The Zingiberaceae plant, Zingiber cassumunar (Z. cassumunar), is widely distributed in the Southeast Asian countries and was called as "phlai" in Thailand. The rhizomes of this plant are used as a spice and also used for treatment of asthma, bronchitis, gastrointestinal distress, etc., in traditional Thai medicine. Recently, several chemical and biological studies on Z. cassumunar have been reported. [1][2][3][4][5] For example, several phenylbutanoids isolated from Z. cassumunar were reported to possess P-glycoprotein inhibitory, 1) cyclooxygenase-2 inhibitory, 4) and anti-inflammatory 5) effects. During the course of our characterization studies on Zingiberaceae natural medicines, [6][7][8][9][10][11][12][13][14][15][16] the MeOH extract from the rhizomes of Z. cassumunar was found to show inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse peritoneal macrophages. From the MeOH extract, six new phenylbutanoids named phlains I-VI were isolated together with 16 known constituents. Furthermore, we examined the inhibitory effects of principal constituents on NO production induced by LPS in mouse peritoneal macrophages. In this paper, we describe the isolation and structure elucidation of the new constituents (1-6) and the NO production inhibitory effects of principal constituents from the rhizomes of Z. cassumunar.The rhizomes of Z. cassumunar were extracted with MeOH. The MeOH extract (24.1% from the rhizomes) was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish an EtOAc-soluble fraction (16.7%) and an aqueous phase (7.4%). The MeOH extract (IC 50 ϭ11 mg/ml) and the EtOAc-
Structures of New Phenylbutanoids and Nitric Oxide Production Inhibitors from the Rhizomes of Zingiber cassumunar
In the course ot a screening program for tyrosine kinase inhibitors, the chloroform extract of a tropical plant, Desmos chinensis, strongly inhibited the enzyme activity. The active substance was purified by silica gel, gel filtration, and finally crystallized. The structure was elucidated by mass spectrometry and X-ray crystallography to be 8-formyl-2,5,7-trihydroxy-6-methylflavanone, and we named it desmal. Desmal competed with peptide substrate and non-competed with ATP. It inhibited tyrosine kinase in situ in epidennal growth factor (EGF) receptor-overexpressing NIH3T3 (ER12) cells. It also inhibited EGF-induced inositol phosphate formation and morphological changes.
Zingiber cassumunar is widely distributed in Asia, and its rhizomes are used for asthma treatment in traditional medicine and as a spice. Five new phenylbutanoids, cassumunols I–M (1-5), were isolated from Z cassumunar rhizomes collected in Thailand, and their structures were characterized on the basis of physiochemical and chemical evidence.
The methanolic extract [inhibition (%): 61.2±3.8 (p<0.01) at 100 g/mL] and its EtOAc-soluble fraction [inhibition (%): 82.5±1.7 (p<0.01) at 100 g/mL] from the sclerotia of Inonotus obliquus collected in Japan significantly inhibited invasion of human fibrosarcoma HT1080 cells through matrigel-coated filters. In addition, the methanolic extract significantly inhibited lung tumor formation fifteen days after injection of B16F10 melanoma cells in mice [inhibition (%) 66.1 ± 12.8 (p < 0.05) at 500 mg/kg/d, p.o.]. Lanostane-type triterpenes were isolated as the common principal constituents from Japanese and Russian I. obliquus. Furtheremore, we examine the inhibitory effects of the constituents on the invasion of HT 1080 cells. Interestingly, 3-hydroxylanosta-8,24-dien-21-al [inhibition (%) 37.9 ± 3.0 (p < 0.05) at 30 M] significantly inhibited the invasion, and no cytotoxic effect at 30 M was observed.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.