دورية أكاديمية
A Pair of Chromone Epimers and an Acetophenone Glucoside from the Mangrove Endophytic Fungus Mycosphaerella sp. L3A1.
العنوان: | A Pair of Chromone Epimers and an Acetophenone Glucoside from the Mangrove Endophytic Fungus Mycosphaerella sp. L3A1. |
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المؤلفون: | Tan Q; School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China., Yang W; School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China., Zhu G; Department of Biochemistry, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, 510080, P. R. China., Chen T; School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China., Wu J; Guangdong Key Laboratory of Natural Medicine Research and Development & College of Pharmacy, Guangdong Medical University, Dongguan, 523808, P. R. China., Zhu Y; School of Public Health, Sun Yat-sen University, Guangzhou, 510080, P. R. China., Wang B; School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China., Yuan J; Department of Biochemistry, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, 510080, P. R. China., She Z; School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China. |
المصدر: | Chemistry & biodiversity [Chem Biodivers] 2022 Dec; Vol. 19 (12), pp. e202200998. Date of Electronic Publication: 2022 Nov 17. |
نوع المنشور: | Journal Article |
اللغة: | English |
بيانات الدورية: | Publisher: Verlag Helvetica Chimica Acta Country of Publication: Switzerland NLM ID: 101197449 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1612-1880 (Electronic) Linking ISSN: 16121872 NLM ISO Abbreviation: Chem Biodivers Subsets: MEDLINE |
أسماء مطبوعة: | Original Publication: Zürich, Switzerland : Hoboken, NJ : Verlag Helvetica Chimica Acta ; Distributed in the USA by Wiley, c2004- |
مواضيع طبية MeSH: | Mycosphaerella* , Chromones*/pharmacology, Fungi ; Crystallography, X-Ray ; Molecular Structure |
مستخلص: | Three new compounds, including a pair of chromone derivatives (1-2), and an acetophenone glucoside (3), together with three known compounds (4-6), were isolated from the mangrove endophytic fungus Mycosphaerella sp. L3A1. Their structures were elucidated by HR-ESI-MS analysis and extensive spectroscopic data. The absolute configurations of new compounds were determined using single-crystal X-ray diffraction analysis, electronic circular dichroism (ECD) calculations and chemical hydrolysis. In bioassays, compound 4 showed moderate cytotoxic activity against MDA-MB-435, HCT116, and SNB19 with IC (© 2022 Wiley-VHCA AG, Zurich, Switzerland.) |
References: | S. Chen, R. Cai, Z. Liu, H. Cui, Z. She, ‘Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities’, Nat. Prod. Rep. 2022, 39, 560-595. S. Yang, A. Mándi, X. Li, H. Liu, X. Li, S. Balázs Király, T. Kurtán, B. Wang, ‘Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370’, Bioorg. Chem. 2021, 106, 104477. M. Bai, C. Zheng, G. Chen, ‘Austins-type meroterpenoids from a mangrove-derived Penicillium sp.’, J. Nat. Prod. 2021, 84, 2104-2110. G. Zou, Q. Tan, Y. Chen, W. Yang, Z. Zang, H. Jiang, S. Chen, B. Wang, Z. She, ‘Furobenzotropolones A and B, 3-hydroxyepicoccone B with antioxidative activity from mangrove endophytic fungus Epicoccum nigrum MLY-3’, Mar. Drugs. 2021, 19, 395. Y. Chen, W. Yang, G. Zou, G. Wang, W. Kang, J. Yuan, Z. She, ‘Cytotoxic bromine and iodine-containing cytochalasins produced by the mangrove endophytic fungus Phomopsis sp. QYM-13 using the OSMAC approach’, J. Nat. Prod. 2022, 85, 1229-1238. Z. Liang, N. Shen, Y. Zheng, J. Wu, L. Miao, X. Fu, M. Chen, C. Wang, ‘Two new unsaturated fatty acids from the mangrove rhizosphere soil-derived fungus Penicillium javanicum HK1-22’, Bioorg. Chem. 2019, 93, 103331. S. Chen, D. Chen, R. Cai, H. Cui, Y. Long, Y. Lu, C. Li, Z. She, ‘Cytotoxic and antibacterial preussomerins from the mangrove endophytic fungus Lasiodiplodia theobromae ZJ-HQ1’, J. Nat. Prod. 2016, 79, 2397-2402. Y. Chen, W. Yang, G. Zou, Z. Yan, P. Qiu, Y. Long, Z. She, ‘Metabolites with anti-inflammatory and alpha-glucosidase inhibitory activities from the mangrove endophytic fungus Phoma sp. SYSU-SK-7’, Tetrahedron Lett. 2020, 61, 152578. J. Peng, T. Lin, W. Wang, Z. Xin, T. Zhu, Q. Gu, D. Li, ‘Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp. PJX-41’, J. Nat. Prod. 2013, 76, 1133-1140. Y. Liu, Q. Yang, G. Xia, H. Huang, H. Li, L. Ma, Y. Lu, L. He, X. Xia, Z. She, ‘Polyketides with α-glucosidase inhibitory activity from a mangrove endophytic fungus, Penicillium sp. HN29-3B1’, J. Nat. Prod. 2015, 78, 1816-1822. J. Lee, J. Lee, G. Kim, I. Yang, W. Wang, J. Nam, H. Choi, S. Nam, H. Kang, ‘Mycousfurans A and B, antibacterial usnic acid congeners from the fungus Mycosphaerella sp., isolated from a marine sediment’, Mar. Drugs. 2019, 17, 422. F. Otálvaro, J. Nanclares, L. Vásquez, W. Quiñones, F. Echeverri, R. Arango, B. Schneider, ‘Phenalenone-type compounds from Musa acuminata var. ‘Yangambi km 5’ (AAA) and their activity against Mycosphaerella fijiensis’, J. Nat. Prod. 2007, 70, 887-890. A. Assante, L. Camarda, L. Merlini, G. Nasini, ‘Secondary metabolites from Mycosphaerella ligulicola’, Phytochemistry. 1981, 20, 1955-1957. D. Oliveira, C. Pereira, G. Mendes, J. Junker, M. Kolloff, L. Rosa, C. Rosa, T. Alves, C. Zani, S. Johann, B. Cota, ‘Two new usnic acid derivatives from the endophytic fungus Mycosphaerella sp.’, Z. Naturforsch. C. 2018, 73, 449-455. Z. Huang, X. Liang, S. Qi, ‘A new iron(III) chelator of coprogen-type siderophore from the deep-sea-derived fungus Mycosphaerella sp. SCSIO z059’, Chin. J. Nat. Med. 2020, 18, 243-249. C. Moreno, T. Varughese, C. Spadafora, A. Arnold, P. Coley, T. Kursar, W. Gerwick, L. Cubilla-Rios, ‘Chemical constituents of the new endophytic fungus Mycosphaerella sp. nov and their anti-parasitic activity’, Nat. Prod. Commun. 2011, 6, 835-840. P. Qiu, Z. Liu, Y. Chen, R. Cai, G. Chen, Z. She, ‘Secondary metabolites with α-glucosidase inhibitory activity from the mangrove fungus Mycosphaerella sp. SYSU-DZG01’, Mar. Drugs. 2019, 17, 483. Z. Liu, Y. Chen, S. Chen, Y. Liu, Y. Lu, D. Chen, Y. Lin, X. Huang, Z. She, ‘Aspterpenacids A and B, two sesterterpenoids from a mangrove endophytic fungus Aspergillus terreus H010’, Org. Lett. 2016, 18, 1406-1409. H. Cui, Y. Lin, M. Luo, Y. Lu, X. Huang, Z. She, ‘Diaporisoindoles A−C: Three isoprenylisoindole alkaloid derivatives from the mangrove endophytic fungus Diaporthe sp. SYSU-HQ3’, Org. Lett. 2017, 19, 5621-5624. H. Cui, Y. Liu, J. Li, X. Huang, T. Yan, W. Cao, H. Liu, Y. Long, Z. She, ‘Diaporindenes A-D: Four unusual 2,3-dihydro-1H-indene analogs with anti-inflammatory activities from the mangrove endophytic fungus Diaporthe sp. SYSU-HQ3’, J. Org. Chem. 2018, 83, 11804-11813. R. Cai, H. Jiang, Z. Xiao, W. Cao, T. Yan, Z. Liu, S. Lin, Y. Long, Z. She, ‘(−)- and (+)-Asperginulin A, a pair of indole diketopiperazine alkaloid dimers with a 6/5/4/5/6 pentacyclic skeleton from the mangrove endophytic fungus Aspergillus sp. SK-28’, Org. Lett. 2019, 21, 9633-9636. J. Kornsakulkarn, T. Pruksatrakul, P. Surawatanawong, C. Thangsrikeattigun, S. Komwijit, N. Boonyuen, C. Thongpanchang, ‘Antimicrobial, antimalarial, and cytotoxic substances from the insect pathogenic fungus Beauveria asiatica BCC 16812’, Phytochem. Lett. 2021, 43, 8-15. K. Masato, A. Hiroshi, ‘A convenient synthesis of substituted γ-pyrones’, Tetrahedron Lett. 1980, 21, 1197-1200. Y. Zhang, X. Li, Y. Feng, B. Wang, ‘Phenethyl-α-pyrone derivatives and cyclodipeptides from a marine algous endophytic fungus Aspergillus niger EN-13’, Nat. Prod. Res. 2010, 24, 1036-1043. B. M. Trost, E. Gnanamani, C. A. Kalnmals, C. Hung, J. S. Tracy, ‘Direct enantio- and diastereoselective vinylogous addition of butenolides to chromones catalyzed by Zn-prophenol’, J. Am. Chem. Soc. 2019, 141, 1489-1493. J. Giner, J. Feng, D. Kiemle, ‘NMR tube degradation method for sugar analysis of glycosides’, J. Nat. Prod. 2016, 79, 2413-2417. F. Smith, ‘The constitution of mesquite gum. Part III. The structure of the monomethyl glucuronic acid component’, J. Chem. Soc. 1951, 2646-2652. T. Mosmann, ‘Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays’, J. Immunol. Methods. 1983, 65, 55-63. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, et al., Gaussian 09 Rev. A.02, Gaussian, Inc.: Wallingford, CT, USA, 2016. T. Bruhn, Y. Hemberger, A. Schaumlöffel, G. Bringmann, SpecDis, Version 1.53, University of Würzburg: Würzburg, Germany, 2011. R. Dennington, T. A. Keith, J. M. Millam, GaussView, Version 6, Semichem Inc.: Shawnee Mission, KS, USA, 2016. |
معلومات مُعتمدة: | U20A2001 National Natural Science Foundation of China; 21877133 National Natural Science Foundation of China; GDNRC [2022]35 Guangdong Provincial Department Foundation of Natural Resources; 2020B1111030005 Key-Area Research and Development Program of Guangdong Province |
فهرسة مساهمة: | Keywords: Mycosphaerella; cytotoxic activity; mangrove endophytic fungus; secondary metabolites |
المشرفين على المادة: | 0 (Chromones) |
تواريخ الأحداث: | Date Created: 20221101 Date Completed: 20221227 Latest Revision: 20221230 |
رمز التحديث: | 20231215 |
DOI: | 10.1002/cbdv.202200998 |
PMID: | 36318651 |
قاعدة البيانات: | MEDLINE |
تدمد: | 1612-1880 |
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DOI: | 10.1002/cbdv.202200998 |