Secondary Metabolites from a Strain of Alternaria tenuissima Isolated from Northern Manitoba Soil

Abstract

Deoxyphomalone (1), dimethyl 4-methyl-2,6-pyridinedicarboxylate (2), stemphyperylenol (3), and N-methyl-2-pyrrolidone (4) were isolated from the fermentation broth of a strain of the fungus, Alternaria tenuissima. This fungus was isolated from the soil underlying the lichen, Peltigera didactyla, which had been collected from Wapusk National Park in Northern Manitoba. The structures of the compounds were determined by comprehensive analysis of their spectroscopic data including FT-IR, 1D and 2D NMR spectroscopy and mass spectrometry; and their bioactivities were tested against E.coli cells. The taxonomic identity of the fungus was confirmed by ITS sequencing of its ribosomal DNA.

Keywords

Soil fungi Alternaria tenuissima Deoxyphomalone Stemphyperylenol N-Methyl pyrollidinone Dimethyl 4-methyl-2,6-pyridinedicarboxylate

References

Pace

. (1997) A molecular view of microbial diversity and the biosphere. Science, 276, 734–740.

Molinari

(2009) Natural products in drug discovery: present status and perspectives. In Pharmaceutical Biotechnology: Advances in Experimental Medicine and Biology. Vol 655, Guzman

, Feuerstein

. (Eds). Springer, New York. 13–27.

Lazzarini

, Cavaletti

, Toppo

, Marinelli

(2000) Rare genera of actinomycetes as potential producers of new antibiotics. Antonie Van Leeuwenhoek, 78, 399–405.

Jefferys

, Brian

, Hemming

, Lowe

(1953) Antibiotic production by the microfungi of acid heath soils. Jornal of General Microbiology, 9, 314–341.

Ayer

, Jimenez

. (1994) Phomalone, an antifungal metabolite of Phoma etheridgei. Canadian Journal of Chemistry, 72, 2326–2332.

Slieman

, Nicholson

. (2001) Role of dipicolinic acid in survival of Bacillus subtilis spores exposed to artificial and solar UV radiation. Applied and Environmental Microbiology, 67, 1274–1279.

Asaff

, Cerda-Garcia-Rojas

, de la Torre

(2005) Isolation of dipicolinic acid as an insecticidal toxin from Paecilomyces fumosoroseus. Applied Microbiology and Biotechnology, 68, 542–547.

Sumi

, Ohosugi

(1999) Anti-bacterial component dipicolic acid measured in natto and natto bacilli. Nippon Nogeikagaku Kaishi, 73, 1289–1291.

Watanabe

, Hattori

, Yokoyama

, Isomura

, Ujita

, Hara

(2006) Entomogenous fungi that produce 2,6-pyridine dicarboxylic acid (dipicolinic acid). Journal of Bioscience and Bioengineering, 102, 365–368.

10.

Arnone

, Nasini

, Merlini

, Assante

(1986) Secondary mould metabolites. Part 16. Stemphyltoxins, new reduced perylenequinone metabolites from Stemphylium botryosum var. lactucum. Journal of the Chemical Society Perkin Transactions 1, 525–530.

11.

Kjer

, Wray

, Edrada-Ebel

, Ebel

, Pretsch

, Lin

, Proksch

(2009) Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba. Journal of Natural Products, 72, 2053–2057.

12.

Gao

S-S

, Li

X-M

, Wang

B-G

. (2009) Perylene derivatives produced by Alternaria alternata, an endophytic fungus isolated from Laurencia species. Natural Product Communications, 4, 1477–1480.

13.

Liu

, Cai

, Yang

, Xia

, Guo

, Yuan

, Li

, She

, Lin

. (2010) The bioactive metabolites of the mangrove endophytic fungus Talaromyces sp. ZH-154 isolated from Kandelia candel (L.) Druce. Planta Medica, 76, 185–189.

14.

Schobert

, Schlenk

(2008) Tetramic and tetronic acids: An update on new derivatives and biological aspects Bioorganic & Medicinal Chemistry, 16, 4203–4221.

15.

Sims

, Fillmore

, Warner

, Schmidt

. (2005) Equisetin biosynthesis in Fusarium heterosporum. Chemical Communications. 186–188.

16.

Aoki

, Higuchi

, Ye

, Satari

, Kobayashi

(2000) Melophlins A and B, novel tetramic acids reversing the phenotype of ras-transformed cells, from the marine sponge Melophlus sarassinorum. Tetrahedron, 56, 1833–1836.

17.

Radhika

, Venkatesan

, Kathiroli

(2007) N-Methylpyrrolidone: Isolation and characterization of the compound from the marine sponge Clathria frondifera (class: Demospongiae). Indian Journal of Marine Sciences, 36, 235–238.

18.

Jouyban

, Fakhree

MAA

, Shayanfar

(2010) Review of pharmaceutical applications of N-methyl-2-pyrrolidone. Journal of Pharmacy & Pharmaceutical Sciences, 13, 524–535.

19.

We have neither purchased nor used N-methyl-2-pyrrolidone (4) as a solvent in our lab, suggesting that 4 is not contamination from external sources.

20.

Nadeau

, Sorensen

(2011) Polyketides produced by Daldinia loculata cultured from Northern Manitoba. Tetrahedron Letters, 52, 1697–1699.

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

4.63 MB