海绵附生真菌Penicillium sp. G5A-11的次级代谢产物研究

doi:10.11978/2024075

热带海洋学报 ›› 2025, Vol. 44 ›› Issue (2): 73-83.doi: 10.11978/2024075CSTR: 32234.14.2024075

海绵附生真菌Penicillium sp. G5A-11的次级代谢产物研究

梁学诚¹^,²(), 畅文军², 戴好富², 周丽华¹(), 曾艳波¹^,²()

1.湖南人文科技学院研究生教育教学部, 湖南娄底 417000
2.中国热带农业科学院热带生物技术研究所, 海南省海洋生物资源功能性成分研究与利用重点实验室, 海南海口 571101

收稿日期:2024-04-03 修回日期:2024-05-21 出版日期:2025-03-10 发布日期:2025-04-11
通讯作者: 周丽华, 曾艳波
作者简介:
梁学诚(1997—), 男, 湖南省郴州市人, 硕士研究生。email: 835923919@qq.com
基金资助:
国家自然科学基金项目(41776093); 农业农村部财政专项(NFZX2021); 湖南省研究生教学平台项目(Xiang Jiao Tong [2019]370)

Secondary metabolites from the sponge-derived fungus Penicillium sp. G5A-11

LIANG Xuecheng¹^,²(), CHANG Wenjun², DAI Haofu², ZHOU Lihua¹(), ZENG Yanbo¹^,²()

1. Department of Graduate Education and Teaching, Hunan University of Humanities, Science and Technology, Loudi 417000, China
2. Hainan Provincial Key Laboratory for Functional Components Research and Utilization of Marine Bio-resources, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China

Received:2024-04-03 Revised:2024-05-21 Online:2025-03-10 Published:2025-04-11
Contact: ZHOU Lihua, ZENG Yanbo
Supported by:
National Natural Science Foundation of China(41776093); Financial Fund of the Ministry of Agriculture and Rural Affairs, P. R. of China(NFZX2021); Project of Postgraduate Teaching Platform in Hunan Province(Xiang Jiao Tong [2019]370)

摘要/Abstract

摘要：

文章对南海海绵共附生真菌Penicillium sp. G5A-11的化学成分及其细胞毒活性进行了研究。综合运用薄层色谱、硅胶柱色谱、凝胶柱色谱以及半制备型高效液相色谱等多种分离技术对海绵共附生真菌Penicillium sp. G5A-11的大米发酵产物进行分离纯化, 依据波谱数据和理化常数分析并结合相关的文献数据比对, 确定所分离化合物的结构, 并用四唑盐比色(methylthiazolyldiphenyl-tetrazolium bromide, MTT)法对所鉴定的化合物进行了细胞毒活性测定。结果显示: 从海绵共附生真菌Penicillium sp. G5A-11中共分离鉴定了17个化合物, 其结构分别鉴定为: N-乙酰酪胺 (1)、methyl 2-(6-hydroxybenzothiazol-4-yl) acetate (2)、R-甲羟内酯 (3)、烟酸 (4)、altechromone A (5)、2, 5-dimethy-7-hydroxychromone (6)、methyl 7-hydroxy-2-methylchromone-5-carboxylate (7)、stagonoculiepine [(2S, 5R)-1-formyl-1, 2, 3, 4-tetrahydro-5H-2, 5-epiminobenzo[b]azepin-5-yl acetates] (8)、(4R, 5S)-5-(hydroxymethyl)-5-methyl-4-(3-oxobutyl)dihydrofuran-2(3H)-one (9)、9α-hydroxy-1, 2, 3, 4, 5, 10, 19-heptanorergosta-7, 22-diene-6, 9-lact (10)、3β, 5α, 9α-trihydroxy-(22E, 24R)-ergosta-7, 22-dien-6-one (11)、过氧化麦角甾醇 (12)、(22E, 24R)-24-methylcholesta-2, 22-diene-3β, 5α, 6β-triol (13)、麦角甾醇(14)、豆甾醇/β-谷甾醇 (15)、3β, 5α-dihydroxy-(22E, 24R)-ergosta-7, 22-dien-6-one (16)和3β, 5α-dihydroxy-6β-methoxyergosta-7, 22-diene (17)。其中, 化合物7和9为新天然产物。肿瘤细胞毒活性测试结果表明, 化合物10对肿瘤细胞K562 (人慢性髓原白血病细胞)和SGC-7901 (人胃癌细胞)显示出细胞毒活性, 其半数最大抑制浓度值分别为(12.07 ± 0.12)μmol·L^-1和(13.17 ± 0.02)μmol·L^-1。

关键词: 海洋真菌, Penicillium sp., 化学成分, 细胞毒活性

Abstract:

This paper investigated the chemical constituents of Penicillium sp. G5A-11, which was isolated from a sponge in the South China Sea, and their cytotoxicity. Various separation methods, including thin layer chromatography, silica gel column chromatography, gel column chromatography, and semi-preparative high-performance liquid chromatography, were used to isolate compounds from solid-rice culture of this marine derived fungus. Spectroscopic data, along with physical and chemical properties, were utilized to identify the structures of the isolated compounds, and compared with literature data. Their cytotoxic activities were tested by the MTT (methylthiazolyldiphenyl-tetrazolium bromide) method. Seventeen compounds were identified from the marine fungus Penicillium jiangxiense, including N-acetyltryptamine (1), methyl 2-(6-hydroxybenzothiazol-4-yl) acetate (2), R-mevalonolactone (3), nicotinic acid (4), altechromone A (5), 2, 5-dimethy-7-hydroxychromone (6), methyl 7-hydroxy-2-methylchromone-5-carboxylate (7), stagonoculiepine [(2S, 5R)-1-formyl-1, 2, 3, 4-tetrahydro-5H-2, 5-epiminobenzo[b]azepin-5-yl acetates] (8), (4R, 5S)-5-(hydroxymethyl)-5-methyl-4-(3-oxobutyl) dihydrofuran-2(3H)-one (9), 9α-hydroxy-1, 2, 3, 4, 5, 10, 19-heptanorergosta-7, 22-diene-6, 9-lact (10), 3β, 5α, 9α-trihydroxy-(22E, 24R)-ergosta-7, 22-dien-6-one (11), ergosterol peroxide (5α, 8α-epidioxy-24(R)-methylcholesta-6, 22-dien-3β-ol) (12), (22E, 24R)-24-methylcholesta-2, 22-diene-3β, 5α, 6β-triol (13), ergosterol (14), stigmasterol/β-sitosterol (15), 3β, 5α-dihydroxy-(22E, 24R)-ergosta-7, 22-dien-6-one (16), and 3β, 5α-dihydroxy-6β-methoxyergosta-7, 22-diene (17). Among them, compounds 7 and 9 were new natural products. Cytotoxic activity tests showed that compound 10 was moderately cytotoxic to human chronic myeloid leukemia cells (K562) and human gastric cancer cells (SGC-7901) with IC₅₀ values of (12.07 ± 0.12) μmol·L^-1 and (13.17 ± 0.02) μmol·L^-1, respectively. However, the results of the anti-inflammatory activity test revealed that none of the compounds exhibited anti-inflammatory activity.

Key words: marine fungus, Penicillium sp., chemical constituent, cytotoxicity

中图分类号:

P734.43

梁学诚, 畅文军, 戴好富, 周丽华, 曾艳波. 海绵附生真菌Penicillium sp. G5A-11的次级代谢产物研究[J]. 热带海洋学报, 2025, 44(2): 73-83.

LIANG Xuecheng, CHANG Wenjun, DAI Haofu, ZHOU Lihua, ZENG Yanbo. Secondary metabolites from the sponge-derived fungus Penicillium sp. G5A-11[J]. Journal of Tropical Oceanography, 2025, 44(2): 73-83.

图/表 3

参考文献 36

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化合物	(IC₅₀ ± SD)/(μmol·L^-1)^a
化合物	K562	BEL-7402	SGC-7901	A549	Hela
10	12.07 ± 0.12	15.81 ± 0.26	13.17 ± 0.02	14.59 ± 0.03	20.92 ± 0.06
14	23.77 ± 0.22	23.20 ± 0.16	22.71 ± 0.11	44.01 ± 0.18	42.72 ± 0.52
顺铂^b	3.08 ± 0.05	4.02 ± 0.06	4.11 ± 0.02	1.93 ± 0.02	11.29 ± 0.15

海绵附生真菌Penicillium sp. G5A-11的次级代谢产物研究

Secondary metabolites from the sponge-derived fungus Penicillium sp. G5A-11

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