Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression

Hitora, Yuki; Takada, Kentaro; Ise, Yuji; Woo, Sau Pinn; Inoue, Seiya; Mori, Nozomu; Takikawa, Hirosato; Nakamukai, Shohei; Okada, Shigeru; Matsunaga, Shigeki

doi:10.1016/j.bmc.2019.115233

Cited by 10 publications

(7 citation statements)

References 27 publications

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“…), and 1054 and 1055 (Dysidea septosa) respectively. [457][458][459] Spiroetherones A 1056 and B 1057, the rst examples of sesquiterpenoids conjugated to naphthoquinone cores via a quaternary carbon spiro centre, were isolated from Dysidea etheria. Both are moderate inhibitors of angiogenesis with weak cytotoxicity against several HTCLs and no overt toxicity to human kidney cells, therefore prompting interest in their bioactivity.…”

Section: Reviewmentioning

confidence: 99%

Marine natural products

et al. 2022

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Section: Reviewmentioning

confidence: 99%

Marine natural products

et al. 2022

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“…as a racemate. 10 The unsymmetrical and symmetrical thorectidiol dimer acetates 4 and 5 and thoractidol acetate (6) were all isolated by normal-phase HPLC as optically inactive materials. When thorectidol acetate (6) was analyzed by chiral-phase HPLC, two peaks were observed in a ratio of 1:1.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Thorectidiol A Isolated from the Marine Sponge Dactylospongia elegans Disrupts Interactions of the SARS-CoV-2 Spike Receptor Binding Domain with the Host ACE2 Receptor

et al. 2023

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Thorectidiols isolated from the marine sponge Dactylospongia elegans (family Thorectidae, order Dictyoceratida) collected in Papua New Guinea are a family of symmetrical and unsymmetrical dimeric biphenyl meroterpenoid stereoisomers presumed to be products of oxidative phenol coupling of a co-occurring racemic monomer, thorectidol (3). One member of the family, thorectidiol A (1), has been isolated in its natural form, and its structure has been elucidated by analysis of NMR, MS, and ECD data. Acetylation of the sponge extract facilitated isolation of additional thorectidiol diacetate stereoisomers and the isolation of the racemic monomer thorectidol acetate (6). Racemic thorectidiol A (1) showed selective inhibition of the SARS-CoV-2 spike receptor binding domain (RBD) interaction with the host ACE2 receptor with an IC50 = 1.0 ± 0.7 μM.

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“…Investigation of such an untapped resource would lead to the discovery of new biologically active secondary metabolites. In our continuing cytotoxic screening of such resources [ 3 , 4 ], the extract of a marine sponge, Cladocroce sp., exhibited activity against HeLa human cancer cervical cells. We have isolated calyxoside B ( 1 ) together with the known compound calyxoside ( 2 ) [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Structure Elucidation of Calyxoside B, a Bipolar Sphingolipid from a Marine Sponge Cladocroce sp. through the Use of Beckmann Rearrangement

et al. 2021

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Marine sponges are an excellent source of biologically active secondary metabolites. We focus on deep-sea sponges for our discovery study. A marine sponge Cladocroce sp. exhibited cytotoxic activity in the bioactivity screening. From this sponge a previously unreported cytotoxic glycosphingolipid, calyxoside B, was isolated and the structure of this compound was elucidated by analyses of MS and NMR spectra and chemical derivatization. We converted the ketone in the middle of a long aliphatic chain into an oxime to which was applied Beckmann rearrangement to afford two positional isomers of amides. The products were subjected to acidic hydrolysis followed by LC-MS analysis, permitting us to assign unequivocally the position of the ketone. Calyxoside B shows cytotoxicity against HeLa cells with an IC50 value of 31 µM and also weakly stimulated the production of cytokines in mice.

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Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression

Cited by 10 publications

References 27 publications

Marine natural products

Marine natural products

Thorectidiol A Isolated from the Marine Sponge Dactylospongia elegans Disrupts Interactions of the SARS-CoV-2 Spike Receptor Binding Domain with the Host ACE2 Receptor

Structure Elucidation of Calyxoside B, a Bipolar Sphingolipid from a Marine Sponge Cladocroce sp. through the Use of Beckmann Rearrangement

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