Alkaloids and Polyketides from Penicillium citrinum, an Endophyte Isolated from the Moroccan Plant Ceratonia siliqua

被引:85
作者
El-Neketi, Mona [1 ,2 ]
Ebrahim, Weaam [1 ,2 ]
Lin, Wenhan [3 ]
Gedara, Sahar [2 ]
Badria, Farid [2 ]
Saad, Hassan-Elrady A. [2 ]
Lai, Daowan [1 ]
Proksch, Peter [1 ]
机构
[1] Univ Dusseldorf, Inst Pharmazeut Biol & Biotechnol, D-40225 Dusseldorf, Germany
[2] Univ Mansoura, Fac Pharm, Dept Pharmacognosy, Mansoura 35516, Egypt
[3] Peking Univ, State Key Lab Nat & Biomimet Drugs, Hlth Sci Ctr, Beijing 100191, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2013年 / 76卷 / 06期
关键词
FUNGAL ENDOPHYTES; METABOLITE; QUINOLACTACIDE; DERIVATIVES; STECKII;
D O I
10.1021/np4001366
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The endophytic fungus Penicillium citrinum was isolated from a fresh stern of the Moroccan plant Ceratonia siliqua. Extracts of P. citrinum grown on rice and white bean media yielded five new compounds, namely, citriquinochroman (1), tanzawaic acids G and H (2 and 3), 6-methylcurvulinic acid (4), 8-methoxy-3,5-dimethylisoquinolin-6-ol (5), and one new natural product, 1,2,3,11b-tetrahydroquinolactacide (6), which had previously been described as a synthetic compound. In addition, 13 known compounds including seven alkaloids and six polyketides were isolated. The structures of the new compounds were unambiguously determined on the basis of one- and two-dimensional NMR spectroscopy as well as by high-resolution mass spectrometry. Citriquinochroman (1) features a new skeleton, consisting of quinolactacide and (3S)-6-hydroxy-8-methoxy-3,5-dimethylisochroman linked by a C-C bond. 1,2,3,11b-Tetrahydroquinolactacide (6) may be a biogenetic precursor of quinolactacide. Citriquinochroman (1) showed cytotoxicity against the murine lymphoma L5178Y cell line with an IC50 value of 6.1 mu M, while the other compounds were inactive (IC50 > 10 mu M) in this assay.
引用
收藏
页码:1099 / 1104
页数:6
相关论文
共 39 条
[1]   Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities [J].
Abe, M ;
Imai, T ;
Ishii, N ;
Usui, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2006, 70 (01) :303-306
[2]   Quinolactacide, a new quinolone insecticide from Penicillium citrinum Thom F 1539 [J].
Abe, M ;
Imai, T ;
Ishii, N ;
Usui, M ;
Okuda, T ;
Oki, T .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2005, 69 (06) :1202-1205
[3]   Fungal endophytes from higher plants: a prolific source of phytochemicals and other bioactive natural products [J].
Aly, Amal H. ;
Debbab, Abdessamad ;
Kjer, Julia ;
Proksch, Peter .
FUNGAL DIVERSITY, 2010, 41 (01) :1-16
[4]   Fungal endophytes: unique plant inhabitants with great promises [J].
Aly, Amal Hassan ;
Debbab, Abdessamad ;
Proksch, Peter .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2011, 90 (06) :1829-1845
[5]  
[Anonymous], DICT FUNGI
[6]   Synthesis and absolute stereochemistry of tanzawaic acid (GS-1302) [J].
Arimoto, H ;
Nishimura, K ;
Kuramoto, M ;
Uemura, D .
TETRAHEDRON LETTERS, 1998, 39 (51) :9513-9516
[7]   Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia [J].
Ashour, Mohamed ;
Edrada, RuAngelie ;
Ebel, Rainer ;
Wray, Victor ;
Waetjen, Wim ;
Padmakumar, K. ;
Mueller, Werner E. G. ;
Lin, Wen Han ;
Proksch, Peter .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (11) :1547-1553
[8]   3,6,8-TRIHYDROXY-1-METHYLXANTHONE - ANTIBACTERIAL METABOLITE FROM PENICILLIUM-PATULUM [J].
BROADBENT, D ;
MABELIS, RP ;
SPENCER, H .
PHYTOCHEMISTRY, 1975, 14 (09) :2082-2083
[9]  
Clinical and Laboratory Standards Institute, 2018, METH DIL ANT SUSC TE
[10]   NEW ISOCHROMAN MYCOTOXIN ISOLATED FROM PENICILLIUM-STECKII [J].
COX, RH ;
HERNANDEZ, O ;
DORNER, JW ;
COLE, RJ ;
FENNELL, DI .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1979, 27 (05) :999-1001