|
|
Two new diterpenoids from the endophytic fungus Trichoderma sp. Xy24 isolated from mangrove plant Xylocarpus granatum |
Min Zhang, Ji-Mei Liu, Jin-Lian Zhao, Ning Li, Ri-Dao Chen, Ke-Bo Xie, Wen-Jing Zhang, Ke-Ping Feng, Zheng Yan, Nan Wang, Jun-Gui Dai |
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China |
|
|
Abstract Two new harziane diterpenoids, named (9R,10R)-dihydro-harzianone (1) and harzianelactone (2), were isolated from the endophytic fungus Trichoderma sp. Xy24 by using various column chromatography techniques. Their structures were determined on the basis of extensive spectroscopic (HR-ESI-MS, 1D NMR, 2D NMR and CD) analyses. Among them, 1 was the reductive product of harzianone and 2 was the Baeyer-Villiger monooxygenase catalyzed oxidation product of harzianone. Compound 1 exhibited cytotoxic activity against HeLa and MCF-7 cell lines with IC50 values of 30.1 mmol/L and 30.7 mmol/L, respectively.
|
Received: 11 December 2015
Published: 02 March 2016
|
Fund:Thisworkwas financially supported by the Science & Technology Project of Guangdong Province (No. 2011A080403020). |
Corresponding Authors:
Jun-Gui Dai
E-mail: jgdai@imm.ac.cn
|
|
|
|
[1] |
G.E. Harman, C.R. Howell, A. Viterbo, I. Chet, M. Lorito, Trichoderma species— opportunistic, avirulent plant symbionts, Nat. Rev. Microbiol. 2 (2004) 43-56.
|
[2] |
J.L. Reino, R.F. Guerrero, R. Hernández-Galá n, I.G. Collado, Secondary metabolites from species of the biocontrol agent Trichoderma, Phytochem. Rev. 7 (2008) 89-123.
|
[3] |
C. Keswani, S. Mishra, B.K. Sarma, S.P. Singh, H.B. Singh, Unraveling the efficient applications of secondary metabolites of various Trichoderma spp., Appl. Microbiol. Biotechnol. 98 (2014) 533-544.
|
[4] |
M. Zhang, N. Li, R.D. Chen, et al., Two terpenoids and a polyketide from the endophytic fungus Trichoderma sp. Xy24 isolated from mangrove plant Xylocarpus granatum, J. Chin. Pharm. Sci. 23 (2014) 421-424.
|
[5] |
F.P. Miao, X.R. Liang, X.L. Yin, G. Wang, N.Y. Ji, Absolute configurations of unique harziane diterpenes from Trichoderma species, Org. Lett. 14 (2012) 3815-3817.
|
[6] |
E.L. Ghisalberti, D.C.R. Hockless, C. Rowland, A.H. White, Harziandione, a new class of diterpene from Trichoderma harzianum, J. Nat. Prod. 55 (1992) 1690-1694.
|
[7] |
E. Adelin, C. Servy, M.T. Martin, et al., Bicyclic and tetracyclic diterpenes from a Trichoderma symbiont of Taxus baccata, Phytochemistry 97 (2014) 55-61.
|
[8] |
Z.L. Xie, H.J. Li, L.Y. Wang, et al., Trichodermaerin, a new diterpenoid lactone from the marine fungus Trichoderma erinaceum associated with the sea star Acanthaster planci, Nat. Prod. Commun. 8 (2013) 67-68.
|
[9] |
N. Li, F.Y. Ruan, Z.S. Wen, et al., Diversity and in vitro antitumor activity of endophytic fungi from mangrove plants Xylocarpus, Chin. J. Chin. Mater. Med. 38 (2013) 2282-2286.
|
[10] |
W. Moffitt, R.B. Woodward, A. Moscowitz, W.T. Klyne, C. Djerassi, Structure and the optical rotatory dispersion of saturated ketones, J. Am. Chem. Soc. 83 (1961) 4013-4018.
|
[11] |
A. Hassner, L.R. Krepski, Cycloadditions. 26. Regio-and stereochemistry of the cycloadditions of dichloroketene to 2-methyl-and 3-methyl-2-cholestene, J. Org. Chem. 44 (1979) 1376-1379.
|
[12] |
T. Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 65 (1983) 55-63.
|
[13] |
J. Carmichael, W.G. Degraff, A.F. Gazdar, J.D. Minna, J.B. Mitchell, Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing, Cancer Res. 47 (1987) 936-943.
|
|
|
|