Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins.
The methanolic extract from guggul-gum resin, the resin of Balsamodendron mukul, was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages (IC(50) = 13 microg/mL). From the methanolic extract, three new polypodane-type triterpenes, myrrhanol B and myrrhanones B and A acetate, and a new octanordammarane-type triterpene, epimansumbinol, were isolated together with 17 known compounds including progesterone and the related steroids. The absolute stereostructures of new triterpenes were elucidated on the basis of chemical and physicochemical evidence. The several constituents showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
Matsuda
Hisashi
H
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
Morikawa
Toshio
T
Ando
Shin
S
Oominami
Hideo
H
Murakami
Toshiyuki
T
Kimura
Ikuko
I
Yoshikawa
Masayuki
M
D000818:Animals; D029744:Commiphora; D008264:Macrophages / Q000201:enzymology; D000432:Methanol / Q000737:chemistry; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis*; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors; D052247:Nitric Oxide Synthase Type II; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D053149:Plant Gums; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D010936:Plant Extracts; D053149:Plant Gums; D014315:Triterpenes; C495010:epimansumbinol; C434796:myrrhanol A; C495009:myrrhanol B; D009569:Nitric Oxide; C018562:guggulu extract; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse; D000432:Methanol