Salvifaricin

Neo-clerodane Diterpenoids with Hypoglycemic Effects in Vivo from the Aerial Parts of Salvia hispanica L.[Pubmed:34292661]

Chem Biodivers. 2021 Sep;18(9):e2100517.

A new neo-clerodane diterpenoid, salvihispin H (1), and six known ones (2-7) were identified from the aerial parts of Salvia hispanica L. The structure and absolute configuration of 1 were elucidated by extensive analysis of spectroscopic ((1) H, (13) C, and 2D NMR, and HR-ESI-MS) and single-crystal X-ray diffraction data. The anti-diabetic effects of salvihispin H (1) and Salvifaricin (2) were evaluated in diabetic db/db mice. The data showed that 1 and 2 could significantly reduce fasting blood glucose level and improve insulin resistance, and compound 1 exerted glucose-lowering effect more quickly than metformin. In addition, 1 and 2 could also reduce serum TG level in db/db mice. These results demonstrated that compounds 1 and 2 could be considered as potent candidates for the therapy of type 2 diabetes mellitus (T2DM).

Isolation and chemical modification of clerodane diterpenoids from Salvia species as potential agonists at the kappa-opioid receptor.[Pubmed:17638340]

Chem Biodivers. 2007 Jul;4(7):1586-93.

The clerodane diterpenoid salvinorin A (1), the main active component of the psychotropic herb Salvia divinorum, has been reported to be a potent agonist at the kappa-opioid receptor. Computer modeling suggested that splendidin (2) from S. splendens, as well as related compounds, might possess similar activities. In the present study, this hypothesis was tested by determination of the binding properties of a series of structural congeners, compounds 2-8, at the mu-, delta-, and kappa-opioid receptors. However, none of these compounds showed significant binding to any of the opioid-receptor subtypes, thus disproving the above hypothesis. The novel compounds 7 and 8 were obtained semi-synthetically by selective modification of salvifarin (5), isolated from Salvia farinacea, upon epoxide-ring opening with AcOH in the presence of indium(III) triflate. Also, the X-ray crystal structure of Salvifaricin (6; Fig.), obtained from S. farinacea, was determined for the first time and used, in combination with in-depth NMR experiments, to elucidate the absolute configurations of the new products. Our experiments demonstrate that the relatively well-accessible diterpenoid 6 could be used as starting material for future studies into the structure-activity relationship at the kappa-opioid receptor.

A novel diterpenoid with a rearranged neoclerodane skeleton from Salvia leucantha CAV.[Pubmed:29435878]

J Nat Med. 2006 Jul;60(3):206-209.

A new diterpenoid with a rearranged neoclerodane skeleton, spiroleucantholide (compound "S1"), along with four known diterpenoids-Salvifaricin (compound "S2"), isosalvipuberulin (compound "S3"), salvileucantholide (compound "S4"), and salviandulin E (compound "S5")-was isolated from the aerial parts of Salvia leucantha CAV.. The structures were established by spectroscopic methods, including the X-ray analysis of spiroleucantholide (S1).

Polystachynes A-E, five cis-neo-clerodane diterpenoids from Salvia polystachya.[Pubmed:10656416]

Phytochemistry. 2000 Jan;53(1):103-9.

From the aerial parts of Salvia polystachya five new neo-clerodane diterpenoids, polystachynes A-E, have been isolated. The structures were established by spectroscopic methods, including the X-ray analysis of polystachynes C and D. The known clerodanes Salvifaricin, linearolactone and dehydrokerlin were also isolated.