Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087.

Fan, Bicheng, Dewapriya, Pradeep , Li, Fengjie , Grauso, Laura , Blümel, Martina , Mangoni, Alfonso and Tasdemir, Deniz (2020) Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087. Open Access Marine Drugs, 18 (6). Art.Nr. 281. DOI 10.3390/md18060281.

[img]
Preview
Text
marinedrugs-18-00281-v2.pdf - Published Version
Available under License Creative Commons: Attribution 4.0.

Download (891Kb) | Preview
[img]
Preview
Text
marinedrugs-18-00281-s001.pdf - Supplemental Material
Available under License Creative Commons: Attribution 4.0.

Download (1950Kb) | Preview

Supplementary data:

Abstract

The fungal genus Pyrenochaetopsis is commonly found in soil, terrestrial, and marine environments, however, has received little attention as a source of bioactive secondary metabolites so far. In a recent work, we reported the isolation and characterization of three new anticancer decalinoyltetramic acid derivatives, pyrenosetins A-C, from the Baltic Fucus vesiculosus-derived endophytic fungus Pyrenochaetopsis sp. FVE-001. Herein we report a new pentacyclic decalinoylspirotetramic acid derivative, pyrenosetin D (1), along with two known decalin derivatives wakodecalines A (2) and B (3) from another endophytic strain Pyrenochaetopsis FVE-087 isolated from the same seaweed and showed anticancer activity in initial screenings. The chemical structures of the purified compounds were elucidated by comprehensive analysis of HR-ESIMS, FT-IR, [a]D, 1D and 2D NMR data coupled with DFT calculations of NMR parameters and optical rotation. Compounds 1-3 were evaluated for their anticancer and toxic potentials against the human malignant melanoma cell line (A-375) and the non-cancerous keratinocyte cell line (HaCaT). Pyrenosetin D (1) showed toxicity towards both A-375 and HaCaT cells with IC50 values of 77.5 and 39.3 μM, respectively, while 2 and 3 were inactive. This is the third chemical study performed on the fungal genus Pyrenochaetopsis and the first report of a pentacyclic decalin ring system from the fungal genus Pyrenochaetopsis.

Document Type: Article
Keywords: Pyrenochaetopsis; pyrenosetin; marine fungus; decalinoyltetramic acid; Fucus vesiculosus; anticancer
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MN Marine natural products chemistry
Refereed: Yes
Open Access Journal?: Yes
DOI etc.: 10.3390/md18060281
ISSN: 1660-3397
Date Deposited: 08 Jun 2020 12:38
Last Modified: 08 Jun 2020 12:38
URI: http://oceanrep.geomar.de/id/eprint/49834

Actions (login required)

View Item View Item

Document Downloads

More statistics for this item...