Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum(Labiatae)

  title={Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum(Labiatae)},
  author={Alfredo R. Ortega and John F. Blount and Percy S. Manchand},
  journal={Journal of The Chemical Society-perkin Transactions 1},
Salvinorin, isolated from Salvia divinorum, has been shown by spectroscopic and X-ray-crystallographic methods to be a trans-neoclerodane diterpene of structure (1). Crystals of compound (1) are orthorhombic, space group P212121 with a= 6.368(2), b= 11.338(3), c= 30.710(6)A, and Z= 4. The structure was refined by leastsquares to R 0.052 and R′ 0.056. 

Tables from this paper

Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum.
Its structure was elucidated on the basis of extensive proton and C-13 NMR experiments, as well as by comparison of the NMR data with those of the mono- and diacetate derivatives 5-7 of the major NaBH(4)-reduction product of salvinorin A (2).
Synthetic 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.
Neo-clerodane diterpenes from Salvia herbacea.
None of the compounds were considered to be cytotoxic; however, compound 7 exhibited anti-inflammatory activity comparable to that of indomethacin.
Isolation and Chemical Modification of Clerodane Diterpenoids from Salvia Species as Potential Agonists at the κ‐Opioid Receptor
None of these compounds showed significant binding to any of the opioid‐receptor subtypes, thus disproving the hypothesis that splendidin from S. splendens might possess similar activities.
Isoscoparins R and S, two new ent-clerodane diterpenoids from Isodon scoparius
Two new ent-clerodane diterpenoids, named isoscoparins R and S (1 and 2), were isolated from the aerial parts of Isodon scoparius and showed weak activity as an autophagic inhibitor.
Microphyllandiolide, a new diterpene with an unprecedented skeleton from Salvia microphylla.
The structure of microphyllandiolide, an unprecedented rearranged clerodane-type diterpene with a 9/3 bicyclic ring system, was elucidated by analysis of its spectroscopic data and confirmed by single crystal X-ray diffraction analysis.
The chemistry of Salvia divinorum
Salvinorin A (1a), a neoclerodane diterpenoid isolated from the plant, is a potent, selective agonist at the κ opioid receptor (KOR), and is the first non-nitrogenous opioid.
Total Synthesis of (-)-Salvinorin A.
A total synthesis has been developed that parlays the stereochemistry of l-(+)-tartaric acid into that of (-)-1 via an unprecedented allylic dithiane intramolecular Diels-Alder reaction to obtain the trans-decalin scaffold.