Alkaloids and Polyketides from Penicillium citrinum, an Endophyte Isolated from the Moroccan Plant Ceratonia siliqua
Alkaloids and Polyketides from Penicillium citrinum, an Endophyte Isolated from the Moroccan Plant Ceratonia siliqua
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DOI：
10.1021/np4001366
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发表时间：
2013-06-01
影响因子：
5.1
通讯作者：
Proksch, Peter
中科院分区：
文献类型：
--
作者：
El-Neketi, Mona;Ebrahim, Weaam;Proksch, Peter
内生真菌桔青霉（Penicillium citrinum）是从摩洛哥植物角豆（Ceratonia siliqua）的新鲜茎中分离得到的。从生长在水稻和白色菜豆培养基上的桔黄孢霉（P. citrinum）提取物中分离得到5个新化合物，即桔喹色满（citriquinochroman，1）、tanzawaic acids G和H（tanzawaic acids G和H，2和3）、6-甲基曲维酸（6-methylcurvulinic acid，4）、8-甲氧基-3，5-二甲基异喹啉-6-醇（8-methoxy-3，5-dimethylisoquinolin-6-ol，5）和1个新的天然产物，1，2，3，11 b-四氢喹啉酸内酯（6），该化合物以前曾被描述为一种合成化合物。此外，还分离得到13个已知化合物，包括7个生物碱和6个聚酮化合物。新化合物的结构是明确确定的基础上的一维和二维NMR光谱以及高分辨率质谱。西喹并色满（1）是一个新的骨架，由喹诺酮和（3S）-6-羟基-8-甲氧基-3，5-二甲基异色满通过C-C键连接而成。1，2，3，11b-四氢喹诺酮（6）可能是喹诺酮的生物前体。西喹并色满（1）显示出对鼠淋巴瘤L5178 Y细胞系的细胞毒性，其IC 50值为6.1 μ M，而其它化合物在该测定中无活性（IC 50> 10 μ M）。
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.