Two new phenolic glycosides, kaempferiaosides A and B were isolated from the rhizomes of Kaempferia parviflora (Zingiberaceae) together with 24 known compounds. Their structures including absolute stereochemistry were elucidated on the basis of chemical and spectroscopic evidence. Among the isolates, 5,3′-dihydroxy-3,7,4′-trimethoxyflavone showed higher activity than silybin, a commercial hepatoprotective agent.Key words Kaempferia parviflora; Zingiberaceae; kaempferiaoside; hepatoprotective activity; Krachai Dum A Zingiberaceae plant, Kaempferia parviflora WALL. ex BAKER, is widely distributed in Thailand and is known as Krachai Dum.1,2) The rhizomes of this plant are tinged with-dark purple to black, and have traditionally been used for the treatment of hypertension, [3][4][5] allergy, 6) gastrointestinal disorders, 7) and impotence. 8,9) The extract of the rhizomes of K. parviflora and its constituents were revealed to exhibit several pharmacological activities, such as antiplasmoidal, antifungal, 2) antiinflammatory, [10][11][12] α-glucosidase inhibitory, 13) and xanthine oxidase inhibitory 1) activities and cytotoxicity of several tumor cell lines 14,15) as well as effect of P-glycoprotein function 16) and modulation of multi-drug resistance in cancer cells.
17)Recently, rhizomes of K. parviflora powder was found to show preventive effect from obesity and its downstream symptoms. 18) By a previous chemical study on K. parviflora, presence of several methoxyflavones and related phenolic constituents have been revealed. 2,5,6,[10][11][12][13][14][15]17,[19][20][21][22] During the course of our characterization studies on Thai natural medicines, [23][24][25][26][27][28][29][30][31][32] two new phenolic glycosides named kaempferiaosides A (1) and B (2) were isolated from the rhizomes of K. parviflora together with 24 known compounds. This paper deals with the structure elucidation of 1 and 2, as well as hepatoprotective effect of the constituents from the rhizomes of K. parviflora on D-galactosamine (D-GalN)-induced cytotoxicity in primary cultured mouse hepatocytes.The dried rhizomes of K. parviflora cultivated at Loei province, Thailand were extracted with methanol to give a methanolic extract (7.10% from the dried rhizomes). The methanolic extract was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish an EtOAc-soluble fraction (3.82%) and an aqueous phase. The aqueous phase was subjected to Diaion HP-20 column chromatography (H 2 O → MeOH) to give H 2 O-and MeOH-eluted fractions (2.04, 1.23%, respectively). As shown in Table 1, the EtOAc-soluble fraction and the MeOH-eluted fraction exhibited hepatoprotective activity, but the H 2 Oeluted fraction lacked the activity. The EtOAc-soluble fraction was subjected to normal-and reversed-phase column chromatographies, and finally HPLC to give 5-hydroxy-7-methoxyflavone 33) (3, 0.113%), 5,7-dimethoxyflavone rel-(5aS, 10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]