Microbial transformation of 20(S)-protopanaxatriol by Mucor spinosus

详细信息    查看全文

• 作者：Xue Yang ; Hongjuan Ge ; Yan Song ; Jianlin Li ; Guangtong Chen
• 关键词：Biocatalysis ; Biotransformation ; Cytotoxic activity ; Dehydrogenation ; Ginsenosides ; Hydroxylation Mucor spinosus ; 20(S) ; Protopanaxatriol
• 刊名：Biotechnology Letters
• 出版年：2015
• 出版时间：February 2015
• 年：2015
• 卷：37
• 期：2
• 页码：397-402
• 全文大小：234 KB
• 参考文献：1. Antonio M, Francisco R, Alberto P et al (2013) Biotransformation of oleanolic and maslinic acids by / Rhizomucor miehei. Phytochemistry 94:229-37 get="_blank" title="It opens in new window">CrossRef
  2. Arifin AA, Don MM, Uzir MH et al (2011) Baker’s yeast mediated biotransformation of geraniol into citronellol using a continuous-closed-gas-loop bioreactor (CCGLB) system. Biochem Eng J 56:219-24 get="_blank" title="It opens in new window">CrossRef
  3. Chen GT, Yang M, Song Y et al (2008) Microbial transformation of ginsenoside Rb₁ by / Acremonium strictum. Appl Microbiol Biotechnol 77:1345-350 get="_blank" title="It opens in new window">CrossRef
  4. Chen GT, Yang X, Li JL et al (2013a) Biotransformation of 20( / S)-protopanaxadiol by / Aspergillus niger AS 3.1858. Fitoterapia 91:256-60 get="_blank" title="It opens in new window">CrossRef
  5. Chen GT, Yang X, Nong SJ et al (2013b) Two novel hydroperoxylated products of 20( / S)- protopanaxadiol produced by / Mucor racemosus and their cytotoxic activities against human prostate cancer cells. Biotechnol Lett 35:439-43 get="_blank" title="It opens in new window">CrossRef
  6. Gao HW, Zhang MM, Liu YL et al (2013) Anticomplement activity of ginsenosides from / Panax ginseng. J Funct Foods 5:498-02 get="_blank" title="It opens in new window">CrossRef
  7. He CY, Zhou DD, Ji Li et al (2014) Identification of 20( / S)-protopanaxatriol metabolites in rats by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry and nuclear magnetic resonance spectroscopy. J Pharm Biomed 88:497-08 get="_blank" title="It opens in new window">CrossRef
  8. Lv X, Liu D, Hou J et al (2013) Biotransformation of imperatorin by / Penicillium janthinellum. Anti-osteoporosis activities of its metabolites. Food Chem 138:2260-266 get="_blank" title="It opens in new window">CrossRef
  9. 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 70:2017-022 get="_blank" title="It opens in new window">CrossRef
  10. 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- get="_blank" title="It opens in new window">CrossRef
  11. 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 18:143-49 get="_blank" title="It opens in new window">CrossRef
  12. Qi LW, Wang CZ, Yuan CS et al (2011) Ginsenosides from American ginseng: chemical and pharmacological diversity. Phytochemistry 72:689-99 get="_blank" title="It opens in new window">CrossRef
  13. Tian Y, Guo HZ, Han J et al (2005) Microbial transformation of 20( / S)-protopanaxatriol by / Mucor spinosus. J Nat Prod 68:678-80 get="_blank" title="It opens in new window">CrossRef
  14. Wang Y, Sun Y, Wang C et al (2013) Biotransformation of 11-keto-β-boswellic acid by / Cunninghamella blakesleana. Phytochemistry 96:330-36 get="_blank" title="It opens in new window">CrossRef
  15. Zhang J, Guo HZ, Tian Y et al (2009) Biotransformation of 20( / S)-protopanaxatriol by / Mucor spinosus and the cytotoxic structure activity relationships of the transformed products. Phytochemistry 68:2523-530 get="_blank" title="It opens in new window">CrossRef
  
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Life Sciences
  Microbiology
  Biotechnology
  Applied Microbiology
  Biochemistry
  
• 出版者：Springer Netherlands
• ISSN：1573-6776

文摘

Microbial transformation of 20(S)-protopanaxatriol (1) by Mucor spinosus afforded two new and eight known metabolites. The structures of the metabolites were identified as 12-oxo-20(S)-protopanaxatriol (2), 23,24-en-25-methoxyl-20(S)-protopanaxatriol (3), 29-hydroxyl-20(S)-protopanaxatriol (4), 20(S),24(S)-epoxy-dammaran-3β,6α,12β,25-triol (5), 12-oxo-27-hydroxyl-20(S)-protopanaxatriol (6), 12-oxo-26-hydroxyl-20(S)-protopanaxatriol (7), 12-oxo-23β-hydroxyl-20(S)-protopanaxatriol (8), 12-oxo-11β-hydroxyl-20(S)-protopanaxatriol (9), 12-oxo-15α-hydroxyl-20(S)-protopanaxatriol (10), and 12-oxo-25,26-en-15α-hydroxyl-20(S)-protopanaxatriol (11). Among them, 3 and 11 are new compounds. The metabolites 3, 10 and 11 showed the more potent inhibitory effects against seven cell lines than the substrate.