Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina

Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Teruhiko Matsubara, Satoshi Shimada, Toshinori Sato, Kiyotake Suenaga

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Mebamamides A and B, new lipopeptides with four d-amino acid residues and a 3,8-dihydroxy-9-methyldecanoic acid residue, were isolated from the green alga Derbesia marina. Their gross structures were elucidated by spectroscopic and ESI-ITMS analyses. The absolute configurations except for the two leucines were revealed based on chiral-phase HPLC analyses of the acid hydrolysate and a modified Mosher's method. A distinction between d-Leu and l-Leu in the sequence was established by the application of a dansyl-Edman method to the partial acid hydrolysate. Mebamamide A did not exhibit any growth inhibitory activity against HeLa and HL60 cells at 10 μM, and mebamamide B did not exhibit any growth inhibitory activity against those cells at 100 μM. Additionally, it was suggested that mebamamide B induced the differentiation of HL60 cells into macrophage-like cells at 100 μM. (Chemical Equation).

Original languageEnglish
Pages (from-to)901-908
Number of pages8
JournalJournal of Natural Products
Volume78
Issue number4
DOIs
Publication statusPublished - 2015 Apr 24

Fingerprint

Lipopeptides
Marinas
Chlorophyta
Algae
HL-60 Cells
Acids
Macrophages
Growth
HeLa Cells
Leucine
High Pressure Liquid Chromatography
Amino Acids
mebamamide B
mebamamide A

ASJC Scopus subject areas

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

Cite this

Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina. / Iwasaki, Arihiro; Ohno, Osamu; Sumimoto, Shinpei; Matsubara, Teruhiko; Shimada, Satoshi; Sato, Toshinori; Suenaga, Kiyotake.

In: Journal of Natural Products, Vol. 78, No. 4, 24.04.2015, p. 901-908.

Research output: Contribution to journalArticle

@article{c989394950fe4524bc0fcde5f1bc2b47,
title = "Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina",
abstract = "Mebamamides A and B, new lipopeptides with four d-amino acid residues and a 3,8-dihydroxy-9-methyldecanoic acid residue, were isolated from the green alga Derbesia marina. Their gross structures were elucidated by spectroscopic and ESI-ITMS analyses. The absolute configurations except for the two leucines were revealed based on chiral-phase HPLC analyses of the acid hydrolysate and a modified Mosher's method. A distinction between d-Leu and l-Leu in the sequence was established by the application of a dansyl-Edman method to the partial acid hydrolysate. Mebamamide A did not exhibit any growth inhibitory activity against HeLa and HL60 cells at 10 μM, and mebamamide B did not exhibit any growth inhibitory activity against those cells at 100 μM. Additionally, it was suggested that mebamamide B induced the differentiation of HL60 cells into macrophage-like cells at 100 μM. (Chemical Equation).",
author = "Arihiro Iwasaki and Osamu Ohno and Shinpei Sumimoto and Teruhiko Matsubara and Satoshi Shimada and Toshinori Sato and Kiyotake Suenaga",
year = "2015",
month = "4",
day = "24",
doi = "10.1021/acs.jnatprod.5b00168",
language = "English",
volume = "78",
pages = "901--908",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "4",

}

TY - JOUR

T1 - Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina

AU - Iwasaki, Arihiro

AU - Ohno, Osamu

AU - Sumimoto, Shinpei

AU - Matsubara, Teruhiko

AU - Shimada, Satoshi

AU - Sato, Toshinori

AU - Suenaga, Kiyotake

PY - 2015/4/24

Y1 - 2015/4/24

N2 - Mebamamides A and B, new lipopeptides with four d-amino acid residues and a 3,8-dihydroxy-9-methyldecanoic acid residue, were isolated from the green alga Derbesia marina. Their gross structures were elucidated by spectroscopic and ESI-ITMS analyses. The absolute configurations except for the two leucines were revealed based on chiral-phase HPLC analyses of the acid hydrolysate and a modified Mosher's method. A distinction between d-Leu and l-Leu in the sequence was established by the application of a dansyl-Edman method to the partial acid hydrolysate. Mebamamide A did not exhibit any growth inhibitory activity against HeLa and HL60 cells at 10 μM, and mebamamide B did not exhibit any growth inhibitory activity against those cells at 100 μM. Additionally, it was suggested that mebamamide B induced the differentiation of HL60 cells into macrophage-like cells at 100 μM. (Chemical Equation).

AB - Mebamamides A and B, new lipopeptides with four d-amino acid residues and a 3,8-dihydroxy-9-methyldecanoic acid residue, were isolated from the green alga Derbesia marina. Their gross structures were elucidated by spectroscopic and ESI-ITMS analyses. The absolute configurations except for the two leucines were revealed based on chiral-phase HPLC analyses of the acid hydrolysate and a modified Mosher's method. A distinction between d-Leu and l-Leu in the sequence was established by the application of a dansyl-Edman method to the partial acid hydrolysate. Mebamamide A did not exhibit any growth inhibitory activity against HeLa and HL60 cells at 10 μM, and mebamamide B did not exhibit any growth inhibitory activity against those cells at 100 μM. Additionally, it was suggested that mebamamide B induced the differentiation of HL60 cells into macrophage-like cells at 100 μM. (Chemical Equation).

UR - http://www.scopus.com/inward/record.url?scp=84928732074&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84928732074&partnerID=8YFLogxK

U2 - 10.1021/acs.jnatprod.5b00168

DO - 10.1021/acs.jnatprod.5b00168

M3 - Article

C2 - 25768725

AN - SCOPUS:84928732074

VL - 78

SP - 901

EP - 908

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 4

ER -