Biotransformation of Ganoderic Acid A to 3-O-Acetyl Ganoderic Acid A by Soil-isolated Streptomyces sp.
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Microorganisms and Chemicals
3.2. Screening and Identifying Soil Bacteria with Biotransformation Activity
3.3. UPLC Analysis
3.4. Candidate Strain Classification Via 16S rRNA Gene Analysis
3.5. Scaled-Up Fermentation, Isolation, and Identification of the Biotransformation Products
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
- Wu, J.W.; Zhao, W.; Zhong, J.J. Biotechnological production and application of ganoderic acids. Appl. Microbiol. Biotechnol. 2010, 87, 457–466. [Google Scholar]
- Xia, Q.; Zhang, H.; Sun, X.; Zhao, H.; Wu, L.; Zhu, D.; Yang, G.; Shao, Y.; Zhang, X.; Mao, X.; et al. A comprehensive review of the structure elucidation and biological activity of triterpenoids from Ganoderma spp. Molecules 2014, 19, 17478–17535. [Google Scholar] [CrossRef]
- Kubota, T.; Asaka, Y. Structures of ganoderic acid A and B, two new lanostane type bitter triterpenes from Ganoderma lucidum (FR.) Karst. Helv. Chim. Acta 1982, 65, 611–619. [Google Scholar] [CrossRef]
- Wang, X.L.; Ding, Z.Y.; Liu, G.Q.; Yang, H.; Zhou, G.Y. Improved production and antitumor properties of triterpene acids from submerged culture of Ganoderma lingzhi. Molecules 2016, 21, 1395. [Google Scholar] [CrossRef] [PubMed]
- Jiang, J.; Grieb, B.; Thyagarajan, A.; Sliva, D. Ganoderic acids suppress growth and invasive behavior of breast cancer cells by modulating AP-1 and NF-κB signaling. Int. J. Mol. Med. 2008, 21, 577–584. [Google Scholar] [CrossRef]
- Yao, X.; Li, G.; Xu, H.; Lu, C. Inhibition of the JAK-STAT3 signaling pathway by ganoderic acid A enhances chemosensitivity of HepG2 cells to cisplatin. Planta Med. 2012, 78, 1740–1748. [Google Scholar] [CrossRef]
- Wang, X.; Sun, D.; Tai, J.; Wang, L. Ganoderic acid A inhibits proliferation and invasion, and promotes apoptosis in human hepatocellular carcinoma cells. Mol. Med. Rep. 2017, 16, 3894–3900. [Google Scholar] [CrossRef][Green Version]
- Akihisa, T.; Nakamura, Y.; Tagata, M.; Tokuba, H.; Yasukawa, K.; Uchiyama, E.; Suzukli, T.; Kimura, Y. Anti-inflammatory and anti-tumor-promoting effects of triterpene acids and sterols from the fungus Ganoderma lucidum. Chem. Biod. 2007, 4, 224–231. [Google Scholar] [CrossRef]
- Koyama, K.; Imaizumi, T.; Akiba, M.; Kinoshita, K.; Takahashi, K.; Suzuki, A.; Yano, S.; Horie, S.; Watanabe, K.; Naoi, Y. Antinociceptive components of Ganoderma lucidum. Planta Med. 1997, 63, 224–227. [Google Scholar] [CrossRef]
- Zhu, M.; Chang, Q.; Wong, L.K.; Chong, F.S.; Li, R.C. Triterpene antioxidants from Ganoderma lucidum. Phytother. Res. 1999, 13, 529–531. [Google Scholar] [CrossRef]
- Shah, S.A.A.; Tan, H.L.; Sultan, S.; Faridz, M.A.B.M.; Shah, M.A.B.M.; Nurfazilah, S.; Hussain, M. Microbial-catalyzed biotransformation of multifunctional triterpenoids derived from phytonutrients. Int. J. Mol. Sci. 2014, 15, 12027–12060. [Google Scholar] [CrossRef] [PubMed]
- Sultana, N.; Saify, Z.S. Enzymatic biotransformation of terpenes as bioactive agents. J. Enzym. Inhib. Med. Chem. 2013, 28, 1113–1128. [Google Scholar] [CrossRef] [PubMed]
- Muffler, K.; Leipold, D.; Scheller, M.C.; Haas, C.; Steingroewer, J.; Bley, T.; Neuhaus, H.E.; Mirata, M.A.; Schrader, J.; Ulber, R. Biotransformation of triterpenes. Process Biochem. 2011, 46, 1–15. [Google Scholar] [CrossRef]
- Parra, A.; Rivas, F.; Garcia-Granados, A.; Martinez, A. Microbial transformation of triterpenoids. Mini-Rev. Org. Chem. 2009, 6, 307–320. [Google Scholar] [CrossRef]
- Chang, T.S. Isolation, bioactivity, and production of ortho-hydroxydaidzein and ortho-hydroxygenistein. Int. J. Mol. Sci. 2014, 15, 5699–5716. [Google Scholar] [CrossRef] [PubMed]
- Chang, T.S.; Chiang, C.M.; Wang, T.Y.; Lee, C.H.; Lee, Y.W.; Wu, J.J. New triterpenoid from novel triterpenoid 15-O-glycosylation on ganoderic acid A by intestinal bacteria of zebrafish. Molecules 2018, 23, 2345. [Google Scholar] [CrossRef] [PubMed]
- Saitou, N.; Nei, M. The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 1987, 4, 406–425. [Google Scholar] [PubMed]
- Felsenstein, J. Confidence limits on phylogenies: An approach using the bootstrap. Evolution 1985, 39, 783–791. [Google Scholar] [CrossRef] [PubMed]
- Tamura, K.; Nei, M.; Kumar, S. Prospects for inferring very large phylogenies by using the neighbor-joining method. Proc. Natl. Acad. Sci. USA 2004, 101, 11030–11035. [Google Scholar] [CrossRef] [PubMed][Green Version]
- Tamura, K.; Kumar, S. Evolutionary distance estimation under heterogeneous substitution pattern among lineages. Mol. Biol. Evol. 2002, 19, 1727–1736. [Google Scholar] [CrossRef]
- Kumar, S.; Stecher, G.; Li, M.; Knyaz, C.; Tamura, K. MEGA X: Molecular Evolutionary Genetics Analysis across computing platforms. Mol. Biol. Evol. 2018, 35, 1547–1549. [Google Scholar] [CrossRef] [PubMed]
- Wubshet, S.G.; Johansen, K.T.; Nyberg, N.T.; Jaroszewski, J.W. Direct 13C NMR detection in HPLC hyphenation mode: Analysis of Ganoderma lucidum terpenoids. J. Nat. Prod. 2012, 75, 876–882. [Google Scholar] [CrossRef] [PubMed]
- Cao, F.R.; Feng, L.; Ye, L.H.; Wang, L.S.; Xiao, B.X.; Tao, X.; Chang, Q. Ganoderic acid A metabolites and their metabolic kinetics. Front. Pharmacol. 2017, 8, 101. [Google Scholar] [CrossRef] [PubMed]
- Chiang, C.M.; Wang, T.Y.; Ke, A.N.; Chang, T.S.; Wu, J.Y. Biotransformation of ergostane triterpenoid antcin K form Antrodia cinnamomea by soil-isolated Psychrobacillus sp. AK 1817. Catalysts 2017, 7, 299. [Google Scholar] [CrossRef]
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Chang, T.-S.; Ko, H.-H.; Wang, T.-Y.; Lee, C.-H.; Wu, J.-Y. Biotransformation of Ganoderic Acid A to 3-O-Acetyl Ganoderic Acid A by Soil-isolated Streptomyces sp. Fermentation 2018, 4, 101. https://doi.org/10.3390/fermentation4040101
Chang T-S, Ko H-H, Wang T-Y, Lee C-H, Wu J-Y. Biotransformation of Ganoderic Acid A to 3-O-Acetyl Ganoderic Acid A by Soil-isolated Streptomyces sp. Fermentation. 2018; 4(4):101. https://doi.org/10.3390/fermentation4040101
Chicago/Turabian StyleChang, Te-Sheng, Horng-Huey Ko, Tzi-Yuan Wang, Chun-Hsien Lee, and Jiumn-Yih Wu. 2018. "Biotransformation of Ganoderic Acid A to 3-O-Acetyl Ganoderic Acid A by Soil-isolated Streptomyces sp." Fermentation 4, no. 4: 101. https://doi.org/10.3390/fermentation4040101