Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

Zhenjian Lin, Malem Flores, Imelda Forteza, Niel M. Henriksen, Gisela P. Concepcion, Gary Rosenberg, Margo Haygood, Baldomero M. Olivera, Alan R. Light, Thomas E. Cheatham, Eric W. Schmidt

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

Original languageEnglish (US)
Pages (from-to)644-649
Number of pages6
JournalJournal of Natural Products
Volume75
Issue number4
DOIs
StatePublished - Apr 27 2012

Fingerprint

Polyketides
Cyclic Peptides
Mollusca
Streptomyces
Bacteria
Gastropoda
Philippines
Glycosides
Nuclear magnetic resonance
Derivatives
Amino Acids
Peptides
totopotensamide B
totopotensamide A
2,3-diaminobutanoic acid

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Lin, Z., Flores, M., Forteza, I., Henriksen, N. M., Concepcion, G. P., Rosenberg, G., ... Schmidt, E. W. (2012). Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp. Journal of Natural Products, 75(4), 644-649. https://doi.org/10.1021/np200886x

Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp. / Lin, Zhenjian; Flores, Malem; Forteza, Imelda; Henriksen, Niel M.; Concepcion, Gisela P.; Rosenberg, Gary; Haygood, Margo; Olivera, Baldomero M.; Light, Alan R.; Cheatham, Thomas E.; Schmidt, Eric W.

In: Journal of Natural Products, Vol. 75, No. 4, 27.04.2012, p. 644-649.

Research output: Contribution to journalArticle

Lin, Z, Flores, M, Forteza, I, Henriksen, NM, Concepcion, GP, Rosenberg, G, Haygood, M, Olivera, BM, Light, AR, Cheatham, TE & Schmidt, EW 2012, 'Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.', Journal of Natural Products, vol. 75, no. 4, pp. 644-649. https://doi.org/10.1021/np200886x
Lin, Zhenjian ; Flores, Malem ; Forteza, Imelda ; Henriksen, Niel M. ; Concepcion, Gisela P. ; Rosenberg, Gary ; Haygood, Margo ; Olivera, Baldomero M. ; Light, Alan R. ; Cheatham, Thomas E. ; Schmidt, Eric W. / Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp. In: Journal of Natural Products. 2012 ; Vol. 75, No. 4. pp. 644-649.
@article{a28df591c6cc4981942d39cdb76726e7,
title = "Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.",
abstract = "Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.",
author = "Zhenjian Lin and Malem Flores and Imelda Forteza and Henriksen, {Niel M.} and Concepcion, {Gisela P.} and Gary Rosenberg and Margo Haygood and Olivera, {Baldomero M.} and Light, {Alan R.} and Cheatham, {Thomas E.} and Schmidt, {Eric W.}",
year = "2012",
month = "4",
day = "27",
doi = "10.1021/np200886x",
language = "English (US)",
volume = "75",
pages = "644--649",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "4",

}

TY - JOUR

T1 - Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

AU - Lin, Zhenjian

AU - Flores, Malem

AU - Forteza, Imelda

AU - Henriksen, Niel M.

AU - Concepcion, Gisela P.

AU - Rosenberg, Gary

AU - Haygood, Margo

AU - Olivera, Baldomero M.

AU - Light, Alan R.

AU - Cheatham, Thomas E.

AU - Schmidt, Eric W.

PY - 2012/4/27

Y1 - 2012/4/27

N2 - Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

AB - Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

UR - http://www.scopus.com/inward/record.url?scp=84860341355&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84860341355&partnerID=8YFLogxK

U2 - 10.1021/np200886x

DO - 10.1021/np200886x

M3 - Article

C2 - 22439622

AN - SCOPUS:84860341355

VL - 75

SP - 644

EP - 649

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 4

ER -