海洋本草软珊瑚共附生真菌Aspergillus terreus EGF7-0-1中γ-芳环丁烯内酯类化合物研究(I)
何悦铭、赵立凝为共同第一作者
何悦铭(1998—), 男, 广东江门人, 硕士研究生, email: 20211110071@stu.gzucm.edu.cn; |
赵立凝(1976—), 女, 河北秦皇岛人, 硕士研究生, 副教授, email: 459036877@qq.com |
Copy editor: 孙翠慈
收稿日期: 2024-03-05
修回日期: 2024-03-17
网络出版日期: 2024-04-02
基金资助
国家自然科学基金项目(82273845)
广东省自然资源厅专项(GDNRC[2023]37)
广东省自然资源厅专项(GDNRC[2020]039)
广东省自然资源厅专项(GDNRC[2021]048)
广东省大学生创新创业项目(202310572224)
广东省大学生创新创业项目(202310572291)
γ-Aromatic butenolides lignans from soft coral-associated symbiotic and epiphytic fungi Aspergillus terreus EGF7-0-1(I)
Copy editor: SUN Cuici
Received date: 2024-03-05
Revised date: 2024-03-17
Online published: 2024-04-02
Supported by
National Natural Science Foundation of China(82273845)
Special Fund of Guangdong Provincial Department of Natural Resources(GDNRC[2023]37)
Special Fund of Guangdong Provincial Department of Natural Resources(GDNRC[2020]039)
Special Fund of Guangdong Provincial Department of Natural Resources(GDNRC[2021]048)
Innovation and Entrepreneurship Program for College Students in Guangdong Province(202310572224)
Innovation and Entrepreneurship Program for College Students in Guangdong Province(202310572291)
为了从海洋微生物中寻找结构新颖的次生代谢产物, 本文采用大米培养基对海洋本草软珊瑚共附生真菌Aspergillus terreus EGF7-0-1进行规模发酵, 运用薄层色谱、柱层析和高效液相色谱等多种色谱技术对发酵产物进行分离纯化, 通过核磁共振波谱、高分辨质谱和旋光光谱等多种光谱学方法, 并结合文献数据比对确定了8个γ-芳环丁烯内酯类化合物: butyrolactones I—V(1—5)、aspernolide E(6)、asperteretal D(7)和 terrusnolide A(8)。首次对化合物1—8进行体外抑制酪氨酰-DNA磷酸二酯酶I (tyrosyl-DNA phosphodiesterase 1, TDP1)活性测试, 均无抑制作用。本研究为TDP1抑制剂的发现提供借鉴。
关键词: 海洋本草软珊瑚; Aspergillus terreus; γ-芳环丁烯内酯类; 结构鉴定; TDP1抑制剂
何悦铭 , 赵立凝 , 陈欣琪 , 何嘉鸿 , 樊浩 , 陈乐怡 , 张翠仙 , 何细新 . 海洋本草软珊瑚共附生真菌Aspergillus terreus EGF7-0-1中γ-芳环丁烯内酯类化合物研究(I)[J]. 热带海洋学报, 2025 , 44(1) : 146 -153 . DOI: 10.11978/2024051
In order to discover the novel and bioactive secondary metabolites, the soft coral-associated symbiotic and epiphytic fungi Aspergillus terreus EGF7-0-1 were fermented in rice media. The secondary metabolites were isolated using various chromatographic technologies, yielding eight γ-aromatic butenolide lignans. Based on nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HR-ESI-MS) and comparison with the literature, their structures were determined to be butyrolactones I−V (1−5), aspernolide E (6), asperteretal D (7) and terrusnolide A (8). In this study, the inhibitory activity of these compounds against TDP1 (Tyrosyl-DNA phosphodiesterase 1) in vitro was studied for the first time, but it was unfortunate that compounds 1−8 did not show any inhibitory abilities against TDP1. This study provides theoretical data for the discovery of TDP1 inhibitors.
表1 化合物1—4的NMR数据表(CD3OD)Tab. 1 NMR data of 1−4 in CD3OD |
No. | 1 | 2 | 3 | 4 | ||||
---|---|---|---|---|---|---|---|---|
δH, mult, (J in Hz) | δC, type | δH, mult, (J in Hz) | δC, type | δH, mult, (J in Hz) | δC, type | δH, mult, (J in Hz) | δC, type | |
2 | / | 170.3, C | / | 171.9, C | / | 171.5, C | / | 171.1, C |
3 | / | 139.4, C | / | 140.3, C | / | 139.8, C | / | 139.8, C |
4 | / | 129.2, C | / | 130.0, C | / | 129.3, C | / | 128.6, C |
5 | / | 86.7, C | / | 86.9, C | / | 86.7, C | / | 86.9, C |
6 | a 3.45, d, 15.0 b 3.55, d, 15.0 | 39.4, CH2 | 3.45, s | 39.4, CH2 | 3.44, s | 39.5, CH2 | a 3.09, d, 14.7 b 3.43, d, 14.7 | 39.6, CH2 |
7 | / | 171.3, C | / | 171.9, C | / | 170.3, C | / | 170.5, C |
8 | 3.70, s | 53.9, CH3 | 3.77, s | 53.8, CH3 | 3.78, s | 53.9, CH3 | 4.26, q, 7.1 | 63.6, CH2 |
9 | / | / | / | / | / | / | 1.22, t, 7.1 | 14.3, CH3 |
1' | / | 122.8, C | / | 123.9, C | / | 123.1, C | / | 123.2, C |
2' | 7.58, d, 8.4 | 130.2, CH | 7.61, d, 8.8 | 130.0, CH | 7.57, d, 8.8 | 130.3, CH | 7.60, d, 8.9 | 130.4, CH |
3' | 6.68, d, 8.4 | 116.5, CH | 6.86, d, 8.8 | 116.5, CH | 6.88, d, 8.8 | 116.6, CH | 6.87, d, 8.9 | 116.6, CH |
4' | / | 158.8, C | / | 158.8, C | / | 159.3, C | / | 159.3, C |
5' | 6.68, d, 8.4 | 116.5, CH | 6.86, d, 8.8 | 116.5, CH | 6.88, d, 8.8 | 116.6, CH | 6.87, d, 8.9 | 116.6, CH |
6' | 7.58, d, 8.4 | 130.2, CH | 7.61, d, 8.8 | 130.0, CH | 7.57, d, 8.8 | 130.3, CH | 7.60, d, 8.9 | 130.4, CH |
1'' | / | 124.9, C | / | 123.9, C | / | 123.1, C | / | 123.6, C |
2'' | 6.45, s | 132.1, CH | 6.65, d, 8.8 | 132.6, CH | 6.46, d, 2.1 | 132.8, CH | 6.50, d, 2.1 | 132.4, CH |
3'' | / | 128.2, C | 6.51, d, 8.8 | 125.5, CH | / | 129.5, C | / | 129.8, C |
4'' | / | 154.6, C | / | 157.4, C | / | 153.4, C | / | 155.1, C |
5'' | 6.48, d, 8.4 | 115.0, CH | 6.51, d, 8.8 | 125.5, CH | 6.55, d, 8.5 | 117.2, CH | 6.56, d, 8.1 | 115.1, CH |
6'' | 6.52, d, 8.4 | 129.6, CH | 6.65, d, 8.8 | 132.6, CH | 6.52, dd, 8.5, 2.1 | 130.4, CH | 6.54, dd, 8.1, 2.1 | 129.3, CH |
7'' | 3.05, br d, 6.2 | 28.5, CH2 | / | / | 2.81, dd, 16.6, 5.20 | 31.9, CH2 | 3.07, br d, 7.4 | 28.7, CH2 |
8'' | 5.02, t, 6.2 | 123.1, CH | / | / | 3.66, m | 70.4, CH | 5.07, m | 123.6, CH |
9'' | / | 133.0, C | / | / | / | 77.9, C | / | 132.9, C |
10'' | 1.52, s | 25.9, CH3 | / | / | 1.26, s | 25.8, CH3 | 1.57, s | 25.9, CH3 |
11'' | 1.61, s | 17.7, CH3 | / | / | 1.17, s | 20.9, CH3 | 1.67, s | 17.8, CH3 |
注: “/”表示无数据 |
表2 化合物5—8的NMR数据表(CD3OD)Tab. 2 NMR data of 5−8 in CD3OD |
No. | 5 | 6 | 7 | 8 | ||||
---|---|---|---|---|---|---|---|---|
δH, mult, (J in Hz) | δC, type | δH, mult, (J in Hz) | δC, type | δH, mult, (J in Hz) | δC, type | δH, mult, (J in Hz) | δC, type | |
1 | / | / | / | / | / | / | 3.61, s | 49.0, CH2 |
2 | / | 170.2, C | / | 171.5, C | / | 173.0, C | / | 210.0, C |
3 | / | 139.4, C | / | 140.1, C | / | 139.7, C | 3.59, s | 49.0, CH2 |
4 | / | 129.4, C | / | 128.9, C | / | 158.2, C | / | / |
5 | / | 86.7, C | / | 86.7, C | 5.50, s | 104.1, CH | / | / |
6 | 3.40, s | 39.4, CH2 | a 3.45, d, 15.0 b 3.55, d, 15.0 | 39.5, CH2 | a 3.57, d, 15.2 b 3.91, d, 15.2 | 32.8, CH2 | / | / |
7 | / | 171.2, C | / | 170.5, C | 3.53, s | 57.4, CH3 | / | / |
8 | 3.72, s | 53.9, CH3 | 3.79, s | 53.9, CH3 | / | / | / | / |
1' | / | 122.9, C | / | 123.2, C | / | 121.5, C | / | 126.4, C |
2' | 7.55, d, 8.4 | 130.2, CH | 7.57, d, 8.5 | 130.3, CH | 7.35, d, 8.7 | 131.6, CH | 6.93, d, 8.8 | 131.6, CH |
3' | 6.86, d, 8.4 | 116.6, CH | 6.87, d, 8.5 | 116.6, CH | 6.87, d, 8.7 | 116.1, CH | 6.72, d, 8.8 | 116.3, CH |
4' | / | 159.1, C | / | 159.3, C | / | 159.4, C | / | 157.3, C |
5' | 6.86, d, 8.4 | 116.6, CH | 6.87, d, 8.5 | 116.6, CH | 6.87, d, 8.7 | 116.1, CH | 6.72, d, 8.8 | 116.3, CH |
6' | 7.55, d, 8.4 | 130.2, CH | 7.57, d, 8.5 | 130.3, CH | 7.35, d, 8.7 | 131.6, CH | 6.93, d, 8.8 | 131.6, CH |
1'' | / | 120.3, C | / | 123.2, C | / | 129.7, C | / | 128.8, C |
2'' | 6.45, s | 132.8, CH | 6.44, d, 2.0 | 132.0, CH | 6.78, m | 130.9, CH | 6.79, m | 129.5, CH |
3'' | / | 125.9, C | / | 129.5, C | / | 128.0, C | / | 155.1, C |
4'' | / | 159.1, C | / | 153.3, C | / | 155.1, C | / | 128.8, C |
5'' | 6.50, d, 8.4 | 117.1, CH | 6.56, d, 8.0 | 116.5, CH | 6.70, d, 8.6 | 116.4, CH | 6.76, m | 131.6, CH |
6'' | 6.44, d, 8.4 | 130.3, CH | 6.54, dd, 8.0, 2.0 | 129.4, CH | 6.83, m | 128.2, CH | 6.67, m | 123.8, CH |
7'' | a 2.50, dd, 16.8, 6.4 b 2.72, dd, 16.8, 6.4 | 39.4, CH2 | 6.10, d, 9.8 | 123.2, CH | 3.25, d, 7.1 | 29.0, CH2 | 3.26, d, 7.2 | 29.1, CH2 |
8'' | 3.64, m | 70.2, CH | 5.78, d, 9.8 | 132.0, CH | 5.27, t, 7.1 | 123.7, CH | 5.28, t, 7.2 | 126.2, CH |
9'' | / | 77.8, C | / | 77.2, C | / | 133.3, C | / | 133.0, C |
10'' | 1.14, s | 25.7, CH3 | 1.33, s | 28.1, CH3 | 1.71, s | 25.9, CH3 | 1.73, s | 25.9, CH3 |
11'' | 1.21, s | 21.0, CH3 | 1.33, s | 28.1, CH3 | 1.66, s | 17.8, CH3 | 1.69, s | 17.8, CH3 |
注: “/”表示无数据 |
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