Journal of Tropical Oceanography >
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)
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.
HE Yueming , ZHAO Lining , CHEN Xinqi , HE Jiahong , FAN Hao , CHEN Leyi , ZHANG Cuixian , HE Xixin . γ-Aromatic butenolides lignans from soft coral-associated symbiotic and epiphytic fungi Aspergillus terreus EGF7-0-1(I)[J]. Journal of Tropical Oceanography, 2025 , 44(1) : 146 -153 . DOI: 10.11978/2024051
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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