Prenylated cyclohexene-type meroterpenoids and sulfur-containing xanthones produced by Pseudopestalotiopsis theae

Sergi Herve Akone; Hao Wang; Eitel Ngoh Misse Mouelle; Attila Mándi; Tibor Kurtán; Pierre Roger Koliye; Rudolf Hartmann; Sanil Bhatia; Jing Yang; Werner E G Müller; Daowan Lai; Zhen Liu; Rainer Kalscheuer; Peter Proksch

doi:10.1016/j.phytochem.2022.113124

Prenylated cyclohexene-type meroterpenoids and sulfur-containing xanthones produced by Pseudopestalotiopsis theae

Phytochemistry. 2022 May:197:113124. doi: 10.1016/j.phytochem.2022.113124. Epub 2022 Feb 7.

Authors

Affiliations

¹ Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-University, Universitaetsstrasse 1, Geb. 26.23, Duesseldorf, 40225, Germany; Department of Chemistry, Faculty of Science, University of Douala, Douala, P.O. Box 24157, Cameroon; Department of Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research and Department of Pharmacy, Saarland University, Saarbrücken, 66123, Germany. Electronic address: sergiherve.akone@helmholtz-hips.de.
² Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, No. 4 Xueyuan Road, Haikou, 571101, Hainan, China.
³ Department of Chemistry, Faculty of Science, University of Douala, Douala, P.O. Box 24157, Cameroon.
⁴ Department of Organic Chemistry, University of Debrecen, Egyetem Tér 1, P.O. Box. 400, 4002, Debrecen, Hungary.
⁵ Institute of Complex Systems: Strukturbiochemie (ICS-6), Forschungszentrum Julich, Wilhelm-Johnen-Strase, 52428, Julich, Germany.
⁶ Department of Pediatric Oncology, Hematology and Clinical Immunology, Heinrich-Heine University Duesseldorf, Medical Faculty, Duesseldorf, Germany.
⁷ Institute of Physiological Chemistry, Universitatsmedizin der Johannes Gutenberg-Universitat Mainz, 55128, Mainz, Germany.
⁸ Department of Plant Pathology, College of Plant Protection, China Agricultural University, Beijing, 100193, China.
⁹ Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-University, Universitaetsstrasse 1, Geb. 26.23, Duesseldorf, 40225, Germany.
¹⁰ Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-University, Universitaetsstrasse 1, Geb. 26.23, Duesseldorf, 40225, Germany. Electronic address: proksch@uni-duesseldorf.de.

PMID: 35144154
DOI: 10.1016/j.phytochem.2022.113124

Abstract

Chemical investigation of the fungal endophyte Pseudopestalotiopsis theae isolated from leaves of Caloncoba welwitschii, collected in Cameroon, resulted in two previously undescribed sulfur-containing xanthone derivatives sydoxanthones D and E, in addition to three previously undescribed monomeric diisoprenyl-cyclohexene-type meroterpenoids biscognienynes D-F and five known natural products. The structures of the undescribed compounds were unambiguously identified by their mass spectra and by extensive 1D and 2D NMR spectroscopic analysis. Mosher's reaction was performed to determine the absolute configuration of sydoxanthones D and E while TDDFT-ECD calculations were used to assign the configuration of biscognienyne D. Biscognienynes B and D showed significant cytotoxicity against the mouse lymphoma cell line L5178Y with IC₅₀ values of 7.7 and 6.7 μM and against the human leukemic cell lines HL60, and Hal-01 with IC₅₀ values ranging from 4.3 to 12.1 μM.

Keywords: Amphisphaeriaceae; Cytotoxicity; Endophytic fungus; Meroterpenoids; Pseudopestalotiopsis theae; Sulfur-containing xanthone.

MeSH terms

Animals
Ascomycota
Cyclohexenes
Mice
Molecular Structure
Sulfur
Xanthones* / chemistry
Xanthones* / pharmacology

Substances

Cyclohexenes
Xanthones
Sulfur

Supplementary concepts

Pseudopestalotiopsis theae