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

Lekshmi Niveditha; Peng Fu; Tiago F. Leao; Te Li; Tingting Wang; Remington X. Poulin; Lorena R. Gaspar; C. Benjamin Naman; Sajeevan Thavarool Puthiyedathu

doi:10.1055/a-1769-8480

Planta Medica, Table of Contents

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^{[
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Authors

Lekshmi Niveditha

¹National Centre for Aquatic Animal Health, Cochin University of Science and Technology, Fine Arts Avenue, Kochi, Kerala, India
Peng Fu

²School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
Tiago F. Leao

³Center for Nuclear Energy in Agriculture, University of São Paulo, Piracicaba, Brazil
Te Li

⁴Li 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

⁴Li 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

⁵Department of Chemistry and Biochemistry, Center for Marine Science, College of Arts and Sciences, University of North Carolina Wilmington, Wilmington, NC, USA
Lorena R. Gaspar

⁶School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Ribeirão Preto, São Paulo, Brazil
C. Benjamin Naman

⁴Li 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

⁵Department of Chemistry and Biochemistry, Center for Marine Science, College of Arts and Sciences, University of North Carolina Wilmington, Wilmington, NC, USA
Sajeevan Thavarool Puthiyedathu

¹National Centre for Aquatic Animal Health, Cochin University of Science and Technology, Fine Arts Avenue, Kochi, Kerala, India

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

Full Text

References

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

Authors

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