Published May 31, 2021
| Version v1
Journal article
Restricted
Biotransformation of artemisinic acid to bioactive derivatives by endophytic Penicillium oxalicum B4 from Artemisia annua L.
- 1. * & ** & College of Pharmaceutical Sciences, Soochow University, Suzhou, 215123, China
Description
Tian, Hao, Li, Xin Ping, Zhao, Jianping, Gao, Hong Wei, Xu, Qiong Ming, Wang, Jian Wen (2021): Biotransformation of artemisinic acid to bioactive derivatives by endophytic Penicillium oxalicum B4 from Artemisia annua L. Phytochemistry (112682) 185: 1-10, DOI: 10.1016/j.phytochem.2021.112682, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112682
Files
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:5074FFC49540852DFF864514FF912228
References
- Bier, M.C.J., Medeiros, A.B.P., Soccol, C.R., 2017. Biotransformation of limonene by an endophytic fungus using synthetic and orange residue-based media. Fungal Biol. 121 (2), 137-144. https://doi.org/10.1016/j.funbio.2016.11.003.
- Blazquez, A.G., Fernandez-Dolon, M., Sanchez-Vicente, L., Maestre, A.D., Gomez-San Miguel, A.B., Alvarez, M., Serrano, M.A., Jansen, H., Efferth, T., Marin, J.J.G., Romero, M.R., 2013. Novel artemisinin derivatives with potential usefulness against liver/colon cancer and viral hepatitis. Bioorg. Med. Chem. 21 (14), 4432-4441. https://doi.org/10.1016/j.bmc.2013.04.059.
- Demyttenaere, J.C.R., De Pooter, H.L., 1998. Biotransformation of citral and nerol by spores of Penicillium digitatum. Flavour Fragrance J. 13 (3), 173-176. https://dio. org/10.1002/(SICI)1099-1026(199805/06)13:3<173::AID-FFJ715>3.0.CO;2-Y.
- Deng, D.A., Cai, J.C., 1991. Derivatives of artemisic acid with antitumor activity. Chin. J. Org. Chem. 5, 540-543 (In Chinese).
- de Queiroz, T.M., Ellena, J., Porto, A.L.M., 2020. Biotransformation of ethinylestradiol by whole cells of Brazilian marine-derived fungus Penicillium oxalicum CBMAI 1996. Mar. Biotechnol. 22, 673-682. https://doi.org/10.1007/s10126-020-09989-w.
- Ekiz, G., Duman, S., Bedir, E., 2018. Biotransformation of cyclocanthogenol by the endophytic fungus Alternaria eureka 1E1BL1. Phytochemistry 151, 91-98. https:// doi.org/10.1016/j.phytochem.2018.04.006.
- Elmarak, S.A., El-Feraly, F.S., Elsohly, H.N., Croom, E.M., Hufford, C.D., 1988. Microbiological transformations of artemisinic acid. Phytochemistry 27 (10), 3089-3091. https://doi.org/10.1016/0031-9422(88)80006-2.
- Galal, A.M., Ross, S.A., Jacob, M., ElSohly, M.A., 2005. Antifungal activity of artemisinin derivatives. J. Nat. Prod. 68 (8), 1274-1276. https://dio.org/10.1021/np050074u.
- Gao, J., Xu, W.J., Fang, Q., Liang, F., Jin, R.T., Wu, D., Tai, G.H., Zhou, Y.F., 2013. Efficient biotransformation for preparation of pharmaceutically active ginsenoside compound K by Penicillium oxalicum sp. 68. Ann. Microbiol. 63 (1), 139-149. https://doi.org/10.1007/s13213-012-0454-3.
- Gaur, R., Tiwari, S., Jakhmola, A., Thakur, J.P., Verma, R.K., Pandey, R., Bhakuni, R.S., 2014. Novel biotransformation processes of artemisinic acid to their hydroxylated derivatives 3β- hydroxyartemisinic acid and 3β, 15-dihydroxyartemisinic by fungus Trichothecium roseum CIMAPN1 and their biological evaluation. J. Mol. Catal. B Enzym. 106, 46-55. https://doi.org/10.1016/j.molcatb.2014.04.008.
- Hu, Y.S., Zhu, J.H., Jiang, B., Yu, R.M., 2010. Biotransformation of artemisinic acid by cell suspension cultures of Cephalotaxusfortunei and Artemisia annua. J. Chin. Med. Mater. 33 (5), 662-665 (In Chinese).
- Huang, L., Liu, J.F., Liu, L.X., Li, D.F., Zhang, Y., Nui, H.Z., Song, H.Y., Zhang, C.Y., Liu, X.H., Tu, Y.Y., 1993. Studies on the antipyretic and anti-inflammatory effects of Artemisia annua L. Chinese J. Chinese Mat. Medica. 18 (1), 44-48 (In Chinese).
- Imran, M., Crowley, D.E., Khalid, A., Hussain, S., Mumtaz, M.W., Arshad, M., 2015. Microbial biotechnology for decolorization of textile wastewaters. Rev. Environ. Sci. Biotechnol. 14 (1), 73-92. https://doi.org/10.1007/s11157-014-9344-4.
- Kawamoto, H., Asada, Y., Sekine, H., Furuya, T., 1998. Biotransformation of artemisinic acid by cultured cells of Artemisia annua. Phytochemistry 48 (8), 1329-1333. https://doi.org/10.1016/S0031-9422(97)01138-2.
- Konkimalla, V.B., Blunder, M., Korn, B., Soomro, S.A., Jansen, H., Change, W., Posner, G. H., Bauer, R., Efferth, T., 2008. Effect of artemisinin and other endoperoxides on nitric oxide-related signaling pathway in RAW 264.7 mouse macrophage cells. Nitric Oxide 19 (2), 184-191. https://doi.org/10.1016/j.niox.2008.04.008.
- Lee, J., Kim, M.H., Lee, J.H., Jung, E., Yoo, E.S., Park, D., 2012. Artemisinic acid is a regulator of adipocyte differentiation and C/EBP δ expression. J. Cell. Biochem. 113 (7), 2488-2499. https://doi.org/10.1002/jcb.24124.
- Li, H.X., Zhang, Q.B., Li, S.M., Zhu, Y.G., Zhang, G.T., Zhang, H.B., Tian, X.P., Zhang, S., Ju, J.H., Zhang, C.S., 2012. Identification and characterization of xiamycin A and oxiamycin gene cluster reveals an oxidative cyclization strategy tailoring indolosesquiterpene biosynthesis. J. Am. Chem. Soc. 134 (21), 8996-9005. https:// doi.org/10.1021/ja303004g.
- Liu, B., Chen, Y., Yu, C.Z., Shen, Z.W., 2003. Highly chemical and regio-selective catalytic oxidation with a novel manganese catalyst. Chin. J. Chem. 21 (7), 833-838. https://doi.org/10.1002/cjoc.20030210723.
- Liu, C.H., Zou, W.X., Lu, H., Tan, R.X., 2001. Antifungal activity of Artemisia annua endophyte cultures against phytopathogenic fungi. J. Biotechnol. 88 (3), 277-282. https://doi.org/10.1016/s0168-1656(01)00285-1.
- Mioso, R., Toledo Marante, F.J., Herrera Bravo de Laguna, I., 2015. Penicillium roqueforti: a multifunctional cell factory of high value-added molecules. J. Appl. Microbiol. 118 (4), 781-791. https://doi.org/10.1111/jam.12706.
- Pareek, N., Vivekanand, V., Dwivedi, P., Singh, R.P., 2011. Penicillium oxalicum SAEM-51: a mutagenised strain for enhanced production of chitin deacetylase for bioconversion to chitosan. N. Biotech. 28 (2), 118-124. https://doi.org/10.1016/j. nbt.2010.09.009.
- Ries, M.I., Ali, H., Lankhorst, P.P., Hankemeier, T., Bovenberg, R.A.L., Driessen, A.J.M., Vreeken, R.J., 2013. Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway. J. Biol. Chem. 288 (52), 37289-37295. https://doi.org/10.1074/jbc.M113.512665.
- Rocha, L.C., Luiz, R.F., Rosset, I.G., Raminelli, C., Seleghim, M.H.R., Sette, L.D., Porto, A. L.M., 2012. Bioconversion of iodoacetophenones by marine fungi. Mar. Biotechnol. 14 (4), 396-401. https://doi.org/10.1007/s10126-012-9463-2.
- Straathof, A.J.J., Panke, S., Schmid, A., 2002. The production of fine chemicals by biotransformations. Curr. Opin. Biotechnol. 13 (6), 548-556. https://doi.org/ 10.1016/s0958-1669(02)00360-9.
- Tian, H., Ma, Y.J., Li, W.Y., Wang, J.W., 2018. Efficient degradation of triclosan by an endophytic fungus Penicillium oxalicum B4. Environ. Sci. Pollut. Res. 25 (9), 8963-8975. https://doi.org/10.1007/s11356-017-1186-5.
- Tu, Y.Y., Ni, M.Y., Zhong, Y.R., Li, L.N., Cui, S.L., Zhang, M.Q., Wang, X.Z., Ji, Z., Liang, X.T., 1982. Studies on the constituents of Artemisia annua. Part II. Planta Med. 44 (3), 143-145. https://doi.org/10.1055/s-2007-971424.
- Vonwiller, S.C., Haynes, R.K., King, G., Wang, H.J., 1993. An improved method for the isolation of Qinghao (Artemisinic) acid from Artemisia annua. Planta Med. 59 (6), 562-563. https://doi.org/10.1055/s-2006-959762.
- Wang, B.J., Won, S.J., Yu, Z.R., Su, C.L., 2005. Free radical scavenging and apoptotic effects of Cordyceps sinensis fractionated by supercritical carbon dioxide. Food Chem. Toxicol. 43 (4), 543-552. https://doi.org/10.1016/j.fct.2004.12.008.
- Wang, J.W., Xia, Z.H., Tan, R.X., 2002. Elicitation on artemisinin biosynthesis in Artemisia annua hairy roots by the oligosaccharide extract from the endophytic Colletotrichum sp. B501. Acta Bot. Sin. 44 (10), 1233-1238.
- Woerdenbag, H.J., Pras, N., Chan, N.G., Bang, B.T., Bos, R., van Uden, W., Van Y, P., Van Boi, N., Batterman, S., Lugt, C.B., 1994. Artemisinin, related sesquiterpenes, and essential oil in Artemisia annua during a vegetation period in Vietnam. Planta Med. 60 (3), 272-275. https://doi.org/10.1055/s-2006-959474.
- Wolken, W.A.M., van der Werf, M.J., 2001. Geraniol biotransformation-pathway in spores of Penicillium digitatum. Appl. Microbiol. Biotechnol. 57 (5-6), 731-737. https://doi.org/10.1007/s002530100821.
- Xu, M.M., Galhano, R., Wiemann, P., Bueno, E., Tiernan, M., Wu, W., Chung, I.M., Gershenzon, J., Tudzynski, B., Sesma, A., Peters, R.J., 2012. Genetic evidence for natural product mediated plant-plant allelopathy in rice (Oryza sativa). New Phytol. 193 (3), 570-575. https://doi.org/10.1111/j.1469-8137.2011.04005.x.
- Yang, L., Zhu, J.H., Song, L.Y., Shi, X.J., Li, X.Y., Yu, R.M., 2012. Three sesquiterpene compounds biosynthesised from artemisinic acid using suspension-cultured cells of Averrhoa carambola (oxalidaceae). Nat. Prod. Res. 26 (15), 1388-1394. https://doi. org/10.1080/14786419.2011.589055.
- Yu, H.S., Zhang, L., Li, L., Zheng, C.J., Guo, L., Li, W.C., Sun, P.X., Qin, L.P., 2010. Recent developments and future prospects of antimicrobial metabolites produced by endophytes. Microbiol. Res. 165 (6), 437-449. https://doi.org/10.1016/j. micres.2009.11.009.
- Zeng, W.L., Li, W.K., Han, H., Tao, Y.Y., Yang, L., Wang, Z.T., Chen, K.X., 2014. Microbial biotransformation of gentiopicroside by the endophytic fungus Penicillium crustosum 2T01Y01. Appl. Environ. Microbiol. 80 (1), 184-192. https://doi.org/10.1128/ AEM.02309-13.
- Zhang, Q.B., Li, H.X., Li, S.M., Zhu, Y.G., Zhang, G.T., Zhang, H.B., Zhang, W.J., Shi, R., Zhang, C.S., 2012. Carboxyl formation from methyl via triple hydroxylations by XiaM in xiamycin A biosynthesis. Org. Lett. 14 (24), 6142-6145. https://doi.org/ 10.1021/ol302782u.
- Zhang, Y.S., Ye, H.C., Liu, B.Y., Wang, H., Li, G.F., 2005. Exogenous GA3 and flowering induce the conversion of artemisinic acid to artemisinin in Artemisia annua plants. Russ. J. Plant Physiol. 52 (1), 58-62. https://doi.org/10.1007/s11183-005-0009-6.
- Zheng, G.Q., 1994. Cytotoxic terpenoids and flavonoids from Artemisia annu a. Planta Med. 60 (1), 54-57. https://doi.org/10.1055/s-2006-959408.
- Zheng, L.P., Tian, H., Yuan, Y.F., Wang, J.W., 2016. The influence of endophytic Penicillium oxalicum B4 on growth and artemisinin biosynthesis of in vitro propagated plantlets of Artemisia annua L. Plant Growth Regul. 80 (1), 93-102. https://doi.org/ 10.1007/s10725-016-0162-2.
- Zhu, J.H., Yu, R.M., 2012. Biotransformation of artemisinic acid by transgenic hairy roots of Polygonum multiflorum. Chin. Tradit. Herb. Drugs 43 (6), 1065-1067 (In Chinese).
- Zhu, J.H., Yu, R.M., Yang, L., Hu, Y.S., Song, L.Y., Huang, Y.J., Li, W.M., Guan, S.X., 2010. Novel biotransformation processes of dihydroartemisinic acid and artemisinic acid to their hydroxylated derivatives by two plant cell culture systems. Process Biochem. 45 (10), 1652-1656. https://doi.org/10.1016/j.procbio.2010.06.014.