Spiroetherones A and B, sesquiterpene naphthoquinones, as angiogenesis inhibitors from the marine sponge Dysidea etheria

Wei-Hua Jiao; Qi-Hang  Xu; Jie Cui; Ru-Yi Shang; Yun Zhang; Jia-Bao Sun; Qi Yang; Ke-Chun Liu; Hou-Wen Lin

doi:10.1039/C9QO01346F

Spiroetherones A and B, sesquiterpene naphthoquinones, as angiogenesis inhibitors from the marine sponge Dysidea etheria

Wei-Hua Jiao, Qi-Hang Xu, Jie Cui, Ru-Yi Shang, Yun Zhang, Jia-Bao Sun, Qi Yang, Ke-Chun Liu, Hou-Wen Lin

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

Spiroetherones A (1) and B (2), a pair of sesquiterpene naphthoquinones with an unprecedented “spiroetherane” carbon skeleton, were isolated from the marine sponge Dysidea etheria collected from the South China Sea. Their structures and absolute configurations were determined by spectroscopic analyses coupled with quantum chemistry DFT GIAO 13C NMR and ECD calculations. Spiroetherone A (1) showed anti-angiogenic activity in a zebrafish model with an IC50 value of 2.4 μM. In addition, the plausible biogenetic pathway of the two metabolites is proposed.

Original language	English
Pages (from-to)	368-373
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	7
Issue number	2
DOIs	https://doi.org/10.1039/C9QO01346F
Publication status	Published - 21 Jan 2020
Externally published	Yes

Keywords

Spiroetherones
sesquiterpene naphthoquinones
angiogenesis inhibitors
marine sponges
Dysidea etheria
anti-angiogenic activity
zebrafish
zebrafish model

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title = "Spiroetherones A and B, sesquiterpene naphthoquinones, as angiogenesis inhibitors from the marine sponge Dysidea etheria",

abstract = "Spiroetherones A (1) and B (2), a pair of sesquiterpene naphthoquinones with an unprecedented “spiroetherane” carbon skeleton, were isolated from the marine sponge Dysidea etheria collected from the South China Sea. Their structures and absolute configurations were determined by spectroscopic analyses coupled with quantum chemistry DFT GIAO 13C NMR and ECD calculations. Spiroetherone A (1) showed anti-angiogenic activity in a zebrafish model with an IC50 value of 2.4 μM. In addition, the plausible biogenetic pathway of the two metabolites is proposed.",

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T1 - Spiroetherones A and B, sesquiterpene naphthoquinones, as angiogenesis inhibitors from the marine sponge Dysidea etheria

AU - Jiao, Wei-Hua

AU - Xu, Qi-Hang

AU - Cui, Jie

AU - Shang, Ru-Yi

AU - Zhang, Yun

AU - Sun, Jia-Bao

AU - Yang, Qi

AU - Liu, Ke-Chun

AU - Lin, Hou-Wen

PY - 2020/1/21

Y1 - 2020/1/21

N2 - Spiroetherones A (1) and B (2), a pair of sesquiterpene naphthoquinones with an unprecedented “spiroetherane” carbon skeleton, were isolated from the marine sponge Dysidea etheria collected from the South China Sea. Their structures and absolute configurations were determined by spectroscopic analyses coupled with quantum chemistry DFT GIAO 13C NMR and ECD calculations. Spiroetherone A (1) showed anti-angiogenic activity in a zebrafish model with an IC50 value of 2.4 μM. In addition, the plausible biogenetic pathway of the two metabolites is proposed.

AB - Spiroetherones A (1) and B (2), a pair of sesquiterpene naphthoquinones with an unprecedented “spiroetherane” carbon skeleton, were isolated from the marine sponge Dysidea etheria collected from the South China Sea. Their structures and absolute configurations were determined by spectroscopic analyses coupled with quantum chemistry DFT GIAO 13C NMR and ECD calculations. Spiroetherone A (1) showed anti-angiogenic activity in a zebrafish model with an IC50 value of 2.4 μM. In addition, the plausible biogenetic pathway of the two metabolites is proposed.

KW - Spiroetherones

KW - sesquiterpene naphthoquinones

KW - angiogenesis inhibitors

KW - marine sponges

KW - Dysidea etheria

KW - anti-angiogenic activity

KW - zebrafish

KW - zebrafish model

U2 - 10.1039/C9QO01346F

DO - 10.1039/C9QO01346F

M3 - Article

VL - 7

SP - 368

EP - 373

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 2

ER -

Spiroetherones A and B, sesquiterpene naphthoquinones, as angiogenesis inhibitors from the marine sponge Dysidea etheria

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Keywords

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