Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732

Klaram, Rotchana; Dethoup, Tida; Machado, Fátima P.; Gales, Luís; Kumla, Decha; Hafez Ghoran, Salar; Sousa, Emília; Mistry, Sharad; Silva, Artur M. S.; Kijjoa, Anake

doi:10.3390/md21060344

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Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732

by

Rotchana Klaram

^1,2,

Tida Dethoup

^2,*

,

Fátima P. Machado

³

,

Luís Gales

^1,4,*

,

Decha Kumla

⁵

,

Salar Hafez Ghoran

⁶

,

Emília Sousa

⁷

,

Sharad Mistry

⁸,

Artur M. S. Silva

⁹

and

Anake Kijjoa

^1,3,*

¹

ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal

²

Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand

³

Interdisciplinary Centre of Marine Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal

⁴

Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal

⁵

Faculty of Pharmaceutical Sciences, Burapha University, 169 Long Had Bangsaen Rd, Chonburi 20131, Thailand

⁶

HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan

⁷

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal

⁸

Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK

⁹

Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal

^*

Authors to whom correspondence should be addressed.

Mar. Drugs 2023, 21(6), 344; https://doi.org/10.3390/md21060344

Submission received: 2 May 2023 / Revised: 31 May 2023 / Accepted: 31 May 2023 / Published: 2 June 2023

(This article belongs to the Special Issue A Theme Issue Honoring Professor Peter Proksch's 70th Birthday: Bioactive Compounds from the Ocean)

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Abstract

Five undescribed pentaketide derivatives, (R)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1H-2-benzopyran-1-one (1), [(3S,4R)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1H-isochromen-3-yl]methyl acetate (2), (R)-5, 7-dimethoxy-3-((S)-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3H)-one (4b), (S)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3H)-one (5), and a p-hydroxyphenyl-2-pyridone derivative, avellaneanone (6), were isolated together with the previously reported (R)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (3), (R)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (4a) and isosclerone (7), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, Hamigera avellanea KUFA0732. The structures of the undescribed compounds were elucidated using 1D and 2D NMR, as well as high-resolution mass spectral analyses. The absolute configurations of the stereogenic carbons in 1, 4b, 5, and 6 were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in 2 were determined by ROESY correlations and on the basis of their common biosynthetic origin with 1. The crude fungal extract and the isolated compounds 1, 3, 4b, 5, 6, and 7 were assayed for their growth inhibitory activity against various plant pathogenic fungi viz. Alternaria brassicicola, Bipolaris oryzae, Colletotrichum capsici, C. gloeosporiodes, Curvularia oryzae, Fusarium semitectum, Lasiodiplodia theobromae, Phytophthora palmivora, Pyricularia oryzae, Rhizoctonia oryzae and Sclerotium rolfsii.

Keywords: Hamigera avellanea; Aspergillaceae; marine sponge-associated fungus; pentaketides; dihydrochromone; 5-p-hydroxy-2-pyridone; anti-plant pathogenic fungal activity

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MDPI and ACS Style

Klaram, R.; Dethoup, T.; Machado, F.P.; Gales, L.; Kumla, D.; Hafez Ghoran, S.; Sousa, E.; Mistry, S.; Silva, A.M.S.; Kijjoa, A. Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732. Mar. Drugs 2023, 21, 344. https://doi.org/10.3390/md21060344

AMA Style

Klaram R, Dethoup T, Machado FP, Gales L, Kumla D, Hafez Ghoran S, Sousa E, Mistry S, Silva AMS, Kijjoa A. Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732. Marine Drugs. 2023; 21(6):344. https://doi.org/10.3390/md21060344

Chicago/Turabian Style

Klaram, Rotchana, Tida Dethoup, Fátima P. Machado, Luís Gales, Decha Kumla, Salar Hafez Ghoran, Emília Sousa, Sharad Mistry, Artur M. S. Silva, and Anake Kijjoa. 2023. "Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732" Marine Drugs 21, no. 6: 344. https://doi.org/10.3390/md21060344

APA Style

Klaram, R., Dethoup, T., Machado, F. P., Gales, L., Kumla, D., Hafez Ghoran, S., Sousa, E., Mistry, S., Silva, A. M. S., & Kijjoa, A. (2023). Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732. Marine Drugs, 21(6), 344. https://doi.org/10.3390/md21060344

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Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732

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