Unusual 2(1 H )-Pyrazinones Isolated from a Culture of a Brazilian Marine-Derived Streptomyces sp

Abstract

Four new secondary metabolites, giovaninones A-D (1–4), were isolated from an ethyl acetate extract of a culture of a marine-derived Streptomyces strain designated SS99BA-2. Chemical analysis was completely conducted in a coupled automated LC-SPE system with the use of a cryogenic NMR probehead and HRMS. The application of this system to identify, purify and elucidate all the structures is described.

Keywords

LC-SPE/NMR Marine Streptomyces Secondary metabolite

References

Berlinck

R.G.S.

, Hadju

, Rocha

R.M.

, Oliveira

Jhhl

, Hernandez

I.L.C.

, Seleghim

M.H.

, Granato

A.C.

, Almeida

E.V.R.

, Nunez

C.V.

, Muricy

, Peixinho

, Pessoa

, Moraes

M.O.

, Cavalcanti

B.C.

, Nascimento

A.G.F.

, Thiemann

, Silva

, Souza

A.O.

, Silva

C.L.

, Minarini

P.R.R.

(2004) Challenges and rewards of research in marine natural products chemistry in Brazil. Journal of Natural Products, 67, 510–522.

Sarkar

, Saha

, Roy

, Jaisankar

, Das

, Roy

L.G.

, Gachhui

, Sen

, Mukherjee

(2008) Enhanced production of antimicrobial compounds by three salt-tolerant actinobacterial strains isolated from the Sundarbans in a niche-mimic bioreactor. Marine Biotechnology, 10, 518–526.

Huang

, Tian

, Fu

, Hua

, Pei

(2006) One new anthraquinone from marine Streptomyces sp. FX-58. Natural Product Research, 20, 1207–1210.

Sobolevskaya

M.P.

, Denisenko

V.A.

, Moiseenko

A.S.

, Shevchenko

L.S.

, Menzorova

N.I.

, Sibirtsev

Y.T.

, Kim

N.Y.

, Kuznetsova

T.A.

(2007) Bioactive metabolities of the marine actinobacterium Streptomyces sp. KMM 7210. Russian Chemical Bulletin, 56, 838–840.

Liana

, Zhang

Indanomycin-related antibiotics from marine Streptomyces antibioticus PTZ0016. (2013) Natural Product Research, 27, 2161–2167.

Hernandez

I.L.C.

, Godinho

M.J.L.

, Magalhães

, Schefer

A.B.

, Ferreira

A.G.

, Berlinck

R.G.S.

(2000) N-Acetyl-γ-hydroxyvaline lactone, an unusual amino acid derivative from a marine streptomycete. Journal of Natural Products, 63, 664–665.

Liras

, Martín

J.F.

(2005) Assay for detection and quantification of antimicrobial metabolites produced by Streptomyces sp. Methods in Biotechnology, 18, 149–163.

Tatsuta

, Fujimoto

, Yamashita

, Tsuchiya

, Umezawa

(1973) Argvalin, a new microbial metabolite: isolation and structure. Journal of Antibiotics, 26, 606–608.

MacDonald

J.C.

, Bishop

G.G.

(1977) Biosynthesis of arglecin and related compounds. Canadian Journal of Biochemistry and Cell Biology, 55, 165–172.

10.

Tatsuta

, Tsuchiya

, Someno

, Umezawa

, Naganawa

(1971) Arglecin, a new microbial metabolite: isolation and chemical structure. Journal of Antibiotics, 25, 674–676.

11.

Tatsuta

, Tsuchiya

, Umezawa

, Naganawa

, Umezawa

(1972) Revised structure for arglecin. Journal of Antibiotics, 25, 674–676.

12.

Alvarez

M.E.

, White

C.B.

, Gregory

, Kydd

G.C.

, Harris

, Sun

H.H.

, Gillum

A.M.

, Cooper

(1995) Phevalin, a new calpain inhibitor, from a Streptomyces sp. Journal of Antibiotics, 48, 1165–1167.

13.

Zimmermann

, Fischbach

M.A.

(2010) A family of pyrazinone natural products from a conserved nonribosomal peptide synthetase in Staphylococcus aureus. Chemistry & Biology, 17, 925–930.

14.

Motohashi

, Inaba

, Fuse

, Doi

, Izumikawa

, Khan

S.T.

, Takagi

, Takahasi

, Shin-ya

(2011) JBIR-56 and JBIR-57, 2(1H)-Pyrazinones from a marine sponge-derived Streptomyces sp. SpD081030SC-03. Journal of Natural Products, 74, 1630–1635.

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