Published August 31, 2021
| Version v1
Journal article
Restricted
Brevianthrones, bianthrones from a Chinese isolate of the endophytic fungus Colletotrichum brevisporum
Authors/Creators
- 1. * & School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin, 300092, People's Republic of China
Description
Lin, Min, Adpressa, Donovon A., Feng, Meiyu, Lu, Ya, Clark, Benjamin R. (2021): Brevianthrones, bianthrones from a Chinese isolate of the endophytic fungus Colletotrichum brevisporum. Phytochemistry (112792) 188: 1-8, DOI: 10.1016/j.phytochem.2021.112792, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112792
Files
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:FFDCFF87FFB0FFD9FFD8FFB1FFD5FFCA
References
- Aly, A.H., Edrada-Ebel, R.A., Indriani, I.D., Wray, V., Muller, W.E.G., Totzke, F., Zirrgiebel, U., Sch¨achtele, C., Kubbutat, M.H.G., Lin, W.H., Proksch, P., Ebel, R., 2008. Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. J. Nat. Prod. 71, 972-980. https://doi.org/10.1021/np070447m.
- Aoyagi, A., Ito-Kobayashi, M., Ono, Y., Furukawa, Y., Takahashi, M., Muramatsu, Y., Umetani, M., Takatsu, T., 2008. Colletoic acid, a novel 11β- hydroxysteroid dehydrogenase type 1 inhibitor from Colletotrichum gloeosporioides SANK 21404. J. Antibiot. (Tokyo) 61, 136-141. https://doi.org/10.1038/ja.2008.122.
- Ayo, R.G., Amupitan, J.O., Zhao, Y., 2007. Trihydroxy-3-methyl-anthraquinone (emodin) isolated from the leaves of Cassia nigricans Vahl. Afr. J. Biotechnol. 6, 1276-1279. https://doi.org/10.4314/ajb.v6i11.57453.
- Bannwarth, C., Ehlert, S., Grimme, S., 2019. GFN2-xTB-An accurate and broadly parametrized self-consistent tight-binding quantum chemical method with multipole electrostatics and density-dependent dispersion contributions. J. Chem. Theor. Comput. 15, 1652-1671. https://doi.org/10.1021/acs.jctc.8b01176.
- Barth´elemy, M., Gu´erineau, V., Genta-Jouve, G., Roy, M., Chave, J., Guillot, R., Pellissier, L., Wolfender, J.L., Stien, D., Eparvier, V., Touboul, D., 2020. Identification and dereplication of endophytic Colletotrichum strains by MALDI TOF mass spectrometry and molecular networking. Sci. Rep. 10, 1-17. https://doi.org/ 10.1038/s41598-020-74852-w.
- Bezerra, J.P., Ferreira, P.V., Barbosa, L., da, F., Ramos-Sobrinho, R., Pinho, D.B., Reis, A., Assunctao, I.P., Lima, G.S.A., 2015. First report of anthracnose on Chayote fruits (Sechium edule) caused by Colletotrichum brevisporum. Plant Dis. 100, 217. https:// doi.org/10.1094/PDIS-07-15-0793-PDN.
- Borghi, S.M., Carvalho, T.T., Staurengo-Ferrari, L., Hohmann, M.S.N., Pinge-Filho, P., Casagrande, R., Verri, W.A., 2013. Vitexin inhibits inflammatory pain in mice by targeting TRPV1, oxidative stress, and cytokines. J. Nat. Prod. 76, 1141-1146. https://doi.org/10.1021/np400222v.
- Bruhn, T., Schaumloffel ¨, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25, 243-249. https://doi.org/10.1002/chir.22138.
- Chiang, Y.M., Szewczyk, E., Davidson, A.D., Entwistle, R., Keller, N.P., Wang, C.C.C., Oakley, B.R., 2010. Characterization of the Aspergillus nidulans monodictyphenone gene cluster. Appl. Environ. Microbiol. 76, 2067-2074. https://doi.org/10.1128/ AEM.02187-09.
- Clark, B.R., Lacey, E., Gill, J.H., Capon, R.J., 2007. The effect of halide salts on the production of Gymnoascus reessii polyenylpyrroles. J. Nat. Prod. 70, 665-667. https://doi.org/10.1021/np0605283.
- De Silva, D.D., Crous, P.W., Ades, P.K., Hyde, K.D., Taylor, P.W.J., 2017. Life styles of Colletotrichum species and implications for plant biosecurity. Fungal Biol. Rev. 31, 155-168. https://doi.org/10.1016/j.fbr.2017.05.001.
- Duval, J., Pecher, V., Poujol, M., Lesellier, E., 2016. Research advances for the extraction, analysis and uses of anthraquinones: a review. Ind. Crop. Prod. 94, 812-833. https:// doi.org/10.1016/j.indcrop.2016.09.056.
- Elbanna, A.H., Khalil, Z.G., Bernhardt, P.V., Capon, R.J., 2021. Neobulgarones revisited: anti and syn bianthrones from an Australian mud dauber wasp nest-associated fungus, Penicillium sp. CMB-MD22. J. Nat. Prod. 84, 762-770. https://doi.org/ 10.1021/acs.jnatprod.0c01035.
- Figueroa, M., Jarmusch, A.K., Raja, H.A., El-Elimat, T., Kavanaugh, J.S., Horswill, A.R., Cooks, R.G., Cech, N.B., Oberlies, N.H., 2014. Polyhydroxy anthraquinones as quorum sensing inhibitors from the guttates of Penicillium restrictum and their analysis by desorption electrospray ionization mass spectrometry. J. Nat. Prod. 77, 1351-1358. https://doi.org/10.1021/np5000704.
- Form, I.C., Bonus, M., Gohlke, H., Lin, W., Daletos, G., Proksch, P., 2019. Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg. Med. Chem. 27, 115005. https://doi.org/10.1016/j. bmc.2019.07.021.
- Fouillaud, M., Venkatachalam, M., Girard-Valenciennes, E., Caro, Y., Dufoss´e, L., 2016. Anthraquinones and derivatives from marine-derived fungi: structural diversity and selected biological activities. Mar. Drugs 14, 64. https://doi.org/10.3390/ md14040064.
- Fredimoses, M., Zhou, X., Ai, W., Tian, X., Yang, B., Lin, X., Liu, J., Liu, Y., 2019. Emerixanthone E, a new xanthone derivative from deep sea fungus Emericella sp SCSIO 05240. Nat. Prod. Res. 33, 2088-2094. https://doi.org/10.1080/ 14786419.2018.1487966.
- Grimme, S., Bannwarth, C., 2016. Ultra-fast computation of electronic spectra for large systems by tight-binding based simplified Tamm-Dancoff approximation (sTDAxTB). J. Chem. Phys. 145 https://doi.org/10.1063/1.4959605.
- Hiruma, K., Gerlach, N., Sacrist´an, S., Nakano, R.T., Hacquard, S., Kracher, B., Neumann, U., Ramirez, D., Bucher, M., O' Connell, R.J., Schulze-Lefert, P., 2016. Root endophyte Colletotrichum tofieldiae confers plant fitness benefits that are phosphate status dependent. Cell 165, 464-474. https://doi.org/10.1016/j. cell.2016.02.028.
- Ji, N.Y., Liang, X.R., Sun, R.R., Miao, F.P., 2014. A rule to distinguish diastereomeric bianthrones by 1H NMR. RSC Adv. 4, 7710-7715. https://doi.org/10.1039/ c3ra47055e.
- Kim, J.W., Shim, S.H., 2019. The fungus Colletotrichum as a source for bioactive secondary metabolites. Arch Pharm. Res. (Seoul) 42, 735-753. https://doi.org/ 10.1007/s12272-019-01142-z.
- Kusari, S., Pandey, S.P., Spiteller, M., 2013. Untapped mutualistic paradigms linking host plant and endophytic fungal production of similar bioactive secondary metabolites. Phytochemistry 91, 81-87. https://doi.org/10.1016/j.phytochem.2012.07.021.
- Lee, M.S., Sohn, C.B., 2008. Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome. Biol. Pharm. Bull. 31, 2154-2157. https://doi.org/10.1248/ bpb.31.2154.
- Lin, X., Yu, M., Lin, T., Zhang, L., 2016. Secondary metabolites of Xylaria sp., an endophytic fungus from Taxus mairei. Nat. Prod. Res. 30, 2442-2447. https://doi. org/10.1080/14786419.2016.1198350.
- Liu, L.P., Zhang, L., Qiu, P.L., Xu, Z., Zhao, Z.M., Ren, S.C., Bai, Q.R., Chen, C.Q., Lu, B. H., Yang, L.N., Li, Y., Gao, J., Hsiang, T., 2017. First report of Colletotrichum brevisporum causing anthracnose on pumpkin in China. Plant Dis. 102, 1038. https:// doi.org/10.1094/PDIS-08-17-1271-PDN.
- Ludewig, H., Molyneux, S., Ferrinho, S., Guo, K., Lynch, R., Gkotsi, D.S., Goss, R.J.M., 2020. Halogenases: structures and functions. Curr. Opin. Struct. Biol. 65, 51-60. https://doi.org/10.1016/j.sbi.2020.05.012.
- Mandelare, P.E., Adpressa, D.A., Kaweesa, E.N., Zakharov, L.N., Loesgen, S., 2018. Coculture of two developmental stages of a marine-derived Aspergillus alliaceus results in the production of the cytotoxic bianthrone allianthrone A. J. Nat. Prod. 81, 1014-1022. https://doi.org/10.1021/acs.jnatprod.8b00024.
- Maor, R., Haskin, S., Levi-Kedmi, H., Sharon, A., 2004. In planta production of indole-3- acetic acid by Colletotrichum gloeosporioides f. sp. aeschynomene. Appl. Environ. Microbiol. 70, 1852-1854. https://doi.org/10.1128/AEM.70.3.1852-1854.2004.
- Mbwambo, Z.H., Apers, S., Moshi, M.J., Kapingu, M.C., Van Miert, S., Claeys, M., Brun, R., Cos, P., Pieters, L., Vlietinck, A., 2004. Anthranoid compounds with antiprotozoal activity from Vismia orientalis. Planta Med. 70, 706-710. https://doi. org/10.1055/s-2004-827199.
- Moraga, J., Gomes, W., Pinedo, C., Cantoral, J.M., Hanson, J.R., Carbu, M., Garrido, C., Dur´an-Patron ´, R., Collado, I.G., 2019. The current status on secondary metabolites produced by plant pathogenic Colletotrichum species. Phytochemistry Rev. 18, 215-239. https://doi.org/10.1007/s11101-018-9590-0.
- Ndjakou Lenta, B., Devkota, K.P., Ngouela, S., Fekam Boyom, F., Naz, Q., Choudhary, M. I., Tsamo, E., Rosenthal, P.J., Sewald, N., 2008. Anti-plasmodial and cholinesterase inhibiting activities of some constituents of Psorospermum glaberrimum. Chem. Pharm. Bull. 56, 222-226. https://doi.org/10.1248/cpb.56.222.
- Noireung, P., Phoulivong, S., Liu, F., Cai, L., Mckenzie, E.H.C., Chukeatirote, E., Jones, E. B.G., Bahkali, A.H., Hyde, K.D., 2012. Novel species of Colletotrichum revealed by morphology and molecular analysis. Cryptogam. Mycol. 33, 1-16. https://doi.org/ 10.7872/crym.v33.iss3.2012.347.
- Ohra, J., Morita, K., Tsujino, Y., Tazaki, H., Fujimori, T., Goering, M., Evans, S., Zorner, P., 1995. Production of the phytotoxic metabolite, ferricrocin, by the fungus Colletotrichum gloeosporioides. Biosci. Biotechnol. Biochem. 59, 113-114. https://doi. org/10.1271/bbb.59.113.
- Powell, V.H., Sutherland, M.D., 1967. Pigments of marine animals. VI. Anthraquinoid pigments of the crinoids Ptilometra australis Wilton and Tropiometra afra Hartlaub. Aust. J. Chem. 20, 541-553. https://doi.org/10.1071/CH9670541.
- Smith, S.G., Goodman, J.M., 2009. Assigning the stereochemistry of pairs of diastereoisomers using GIAO NMR shift calculation. J. Org. Chem. 74, 4597-4607. https://doi.org/10.1021/jo900408d.
- Song, J.H., Lee, C., Lee, D., Kim, S., Bang, S., Shin, M.S., Lee, J., Kang, K.S., Shim, S.H., 2018. Neuroprotective compound from an endophytic fungus, Colletotrichum sp. JS-0367. J. Nat. Prod. 81, 1411-1416. https://doi.org/10.1021/acs.jnatprod.8b00033.
- Sureram, S., Kesornpun, C., Mahidol, C., Ruchirawat, S., Kittakoop, P., 2013. Directed biosynthesis through biohalogenation of secondary metabolites of the marine-derived fungus Aspergillus unguis. RSC Adv. 3, 1781-1788. https://doi.org/10.1039/ c2ra23021f.
- Tianpanich, K., Prachya, S., Wiyakrutta, S., Mahidol, C., Ruchirawat, S., Kittakoop, P., 2011. Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp. J. Nat. Prod. 74, 79-81. https://doi. org/10.1021/np1003752.
- Vieira, W.A.S., Nascimento, R.J., Michereff, S.J., Hyde, K.D., Cˆamara, M.P.S., 2013. First report of papaya fruit anthracnose caused by Colletotrichum brevisporum in Brazil. Plant Dis. 97, 1659. https://doi.org/10.1094/PDIS-05-13-0520-PDN.
- Wang, F., Zhu, H., Ma, H., Jiang, J., Sun, W., Cheng, L., Zhang, G., Zhang, Y., 2016. Citrinal B, a new secondary metabolite from endophytic fungus Colletotrichum capsici and structure revision of citrinal A. Tetrahedron Lett. 57, 4250-4253. https://doi. org/10.1016/j.tetlet.2016.08.029.
- You, X., Feng, S., Luo, S., Cong, D., Yu, Z., Yang, Z., Zhang, J., 2013. Studies on a rheinproducing endophytic fungus isolated from Rheum palmatum L. Fitoterapia 85, 161-168. https://doi.org/10.1016/j.fitote.2012.12.010.
- Zou, W.X., Meng, J.C., Lu, H., Chen, G.X., Shi, G.X., Zhang, T.Y., Tan, R.X., 2000. Metabolites of Colletotrichum gloeosporioides, an endophytic fungus in Artemisia mongolica. J. Nat. Prod. 63, 1529-1530. https://doi.org/10.1021/np000204t.