Clerodane Diterpenoids from Salvia splendens

Abstract

Four new clerodane diterpenoids, salvisplendins A-D (1-4), have been isolated from an acetone extract of the flowers of Salvia splendens, together with an artifact (5), arising from salvisplendin D (4) by addition of diazomethane, and the already known clerodane olearin (6). The structures of the new compounds (1-5) were established mainly by 1D and 2D NMR spectroscopic studies and, in the case of salvisplendin A (1), by chemical correlation with splenolide B (7). Complete 1H and 13C NMR assignments for olearin (6), not published hitherto, are also reported.

Neuropharmacology of the Naturally Occurring κ-Opioid Hallucinogen Salvinorin A

“…and Schult. also identified several neoclerodanes that are structurally similar to those found in S. divinorum (Fontana et al, 2006), although these and most semisynthetic analogs (Li et al, 2007;Fontana et al, 2008Fontana et al, , 2009 proved to be largely inactive at KOP receptors (see section IV.A).…”

Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity

“…Recently,9 some of us have reinvestigated the diterpene constituents of Salvia splendens Sellow ex Roem. &.…”

“…&. Schult isolating four new neoclerodanes (salvisplendins A–D, 4 , 6 , 7 , and 8 , respectively) together with the artifact 9 , that results from 8 by treatment of the crude extract with diazomethane,9 and salviarin ( 2 ),10 splendidin ( 3 ),11 and splenolides A and B ( 5 ),12 all of them previously reported as constituents of this species 9–13. Taking into account the structural similarity between salvinorin A ( 1 ) and the diterpenes found in S. splendens ( 2–9 ), we decided to test these substances and two of their available derivatives ( 10 and 11 )9 in order to explore whether such compounds may be useful as neuropharmacological agents.…”

“…Moreover, we have now obtained several new semisynthetic derivatives ( 12 – 24 ) starting from the more abundant constituents of S. splendens ( 2 , 3 , 5 , 7 , and 9 ),9,13 and these compounds were also assayed as potential agonists at the opioid receptors. Three clerodanes of S. splendens , salviarin ( 2 ), splendidin ( 3 ), and splenolide B ( 5 ), have recently been tested for affinity at opioid receptors and none of these diterpenes showed significant binding to any of the opioid-receptor subtypes 14.…”

Antibacterial peptides from thermophilic bacteria

“…Only bacteriocins type I nisin, mutacin (Fig. 1C) and planeosporin are active against multidrug resistant Gram-positive bacteria (Severina et al, 1998;Fontana et al, 2006). Bacteriocin production is stabile even at 55 °C and is dependent on the time of incubation, pH and concentrations of nitrogen.…”