北部湾软珊瑚共附生真菌Scopulariopsis sp. SCSIO 41229次级代谢产物研究

doi:10.11978/2024184

热带海洋学报 ›› 2025, Vol. 44 ›› Issue (4): 170-176.doi: 10.11978/2024184

北部湾软珊瑚共附生真菌Scopulariopsis sp. SCSIO 41229次级代谢产物研究

何燕春¹^,²(), 徐淑娜¹^,², 刘永宏¹, 杨斌¹()

1.中国科学院南海海洋研究所, 热带海洋生物资源与生态重点实验室, 广东广州 510301
2.中国科学院大学, 北京 100049

收稿日期:2024-09-29 修回日期:2024-10-18 出版日期:2025-07-10 发布日期:2025-07-31
通讯作者: 杨斌
作者简介:
何燕春(2000—), 女, 湖北省随州市人, 在读硕士, 研究方向: 海洋药物化学。email: heyanchun22@mails.ucas.ac.cn
基金资助:
国家自然科学基金项目(42276128)

Study on the secondary metabolites of the soft coral-derived fungus Scopulariopsis sp. SCSIO 41229 from the Beibu Gulf

HE Yanchun¹^,²(), XU Shuna¹^,², LIU Yonghong¹, YANG Bin¹()

1. Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
2. University of Chinese Academy of Sciences, Beijing 100049, China

Received:2024-09-29 Revised:2024-10-18 Online:2025-07-10 Published:2025-07-31
Contact: YANG Bin
Supported by:
National Natural Science Foundation of China(42276128)

摘要/Abstract

摘要：

本文旨在研究北部湾软珊瑚共附生真菌Scopulariopsis sp. SCSIO 41229的次级代谢产物。采用正相硅胶柱层析、反相硅胶柱层析、薄层色谱、高效液相色谱等多种方法对该菌株的发酵产物进行分离纯化, 通过核磁共振、质谱等波谱学方法并结合理化性质、文献数据比对进行结构鉴定。从中分离得到9个化合物, 分别为neocyclocitrinols A—D(1—4)、penicillenol A₂(5)、环(D-苯丙-L-异亮)二肽(6)、环(L-色-L-苯丙)二肽(7)、(+)-penicilactam A(8)和(8E, 10E)-7-oxo-8, 10-heptadecadienoic acid(9)。化合物1—9均为首次从Scopulariopsis sp.真菌中分离得到。生物活性测试显示, 化合物2、4具有弱抗氧化活性, 化合物2、4和8具有弱乙酰胆碱酯酶抑制活性。

关键词: 珊瑚共附生真菌, 次级代谢产物, Scopulariopsis sp., C25甾体化合物

Abstract:

In this study, we aimed to investigate the secondary metabolites from the coral-derived fungus Scopulariopsis sp. SCSIO 41229, collected from the Beibu Gulf. The fungal extract was isolated using silica gel column chromatography, reverse-phase silica gel column chromatography, thin-layer chromatography (TLC), and high-performance liquid chromatography (HPLC). The structures of the isolated compounds were elucidated through nuclear magnetic resonance (NMR), mass spectrometry (MS), and literature comparison. Nine known compounds were identified, including neocyclocitrinols A-D (1-4), penicillenol A₂ (5), cyclo-(D-Phe-L-Ile) (6), cyclo-(L-tryptophyl-L-phenylalanyl) (7), (+)-penicilactam A (8), and (8E, 10E)-7-oxo-8, 10-heptadecadienoic acid (9). Notably, these compounds were reported from Scopulariopsis sp. for the first time. Bioassays indicated that compounds 2 and 4 exhibited weak antioxidant activity, while compounds 2, 4, and 8 showed weak acetylcholinesterase inhibitory activity.

Key words: coral-derived fungus, secondary metabolites, Scopulariopsis sp., C25 steroids

中图分类号:

O629

何燕春, 徐淑娜, 刘永宏, 杨斌. 北部湾软珊瑚共附生真菌Scopulariopsis sp. SCSIO 41229次级代谢产物研究[J]. 热带海洋学报, 2025, 44(4): 170-176.

HE Yanchun, XU Shuna, LIU Yonghong, YANG Bin. Study on the secondary metabolites of the soft coral-derived fungus Scopulariopsis sp. SCSIO 41229 from the Beibu Gulf[J]. Journal of Tropical Oceanography, 2025, 44(4): 170-176.

图/表 3

图1

图2

表1

化合物1—4的1H NMR和13C NMR数据表"

No.	1		2		3		4
No.	δ_H, mult, J/Hz	δ_C, mult	δ_H, mult, J/Hz	δ_C, mult	δ_H, mult, J/Hz	δ_C, mult	δ_H, mult, J/Hz	δ_C, mult
1	5.55, dd, 8.4, 6.2	122.1, CH	5.55, dd, 8.4, 6.2	122.1, CH	5.55, dd, 8.3, 6.2	122.1, CH	5.55, dd, 8.4, 6.2	122.1, CH
2a	2.07, ddt, 13.0, 9.0, 2.2	36.0, CH₂	2.07, ddt, 13.0, 8.3, 2.2	36.0, CH₂	2.07, ddt, 13.0, 8.4, 2.2	36.0, CH₂	2.07, ddt, 13.1, 8.4, 2.2	36.0, CH₂
2b	2.34, ddd, 13.2, 11.1, 6.2	36.0, CH₂	2.34, ddd, 13.3, 11.1, 6.3	36.0, CH₂	2.34, ddd, 13.3, 11.1, 6.3	36.0, CH₂	2.39~2.30, m	36.0, CH₂
3	3.15~3.08, m	63.1, CH	3.15~3.09, m	63.1, CH	3.14~3.09, m	63.1, CH	3.16~3.07, m	63.1, CH
4a	2.60, m	41.4, CH₂	2.66~2.59, m	41.4, CH₂	2.65~2.60, m	41.4, CH₂	2.65~2.60, m	41.4, CH₂
4b	1.53~1.49, m	41.4, CH₂	1.57~1.51, m	41.4, CH₂	1.55~1.53, m	41.4, CH₂	1.54~1.51, m	41.4, CH₂
5	2.71~2.66, m	48.1, CH	2.70~2.66, m	48.1, CH	2.70~2.67, m	48.1, CH	2.68, m	48.1, CH
6		204.1, C		204.2, C		204.2, C		204.2, C
7	5.43~5.41, s	124.3, CH	5.42, s	124.3, CH	5.43~5.41, s	124.3, CH	5.42, s	124.3, CH
8		157.0, C		157.0, C		157.1, C		157.0, C
9	2.84, dd, 11.9, 5.8	53.3, CH	2.85, dd, 12.0, 5.7	53.2, CH	2.85, dd, 11.8, 5.7	53.3, CH	2.85, dd, 11.8, 5.7	53.3, CH
10		145.6, C		145.6, C		145.6, C		145.6, C
11a	1.56, dt, 15.9, 6.3	27.4, CH₂	1.57~1.51, m	27.5, CH₂	1.59~1.55, m	27.4, CH₂	1.59~1.53, m	27.5, CH₂
11b	1.86~1.78, m	27.4, CH₂	1.86~1.79, m	27.5, CH₂	1.86~1.78, m	27.4, CH₂	1.86~1.78, m	27.5, CH₂
12a	1.43, td, 13.6, 13.2, 4.8	36.9, CH₂	1.51~1.47, m	37.3, CH₂	1.53~1.49, m	36.9, CH₂	1.51~1.46, m	37.3, CH₂
12b	1.75, ddd, 12.4, 8.6, 3.9	36.9, CH₂	1.75, td, 12.8, 4.3	37.3, CH₂	1.77, m	36.9, CH₂	1.76, dd, 12.7, 4.3	37.3, CH₂
13		47.0, C		46.7, C		46.9, C		46.6, C
14	2.27, t, 9.7	54.3, CH	2.25, q, 9.5, 8.9	54.5, CH	2.26, t, 9.8	54.3, CH	2.28~2.20, m	54.5, CH
15	1.56, dt, 15.9, 6.3	22.4, CH₂	1.57~1.51, m	22.3, CH₂	1.59~1.55, m	22.4, CH₂	1.59~1.53, m	22.3, CH₂
15	1.56, dt, 15.9, 6.3	22.4, CH₂	1.57~1.51, m	22.3, CH₂	1.59~1.55, m	22.4, CH₂	1.54~1.51, m	22.3, CH₂
16a	1.75, ddd, 12.4, 8.6, 3.9	23.7, CH₂	1.81, ddd, 10.7, 4.3, 2.4	23.8, CH₂	1.86~1.78, m	23.7, CH₂	1.86~1.78, m	23.8, CH₂
16b	1.70~1.67, m	23.7, CH₂	1.70~1.65, m	23.8, CH₂	1.70~1.65, m	23.7, CH₂	1.59~1.53, m	23.8, CH₂
17	2.22, td, 9.3, 8.7, 2.0	59.0, CH	2.25, q, 9.5, 8.9	58.6, CH	2.22, td, 9.3, 8.6, 2.0	58.9, CH	2.28~2.20, m	58.6, CH
18	2.47, d, 5.9	27.2, CH₂	2.47, d, 5.8	27.2, CH₂	2.47, d, 5.8	27.2, CH₂	2.47, d, 4.1	27.2, CH₂
19	0.53, s	13.5, CH₃	0.49, s	13.3, CH₃	0.53, s	13.4, CH₃	0.49, s	13.3, CH₃
20		135.8, C		135.8, C		135.0, C		135.0, C
21	1.66, d, 1.3	17.4, CH₃	1.68, d, 1.2	18.9, CH₃	1.63, d, 1.3	17.3, CH₃	1.65, s	18.8, CH₃
22	5.15, dt, 8.8, 1.2	128.2, CH	5.16, dt, 8.8, 1.3	127.1, CH	5.21, dt, 8.4, 1.3	128.3, CH	5.22, d, 8.3	127.3, CH
23	3.95, t, 7.8	72.0, CH	3.97~3.93, m	72.2, CH	4.05, dd, 8.4, 4.1	71.5, CH	4.08, d, 7.9	71.7, CH
24	3.40, d, 6.6	70.3, CH	3.39, d, 6.5	70.4, CH	3.50, s	69.8, CH	3.4, d, 5.0	69.8, CH
25	0.96, d, 6.3	18.9, CH₃	0.94, d, 6.3	19.1, CH₃	0.97, d, 6.3	18.6, CH₃	0.96, d, 6.3	18.3, CH₃
3-OH	4.62, d, 4.3		4.62, d, 4.3		4.63, d, 4.3		4.62, d, 4.4
23-OH	4.48, s		4.50, d, 4.2		4.39, s		4.42~4.36, m
24-OH	4.38, s		4.36, s		4.32~4.29, m		4.28, s

表1

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北部湾软珊瑚共附生真菌Scopulariopsis sp. SCSIO 41229次级代谢产物研究

Study on the secondary metabolites of the soft coral-derived fungus Scopulariopsis sp. SCSIO 41229 from the Beibu Gulf

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