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Planta Med 2022; 88(09/10): 774-782
DOI: 10.1055/a-1769-8480
Biological and Pharmacological Activity
Original Papers

Targeted Isolation of Two New Anti-inflammatory and UV-A Protective Dipyrroloquinones from the Sponge-associated Fungus Aspergillus tamarii MCCF102[ # ]

Lekshmi Niveditha
1   National Centre for Aquatic Animal Health, Cochin University of Science and Technology, Fine Arts Avenue, Kochi, Kerala, India
,
Peng Fu
2   School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
,
Tiago F. Leao
3   Center for Nuclear Energy in Agriculture, University of São Paulo, Piracicaba, Brazil
,
Te Li
4   Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Department of Marine Pharmacy, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo, China
,
Tingting Wang
4   Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Department of Marine Pharmacy, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo, China
,
Remington X. Poulin
5   Department of Chemistry and Biochemistry, Center for Marine Science, College of Arts and Sciences, University of North Carolina Wilmington, Wilmington, NC, USA
,
Lorena R. Gaspar
6   School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Ribeirão Preto, São Paulo, Brazil
,
C. Benjamin Naman 
4   Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Department of Marine Pharmacy, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo, China
5   Department of Chemistry and Biochemistry, Center for Marine Science, College of Arts and Sciences, University of North Carolina Wilmington, Wilmington, NC, USA
,
Sajeevan Thavarool Puthiyedathu
1   National Centre for Aquatic Animal Health, Cochin University of Science and Technology, Fine Arts Avenue, Kochi, Kerala, India
› Author AffiliationsSupported by: Higher Education Discipline Innovation Project D16013
Supported by: Department of Biotechnology, Ministry of Science and Technology, India BT/PR26905/AAQ/3/883/2017
Supported by: Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund
Supported by: National Natural Science Foundation of China 41906093
Supported by: National Natural Science Foundation of China 82050410451
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2021/06619-9
› Further Information
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Abstract

In following up on observed in vitro anti-inflammatory activity of the organic extract of the marine sponge-derived fungus Aspergillus tamarii MCCF102, two new dipyrrolobenzoquinones, terreusinone B and C (1 and 2), were discovered along with the known analogue, terreusinone (3). The structures of 1–3 were determined by spectroscopic and spectrometric analyses, along with chemical inter-conversion. In vitro testing on lipopolysaccharide (LPS) stimulated RAW 264.7 murine macrophage cells revealed that 1–3 exhibit anti-inflammatory activity by inhibiting nitric oxide production in a dose-dependent manner (IC50 < 1 µM) without any cytotoxicity observed at the same concentrations. Due to this and the UV-A absorptive properties imparted by the highly conjugated structures of these molecules, the potential for using 1–3 or related analogues as natural sunscreen components is suggested. Gene sequencing and informatics biosynthetic gene cluster comparisons were insufficient to confidently elucidate the biosynthetic origins of these compounds, possibly suggesting the occurrence of a gene cluster not detected in the initial sequencing or a non-canonical pathway that should be further investigated.

Key words

Aspergillus tamarii - sponge-associated fungi - terreusinone - dipyrroloquinone - anti-inflammatory - sunscreen

# Dedicated to Professor Dr. A. Douglas Kinghorn on the occasion of his 75th birthday.


Supporting Information

    1D 1H, 13C, and 2D 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC NMR spectra of compounds 1–3 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 19 November 2021

Accepted after revision: 08 February 2022

Accepted Manuscript online:
11 February 2022

Article published online:
30 March 2022

© 2022. Thieme. All rights reserved.

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