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 shu

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

1.
a Jiangxi Key Labrotory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China;
2.
b College of Science, Jiangxi Agricultural University, Nanchang 330045, China

Corresponding author: Bin-Gui Wang,
Received Date: 13 November 2014
Available Online: 12 January 2015
Fund Project: Financial support from the National Natural Science Foundation of China (No. 31270403) (No. 31270403)

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.
- Mangrove-derived fungus,
- Penicillium brocae,
- Secondary metabolites,
- Pyranonigrin F,
- Antibacterial activity
1. [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [11] G.M. Sheldrick, SADABS, Software for empirical absorption correction, University of Gottingen, Germany, 1996.
12. [12]
  [12] G.M. Sheldrick, SHELXTL, Structure determination software programs, Bruker Analytical X-ray System Inc., Wisconsin, 1997.
13. [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]
  [14] G. Schlingmann, T. Taniguchi, H.Y. He, et al., Reassessing the structure of pyranonigrin, J. Nat. Prod. 70 (2007) 1180-1187.
15. [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]
  [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. [2]
  Jiaxi Wang , Zhiwei Gao , Hao Liang , Qianyue Liu , Weiqian Jin , Huyang Gao , Bailei Wang , Ruikai Zhu , Jiahao Huang , Xiaowen Li , Xingmou Wu , Weijiu Mo , Yinhan Liao , Ming Gao , Xiaojie Li , Cuiping Li . NIR stimulated epigallocatechin gallate loaded polydopamine with enhanced antibacterial and ROS scavenging abilities for improved infectious wound healing. Chinese Chemical Letters, 2025, 36(7): 110569-. doi: 10.1016/j.cclet.2024.110569
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Yang Li , Jiachen Li , Daidi Fan . 二硫化钼纳米片的制备及其纳米酶性能探究——介绍一个大学化学综合实验. University Chemistry, 2025, 40(8): 233-240. doi: 10.12461/PKU.DXHX202410016
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
11. [11]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  Yuyao Guan , Baoting Yu , Jun Ding , Tingting Sun , Zhigang Xie . BODIPY photosensitizers for antibacterial photodynamic therapy. Chinese Chemical Letters, 2025, 36(8): 110645-. doi: 10.1016/j.cclet.2024.110645
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1229)
HTML views(37)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142