Sage Journals: Discover world-class research

Abstract

For the past fifteen years we have studied the secondary metabolites of extremophilic fungi from the Berkeley Pit, an abandoned acid mine waste lake. Fungi associated with an acid-tolerant alga have also been harvested from the Pit. Penicillium clavigerum Demelius was isolated from the green alga Chlorella vulgaris Beyerinck [Beijerinck]. In culture it produced the known compounds phomfuranone (1), patulin (2), dimethylphthalides (3) and (4), phomopsolide A (5), phomopsolide C (6), phomopsolide B (7), phomopsolide E (8), phomopsolide F (9), and phompyrone (10) and the new compound berkbenzofuran thioester (11). Compounds 5 and 6 were potent inhibitors (IC₅₀ < 10 μM) of specific and established human cancer cell lines.

Keywords

Phomopsolides Extremophiles Secondary metabolites Matrix metalloproteinase-3 inhibitors Thioesters

References

Montana Bureau of Mines and Geology, Berkeley Pit and Butte Mine-Flooding Operable Unit website: http://www.mbmg.mtech.edu/env/env-berkeley.asp. (accessed November 12, 2007).

Mitman

G.G.

(1999) A final report: biological survey of the Berkeley Pit Lake system. Mine Waste Technology Program Activity IV, Project 10. US EPA National Risk Management Lab, IAG ID# W89938513-01-0; (b) Beyerinck [Beijerinck] MW. (1890) Culturversuche mit zoochlorellen, lichenengonidien und anderen niederen algen, Botanische Zeitung, 47, 725–739, 741–754, 757–768, 781–785.

Stierle

D.B.

, Stierle

A.A.

, Hobbs

J.D.

, Stokken

, Clardy

(2004) Berkeleydione and berkeleytrione, new bioactive metabolites from an acid mine organism. Organic Letters, 6, 1049–1052.

Stierle

D.B.

, Stierle

A.A.

, Patacini

(2007) The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium. Journal of Natural Products, 70, 1820–1823.

Stierle

A.A.

, Stierle

D.B.

, Patacini

(2008) The berkeleyamides, amides from the acid lake fungus Penicillium rubrum. Journal of Natural Products, 71, 856–860.

Sternlicht

M.D.

, Werb

(2001) How matrix metalloproteinases regulate cell behavior. Annual Review of Cell and Developmental Biology, 17, 463–516.

Sternlicht

M.D.

, Lochter

, Sympson

C.J.

, Huey

, Rougier

J.P.

, Gray

J.W.

, Pinkel

, Bissell

M.J.

(1999) The stromal proteinase MMP3/ stromelysin-1 promotes mammary carcinogenesis. Cell, 98, 137–146.

Radisky

D.C.

, Levy

D.D.

, Littlepage

L.E.

, Liu

, Nelson

C.M.

, Fata

J.E.

, Leake

, Godden

E.L.

, Albertson

D.G.

, Nieto

M.A.

, Werb

, Bissell

M.J.

(2005) Rac1b and reactive oxygen species mediate MMP-3-induced EMT and genomic instability. Nature, 436, 123–127.

Bissell

M.J.

, Radisky

(2001) Putting tumours in context. Nature Reviews: Cancer, 1, 46–54.

10.

Brown

P.D.

(1995) Matrix metalloproteinase inhibitors: a novel class of anticancer agents. Advances in Enzyme Regulation, 35, 293–301.

11.

Liedtke

, Cannella

, Mazzaccaro

R.J.

, Clements

J.M.

, Miller

K.M.

, Wucherpfennig

K.W.

, Gearing

A.J.

, Raine

C.S.

(1998) Effective treatment of models of multiple sclerosis by matrix metalloproteinase inhibitors. Annals of Neurology, 44, 35–46.

12.

Stierle

D.B.

, Stierle

A.A.

, Ganser

(1997) New phomopsolides from a Penicillium sp. Journal of Natural Products, 52, 1207–1209.

13.

Chain

, Florey

H.W.

, Jennings

M.A.

(1944) The identification of claviformin and patulin. The Lancet, 243, 112–114; (b) Walker K, Wiesner BP. (1944) Patulin and clavicin. The Lancet, 246, 294.

14.

Nozawa

, Udagawa

, Nakajima

, Kawai

(1989) A dioxopiperazine derivative from Penicillium megasporum. Phytochemistry, 28, 929–931.

15.

Grove

J.F.

(1985) Metabolic products of Phomopsis oblonga. Part 2. Phomopsolide A and B, tiglic esters of two 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones. Journal of the Chemical Society, Perkin Transactions 1, 865–869.

16.

Honma

, Fujimoto

(1993) Fungicides containing pyranones of Diaporthe citri. Japanese Kokai Tokkyo Koho, JP 05213703 A 19930824.

17.

Tahara

, Okabe

, Furihata

, Tanaka

, Yamaguchi

, Nishimura

, Suzuki

(1990) Resorthiomycin, a novel antitumor antibiotic. II. Physico-chemical properties and structure elucidation. Journal of Antibiotics, 43, 135–137; (b) Tahara M, Okabe T, Furihata K, Tanaka N, Yamaguchi H, Nishimura T, Suzuki H. (1991) Revised structure of resorthiomycin. Journal of Antibiotics, 44, 255.

18.

Mahyudin

N.A.

, Blunt

J.W.

, Cole

A.L.J.

, Munro

M.H.G.

(2012) The isolation of a new S-methyl benzothioate compound from a marine-derived Streptomyces sp. Journal of Biomedicine and Biotechnology, 2012, ID 894708, 4 pages.

19.

Pavia

D.L.

, Lampman

G.M.

, Kriz

G.S.

(2001) Introduction to Spectroscopy, 3rd edition. Harcourt College, Orlando, FL, p 65.

20.

Soman

A.G.

, Gloer

J.B.

, Wicklow

D.T.

(1999) Antifungal and antibacterial metabolites from a sclerotium-colonizing isolate of Mortierella vinacea. Journal of Natural Products, 62, 386–388.

21.

Shum

, Radu

, Kim

, Cajuste

, Shao

, Seshan

V E.

, Djaballah

(2008) A high density assay format for the detection of novel cytotoxic agents in large chemical libraries. Journal of Enzyme Inhibition and Medicinal Chemistry, 23, 931–945.

22.

Mahida

J.P.

, Antczak

, DeCarlo

, Champ

K.G.

, Francis

J.H.

, Marr

, Polans

A.S.

, Albert

D.M.

, Abramson

D.H.

, Djaballah

(2013) PLoS ONE, 8, e59156. doi:10.1371/journal.pone.0059156.

23.

Bhinder

, Antczak

, Ramirez

C.N.

, Shum

, Radu

, Liu-Sullivan

, Frattini

M.G.

, Djaballah

(2013) Assay and Drug Development Technologies, 11, 173–190.

24.

, Scott

, O'Doherty

G.A.

(2004) Synthesis of 7-oxa-phomopsolide E and its C-4 epimer. Tetrahedron Letters, 45, 1005–1009.

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

0.13 MB

Phomopsolides and Related Compounds from the Alga-associated Fungus,Penicillium clavigerum

Abstract

Keywords

References

Supplementary Material