Talarolide A, a Cyclic Heptapeptide Hydroxamate from an Australian Marine Tunicate-Associated Fungus, Talaromyces sp (CMB-TU011)

被引：40

作者：

Dewapriya, Pradeep ^{[1
]}

Prasad, Pritesh ^{[1
]}

Damodar, Rakesh ^{[1
]}

Salim, Angela A. ^{[1
]}

Capon, Robert J. ^{[1
]}

机构：

[1] Univ Queensland, Inst Mol Biosci, St Lucia, Qld 4072, Australia

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 08期

基金：

澳大利亚研究理事会;

关键词：

SORDARINS;

D O I：

10.1021/acs.orglett.7b00638

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A miniaturized 24-well plate microbioreactor approach was used to explore secondary metabolite media dependence in an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB TU011). Detailed chemical investigations of an antifungal M1-saline cultivation yielded talarolide A (1), only the second reported natural cyclic peptide hydroxamate, and the first from a fungus. The antifungal properties of the M1-saline extract were attributed to the known diterpene glycoside sordarin (2). Structure elucidation of 1 and 2 was achieved by detailed spectroscopic analysis, with amino acid configurations in 1 assigned by the C-3 and C-18 Marfey's methods, and L-Ala and D-Ala regiochemistry by the recently reported 2D C-3 Marfey's method.

引用

页码：2046 / 2049

页数：4

共 9 条

[1] Talaromins A and B, new cyclic peptides from the endophytic fungus Talaromyces wortmannii [J].

Bara, Robert ;

Aly, Amal H. ;

Wray, Victor ;

Lin, WenHan ;

Proksch, Peter ;

Debbab, Abdessamad .

TETRAHEDRON LETTERS, 2013, 54 (13) :1686-1689

[2] Synthesis of (-)-sordarin [J].

Chiba, Shunsuke ;

Kitamura, Mitsuru ;

Narasaka, Koichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6931-6937

[3] Sordarins:: A new class of antifungals with selective inhibition of the protein synthesis elongation cycle in yeasts [J].

Domínguez, JM ;

Kelly, VA ;

Kinsman, OS ;

Marriott, MS ;

De Las Heras, FG ;

Martín, JJ .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (09) :2274-2278

[4] SORDARIN .1. ISOLATION AND DEGRADATION OF SORDARIN [J].

HAUSER, D ;

SIGG, HP .

HELVETICA CHIMICA ACTA, 1971, 54 (04) :1178-&

[5] Pargamicin a, a novel cyclic peptide antibiotic from Amycolatopsis sp. [J].

Igarashi, Masayuki ;

Sawa, Ryuichi ;

Kinoshita, Naoko ;

Hashizurne, Hideki ;

Nakagawa, Naoko ;

Homma, Yoshiko ;

Nishimura, Yoshio ;

Akamatsu, Yuzuru .

JOURNAL OF ANTIBIOTICS, 2008, 61 (06) :387-393

[6] Bioactive Compounds Produced by Strains of Penicillium and Talaromyces of Marine Origin [J].

Nicoletti, Rosario ;

Trincone, Antonio .

MARINE DRUGS, 2016, 14 (02)

[7] Distribution of the antifungal agents sordarins across filamentous fungi [J].

Vicente, Francisca ;

Basilio, Angela ;

Platas, Gonzalo ;

Collado, Javier ;

Bills, Gerald F. ;

Gonzalez Del Val, Antonio ;

Martin, Jesus ;

Tormo, Jose R. ;

Harris, Guy H. ;

Zink, Deborah L. ;

Justice, Michael ;

Kahn, Jennifer Nielsen ;

Pelaez, Fernando .

MYCOLOGICAL RESEARCH, 2009, 113 :754-770

[8] C3 and 2D C3 Marfey's Methods for Amino Acid Analysis in Natural Products [J].

Vijayasarathy, Soumini ;

Prasad, Pritesh ;

Fremlin, Leith J. ;

Ratnayake, Ranjala ;

Salim, Angela A. ;

Khalil, Zeinab ;

Capon, Robert J. .

JOURNAL OF NATURAL PRODUCTS, 2016, 79 (02) :421-427

[9] The Bioactive Secondary Metabolites from Talaromyces species [J].

Zhai M.-M. ;

Li J. ;

Jiang C.-X. ;

Shi Y.-P. ;

Di D.-L. ;

Crews P. ;

Wu Q.-X. .

Natural Products and Bioprospecting, 2016, 6 (1) :1-24

← 1 →