Neoclerodanes

Bruno M, Piozzi F, Rosselli S. Natural and hemisynthetic neoclerodane diterpenoids from Scutellaria and their antifeedant activity. Nat Prod Rep 2002 19 357-78. 

One of the most exiting findings in this area is perhaps the isolation of Bt-CD, a neoclerodane diterpenoid from Baccharis trimera (Less) DC or carqueja (Brazil) used to treat rheumatism and diabetes that shows anti-phospholipase A2 activity (11). Note also the anti-phospholipase A2 and anti-inflammatory activity of Santolina chamaecy-parissus (12). Cirsium japonicum DC, Crossotephium chinense L. Makino, Inula chinensis Rupr. ex Maxim., and Sigesbeckia orientalis L. are used in Asia for the treatment of inflammatory conditions. 

The discovery of a potent and selective K-opioid receptor agonist compound, salvinorin A (54), a hallucinogenic neoclerodane diterpenoid from Salvia divinorum Epling and Jativa, has created particular interest in recent years, since it is the first nonnitrogenous compound found to demonstrate this type of activity. 

A. Salvia contains a substance called salvinorin A. Salvinorin A is the most potent naturally occurring vision inducer. Salvinorin A is not an alkaloid—its molecule contains only carbon, hydrogen and oxygen atoms. Technically it is a neoclerodane diterpenoid. Salvinorin A is a unique vision inducing substance, of great power. It is NOT an analog of any other drug. 

Ortega, A. etal. 1982. Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum (Labiatae). Journal of the Chemical Society Perkins Transactions. 1 1982 2505-2508. 

Salvinorin, a New trans-Neoclerodane Diterpene from Salvia divinorum (Labiatae) J. Chem. Soc. Perkin Trans. 1 2505-2508. 

Salvinorin, isolated from Salvia divinorum has been shown by spectroscopic and X-ray-crystallographic methods to be a tran -neoclerodane diterpene of structure (1). Crystals of compound (1) are orthorhombic, space group P2iP2iP27 with a = 6.368 (2), h = 11.338(3), c = 30.7100 (6) A, and Z = 4. The structure was refined by least-squares to R 0.052 and R 0.056. 

Salvinorin (1) thus belongs to the neoclerodane class of diterpenes, a group of compounds that has... 

Divinorin C," a New Neoclerodane Diterpene from a Bioactive TLC Fraction of Salvia divinorum... 

Ortega. A 1982 Salvinorin, A New Trans-Neoclerodane Diterpene from... 

The active principle of Salvia divinorum, salvinorin A, is derived from the leaves of the plant. Chemically, salvinorin A is a neoclerodane diterpene, one of a group of nitrogen-containing terpene compounds that have psychotropic properties. Two other such compounds are tetrahydrocannabinol and absinthe. Purified salvinorin A can be obtained from an ether extract of the leaves, which is then concentrated by chromatography and repeated crystallization. 

Epling and Jativa-M) containing the neoclerodane diterpene divinorin A or salvinorin A (Fig. 12.1). It was the first documented non-alkaloidal diterpene hallucinogen. It is inactivated by the gastrointestinal system if orally ingested, and the effect is produced after absorption through the oral mucous. 9... 

VALDES, L.J., CHANG, H.M., VISGER, D.C., KOREEDA, M., Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum., Org. Lett., 2001, 3, 3935-3937. 

The neoclerodane type diterpenoids (listed in Table 3 with corresponding Salvia species and references) may be divided into 4 categories. 

Neoclerodan-16,15,20,19-diolides (41-43) which have been isolated from S. madrensis [69]. 

Neoclerodan-18,19-olides with a furan group on C-12 and Me-17 in a-configuration (50-52). 

Neoclerodan-18,19-olides with a double bond or more in the decalin skeleton or one double bond and an epoxyde. The C-10 substituent has a -configuration (62-78). 

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