Abstract
Microbial transformation of 20(S)-protopanaxadiol (1) by Mucor racemosus AS 3.205 yielded two novel hydroperoxylated metabolites and three known hydroxylated metabolites. The structures of the metabolites were identified as 26-hydroxyl-20(S)-protopanaxadiol (2), 23,24-en-25-hydroxyl-20(S)-protopanaxadiol (3), 25,26-en-24(R)-hydroperoxyl-20(S)-protopanaxadiol (4), 23,24-en-25-hydroperoxyl-20(S)-protopanaxadiol (5), and 25-hydroxyl-20(S)-protopanaxadiol (6). 4 and 5 are new compounds. Metabolites 2, 4, and 5 showed the more potent inhibitory effects against DU-145 and PC-3 cell lines than the substrate.
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References
Asai T, Hara N, Fujimoto Y (2010) Fatty acid derivatives and dammarane triterpenes from the glandular trichome exudates of Ibicella lutea and Proboscidea louisiana. Phytochemistry 71:877–894
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
Cui JF, Eneroth P, Beuhn JG, Arihara S, Yoshikawa K (1998) Alkaline cleavage of gypenosides and characterization of dammarane-type aglycones by gas chromatography-mass spectrometry. Phytochem Anal 9(3):128–133
Homhual S, Bunyapraphatsara N, Kondratyuk T et al (2006) Bioactive dammarane triterpenes from mangrove plant Bruguiera gymnorrhiza. J Nat Prod 69:421–424
Hung TM, Hoang DM, Kim JC, Jang HS, Ahn JS, Min BS (2009) Protein tyrosine phosphatase 1B inhibitory by dammaranes from Vietnamese Giao-Co-Lam tea. J Ethnopharmacol 124:240–245
Mao SH, Hu XJ, Hua BY, Wang N, Liu XG, Lu FP (2012) 15α-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
Marquina S, Parra JL, González M et al (2009) Hydroxylation of the diterpenes ent-kaur-16-en-19-oic and ent-beyer-15-en-19-oic acids by the fungus Aspergillus niger. Phytochemistry 70:2017–2022
Pakhathirathien C, Karalai C, Ponglimanont C, Subhadhiraskul S, Chantrapromma K (2005) Dammarane triterpenes from hypocotyls and fruits of Ceriops tagal. J Nat Prod 68:1787–1789
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
Saklani A, Kutty SK (2008) Plant-derived compounds in clinical trials. Drug Disc Today 13:161–171
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
Zhao YQ, Wu CF, Zhang RW et al (2008) Preparation and application of two protopanaxadiol derivatives. Faming Zhuangli Shenqing Gongkai Shuomingshu 7
Acknowledgments
This work was financially supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (10KJB350003), National Natural Science Foundation of China (No. 81102327), and A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
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Chen, G., Yang, X., Nong, S. et al. Two novel hydroperoxylated products of 20(S)-protopanaxadiol produced by Mucor racemosus and their cytotoxic activities against human prostate cancer cells. Biotechnol Lett 35, 439–443 (2013). https://doi.org/10.1007/s10529-012-1098-x
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DOI: https://doi.org/10.1007/s10529-012-1098-x