Studies On The Chemical Constituents Of The Resins Of Commiphora Opobalsamum

Myrrh is one of the oldest herbal medicines and flavoring agents, and was first described in the Chinese medical literature Kai Bao Ben Cao. It is the oleo-gum-resin obtained from trees of Commiphora species of the Burseraceae family (such as Commiphora myrrha Engl.). As a Chinese traditional medicine, its nature and flavor is balanced and bitter respectively. Its main effect is to relieve painful swelling and pains due to blood stagnation, traumatic injury or other kinds of wounds, etc. The modern pharmacology researches show that myrrh and its constituents possess various bioactivities, such as cytotoxic, antifungal, antibacterial, antalgic, antioxidant, anti-inflammatory effects, etc. It is known as a rich source of secondary metabolites such as sesquiterpenes, triterpenes, steroids and lignans, etc.The chemical constituents of the CHCl3 extract from the resins of Commiphora opobalsamum were studied. Seventeen compounds were isolated by repeated silica gel, Sephadex LH-20 column chromatography and preparative HPLC. On the basis of spectral data and physico-chemical characters, the structures of these compounds were identified as:(4α,11α)-2-oxo-8, 11-dihydroxycadina-1(6),7,9-trien-12-oic acidγ-lactone(1), (4α,11β)-2-oxo-8, 11-dihydroxycadina-1(6),7,9-trien-12-oic acidγ-lactone(2),9-methoxymyrrhone(3), myrrhone(4), dihydropyrocurzerenone(5); orientalol E(6), alismol(7), guaianediol(8); (1(10)E,2R*,4R*,5S*)-2-methoxy-5-acetoxy-furanogermacr-1(10)E-en-6-one(9), (1(10)E,2R*,4R*)-2-methoxy-8, 12-epoxygermacra-1(10)E,7, 11-trien-6-one(10); proximadiol(11); cycloartane-1α,2α, 3β,25-tetrol(12), cycloartan-24-ene-1α,2α,3β-triol(13), cycloartan-24-ene-1α, 3β-diol(14); 29-norlanost-8,24-dien-1α,2α,3β-triol(15); octadecane-1,2S,3S, 4R-tetrol-1-O-α-L-rhamnopyranoside(16) andβ-sitosterol(17). Among them, compounds 1-5,6-8,9-10,11 belong to cadinane type, guaiane type, furanogermacrane type and eudesmane type sesquiterpenes, respectively, and compounds 12-14,15 are cycloartane type and norlanostane type triterpenes, respectively. In addition, compounds 1,2 and 3 are three new compounds, and compounds 6,7 and 11 were obtained for the first time from Commiphora genus.The isolated compounds 4-16 were tested against human prostate cancer PC-3 cell lines. Among them, compounds 13,15 and 16 showed moderate antiproliferative effects on PC-3 cell lines with IG50 values ranging from 22.9 to 39.3μM. The all eight tested sesquiterpenoids and compounds 12 and 14 were inactive in the bioassay.