Citation:
Ling-Hong Meng, Xiao-Ming Li, Yang Liu, Bin-Gui Wang. Polyoxygenated dihydropyrano[2,3-c]pyrrole-4,5-dione derivatives from the marine mangrove-derived endophytic fungus Penicillium brocae MA-231 and their antimicrobial activity[J]. Chinese Chemical Letters,
;2015, 26(5): 610-612.
doi:
10.1016/j.cclet.2015.01.024
-
A new polyoxygenated dihydropyrano[2,3-c]pyrrole-4,5-dione derivative, pyranonigrin F (1), together with a related known compound, pyranonigrin A (2), were isolated and identified from Penicillium brocae MA-231, an endophytic fungus obtained from the fresh tissue of the marine mangrove plant Avicennia marina. The structures of these metabolites were determined based on comprehensive spectral interpretation and the absolute configuration of compound 1 was established by X-ray crystallographic analysis. Compounds 1, and 2 showed potent activity against a broad spectrum of human-, aqua-, and plant-pathogens.
-
-
-
[1]
[1] R.D. Chen, Z. Yan, J.H. Zou, N. Wang, J.G. Dai, Rubratoxin C, a new nonadride derivative from an endophytic fungus Penicillium sp. F-14, Chin. Chem. Lett. 25 (2014) 1308-1310.
-
[2]
[2] J. Hiort, K. Maksimenka,M. Reichert, et al., New natural products from the spongederived fungus Aspergillus niger, J. Nat. Prod. 67 (2004) 1532-1543.
-
[3]
[3] Y. Miyake, C. Ito, H. Tokuda, T. Osawa, M. Itoigawa, Evaluation of flavoglaucin, its derivatives and pyranonigrins produced by molds used in fermented foods for inhibiting tumor promotion, Biosci. Biotechnol. Biochem. 74 (2010) 1120- 1122.
-
[4]
[4] R. Riko, H. Nakamura, K. Shindo, Studies on pyranonigrins-isolation of pyranonigrin E and biosynthetic studies on pyranonigrin A, J. Antibiot. 67 (2014) 179-181.
-
[5]
[5] Y. Miyake, M. Muchizuki, C. Ito, M. Itoigawa, T. Osawa, Antioxidative pyranonigrins in rice mold starters and their suppressive effect on the expression of blood adhesion molecules, Biosci. Biotechnol. Biochem. 72 (2008) 1580-1585.
-
[6]
[6] M.H. Wang, X.M. Li, C.S. Li, N.Y. Ji, B.G. Wang, Secondary metabolites from Penicillium pinophilium SD-272, a marine sediment-derived fungus, Mar. Drugs 11 (2013) 2230-2238.
-
[7]
[7] L.H. Meng, X.M. Li, C.T. Lü, et al., Sulfur-containing cytotoxic curvularin macrolides from Penicillium sumatrense MA-92, a fungus obtained from the rhizosphere of the mangrove Lumnitzera recemosa, J. Nat. Prod. 76 (2013) 2145-2149.
-
[8]
[8] C.Y. An, X.M. Li, H. Luo, et al., 4-Phenyl-3,4-dihydroquinolone derivatives from Aspergillus nidulans MA-143, an endophytic fungus isolated from the mangrove plant Rhizophora stylosa, J. Nat. Prod. 76 (2013) 1896-1901.
-
[9]
[9] L.H. Meng, X.M. Li, C.T. Lü, C.G. Huang, B.G. Wang, Brocazines A-F, cytotoxic bisthiodiketopiperazine derivatives from Penicillium brocae MA-231, an endophytic fungus derived from the marine mangrove plant Avicennia marina, J. Nat. Prod. 77 (2014) 1921-1927.
-
[10]
[10] Crystallographic data of compound 1 have been deposited in the Cambridge Crystallographic Data Centre as CCDC 1032043. The data can be obtained free of charge via http://www.ccdc.cam.ac.uk/data_request/cif (or from the CCDC, 12 Union Road, Cambridge CB21EZ, UK; fax: +44-1223-336-033; e-mail: deposit@_ccdc.cam.ac.uk).
-
[11]
[11] G.M. Sheldrick, SADABS, Software for empirical absorption correction, University of Gottingen, Germany, 1996.
-
[12]
[12] G.M. Sheldrick, SHELXTL, Structure determination software programs, Bruker Analytical X-ray System Inc., Wisconsin, 1997.
-
[13]
[13] G.M. Sheldrick, SHELXL-97 and SHELXS-97, Program for X-ray crystal structure solution and refinement, University of Gottingen, Germany, 1997.
-
[14]
[14] G. Schlingmann, T. Taniguchi, H.Y. He, et al., Reassessing the structure of pyranonigrin, J. Nat. Prod. 70 (2007) 1180-1187.
-
[15]
[15] B.N. Meyer, N.R. Ferrigni, J.E. Putnam, et al., Brine shrimp: a convenient general bioassay for active plant constituents, Planta Med. 45 (1982) 31-34.
-
[16]
[16] S.K.S. Al-Burtamani, M.O. Fatope, R.G. Marwash, A.K. Onifade, S.H. Al-Saidi, Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman, J. Ethnopharmacol. 96 (2005) 107-112.
-
[1]
-
-
-
[1]
Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
-
[2]
Yanye Fan , Jingjing Chen , Bichun Chen , Jinyu Bai , Bowen Yang , Feng Liang , Lijing Fang . Design, synthesis and biological evaluation of Leu10-teixobactin analogues. Chinese Chemical Letters, 2025, 36(4): 110075-. doi: 10.1016/j.cclet.2024.110075
-
[3]
Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
-
[4]
Zheng-Biao Zou , Tai-Zong Wu , Chun-Lan Xie , Yuan Wang , Yan Li , Gang Zhang , Rong Chao , Lian-Zhong Luo , Li-Sheng Li , Xian-Wen Yang . neo-Dicitrinols A–C: Unprecedented PKS-NRPS hybrid citrinin dimers with ferroptosis inhibitory activity from the deep-sea-derived Penicillium citrinum W22. Chinese Chemical Letters, 2024, 35(12): 109723-. doi: 10.1016/j.cclet.2024.109723
-
[5]
Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
-
[6]
Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
-
[7]
Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
-
[8]
Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
-
[9]
Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
-
[10]
Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
-
[11]
Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
-
[12]
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
-
[13]
Aolei Tan , Xiaoxiao Ma . Exploring the functional roles of small-molecule metabolites in disease research: Recent advancements in metabolomics. Chinese Chemical Letters, 2024, 35(8): 109276-. doi: 10.1016/j.cclet.2023.109276
-
[14]
Ran Wu , Dongxu Jiang , Hao Hu , Chenyu Yang , Liang Qin , Lulu Chen , Zehui Hu , Hualei Xu , Jinrong Li , Haiqiang Liu , Hua Guo , Jinxiang Fu , Qichen Hao , Yijun Zhou , Jinchao Feng , Qiang Wang , Xiaodong Wang . 4-Aminoazobenzene: A novel negative ion matrix for enhanced MALDI tissue imaging of metabolites. Chinese Chemical Letters, 2024, 35(11): 109624-. doi: 10.1016/j.cclet.2024.109624
-
[15]
Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
-
[16]
Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
-
[17]
Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
-
[18]
Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
-
[19]
Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
-
[20]
Mianling Yang , Meehyein Kim , Peng Zhan . Modular miniaturized synthesis and in situ biological evaluation facilitate rapid discovery of potent MraY inhibitors as antibacterial agents. Chinese Chemical Letters, 2025, 36(2): 110455-. doi: 10.1016/j.cclet.2024.110455
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(744)
- HTML views(25)