Bioactive Terpenoids and Guggulusteroids from Commiphora mukul Gum Resin of Potential Anti‐Inflammatory Interest

Abstract

Guggulu, the gum resin from Commiphora mukul, is one of the components of various formulations of traditional Ayurvedic medicine to treat inflammation, obesity, and lipid disorders. In most preparations of Ayurvedic medicine in India, guggulu is boiled prior to its use. Therefore, guggulu was boiled with H2O prior to extractions in our study. Bioassay-guided isolation of compounds from the hexane-soluble portion of the MeOH extract of guggulu yielded cembrenoids, 1-6, a bicyclic diterpene, 7, guggulusterone derivatives, 8-11, myrrhanone derivatives, 12, myrrhanol derivative, 13, and a lignan, 14. The structures of these compounds were confirmed by spectroscopic methods. Compounds 5, 6, 7, 10, and 12-14 are novel. These compounds were assayed for lipid peroxidation and cyclooxygenase (COX) enzyme inhibitory activities. At 100 ppm, compounds 3, 6, and 14 inhibited the lipid peroxidation by 79, 57, and 58%, respectively, and the rest of isolated compounds showed 20-40% inhibitory activity with respect to the controls. In COX-1 and COX-2 enzyme inhibitory assays, compound 3 showed 79 and 83%, and compound 8 gave 67 and 54% of inhibition, respectively, at 100 ppm. All fourteen compounds inhibited COX-1 enzyme at 100 ppm. The lipid peroxidation and COX enzyme inhibitory activities exhibited by compounds isolated from C. mukul may substantiate its use in traditional medicine.

1H and 13C assignments of five cembrenes from guggul

“…[8] Verticillol (#5) has been isolated from olibanum oil [9] and guggul. [10] Our NMR assignments are in general agreement with those reported previously except the 13 C assignments for methyl groups at position C18 and C20 for Cembrene A (#2), [8] and at C18 and C19 for mukulol (#4). [8] The discrepancy is attributed to the heteronuclear chemical shift correlation methods used in this report, which provide accurate information on the correlation between 1 H and 13 C and were not available to the earlier reports.…”

Anti-inflammatory and analgesic activity of different extracts of Commiphora myrrha

“…It was reported that Zguggulsterone, E-guggulsterone, myrrhanone A, and myrrhanol A inhibited nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages (Matsuda et al, 2004). Moreover, E-guggulsterone possessed the cyclooxygenase (COX) enzyme inhibitory activities (Francis et al, 2004). In this present study, seven major constituents including three sesquiterpenes, one diterpene and three diterpenic acids were identified by UPLC-MS/MS from the analgesic and anti-inflammatory fraction.…”

The genus Commiphora: A review of its traditional uses, phytochemistry and pharmacology

“…Myrrhanol A (23) and mukulol (25) inhibited the induction of inducible nitric oxide synthase (iNOS) in LPS-activated mouse peritoneal macrophages (Matsuda et al, 2004a). Concerning the COX inhibitory effect, cembrene (26) and E-guggulsterone (22) are most active, with 79% and 67% inhibition against COX-1, and with 83% and 54% inhibition against COX-2 at 100 ppm (Francis et al, 2004).…”