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Marine Drugs
Volume 18
Issue 11
10.3390/md18110575
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Article

New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects

by
Wenjuan Ding
1,†,
Chokkalingam Uvarani
1,†,
Fangfang Wang
1,†,
Yaxin Xue
2,
Ning Wu
2,
Liming He
2,
Danmei Tian
1,
Mei Chen
1,
Youwei Zhang
3,
Kui Hong
2,* and
Jinshan Tang
1,*
1
International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China
2
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China
3
Case Comprehensive Cancer Center, Department of Pharmacology, School of Medicine, Case Western Reserve University, Cleveland, OH 44106, USA
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Mar. Drugs 2020, 18(11), 575; https://doi.org/10.3390/md18110575
Submission received: 21 October 2020 / Revised: 16 November 2020 / Accepted: 18 November 2020 / Published: 20 November 2020
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Abstract

Deep-sea fungi have become a new arsenal for the discovery of leading compounds. Here five new ophiobolins 1–5, together with six known analogues 6–11, obtained from a deep-sea derived fungus WHU0154. Their structures were determined by analyses of IR, HR-ESI-MS, and NMR spectra, along with experimental and calculated electronic circular dichroism (ECD) analysis. Pharmacological studies showed that compounds 4 and 6 exhibited obvious inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine macrophage RAW264.7 cells. Mechanical study revealed that compound 6 could inhibit the inducible nitric oxide synthase (iNOS) level in LPS-stimulated RAW264.7 cells. In addition, compounds 6, 9, and 10 could significantly inhibit the expression of cyclooxygenase 2 (COX 2) in LPS-induced RAW264.7 cells. Preliminary structure-activity relationship (SAR) analyses revealed that the aldehyde group at C-21 and the α, β-unsaturated ketone functionality at A ring in ophiobolins were vital for their anti-inflammatory effects. Together, the results demonstrated that ophiobolins, especially for compound 6, exhibited strong anti-inflammatory effects and shed light on the discovery of ophiobolins as new anti-inflammatory agents.
Keywords: deep-sea derived fungus; secondary metabolites; ophiobolin; anti-inflammatory effect deep-sea derived fungus; secondary metabolites; ophiobolin; anti-inflammatory effect
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MDPI and ACS Style

Ding, W.; Uvarani, C.; Wang, F.; Xue, Y.; Wu, N.; He, L.; Tian, D.; Chen, M.; Zhang, Y.; Hong, K.; et al. New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects. Mar. Drugs 2020, 18, 575. https://doi.org/10.3390/md18110575

AMA Style

Ding W, Uvarani C, Wang F, Xue Y, Wu N, He L, Tian D, Chen M, Zhang Y, Hong K, et al. New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects. Marine Drugs. 2020; 18(11):575. https://doi.org/10.3390/md18110575

Chicago/Turabian Style

Ding, Wenjuan, Chokkalingam Uvarani, Fangfang Wang, Yaxin Xue, Ning Wu, Liming He, Danmei Tian, Mei Chen, Youwei Zhang, Kui Hong, and et al. 2020. "New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects" Marine Drugs 18, no. 11: 575. https://doi.org/10.3390/md18110575

APA Style

Ding, W., Uvarani, C., Wang, F., Xue, Y., Wu, N., He, L., Tian, D., Chen, M., Zhang, Y., Hong, K., & Tang, J. (2020). New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects. Marine Drugs, 18(11), 575. https://doi.org/10.3390/md18110575

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