New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081

被引:25
|
作者
Prompanya, Chadaporn [1 ,2 ]
Dethoup, Tida [3 ]
Gales, Luis [1 ,4 ]
Lee, Michael [5 ]
Pereira, Jose A. C. [1 ]
Silva, Artur M. S. [6 ,7 ]
Pinto, Madalena M. M. [2 ,8 ]
Kijjoa, Anake [1 ,2 ]
机构
[1] Univ Porto, ICBAS Inst Ciencias Biomed Abel Salazar, Rua Jorge Viterbo Ferreira 228, P-4050313 Oporto, Portugal
[2] Interdisciplinary Ctr Marine & Environm Res CIIMA, Rua Bragas 289, P-4050313 Oporto, Portugal
[3] Kasetsart Univ, Dept Plant Pathol, Fac Agr, Bangkok 10900, Thailand
[4] Univ Porto, IBMC, Rua Jorge Viterbo Ferreira 228, P-4050313 Oporto, Portugal
[5] Univ Leicester, Dept Chem, Univ Rd, Leicester LE7 RH, Leics, England
[6] Univ Aveiro, Dept Quim, P-3810193 Aveiro, Portugal
[7] Univ Aveiro, QOPNA, P-3810193 Aveiro, Portugal
[8] Univ Porto, Dept Ciencias Quim, Fac Farm, Lab Quim Organ, Rua Jorge Viterbo Ferreira 228, P-4050313 Oporto, Portugal
来源
MARINE DRUGS | 2016年 / 14卷 / 07期
关键词
Neosartorya quadricincta KUFA 0081; marine-derived fungus; polyketides; pentaketides; benzoic acid derivatives; Clathria reinwardti; SOIL FUNGI; ASPERGILLUS; CONSTITUENTS; FOMANNOXIN;
D O I
10.3390/md14070134
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two new pentaketides, including a new benzofuran-1-one derivative (1) and a new isochromen-1-one (5), and seven new benzoic acid derivatives, including two new benzopyran derivatives (2a, b), a new benzoxepine derivative (3), two new chromen-4-one derivatives (4b, 7) and two new benzofuran derivatives (6a, b), were isolated, together with the previously reported 2,3-dihydro-6-hydroxy-2,2-dimethyl-4H-1-benzopyran-4-one (4a), from the culture of the marine sponge-associated fungus Neosartorya quadricincta KUFA 0081. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compounds 1, 2a, 4b, 5, 6a and 7, the absolute configurations of their stereogenic carbons were determined by an X-ray crystallographic analysis. None of the isolated compounds were active in the tests for antibacterial activity against Gram-positive and Gram-negative bacteria, as well as multidrug-resistant isolates from the environment (MIC > 256 mu g/mL), antifungal activity against yeast (Candida albicans ATTC 10231), filamentous fungus (Aspergillus fumigatus ATTC 46645) and dermatophyte (Trichophyton rubrum FF5) (MIC > 512 mu g/mL) and in vitro growth inhibitory activity against the MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma) cell lines (GI(50) > 150 mu M) by the protein binding dye SRB method.
引用
收藏
页数:26
相关论文
共 50 条
  • [31] Erubescensoic Acid, a New Polyketide and a Xanthonopyrone SPF-3059-26 from the Culture of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA 0220 and Antibacterial Activity Evaluation of Some of Its Constituents
    Kumla, Decha
    Dethoup, Tida
    Gales, Luis
    Pereira, Jose A.
    Freitas-Silva, Joana
    Costa, Paulo M.
    Silva, Artur M. S.
    Pinto, Madalena M. M.
    Kijjoa, Anake
    MOLECULES, 2019, 24 (01):
  • [32] New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C28 Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767
    Machado, Fatima P.
    Rodrigues, Ines C.
    Georgopolou, Aikaterini
    Gales, Luis
    Pereira, Jose A.
    Costa, Paulo M.
    Mistry, Sharad
    Ghoran, Salar Hafez
    Silva, Artur M. S.
    Dethoup, Tida
    Sousa, Emilia
    Kijjoa, Anake
    MARINE DRUGS, 2023, 21 (03)
  • [33] Brasilianoids A-F, New Meroterpenoids From the Sponge-Associated Fungus Penicillium brasilianum
    Zhang, Jianping
    Yuan, Bochuan
    Liu, Dong
    Gao, Shuang
    Proksch, Peter
    Lin, Wenhan
    FRONTIERS IN CHEMISTRY, 2018, 6
  • [34] Induction of new metabolites from sponge-associated fungus Aspergillus carneus by OSMAC approach
    Ozkaya, Ferhat Can
    Ebrahim, Weaam
    El-Neketi, Mona
    Tanrikul, T. Tansel
    Kalscheuer, Rainer
    Mueller, Werner E. G.
    Guo, Zhiyong
    Zou, Kun
    Liu, Zhen
    Proksch, Peter
    FITOTERAPIA, 2018, 131 : 9 - 14
  • [35] Structurally diverse sesquiterpenoids and polyketides from a sponge-associated fungus Aspergillus sydowii SCSI041301
    Liu, Nianzhen
    Peng, Shuai
    Yang, Jie
    Cong, Ziwen
    Lin, Xiuping
    Liao, Shengrong
    Yang, Bin
    Zhou, Xuefeng
    Zhou, Xiaojiang
    Liu, Yonghong
    Wang, Junfeng
    FITOTERAPIA, 2019, 135 : 27 - 32
  • [36] Isocoumarin Derivatives from the Sponge-Associated Fungus Peyronellaea glomerata with Antioxidant Activities
    Zhao, Yang
    Liu, Dong
    Proksch, Peter
    Yu, Siwang
    Lin, Wenhan
    CHEMISTRY & BIODIVERSITY, 2016, 13 (09) : 1186 - 1193
  • [37] New polyketides and norterpenoids from the marine sponge Diacarnus megaspinorhabdosa
    Miao, Xian-Xian
    Chen, Meng-Xuan
    Zhu, Hong-Rui
    Sun, Fan
    Hong, Li-Li
    Wu, Wen-Hui
    Lin, Hou-Wen
    Yang, Fan
    TETRAHEDRON, 2020, 76 (14)
  • [38] Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri
    Lan, Wen-Jian
    Fu, Sheng-Jiao
    Xu, Meng-Yang
    Liang, Wan-Ling
    Lam, Chi-Keung
    Zhong, Guo-Hua
    Xu, Jun
    Yang, De-Po
    Li, Hou-Jin
    MARINE DRUGS, 2016, 14 (01):
  • [39] Varioxiranols I-L, new lactones from a sponge-associated Emericella variecolor fungus
    Wu, Qi
    Long, Hai-Lin
    Liu, Dong
    Proksch, Peter
    Lin, Wen-Han
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2015, 17 (12) : 1137 - 1145
  • [40] Lobophorin C and D, New Kijanimicin Derivatives from a Marine Sponge-Associated Actinomycetal Strain AZS17
    Wei, Rong-Bian
    Xi, Tao
    Li, Jing
    Wang, Ping
    Li, Fu-Chao
    Lin, Yong-Cheng
    Qin, Song
    MARINE DRUGS, 2011, 9 (03): : 359 - 368