Two Onnamide Analogs from the Marine Sponge Theonella conica: Evaluation of Geometric Effects in the Polyene Systems on Biological Activity

Fumiaki Nakamura; Hiroshi Kimura; Nobuhiro Fusetani; Yoichi Nakao

doi:10.3390/molecules28062524

Two Onnamide Analogs from the Marine Sponge Theonella conica: Evaluation of Geometric Effects in the Polyene Systems on Biological Activity

Molecules. 2023 Mar 9;28(6):2524. doi: 10.3390/molecules28062524.

Authors

Fumiaki Nakamura¹, Hiroshi Kimura², Nobuhiro Fusetani³, Yoichi Nakao^{1

3}

Affiliations

¹ Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
² Cell Biology Center, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.
³ Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.

Abstract

Two previously unreported onnamide analogs, 2Z- and 6Z-onnamides A (1 and 2), were isolated from the marine sponge Theonella conica collected at Amami-Oshima Is., Kagoshima Prefecture, Japan. Structures of compounds 1 and 2 were elucidated by spectral analysis. Structure-activity relationships (SARs) for effects on histone modifications and cytotoxicity against HeLa and P388 cells were characterized. The geometry in the polyene systems of onnamides affected the histone modification levels and cytotoxicity.

Keywords: Theonella sp.; cytotoxicity; histone modifications; marine natural products; marine sponges; onnamides.

MeSH terms

Animals
HeLa Cells
Humans
Molecular Structure
Polyenes / pharmacology
Porifera* / chemistry
Pyrans
Theonella* / chemistry

Substances

onnamide
Pyrans
Polyenes

Abstract

MeSH terms

Substances

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