Two new benzophenones and one new natural amide alkaloid isolated from a mangrove-derived Fungus Penicillium citrinum

被引:31
作者
Zheng, Cai-Juan [1 ]
Liao, Hai-Xia [1 ,2 ,3 ]
Mei, Rong-Qing [1 ]
Huang, Guo-Lei [1 ]
Yang, Lu-Jia [2 ,3 ]
Zhou, Xue-Ming [1 ]
Shao, Tai-Ming [1 ,4 ]
Chen, Guang-Ying [1 ]
Wang, Chang-Yun [2 ,3 ]
机构
[1] Hainan Normal Univ, Coll Chem & Chem Engn, Key Lab Trop Med Plant Chem, Minist Educ, Haikou, Hainan, Peoples R China
[2] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao, Shandong, Peoples R China
[3] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao, Shandong, Peoples R China
[4] Hainan Inst Sci & Technol, Coll Chem & Mat Engn, Haikou, Hainan, Peoples R China
基金
中国国家自然科学基金;
关键词
Penicillium citrinum; penibenzophenone; amide alkaloid; cytotoxic activity; antibacterial activity; DERIVATIVES; GROWTH; POLYKETIDES; METABOLITES; ACID;
D O I
10.1080/14786419.2018.1460832
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two new compounds penibenzophenones A-B (1-2), and the synthetic alpha,beta-unsaturated amide alkaloid (E)-tert-butyl(3-cinnamamidopropyl)carbamate (4), newly identified as a natural product, alone with three known ones (3, 5-6) were isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Compound 1 was a chlorinated benzophenone. The structures of 1-6 were elucidated by extensive NMR spectral interpretation, MS data and X-ray analysis. The new compound 2 displayed cytotoxic activity against human A549 cell lines with an IC50 value of 15.7 mu g/mL, and 1 showed antibacterial activity against Staphylococcus aureus with a MIC value of 20 mu g/mL. [GRAPHICS] .
引用
收藏
页码:1127 / 1134
页数:8
相关论文
共 25 条
[1]   Biology-Orientated Synthesis of Putrescine Bisamides Gigantamide A, Dasyclamide, and Cucullamide [J].
Batwal, Ramesh U. ;
Argade, Narshinha P. .
SYNTHESIS-STUTTGART, 2013, 45 (20) :2888-2892
[2]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Keyzers, Robert A. ;
Munro, Murray H. G. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2017, 34 (03) :235-294
[3]   Complexity Generation in Fungal Polyketide Biosynthesis: A Spirocycle-Forming P450 in the Concise Pathway to the Antifungal Drug Griseofulvin [J].
Cacho, Ralph A. ;
Chooi, Yit-Heng ;
Zhou, Hui ;
Tang, Yi .
ACS CHEMICAL BIOLOGY, 2013, 8 (10) :2322-2330
[4]   PROTECTION OF AMINES BY THE PYRIDINE-2-SULFONYL GROUP AND ITS CLEAVAGE UNDER MILD CONDITIONS (SMI2 OR ELECTROLYSIS) [J].
GOULAOUICDUBOIS, C ;
GUGGISBERG, A ;
HESSE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5969-5972
[5]   New chlorinated diphenyl ethers from an Aspergillus species [J].
Hargreaves, J ;
Park, JO ;
Ghisalberti, EL ;
Sivasithamparam, K ;
Skelton, BW ;
White, AH .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (01) :7-10
[6]   New chlorinated xanthone and anthraquinone produced by a mangrove-derived fungus Penicillium citrinum HL-5126 [J].
He, Ke-Yao ;
Zhang, Cheng ;
Duan, Yi-Ru ;
Huang, Guo-Lei ;
Yang, Chun-Yan ;
Lu, Xing-Rui ;
Zheng, Cai-Juan ;
Chen, Guang-Ying .
JOURNAL OF ANTIBIOTICS, 2017, 70 (07) :823-827
[7]   Dihydroisocoumarins from the Mangrove-Derived Fungus Penicillium citrinum [J].
Huang, Guo-Lei ;
Zhou, Xue-Ming ;
Bai, Meng ;
Liu, Yu-Xin ;
Zhao, Yan-Lei ;
Luo, You-Ping ;
Niu, Yan-Yan ;
Zheng, Cai-Juan ;
Chen, Guang-Ying .
MARINE DRUGS, 2016, 14 (10)
[8]   Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum [J].
Huang, Song ;
Chen, Haiyan ;
Li, Wensheng ;
Zhu, Xinwei ;
Ding, Weijia ;
Li, Chunyuan .
MARINE DRUGS, 2016, 14 (10)
[9]  
INAMORI Y, 1983, CHEM PHARM BULL, V31, P4543
[10]   Solid phase synthesis of alkenes using the Horner-Wadsworth-Emmons reaction and monitoring by gel phase P-31 NMR [J].
Johnson, CR ;
Zhang, BR .
TETRAHEDRON LETTERS, 1995, 36 (51) :9253-9256