Natural Products and Bioprospecting    2012, Vol. 2 Issue (5) : 222-226     DOI: 10.1007/s13659-012-0059-3
Short Communication |
Two new tirucallane triterpenoids from Aphanamixis grandifolia
Xiao-Ying WANGa,b, Gui-Hua TANGa, Chun-Mao YUANa, Yu ZHANGa, Li HOUa,b, Qing ZHAOb, Xiao-Jiang HAOa, Hong-Ping HEa
a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Faculty of Pharmacy, Yunnan University of TCM, Kunming 650500, China
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Abstract  Two new tirucallane triterpenoids, 2α-ethoxy-2, 3-secotirucalla-2, 29-epoxy-7-ene-23-oxo-3-oic acid(1) and(23E)-2α-hydroxytirucalla-7, 23, 25-triene-3-one(2), along with the known 2, 3-secotirucalla-2, 3; 2, 29-diepoxy-7-ene-3, 23-dione(3), were isolated from the leaves and twigs of Aphanamixis grandifolia. Their structures were elucidated by extensive NMR and MS data, and compound 3 was further confirmed by X-ray crystal diffraction analysis. Antimicrobial activities and insecticidal activities of these three compounds were also evaluated. Compound 1 showed good antimicrobial activity against Staphylococcus aureus with the MIC value of 1.56 μg/mL, while compounds 1 and 2 showed insecticidal activity at 100 ppm, with the corrected mortality 79.1% and 60.6%, respectively.
Keywords Aphanamixis grandifolia      Meliaceae      2,3-seco-tirucallane triterpenoid      bioassays     
Fund:This work was financially supported by grants from the National Basic Research Program of China(973 Program, 2009CB522300 and 2009CB940900), National Natural Science Funding of China(31170332), and the Young Academic and Technical Leader Raising Foundation of Yunnan Province(2010CI047).
Issue Date: 11 February 2018
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Xiao-Ying WANG
Gui-Hua TANG
Chun-Mao YUAN
Yu ZHANG
Li HOU
Qing ZHAO
Xiao-Jiang HAO
Hong-Ping HE
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Xiao-Ying WANG,Gui-Hua TANG,Chun-Mao YUAN, et al. Two new tirucallane triterpenoids from Aphanamixis grandifolia[J]. Natural Products and Bioprospecting, 2012, 2(5): 222-226.
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http://npb.kib.ac.cn/EN/10.1007/s13659-012-0059-3     OR     http://npb.kib.ac.cn/EN/Y2012/V2/I5/222
[1] (a) Fang, X.; Di, Y. T.; Hao, X. J. Curr. Org. Chem. 2011, 15, 1363-1391. (b) Tan, Q. G.; Luo, X. D. Chem. Rev. 2011, 111, 7437-7522.
[2] Chen, S. K.; Li, H.; Chen, P. Y. Flora of China; Science Press:Beijing, 1997; Vol. 43, Chapter 3, pp 75-80.
[3] (a) Zhang, Y.; Wang, J. S.; Luo, J.; Kong, L. Y. Chem. Pharm. Bull. 2011, 59, 282-286. (b) Liu, Q. A.; Chen, C. J.; Shi, X. A.; Zhang, L.; Chen, H. J.; Gao, K. Chem. Pharm. Bull. 2010, 58, 1431-1435. (c) Wang, J. S.; Zhang, Y.; Wang, X. B.; Wei, D. D.; Luo, J.; Luo, J. G.; Yang, M. H.; Yao, H. Q.; Sun, H. B.; Kong, L. Y. Tetrahedron Lett. 2012, 53, 1705-1709. (d) Kundu, A. B.; Ray, S.; Chatterjee, A. Phytochemistry 1985, 24, 2123-2125.
[4] (a) Yang, S. P.; Chen, H. D.; Liao, S. G.; Xie, B. J.; Miao, Z. H.; Yue, J. M. Org. Lett. 2011, 13, 150-153. (b) Zhang, Y.; Wang, J. S.; Wang, X. B.; Wei, D. D.; Luo, J. G.; Luo, J.; Yang, M. H.; Kong, L. Y. Tetrahedron Lett. 2011, 52, 2590-2593. (c) Tong, L.; Zhang, Y.; He, H. P.; Hao, X. J. Chin. J. Chem. 2012, 30, 1261-1264. (d) Cai, J. Y.; Zhang, Y.; Luo, S. H.; Chen, D. Z.; Tang, G. H.; Yuan, C. M.; Di, Y. T.; Li, S. H.; Hao, X. J.; He, H. P. Org. Lett. 2012, 14, 2524-2527.
[5] Sadhu, S. K.; Phattanawasin, P.; Choudhuri, M. S. K.; Ohtsuki, T.; Ishibashi, M. J. Nat. Med. 2006, 60, 258-260.
[6] Harmon, A. D.; Weiss, U.; Silverton, J. V. Tetrahedron Lett. 1979, 8, 721-724.
[7] (a) Yin, J. L.; Di, Y. T.; Fang, X.; Liu, E. D.; Liu, H. Y.; He, H. P.; Li, S. L.; Li, S. F.; Hao, X. J. Tetrahedron Lett. 2011, 52, 3083-3085. (b) Fang, X.; Di, Y. T.; He, H. P.; Liu, H. Y.; Zhang, Z.; Ren, Y. L.; Gao, Z. L.; Gao, S.; Hao, X. J. Org. Lett. 2008, 10, 1905-1908. (c) Yang, W.; Kong, L. M.; Li, S. F.; Li, Y.; Zhang, Y.; He, H. P.; Hao, X. J. Nat. Prod. Bioprospect. 2012, 2, 145-149. (d) Liu, W. X.; Tang, G. H.; He, H. P.; Zhang, Y.; Li, S. L.; Hao, X. J. Nat. Prod. Bioprospect. 2012, 2, 29-34.
[8] Zeng, Q.; Guan, B.; Qin, J. J.; Wang, C. H.; Cheng, X. R.; Ren, J.; Yan, S. K.; Jin, H. Z.; Zhang, W. D. Phytochemistry 2012, 80, 148-155.
[9] Luo, X. D.; Wu, S. H.; Ma, Y. B.; Wu, D. G. Phytochemistry 2000, 54, 801-805.
[10] Solis, P. N.; Wright, C. W.; Anderson, M. M.; Gupta, M. P.; Phillipson, J. D. Planta Med. 1993, 59, 250-252.
[11] X-ray crystallographic analysis of 3:a colorless cylinder crystal (in Acetone-H2O), C30H46O4, MW=470.7. All measurements were made on a Bruker APEX DUO detector employing graphite monochromated Cu Ka radiation λ=1.54178Å at 100 K, and operating in the Ф/σ scan mode. Space group P 21 with a=8.2806(13) Å, b=10.4107(17) Å, c=15.285(3) Å, α=γ=90°, β=99.515(8)°. Crystal dimensions 0.28×0.07×0.07 mm, V=1299.6(4) Å, Z=2, dx=1.203 mg/m3, F (000)=516. The structure was solved by direct methods using Shelxs97 and fullmatrix least-squares calculations. The total number of independent reflections measured was 3980, of which 3823 were observed. Final indices (|F|2 ≥ 2σ|F|2):And the final agreement factors were R1=0.0712, ω R2=0.1961(w=1/σ|F|2), S=1.092, Flack x=σ 0.7(4). The crystallographic data for 3 has been deposited at the Cambridge Crystallographic Data Centre with the deposition number CCDC 895143. These data can be obtained free of charge from the Cambridge Crystallographic Data centre via https://www.ccdc.cam.ac.uk/services/structure_deposit/
[12] Xu, S. Y.; Bian, R. L.; Chen, X. Pharmacological Experiment Methodology, 3rd ed; People's Medical Publishing House:Beijing, 2002, pp 1647-1719.
[13] Tang, G. H.; Zhang, Y.; Gu, Y. C.; Li, S. F.; Di, Y. T.; Wang, Y. H.; Yang, C. X.; Zuo, G. Y.; Li, S. L.; He, H. P.; Hao, X. J. J. Nat. Prod. 2012, 75, 996-1000.
[14] Michael, A. S.; Thompson, C. G. Abramovitz, M. Science. 1956, 123, 464.
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