neo-Clerodane Diterpenoids from Salvia polystachya Stimulate the Expression of Extracellular Matrix Components in Human Dermal Fibroblasts

Abstract

Eleven neo-clerodane diterpenoids (1-11) including the new analogues 1, 2, and 10, and 3',5,6,7-tetrahydroxy-4'-methoxyflavone (12) were isolated from the aerial parts of Salvia polystachya. Polystachyne G (1) and 15-epi-polystachyne G (2) were isolated as an epimeric mixture, containing a 5-hydroxyfuran-2(5H)-one unit in the side chain at C-12 of the neo-clerodane framework. Polystachyne H (10) contains a 1(10),2-diene moiety and a tertiary C-4 hydroxy group. The structures of these compounds were established by analysis of their NMR spectroscopic and MS spectrometric data. The absolute configurations of compounds 3, 4, and 10 were determined through single-crystal X-ray diffraction analysis. The antibacterial, antifungal, and phytotoxic activities of the diterpenoids were determined. In addition, the stimulatory effect of the expression of extracellular matrix components of nine of the isolates (1-8 and 11) was assayed. Compounds 1-4, 8, and 11 increased the expression of the genes codifying for type I, type III, and type V collagens and for elastin.

Antioxidant Properties and Protective Effects of Some Species of the Annonaceae, Lamiaceae, and Geraniaceae Families against Neuronal Damage Induced by Excitotoxicity and Cerebral Ischemia

“…We postulated that compounds present on Sp extract, besides lowering the stress oxidative-induced damage, might allow adaptations on gene regulation. For example, aerial parts of Sp contain eleven neo-cleorodane difepenoids; some of these compounds augmented the expression of extracellular matrix components (e.g., genes codifying type I, II, and V collagens and elastin) [57], which are critical for vascular basement membrane function and play a central role in cerebrovascular diseases [58]. Compounds in S. mitiorrhiza can also inhibit the expression of adhesion molecules in vascular endothelium and in leukocytes that help to prevent the development of vascular damage induced by ischemia and reperfusion [59].…”

Antihyperglycemic Effects of Salvia polystachya Cav. and Its Terpenoids: α-Glucosidase and SGLT1 Inhibitors

“…From the leaves, neo-clerodane diterpenes, such as polystachynes A–H, 15-epi-polystachine G, salvifiline A and C, 15-epi-salvifiline A, and linearolactone, and the flavone 3’,5,6,7-tetrahydroxy-4’-methoxyflavone, were isolated [ 33 , 34 ]. Among these, the diterpene linearolactone exhibited antiprotozoal activity in Entamoeba histolytica and Giardia lamblia [ 35 ]; moreover, polystachynes B and G, linearolactone and 15-epi-salvifiline A increased the gene expression of elastin and the type I, III, and V of collagens [ 36 ]. Although several species of the Salvia genus have been reported to have antidiabetic properties, there are no scientific reports that support S. polystachya ’s effects on hyperglycemia yet.…”

Salvia connivens, a Source of Bioactive Flavones with Amoebicidal and Giardicidal Activity

“…The structures of the isolated compounds were established by the analyses of their NMR spectroscopic and MS spectrometric data and were compared with those described in the literature (Nagao et al 2002;Gecibesler et al 2019). Curiously, during the isolation procedure, sesquiterpenoids and diterpenoids were not isolated as is common in Salvia species (Bautista et al 2017;Fragoso-Serrano et al 2019). The subsequent evaluation of the antiprotozoal properties of isolates 1-3 showed that compounds 1 and 2 had moderate antiprotozoal activity against both protozoa, with IC 50 values of 40.4 (40.9-39.8) and 42.7 (43.1-41.8) μM against E. histolytica; and 61.6 (66.1-60.4) and 60.3 (62.1-59.4) μM against G. lamblia, respectively.…”