A New Polyoxypregnane Glycoside from the Roots of Dregea volubilis (L.f) Benth. ex Hook. f and its Chondroprotective Effect

Abstract

Problem statement: Dregea genus (Asclepiadaceae) is well known for the rich of steroid pregnane contents and these plants are famous for the potential to be applied as alternative biological activities. Dregea volubilis is the only species of Dregea genus in Thailand. The chemical and biological investigations of this plant are interesting to bioassay-guided fractionation, particularly chondroprotective effect. Approach: The research was carried out to extract, isolate, purify and elucidate structure of the active compound from the roots Dregea volubilis. Both of the solvent extracts and isolated compound were evaluated with kinds of chondroprotection. i.e., S-GAG), HA, UA and production of matrix metalloproteinase-2 (MMP-2). Results: Polyoxypregnane glycoside (PGG) or 12-0-benzoyl-8, 11-ditigloyl-3β, 8β, 11α, 12β, 14β-pentahydroxy-pregn-14-ol, 20-one,-3-0-methyl-β-D-allopyranosyl (1→4)-β-D-thevetopyranoside was isolated from the active ethyl acetate extract of the roots Dregea volubilis. The spectroscopic techniques were provided for success in structure determination. In addition, a new compound was the most powerful to biological activities. Chondroprotective effect of PPG on the degradation of sulfated glycosaminoglycan (S-GAG), hyaluronan (HA), uronic acid (UA) and production of matrix metalloproteinase-2 (MMP-2) in interleukin-1β (IL-1β)-stimulated porcine articular cartilage were also assessed. PGG was interestingly effective in reducing IL-1β induced S-GAG, HA release from cartilage explant and MMP-2 activity. Furthermore, PPG can reverse effect of IL-1β-reduced the levels of uronic acid remaining in cartilage tissue. Conclusion: The PGG was possessed a potent chondroprotective activity using the IL-1β stimulated cartilage explant model. Therefore, it is possible to use this compound as a new pharmacological agent for the management of degenerative joint diseases.

Polyoxypregnane glycoside from Dregea volubilis extract inhibits IL-1β-induced expression of matrix metalloproteinase via activation of NF-κB in human chondrocytes

“…Recently, this compound was shown to inhibit IL-1β-induced extracellular matrix (ECMs) degradation in porcine cartilage explants, by decreased sulfated-glycosaminoglycan (s-GAG), hyaluronan (HA) released in culture medium and increased uronic acid content in cartilage tissue when compared with IL-1β treatment group (Sanyacharernkul et al 2009). However, no studies have been undertaken to investigate at the molecular level whether PPG constituents protect the articular chondrocyte.…”

“…1) and were isolated as a white solids powder, melting point 270-271.6°C. Therefore, the molecular formula was established to be C 51 H 72 O 17 by ESIMS and 13 C NMR analyses (Sanyacharernkul et al 2009). …”

Anthelmintic effect of a methanol extract of leaves of Dregea volubilis on Paramphistomum explanatum

“…The leaves and flowers are also used as vegetables (Anonymous 1976). Drevogenin D and kaempferol have been isolated from its leaves whereas dregeosides, hyperoside, drevogenin A, drebbysogenin, and polyoxypregnane glycoside were isolated from its seeds, stem, and roots, respectively (Anonymous 1976;Sanyacharernkul et al 2009;Yoshimura et al 1983Yoshimura et al , 1985. Methanol extract of leaves possess anti-inflammatory activity and was nontoxic up to a dose of 2 g/kg for mice and rat orally (Hossain et al 2010).…”

Stimulation of human osteoblast cells (MG63) proliferation using decanoic acid and isopropyl amine fractions of Wattakaka volubilis leaves

“…[9] The effect of these active principles has also been studied for its anti-diabetic, [8] anti-diarrheal and anti-ulcer, [10] anti-tumour, antioxidant, [11] antiinflammatory and anti-arthritic activities. [12] Sanyacharenkul et al [13] reported that the W. volubilis plant extract showed enhanced chondroprotective effect during cartilage degradation studies in 20-to 24-week-old pigs due to the presence of polyoxypregnane glycosides. The phytochemical constituents present in this medicinal plant like alkaloids, flavonoids, tannin and phenols are highly used for treating ailments.…”

“…The effect of these active principles has also been studied for its anti‐diabetic, anti‐diarrheal and anti‐ulcer, anti‐tumour, antioxidant, anti‐inflammatory and anti‐arthritic activities . Sanyacharenkul et al . reported that the W. volubilis plant extract showed enhanced chondroprotective effect during cartilage degradation studies in 20‐ to 24‐week‐old pigs due to the presence of polyoxypregnane glycosides.…”