetic studies of neoclerodane diterpenes from Salvia divinorum: preparation and opioid receptor activity of salvinicin analogues.
Further modification of salvinorin A (1a), the major active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study that oxadiazole 11a and salvidivin A (12a), a photooxygenation product of 1a, have been identified as the first neoclerodane diterpenes with kappa antagonist activity. This in...
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عنوان ژورنال:
- Organic letters
دوره 7 14 شماره
صفحات -
تاریخ انتشار 2005