Two new compounds, (+)-rumphiin (3) and polyalthurea (7), together with seven known ones, 3,4,5-trimethoxy benzoic acid (1), (-)-seselinone (2), cannabisin D (4), allantoin (5), oxostephanine (6) and a mixture of β-sitosterol (8) and stigmasterol (9) were isolated from the stems of Polyalthia rumphii. The chemical structures of 3 and 7 were elucidated by the combination of spectroscopic data, and the absolute configuration of 3 at C-2 was determined by the matrix method to be R. All compounds were evaluated for their cytotoxicity on four human cancer cell lines, which demonstrated that 3 was a moderate bioactive lignan, and 6 showed significant anticancer activity against SPC-A-1 and BEL-7402 cell lines with IC50 values of 1.47 and 1.73 μg/mL, respectively.
WuZ.Y. (2011) Flora of China, Vol. 19, Science Press, Peking, p 696.
2.
LuZ.M., ZhangQ.J., ChenR.Y., YuD.Q. (2011) Study on chemical constituents from branches and leaves of Polyalthia nemoralis. China Journal of Chinese Material Medica, 136, 1024–1027; (b) Yuan Y, Huang GJ, Wang TS, Chen GY. (2011) In vitro screening of five Hainan plants of Polyalthia (Annonaceae) against human cancer cell lines with MTT assay. Journal of Medicinal Plant Research, 5, 837–841; (c) Prayong P, Barusrux S, Weerapreeyakul N. (2008) Cytotoxic activity screening of some indigenous Thai plants. Fitoterapia, 79, 598–601.
3.
WangT.S., YuanY., WangJ., HanC.R., ChenG.Y. (2012) Anticancer activities of constituents from the stem of Polyalthia rumphii. Pakistan Journal of Pharmaceutical Science, 25, 353–356.
4.
ChenC.Y., ChangF.R., WuY.C. (1997) The constituents from the stems of Annona cherimola. Journal of the Chinese Chemical Society, 44, 313–319; (b) Chang FR, Chen CY, Wu PH, Kuo RY, Chang YC, Wu YC. (2000) New alkaloids from Annona purpurea. Journal of Natural Products, 63, 746–748.
5.
SDBS No. 6709HSP-01–346 (http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng); (b) VučkovićI., TrajkovićV., MacuraS., TeševićV., JanaćkovićP., MilosavljevićS. (2007) A novel cytotoxic lignan from Seseli annuum L. Phytotherapy Research, 21, 790–792; (c) Sakakibara I, Ikeya Y, Hayashi K, Mitruhashi H. (1992) Three phenyldihydronaphthalene lignanamides from fruits of Cannabis sativa. Phytochemistry, 31, 3219–3223; (d) Zhu XD, Ju P, Wang YF, Wang Q, Luo SD. (2006) Chemical study on Pseuderanthemum latifolim (Vahl) B. Hansen. Natural Products Research & Development, 18, 951–953; (e) Fujita S, Ninomiya M, Efdi M, Ohguchi K, Nozawa Y, Koketsu M. (2010) Isolation of chemical constituents from Enicosanthum cupulare (King) Airy-Shaw. Natural Products Research, 24, 1630–1636; (f) Kongduang D, Wungsintaweekul J, De-Eknamkul W. (2008) Biosynthesis of β-sitosterol and stigmasterol proceeds exclusively via the mevalonate pathway in cell suspension cultures of Croton stellatopilosus. Tetrahedron Letters, 49, 4067–4072.
6.
ZhuH.J., RenJ., PittmanC.U.Jr.. (2007) Matrix model to predict specific optical rotations of acyclic chiral molecules, Tetrahedron, 63, 2292–2314; (b) Liao TG, Ren J, Fan HF, Xie MJ, Zhu HJ. (2008) Study of syntheses and specific rotations of (S)–3-phenylhexan-3-ol and its derivatives, Tetrahedron: Asymmetry, 19, 808–815; (c) Zhou ZY, Shi GQ, Fontaine R, Wei K, Feng T, Wang F, Wang GQ, Qu Y, Li ZH, Dong ZJ, Zhu HJ, Yang ZL, Zeng G, Liu JK. (2012) Evidence for the natural toxins from the mushroom Trogia venenata as a cause of sudden unexpected death in Yunnan Province, China. Angewandte Chemie International Edition in English, 51, 2368–2370; (d) Tong XG, Wu GS, Huang CG, Lu Q, Wang YH, Long CL, Luo HR, Zhu HJ, Cheng YX. (2010) Compounds from Acorus tatarinowii: Determination of absolute configuration by quantum computations and cAMP regulation activity. Journal of Natural Products, 73, 1160–1163.
7.
WangL., ChenG.Y., HanC.R., YuanY., YangB., ZhangY., WangJ., ZhongX.Q., HuangX. (2011) Two novel alkaloids from the stem of Saprosma hainanense and their cytotoxic activities in vitro. Chemical and Pharmaceutical Bulletin, 59, 338–340.