海洋真菌Phaeosphaeriopsis sp. ZYX-Z-811次生代谢产物研究

doi:10.11978/2023095

热带海洋学报 ›› 2024, Vol. 43 ›› Issue (2): 121-127.doi: 10.11978/2023095CSTR: 32234.14.2023095

海洋真菌Phaeosphaeriopsis sp. ZYX-Z-811次生代谢产物研究

全苗苗¹(), 马青云², 杨理², 谢晴宜², 戴好富², 郝玉娥¹(), 赵友兴²()

1.南华大学衡阳医学院公共卫生学院卫生检验与检疫系, 湖南衡阳 421000
2.中国热带农业科学院热带生物技术研究所海口市热带天然产物研究与利用重点实验室, 海南海口 571101

收稿日期:2023-07-10 修回日期:2023-08-25 出版日期:2024-03-10 发布日期:2024-03-26
作者简介:
全苗苗(1997—), 女, 湖南省衡阳市人, 硕士研究生, 研究方向为海洋微生物。email: 1345610909@qq.com
基金资助:
农业农村部财政专项项目(NFZX2021); 财政部和农业农村部国家现代农业产业技术体系专项(CARS-21); 社会公益类科研机构改革专项(ITBBQDF2023004)

Study on the secondary metabolites of marine fungus Phaeospheriopsis sp. ZYX-Z-811

QUAN Miaomiao¹(), MA Qingyun², YANG Li², XIE Qingyi², DAI Haofu², HAO Yu’e¹(), ZHAO Youxing²()

1. Department of Public Health Laboratory Sciences, School of Public Health, Hengyang Medical School, University of South China, Hengyang 421000, China
2. Haikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101,China

Received:2023-07-10 Revised:2023-08-25 Online:2024-03-10 Published:2024-03-26
Supported by:
Special Finance Project of Ministry of Agriculture and Rural Affairs(NFZX2021); Special Project of the Ministry of Finance and the Ministry of Agriculture and Rural Affairs on the National Modern Agricultural Industrial Technology System(CARS-21); Special projects for the reform of public scientific research institutions(ITBBQDF2023004)

摘要/Abstract

摘要：

对海洋真菌Phaeosphaeriopsis sp. ZYX-Z-811发酵液中次生代谢产物进行分离鉴定, 并评价其生物活性。采用正相硅胶柱色谱、反向C18柱色谱、高效液相色谱、SephadexLH-20凝胶柱色谱等技术进行分离纯化, 共分离得到10个化合物, 利用核磁及红外和紫外波谱技术对分离的单体化合物进行结构鉴定, 分别为4-epi-lignicol (1)、lignicol (2)、6-demethylkigelin (3)、6,8-dihydroxy-3,4,7-trimethylisocoumarin (4)、6,7-dimethoxymellein (5)、musaone A (6)、2-(4-hydroxyphenyl)ethylacetate (7)、3-吲哚甲醛 (8)、吲哚-3-乙酸甲酯 (9)、对羟基苯甲酸甲酯(10), 其中化合物1为未发表的化合物, 文章通过电子圆二色谱(electrostatic circular dichroism, ECD)计算确定了其绝对构型。对这些化合物分别进行抗氧化和α-糖苷酶抑制活性评价, 发现化合物10有弱的抗氧化活性。

关键词: 海洋真菌, Phaeosphaeriopsis sp., 次生代谢产物, 生物活性

Abstract:

The secondary metabolites of marine fungus Phaeosporiopsis sp. ZYX-Z-811 were isolated and identified, and their biological activities were evaluated. The compounds were separated and purified by Silica gel, C18, Sephadex LH-20 column chromatography and high performance liquid chromatography (HPLC), ten compounds were separated, and their structures were identified by NMR, IR and UV spectroscopic methods. Ten compounds were identified as 4-epi-lignicol (1), lignicol (2), 6-demethylkigelin (3), 6, 8-dihydroxy-3, 4, 7-trimethylisocoumarin (4), 6, 7-dimethoxymellein (5), musaone A (6), 2-(4-hydroxyphenyl)ethylacetate (7), 3-indole formaldehyde (8), indole-3-acetic acid methyl ester (9), methyl p-hydroxybenzoate (10), among which compound 1 was not published in journal, and the absolute configuration was determined by ECD calculation. These compounds were evaluated for antioxidant activity and α-glucosidase in hibitoryactivity, respectively, compound 10 showed weak antioxidant activities.

Key words: marine-derived fungus, Phaeosphairiopsis sp., secondary metabolites, bioactivity

全苗苗, 马青云, 杨理, 谢晴宜, 戴好富, 郝玉娥, 赵友兴. 海洋真菌Phaeosphaeriopsis sp. ZYX-Z-811次生代谢产物研究[J]. 热带海洋学报, 2024, 43(2): 121-127.

QUAN Miaomiao, MA Qingyun, YANG Li, XIE Qingyi, DAI Haofu, HAO Yu’e, ZHAO Youxing. Study on the secondary metabolites of marine fungus Phaeospheriopsis sp. ZYX-Z-811[J]. Journal of Tropical Oceanography, 2024, 43(2): 121-127.

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碳位	化合物1		化合物2
碳位	δ_C	δ_H	δ_C	δ_H
1	169.3		169.0
3	78.1	4.63, qd (J=6.5, 2.0Hz)	80.0	4.45, m
4	65.2	4.34, d (J=2.1Hz)	67.7	4.38, d (J=5.2Hz)
5	138.2		139.8
6	107.4	6.46, s	105.8	6.65, s
7	157.0		158.0
8	134.5		134.4
9	155.6		156.0
10	99.9		99.6
11	15.8	1.35, d (J=6.5Hz)	18.1	1.35, d (J=6.0Hz)
12	59.9	3.71, s	60.3	3.70, s

海洋真菌Phaeosphaeriopsis sp. ZYX-Z-811次生代谢产物研究

Study on the secondary metabolites of marine fungus Phaeospheriopsis sp. ZYX-Z-811

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化合物	清除率/%
4-epi-lignicol	25.2
lignicol	12.7
6-demethylkigelin	16.2
6,8-dihydroxy-3,4,7-trimethylisocoumarin	17.8
6,7-dimethoxymellein	25.8
musaone A	6.9
2-(4-hydroxyphenyl)ethylacetate	25.8
3-吲哚甲醛	18.9
吲哚-3-乙酸甲酯	2.1
对羟基苯甲酸甲酯	50.6
抗坏血酸	96.8

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