Depsidones and a dihydroxanthenone from the endophytic fungi Simplicillium lanosoniveum (J.F.H. Beyma) Zare & W. Gams PSU-H168 and PSU-H261

Vatcharin Rukachaisirikul; Supaporn Chinpha; Praphatsorn Saetang; Souwalak Phongpaichit; Siriporn Jungsuttiwong; Sarinya Hadsadee; Jariya Sakayaroj; Sita Preedanon; Prapapan Temkitthawon; Kornkanok Ingkaninan

doi:10.1016/j.fitote.2019.104286

Depsidones and a dihydroxanthenone from the endophytic fungi Simplicillium lanosoniveum (J.F.H. Beyma) Zare & W. Gams PSU-H168 and PSU-H261

Fitoterapia. 2019 Oct:138:104286. doi: 10.1016/j.fitote.2019.104286. Epub 2019 Aug 5.

Affiliations

¹ Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand. Electronic address: vatcharin.r@psu.ac.th.
² Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand.
³ Department of Microbiology, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand.
⁴ Department of Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani 34190, Thailand.
⁵ School of Science, Walailak University, Thasala, Nakhonsithammarat 80161, Thailand.
⁶ National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Klong Luang, Pathumthani 12120, Thailand.
⁷ Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University, Phitsanulok 65000, Thailand.

PMID: 31394164
DOI: 10.1016/j.fitote.2019.104286

Abstract

Three new compounds including two depsidones (simplicildones J and K) and one dihydroxanthenone (globosuxanthone E) together with nine known compounds were obtained from the crude extracts of two endophytic fungi Simplicillium lanosoniveum (J.F.H. Beyma) Zare & W. Gams PSU-H168 and PSU-H261 which were isolated from the leaves of Hevea brasiliensis. The structures were elucidated by spectroscopic evidence. The absolute configuration of globosuxanthone E was established by means of experimental and calculated TDDFT ECD data. Simplicildone K exhibited antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with equal MIC values of 128 μg/mL. Simplicildone K and globosuxanthone E displayed antifungal activity against Cryptococcus neoformans ATCC90113 with the same MIC values of 32 μg/mL. In addition, known botryohordine C and simplicildone A showed phosphodiesterase 5 inhibitory activity with the IC₅₀ values of 5.69 and 9.96 μM, respectively, and were noncytotoxic toward noncancerous Vero cells.

Keywords: Antimicrobial activity; Depsidones; Dihydroxanthenone; PDE5 inhibition; Simplicillium lanosoniveum.

MeSH terms

Animals
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology
Antifungal Agents / isolation & purification
Antifungal Agents / pharmacology
Chlorocebus aethiops
Cryptococcus neoformans / drug effects
Depsides / isolation & purification
Depsides / pharmacology*
Endophytes / chemistry
Hevea / microbiology*
Hypocreales / chemistry*
Lactones / isolation & purification
Lactones / pharmacology*
Methicillin-Resistant Staphylococcus aureus / drug effects
Microbial Sensitivity Tests
Molecular Structure
Phosphodiesterase 5 Inhibitors / isolation & purification
Phosphodiesterase 5 Inhibitors / pharmacology
Plant Leaves / microbiology
Thailand
Vero Cells
Xanthones / isolation & purification
Xanthones / pharmacology*

Substances

Anti-Bacterial Agents
Antifungal Agents
Depsides
Lactones
Phosphodiesterase 5 Inhibitors
Xanthones
depsidone