Asporychalasin, a bioactive cytochalasan with an unprecedented 6/6/11 skeleton from the Red Sea sediment Aspergillus oryzae

Raha Orfali; Shagufta Perveen; Muhammad F Khan; Atallah F Ahmed; Sobia Tabassum; Paolo Luciano; Giuseppina Chianese; Orazio Taglialatela-Scafati

doi:10.1016/j.phytochem.2021.112952

Asporychalasin, a bioactive cytochalasan with an unprecedented 6/6/11 skeleton from the Red Sea sediment Aspergillus oryzae

Phytochemistry. 2021 Dec:192:112952. doi: 10.1016/j.phytochem.2021.112952. Epub 2021 Sep 14.

Authors

Raha Orfali¹, Shagufta Perveen², Muhammad F Khan³, Atallah F Ahmed⁴, Sobia Tabassum⁵, Paolo Luciano⁶, Giuseppina Chianese⁶, Orazio Taglialatela-Scafati⁷

Affiliations

¹ Department of Pharmacognosy, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh, 11451, Saudi Arabia.
² Department of Pharmacognosy, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh, 11451, Saudi Arabia. Electronic address: shagufta792000@yahoo.com.
³ Bio-products Research Chair, Department of Zoology, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi Arabia.
⁴ Department of Pharmacognosy, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh, 11451, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt.
⁵ Interdisciplinary Research Centre in Biomedical Materials (IRCBM), COMSATS University Islamabad, Lahore Campus, Pakistan.
⁶ Department of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131, Naples, Italy.
⁷ Department of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131, Naples, Italy. Electronic address: scatagli@unina.it.

PMID: 34534713
DOI: 10.1016/j.phytochem.2021.112952

Abstract

The cytochalasan asporychalasin (1) was obtained from the marine fungus Aspergillus oryzae, isolated from the Red Sea sediments collected off Jeddah, Saudi Arabia. The chemical structure of 1 was elucidated by extensive spectroscopic analysis and quantum-mechanical calculations of ¹³C NMR resonances and ECD to possess an unprecedented 6/6/11-fused tricyclic skeleton, including an isoquinolindione ring in place of the typical isoindolone. Asporychalasin exhibited moderate antiproliferative activity against three human cancer cell lines, lung carcinoma (A549), liver carcinoma (HepG2), and breast carcinoma (MCF7), and no toxicity on zebrafish embryos.

Keywords: Aspergillus oryzae; Computational calculation; Cytochalasan; Cytotoxicity; Structure elucidation; Trichocomaceae.

MeSH terms

Animals
Aspergillus oryzae*
Cytochalasins
Indian Ocean
Molecular Structure
Skeleton
Zebrafish

Substances

Cytochalasins