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Vol. 26 No. 12 (2014): Vol 26 Issue 12

Copyright (c) 2014 AJC

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Biotransformation of Neoandrographolide by Endophytic Fungus from Dendrobium officinale Kimura et Migo

https://doi.org/10.14233/ajchem.2014.15936
Jie-Hua Wang
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Zheng-Tao Wang
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Li-Li Wang
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Zhe-Jian Wang
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Zhao Ma
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Gui-Xin Chou
The MOE Key Laboratory for Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Zhi-Bi Hu
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China
Wan-Kui Li
The SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201210, P.R. China

Corresponding Author(s) : Wan-Kui Li

bio5210@126.com

Asian Journal of Chemistry, Vol. 26 No. 12 (2014): Vol 26 Issue 12

Abstract

Neoandrographolide is one of the principal constituents of ent-labdane diterpenoid lactones isolated from the aerial parts of the traditional herbal medicine Andrographis paniculata (Burm. F.) Nees. To obtain more types of diterpenoid derivatives and acquire compounds with better activities than the substrate, we used endophytic fungi to transform neoandrographolide for the first time. An endophytic fungus, namely, 2T12J01A, which was identified as Fusarium oxysporum based on 18S ribosomal DNA and the inte DNAl transcribed spacer of ribosomal DNA, was used to transform neoandrographolide and obtain four compounds: (2) isoneoandrographolide, (3) 14-deoxyandrographolide, (4) 8a,17b-epoxy-3,14-dideoxyandrographolide and (5) andrograpanin. The structural elucidation of compounds was achieved mainly by 1H- and 13C-nuclear magnetic resonance (NMR), distortionless enhancement by polarization transfer (DEPT), heteronuclear singular quantum correlation (HSQC), 1H detected heteronuclear multiple quantum coherence (HMQC), nuclear overhauser spectroscopy and high-resolution electrospray ionization mass spectrometry experiments. Finally, the proposed biosynthetic pathways of neoandrographolide by 2T12J01A were established.

Keywords

Biotransformation Neoandrographolide Endophytic fungus Fusarium oxysporum
Wang, J.-H., Wang, Z.-T., Wang, L.-L., Wang, Z.-J., Ma, Z., Chou, G.-X., … Li, W.-K. (2014). Biotransformation of Neoandrographolide by Endophytic Fungus from Dendrobium officinale Kimura et Migo. Asian Journal of Chemistry, 26(12), 3457–3460. https://doi.org/10.14233/ajchem.2014.15936
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