Isolation, Purification, and Identification of Taxol and Related Taxanes from Taxol-Producing Fungus Aspergillus niger subsp. taxi
2
조회
0
다운로드
1
인용
0
참고문헌
키워드
초록
The content of taxol in the bark of yews is very low, and this is not affordable from the environmental point of view. Thus, it is a necessity to look for alternative sources of taxol production to solve its supply. Currently, a large portion of the taxol in the market comes from chemical semi-synthesis, but the semi-synthetic precursors such as baccatin III and 10- deacetyl-baccatin III are extracted from needles and twigs of yew trees. Taxol-producing fungi as a renewable resource is a very promising way to increase the scale of taxol production. Our group has obtained a taxol-producing endophytic fungus, Aspergillus niger subsp. taxi HD86-9, to examine if A. niger can produce the taxanes. Six compounds from the fermentation broth of strain HD86-9 were isolated and identified by 1H NMR, 13C NMR, and ESI-MS. The results showed that the six compounds included four taxane diterpenoids (taxol, cephalomannine, baccatin III, and 10-deacetyl-baccatin III) and two non-taxane compounds (β-sitosterol and flavonoid isovitexin). The study verified that the taxanes can be produced by the A. niger, which is very important to taxol production via chemical semi-synthesis. Additionally, the finding is potentially very significant to solve the taxol semi-synthetic precursors extracted from needles and twigs of yew trees, and the precursor production can be easily increased through the culture condition optimization, genetic breeding, and metabolic engineering of the A. niger.
Abstract
The content of taxol in the bark of yews is very low, and this is not affordable from the environmental point of view. Thus, it is a necessity to look for alternative sources of taxol production to solve its supply. Currently, a large portion of the taxol in the market comes from chemical semi-synthesis, but the semi-synthetic precursors such as baccatin III and 10- deacetyl-baccatin III are extracted from needles and twigs of yew trees. Taxol-producing fungi as a renewable resource is a very promising way to increase the scale of taxol production. Our group has obtained a taxol-producing endophytic fungus, Aspergillus niger subsp. taxi HD86-9, to examine if A. niger can produce the taxanes. Six compounds from the fermentation broth of strain HD86-9 were isolated and identified by 1H NMR, 13C NMR, and ESI-MS. The results showed that the six compounds included four taxane diterpenoids (taxol, cephalomannine, baccatin III, and 10-deacetyl-baccatin III) and two non-taxane compounds (β-sitosterol and flavonoid isovitexin). The study verified that the taxanes can be produced by the A. niger, which is very important to taxol production via chemical semi-synthesis. Additionally, the finding is potentially very significant to solve the taxol semi-synthetic precursors extracted from needles and twigs of yew trees, and the precursor production can be easily increased through the culture condition optimization, genetic breeding, and metabolic engineering of the A. niger.
참고문헌 (39)
- Wani MC, "Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia", J. Am. Chem. Soc, 93, pp.2325~2327 (1971)
- Liu WC, "Advances in exploring alternative taxol sources", RSC Adv, 6, pp.48800~48809 (2016)
- Ajikumar PK, "Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli", Science, 330, pp.70~74 (2010)
- Kim J, "Exploration of paclitaxel (Taxol) as a treatment for malignant tumors in cats: a descriptive case series", J. Feline Med. Surg, 17, pp.186~190 (2015)
- Roberts SC., "Production and engineering of terpenoids in plant cell culture", Nat. Chem. Biol, 3, pp.387~395 (2007)
- Long RM, "Specificity of the N-benzoyl transferase responsible for the last step of taxol biosynthesis", Arch. Biochem. Biophys, 477, pp.384~389 (2008)
- Hirasuna TJ, "Taxol production in suspension cultures of Taxus baccata", Plant Cell Tiss. Org, 44, pp.95~102 (1996)
- Mandai T, "A semisynthesis of paclitaxel via a 10-deacetyl baccatin III derivative bearing a beta-keto ester", Tetrahedron Lett, 41, pp.243~246 (2000)
- Wu J, "Enhancement of taxol production and release in Taxus chinensis cell cultures by ultrasound methyl jasmonate and in situ solvent extraction", Appl. Microbiol. Biotechnol, 62, pp.151~155 (2003)
- Stierle A, "Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew", Science, 260, pp.214~216 (1993)
- Xu D, "Antifungal monoterpene derivatives from the plant endophytic fungus Pestalotiopsis foedan", Chem. Biodivers, 13, pp.1422~1425 (2016)
- Malik S, "Production of the anticancer drug taxol in Taxus baccata suspension cultures: a review", Process Biochem, 46, pp.23~34 (2011)
- Ketchum REB, "The Taxus metabolome and the elucidation of the taxol biosynthetic pathway in cell suspension cultures", Biotechnol. Agric. Forest, 57, pp.291~309 (2006)
- Xu M, "Abscisic acid plays critical role in ozone-induced taxol production of Taxus chinensis suspension cell cultures", Biotechnol. Prog, 27, pp.1415~1420 (2011)
- Stierle A, "Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew", Science, 260, pp.214~216 (1993)
- Li JY, "Endophytic taxol-producing fungi from bald cypress, Taxodium distichum", Microbiology, 142, pp.2223~2226 (1996)
- Ganley RJ, "A community of unknown, endophytic fungi in western white pine", Proc. Natl. Acad. Sci. USA, 101, pp.10107~10112 (2004)
- Zhang CL, "Trichoderma taxi sp. nov., an endophytic fungus from Chinese yew Taxus mairei", FEMS Microbiol. Lett, 270, pp.90~96 (2007)
- Deng BW, "Fusarium solani, Tax-3, a new endophytic taxol-producing fungus from Taxus chinensis", World J. Microbiol. Biotechnol, 25, pp.139~143 (2009)
- 센딜쿠마란, "Isolation and Identification of an Anticancer Drug, Taxol from Phyllosticta tabernaemontanae, a Leaf Spot Fungus of an Angiosperm, Wrightia tinctoria", The Journal of Microbiology, 47(1), pp.40~49 (2009), 한국미생물학회
- Jae-Won Yoon, "Establishment of a solvent map for formation of crystalline and amorphous paclitaxel by solvent evaporation process", Korean Journal of Chemical Engineering, 28(9), pp.1918~1923 (2011), 한국화학공학회
- Zhou DP, "Nodulisporium, a genus new to China", Mycosystema, 20, pp.277~278 (2001)
- Sun JQ, "A new species of the genus Pleurocytospora", Mycosystema, 22, pp.12~13 (2013)
- Ge JP, "Identification of taxol-producing strain HU1353", J. Microbiol, 24, pp.19~21 (2004)
- Zhao K, "Isolation of a taxol-producing endophytic fungus and inhibiting effect of the fungus metabolites on HeLa cell", Mycosystema, 27, pp.735~744 (2008)
- Zhao K, "Aspergillus niger subsp. taxi, a new species variant of taxolproducing fungus isolated from Taxus cuspidata in China", J. Appl. Microbiol, 107, pp.1202~1207 (2009)
- Exposito O, "Biotechnological production of taxol and related taxoids: current state and prospects", Anti Cancer Agents Med. Chem, 9, pp.109~121 (2009)
- Guo BH, "An endophytic taxol-producing fungus BT2 isolated from Taxus chinensis var. mairei", Afr. J. Biotechnol, 5, pp.875~877 (2006)
- Jian ZY, "Isolation of an endophytic fungus producing baccatin III from Taxus wallichiana var. mairei", J. Ind. Microbiol. Biotechnol, 40, pp.1297~1302 (2013)
- Wang Y, "A new endophytic taxol- and baccatin III-producing fungus isolated from Taxus chinensis var. mairei", Afr. J. Biotechnol, 10, pp.16379~16386 (2011)
- Facundo VA, "Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana", Rev. Bras. Farmacogn, 22, pp.1134~1139 (2012)
- Li YC, "Isolation and identification of a 10-deacetyl baccatin-III-producing endophyte from Taxus wallichiana", Appl. Biochem. Biotechnol, 175, pp.2224~2231 (2015)
- Liang ZK, "Application of high-speed counter-current chromatography for isolation and purification of paclitaxel and related taxanes from Taxus chinensis cell culture", Sep. Sci. Technol, 50, pp.851~858 (2015)
- Gokul Raj K, "Anti-proliferative effect of fungal taxol extracted from Cladosporium oxysporum against human pathogenic bacteria and human colon cancer cell line HCT 15. Spectrochim", Acta A Mol. Biomol. Spectrosc, 138, pp.667~674 (2015)
- Bhatt V, "Simultaneous quantification and identification of flavonoids, lignans, coumarin and amides in leaves of Zanthoxylum armatum using UPLC-DAD-ESI-QTOF-MS", MS, 2016, pp.132, 46~55
- Tomasz M, "Screening for pharmaceutically important taxoids in Taxus baccata var. Aurea Corr. with CC", SPE, Biomed. Chromatogr, pp.2000, 14[DOI]
- Tatini LK, "Concomitant Pseudopolymorphs of 10-deacetyl baccatin III", AAPS PharmSciTech, 14, pp.558~568 (2013)
- Zielinska-Pisklak MA, "Activity-guided isolation, identification and quantification of biologically active isomeric compounds from folk medicinal plant Desmodium adscendens using high performance liquid chromatography with diode array detector, mass spectrometry and multidimentional nuclear magnetic resonance spectroscopy", Pharm. Biomed. Anal, 102, pp.54~63 (2015)
- Wei Y, "Engineering taxol biosynthetic pathway for improving taxol yield in taxol-producing endophytic fungus EFY-21 (Ozonium sp.)", Afr. J. Biotechnol, 11, pp.9094~9101 (2012)