Abstract
Seven hydroxylates of 20(S)-protopanaxatriol (1) transformed by Absidia corymbifera AS 3.3387 were isolated and identified by spectral methods including 2D-NMR. Among them, 7β-hydroxyl-20(S)-protopanaxatriol (2), 7α-hydroxyl-20(S)-protopanaxatriol (3), and 7β, 15α-dihydroxyl-20(S)-protopanaxatriol (7) are new compounds. The metabolites 2, 6, 7, and 8 showed the more potent inhibitory effects against DU-145 and PC-3 cell lines than the substrate.
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References
Chen GT, Yang M, Lu ZQ et al (2007) Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea. J Nat Prod 70:1203–1206
Chen GT, Yang M, Song Y et al (2008) Microbial transformation of ginsenoside Rb1 by Acremonium strictum. Appl Microbiol Biotechnol 77:1345–1350
Chi H, Ji GE (2005) Transformation of ginsenosides Rb1 and Re from Panax ginseng by food microorganisms. Biotechnol Lett 27:765–771
Hasegawa H, Suzuki R, Nagaoka T, Tezuka Y, Kadota S, Saiki I (2002) Prevention of growth and metastasis of murine melanoma through enhanced natural-killer cytotoxicity by fatty acid-conjugate of protopanaxatriol. Biol Pharm Bull 25:861–866
Ma HY, Gao HY, Huang J, Sun BH, Yang B (2012) Three new triterpenoids from Panax ginseng exhibit cytotoxicity against human A549 and Hep-3B cell lines. J Nat Med. doi:10.1007/s11418-012-0662-y
Mao SH, Hu XJ, Hua BY, Wang N, Liu XG, Lu FP (2012) 15a-Hydroxylation of a steroid (13-ethyl-gon-4-en-3,17-dione) by Penicillium raistrickii in an ionic liquid/aqueous biphasic system. Biotechnol Lett. doi:10.1007/s10529-012-1016-2
Oh GS, Pae HO, Choi BM et al (2004) 20(S)-Protopanaxatriol, one of ginsenoside metabolites, inhibits inducible nitric oxide synthase and cyclooxygenase-2 expressions through inactivation of nuclear factor-κB in RAW 264.7 macrophages stimulated with lipopolysaccharide. Cancer Lett 205:23–29
Popovich DG, Kitts DD (2002) Structure–function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line. Arch Biochem Biophys 406:1–8
Popovich DG, Kitts DD (2004) Mechanistic studies on protopanaxadiol, Rh2, and ginseng (Panax quinquefolius) extract induced cytotoxicity in intestinal Caco-2 cells. J Biochem Mol Toxicol 18:143–149
Sargent JM, Taylor CG (1989) Appraisal of the MTT assay as a rapid test of chemosensitivity in acute myeloid-leukemia. Br J Cancer 60:206–210
Tian Y, Guo HZ, Han J, Guo DA (2005) Microbial transformation of 20(S)-protopanaxatriol by Mucor spinosus. J Nat Prod 68:678–680
Zhang J, Guo HZ, Tian Y, Liu P, Li N, Zhuo JP, Guo DA (2007) Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products. Phytochemistry 68:2523–2530
Acknowledgments
We thank National Natural Science Foundation of China (No. 81102327) and A project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) for financial support.
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Chen, G., Yang, X., Zhai, X. et al. Microbial transformation of 20(S)-protopanaxatriol by Absidia corymbifera and their cytotoxic activities against two human prostate cancer cell lines. Biotechnol Lett 35, 91–95 (2013). https://doi.org/10.1007/s10529-012-1053-x
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DOI: https://doi.org/10.1007/s10529-012-1053-x