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Appl Microbiol Biotechnol. 2017 Jun 5. doi: 10.1007/s00253-017-8351-0. [Epub ahead of print]
New cryptotanshinone derivatives with anti-influenza A virus activities obtained via biotransformation by Mucor rouxii.
He W1,2, Li Y1,3, Qin Y1, Tong X1, Song Z1,3, Zhao Y1,3, Wei R1, Li L4, Dai H1, Wang W5, Luo H6, Ye X1, Zhang L7,8, Liu X9.
Author information
Abstract
This paper provides an efficient platform to diversify the structure and pharmaceutical potentials of known natural products. Seven metabolites were obtained via the biotransformation of cryptotanshinone by the fungus Mucor rouxii AS 3.3447, and assigned as 13R-14R-hydroxy-anhydride of 16R-cryptotanshinone (1), 1S-hydroxy-anhydride of 16R-cryptotanshinone (2), 1R-hydroxy-anhydride of 16R-cryptotanshinone (3), 3S-hydroxy-epicryptoacetalide (4), 3S-hydroxy-cryptoacetalide (5), epicryptoacetalide (6), and cryptoacetalide (7). Among these compounds, 1-5 are novel. The ortho-naphthoquinone chromophore of cryptotanshinone was degraded and rearranged by M. rouxii. 1 and 3 showed good anti-influenza A virus activities with the reduced cytotoxic activities compared to the parent substrate cryptotanshinone (8). The structures of all the new compounds were determined on the basis of HRESIMS (high-resolution electrospray ionization mass spectroscopy) spectrometry, NMR (nuclear magnetic resonance) spectroscopy, ECD (electronic circular dichroism) calculations, and the CD (circular dichroism) of "in situ" method with [Rh2(OCOCF3)4].
KEYWORDS:
Anti-influenza A virus activity; Biotransformation; Cryptotanshinone; Mucor rouxii
PMID: 28584912 DOI: 10.1007/s00253-017-8351-0
New cryptotanshinone derivatives with anti-influenza A virus activities obtained via biotransformation by Mucor rouxii.
He W1,2, Li Y1,3, Qin Y1, Tong X1, Song Z1,3, Zhao Y1,3, Wei R1, Li L4, Dai H1, Wang W5, Luo H6, Ye X1, Zhang L7,8, Liu X9.
Author information
Abstract
This paper provides an efficient platform to diversify the structure and pharmaceutical potentials of known natural products. Seven metabolites were obtained via the biotransformation of cryptotanshinone by the fungus Mucor rouxii AS 3.3447, and assigned as 13R-14R-hydroxy-anhydride of 16R-cryptotanshinone (1), 1S-hydroxy-anhydride of 16R-cryptotanshinone (2), 1R-hydroxy-anhydride of 16R-cryptotanshinone (3), 3S-hydroxy-epicryptoacetalide (4), 3S-hydroxy-cryptoacetalide (5), epicryptoacetalide (6), and cryptoacetalide (7). Among these compounds, 1-5 are novel. The ortho-naphthoquinone chromophore of cryptotanshinone was degraded and rearranged by M. rouxii. 1 and 3 showed good anti-influenza A virus activities with the reduced cytotoxic activities compared to the parent substrate cryptotanshinone (8). The structures of all the new compounds were determined on the basis of HRESIMS (high-resolution electrospray ionization mass spectroscopy) spectrometry, NMR (nuclear magnetic resonance) spectroscopy, ECD (electronic circular dichroism) calculations, and the CD (circular dichroism) of "in situ" method with [Rh2(OCOCF3)4].
KEYWORDS:
Anti-influenza A virus activity; Biotransformation; Cryptotanshinone; Mucor rouxii
PMID: 28584912 DOI: 10.1007/s00253-017-8351-0