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Benzopyranone and cytotoxic constituents from the root of Antidesma japonicum
Antidesma japonicum Sieb. & Zucc. (Euphorbiaceae) is an evergreen shrub distributed in the northern and central parts of Taiwan, Japan, the Ryukyus, and southern China . The chemical constituents and biological activities of this species have never been studied. In a screening program of Formosan plants, the MeOH extract of the root of this plant showed significant cytotoxic activity and was partitioned into EtOAc, n-BuOH and H2O-soluble layers. Investigation of the active EtOAc-soluble layer led to the isolation of a new benzopyranone, antidesmanone A, along with 17 known compounds, including a benzopyranone: 5,7-dihydroxy-2-heneicosyl-chromone; 2 phenylalkanoids: corylifolin, vanillic acid; 1 coumarin: 3-(1,1-dimethylallyl)-scopoletin; 2 lignans: (–)-syringaresinol, (–)-(2R,3R)-1,4-O-diferuloylsecoisolariciresinol; 2 alkaloids: antidesmone, N-trans-feruloyltyramine; 3 flavans: epicatechin, catechin, gallocatechin; 2 triterpenoids: β-amyrin, betulinic acid, and 4 steroids: β-sitosterol, stigmasterol, β-sitosteryl 3-O-β-D-glucopyranoside, stigmasteryl 3-O-β-D-glucopyranoside. (–)-(2R,3R)-1,4-O-Diferuloylsecoisolariciresinol showed cytotoxicity against four colon cancer cell lines, HT-29, CT-26, Colo 205 and HCT-25, with IC50 values of 7.02, 9.62, 10.11 and 12.25µM, respectively.
Acknowledgements: This work was kindly supported by a grant (NSC 97–2320-B-039–025) from the National Science Council of the Republic of China.
References: 1. Hsieh, C.F., Chaw, S.M., Wang, J.C. (1996) Euphorbiaceae in Flora of Taiwan, 2nd edition. Editorial Committee of the Flora of Taiwan, Taipei, Taiwan: Vol. 3: 414–504.