Four New Sesquiterpenes from Curcuma wenyujin and Their Inhibitory Effects on Nitric‐Oxide Production

Abstract

Four new sesquiterpenes including the novel sesquiterpene lactone (6R)-dehydroxysipanolinolide (1), two new eudesmane-type sesquiterpenes, curcolide (2) and curcodione (3), and a new xanthane-type sesquiterpene, curcumadionol (4), were isolated from Curcuma wenyujin Y. H. Chen et C. Ling, together with five known ones, 5-9. The structures of the new compounds were elucidated by spectroscopic methods. The inhibitory effects of compounds 1-9 on nitric-oxide production in lipopolysaccaride-activated macrophages were evaluated.

Natural nitric oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis

“…The molecular formula C 16 Table 2), suggesting that 6 was an elemane-type sesquiterpene possessing a lactone moiety. The molecular formula C 16 Table 2), suggesting that 6 was an elemane-type sesquiterpene possessing a lactone moiety.…”

“…Cell viability in the present experiment was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2Htetrazolium bromide (MTT) method to find out whether inhibition of NO production was due to cytotoxicity of the test compounds (data not shown). Compound 6 and β-hydroxy-isogermafurenolide 16 showed weak inhibitory effects since the H-8 was substituted by methoxy and hydroxy groups, respectively. Com-pounds 1, 3, 4 and 8 exhibited potent inhibitory activities against NO production with an IC 50 of 7.46 ± 0.69, 2.35 ± 0.17, 3.49 ± 0.31 and 16.49 ± 1.16 μM, respectively.…”

“…7 Though their pharmacological activities and chemical characteristics are obviously different, it is difficult to distinguish the origins of these raw materials in the clinic due to the similarities in morphological characteristics. [12][13][14][15][16][17][18] We found that sesquiterpenes were mainly isolated from C. wenyujin and C. phaeocaulis, while diarylheptanoids were the major compounds from C. kwangsiensis. Recently, our research group has been examining the constituents of C. kwangsiensis, C. phaeocaulis and C. wenyujin as well as their inhibitory activities against LPS-induced nitric oxide production, and has hitherto reported the isolation and identification of several new sesquiterpenoids and diarylheptanoids.…”

Four new sesquiterpenes from the rhizomes ofCurcuma phaeocaulisand their iNOS inhibitory activities

“…The IR spectrum showed absorptions belonging to double bonds (1611, 1544, 1512, 1451 cm 21 ) and conjugated carbonyl (1763 cm 21 ) group, and the UV spectrum revealed a characteristic absorption maxima at 234 and 326 nm (MeOH, log 1 4.21 and 3.64, respectively) indicating the presence of a tropone chromophore [4]. The 1 H and 13 C NMR spectra of 2 were similar to those of phaeocaulisin D, which had been obtained previously from C. phaeocaulis by our research group [6].…”

Eudesmane‐Type Sesquiterpenes from Curcuma phaeocaulis and Their Inhibitory Activities on Nitric Oxide Production in RAW 264.7 Cells

“…Recently, much attention has been paid to Curcuma species owing to their diverse biological activities that include antiinflammatory, [2][3][4] anticancer, [5][6][7][8][9] antioxidant, [10,11] vaso-relaxant, [12] hepatoprotective [13] and neuroprotective [14] effects, which have motivated a number of studies on the main bioactive constituents of this genus. [17][18][19][20][21][22][23] As reported in the Chinese Pharmacopoeia, three species of Rhizoma Curcumae (Curcuma phaeocaulis Valeton, Curcuma kwangsiensis S. G. Lee et C. F. Liang, and Curcuma wenyujin Y. H. Chen et C. Ling) are officially approved as Chinese medicine. [17][18][19][20][21][22][23] As reported in the Chinese Pharmacopoeia, three species of Rhizoma Curcumae (Curcuma phaeocaulis Valeton, Curcuma kwangsiensis S. G. Lee et C. F. Liang, and Curcuma wenyujin Y. H. Chen et C. Ling) are officially approved as Chinese medicine.…”