Aurantoside L, a New Tetramic Acid Glycoside with Anti-Leishmanial Activity Isolated from the Marine Sponge Siliquariaspongia japonica

Yasumoto Oyadomari; Yasuyuki Goto; Keisuke Suganuma; Shin-Ichiro Kawazu; Leontine E Becking; Nobuhiro Fusetani; Yoichi Nakao

doi:10.3390/md22040171

Aurantoside L, a New Tetramic Acid Glycoside with Anti-Leishmanial Activity Isolated from the Marine Sponge Siliquariaspongia japonica

Mar Drugs. 2024 Apr 12;22(4):171. doi: 10.3390/md22040171.

Authors

Yasumoto Oyadomari¹, Yasuyuki Goto², Keisuke Suganuma³, Shin-Ichiro Kawazu³, Leontine E Becking^{4

5}, Nobuhiro Fusetani⁶, Yoichi Nakao^{1

6}

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 Graduate School of Agricultural and Life Science, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
³ National Research Center for Protozoan Diseases, Obihiro University of Agriculture and Veterinary Medicine, Inada-cho, Obihiro 080-8555, Japan.
⁴ Aquaculture & Fisheries Group, Wageningen University & Research, P.O. Box 338, Bode 32, 6700 AH Wageningen, The Netherlands.
⁵ Naturalis Biodiversity Center, Darwinweg 2, 23333 CR Leiden, The Netherlands.
⁶ Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.

Abstract

A new tetramic acid glycoside, aurantoside L (1), was isolated from the sponge Siliquariaspongia japonica collected at Tsushima Is., Nagasaki Prefecture, Japan. The structure of aurantoside L (1) composed of a tetramic acid bearing a chlorinated polyene system and a trisaccharide part was elucidated using spectral analysis. Aurantoside L (1) showed anti-parasitic activity against L. amazonensis with an IC₅₀ value of 0.74 µM.

Keywords: Siliquariaspongia japonica; anti-leishmanial activity; aurantosides; marine natural products; marine sponge; mass spectrometry; nuclear magnetic resonance.

MeSH terms

Animals
Antiprotozoal Agents / chemistry
Antiprotozoal Agents / isolation & purification
Antiprotozoal Agents / pharmacology
Glycosides* / chemistry
Glycosides* / isolation & purification
Glycosides* / pharmacology
Inhibitory Concentration 50
Japan
Leishmania* / drug effects
Porifera* / chemistry
Pyrrolidinones / chemistry
Pyrrolidinones / isolation & purification
Pyrrolidinones / pharmacology

Substances

Glycosides
tetramic acid
Antiprotozoal Agents
Pyrrolidinones

Abstract

MeSH terms

Substances

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