Isolation of heptadepsin, a novel bacterial cyclic depsipeptide that inhibits lipopolysaccharide activity

Osamu Ohno, Yoko Ikeda, Ryuichi Sawa, Masayuki Igarashi, Naoko Kinoshita, Yoshikazu Suzuki, Kensuke Miyake, Kazuo Umezawa

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Lipopolysaccharide (LPS) is considered to cause various inflammatory reactions. We searched among microbial secondary metabolites for compounds that could inhibit LPS-stimulated adhesion between human umbilical vein endothelial cells (HUVEC) and human myelocytic cell line HL-60 cells. In the course of our screening, we isolated a novel cyclic depsipeptide, which we named heptadepsin, from the whole culture broth of Paenibacillus sp. The addition of heptadepsin prior to LPS stimulation decreased HL-60 cell-HUVEC adhesion without showing any cytotoxicity. It also inhibited the cellular adhesion induced by lipid A, the active component of LPS, but it did not inhibit TNF-α or IL-1β-induced cell adhesion. The result of surface plasmon resonance (SPR) analysis revealed that heptadepsin interacted with lipid A directly. Thus, heptadepsin, a novel naturally occurring cyclic heptadepsipeptide, was shown to inactivate LPS by direct interaction with LPS.

Original languageEnglish
Pages (from-to)1059-1070
Number of pages12
JournalChemistry and Biology
Volume11
Issue number8
DOIs
Publication statusPublished - 2004 Aug

Fingerprint

Depsipeptides
Lipopolysaccharides
Lipid A
HL-60 Cells
Cell adhesion
Endothelial cells
Human Umbilical Vein Endothelial Cells
Cell Adhesion
Adhesion
Paenibacillus
Surface Plasmon Resonance
Surface plasmon resonance
Cytotoxicity
Metabolites
Interleukin-1
Screening
Cells
Cell Line

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ohno, O., Ikeda, Y., Sawa, R., Igarashi, M., Kinoshita, N., Suzuki, Y., ... Umezawa, K. (2004). Isolation of heptadepsin, a novel bacterial cyclic depsipeptide that inhibits lipopolysaccharide activity. Chemistry and Biology, 11(8), 1059-1070. https://doi.org/10.1016/j.chembiol.2004.05.016

Isolation of heptadepsin, a novel bacterial cyclic depsipeptide that inhibits lipopolysaccharide activity. / Ohno, Osamu; Ikeda, Yoko; Sawa, Ryuichi; Igarashi, Masayuki; Kinoshita, Naoko; Suzuki, Yoshikazu; Miyake, Kensuke; Umezawa, Kazuo.

In: Chemistry and Biology, Vol. 11, No. 8, 08.2004, p. 1059-1070.

Research output: Contribution to journalArticle

Ohno, O, Ikeda, Y, Sawa, R, Igarashi, M, Kinoshita, N, Suzuki, Y, Miyake, K & Umezawa, K 2004, 'Isolation of heptadepsin, a novel bacterial cyclic depsipeptide that inhibits lipopolysaccharide activity', Chemistry and Biology, vol. 11, no. 8, pp. 1059-1070. https://doi.org/10.1016/j.chembiol.2004.05.016
Ohno, Osamu ; Ikeda, Yoko ; Sawa, Ryuichi ; Igarashi, Masayuki ; Kinoshita, Naoko ; Suzuki, Yoshikazu ; Miyake, Kensuke ; Umezawa, Kazuo. / Isolation of heptadepsin, a novel bacterial cyclic depsipeptide that inhibits lipopolysaccharide activity. In: Chemistry and Biology. 2004 ; Vol. 11, No. 8. pp. 1059-1070.
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