nach oben

Journal of Natural Medicines

Erschienen in:

01.10.2017 | Note

Ceylonins G–I: spongian diterpenes from the marine sponge Spongia ceylonensis

verfasst von: Ahmed H. El-Desoky, Hikaru Kato, Sachiko Tsukamoto

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2017

Einloggen, um Zugang zu erhalten

Abstract

Three new spongian diterpenes, ceylonins G–I (1–3), were isolated from the marine sponge Spongia ceylonensis collected in Indonesia, together with five known spongian diterpenes (4–8). Only 4 inhibited USP7 with an IC₅₀ value of 8.2 μM.

In reference [3], two hydrogens (H-15 and H-16) on the furan ring of 9 were observed at δ _H 7.03 and 7.06, whereas each chemical shift was not assigned.

Although the positive Cotton effect was not observed for 3, the presence of the negative Cotton effect and biogenetic relationship with 1, 2, and 9 unambiguously supported the absolute configuration.

Due to the limited amount, 2 was not tested.

When we isolated ceylonamides A–F (10–15) from the sponge S. ceylonensis (RMNH POR 8676), spongian diterpenes 5–8 were also obtained [1].

El-Desoky AH, Kato H, Angkouw ED, Mangindaan REP, de Voogd NJ, Tsukamoto S (2016) Ceylonamides A–F, nitrogenous spongian diterpenes that inhibit RANKL-induced osteoclastogenesis, from the marine sponge Spongia ceylonensis. J Nat Prod 79:1922–1928CrossRef

El-Desoky AH, Kato H, Kagiyama I, Hitora Y, Losung F, Mangindaan REP, de Voogd NJ, Tsukamoto S (2017) Ceylonins A–F, spongian diterpene derivatives that inhibit RANKL-induced formation of multinuclear osteoclasts, from the marine sponge Spongia ceylonensis. J Nat Prod 80:90–95CrossRef

Capelle N, Braekman JC, Daloze D, Tursch B (1980) Chemical studies of marine invertebrates. XLIV. Three new spongian diterpenes from Spongia officinalis. Bull Soc Chim Belg 89:399–404CrossRef

Hyosu M, Kimura J (2000) Two new spongian diterpenes from Coscinoderma mathewsi. J Nat Prod 63:422–423CrossRef

Li CJ, Schmitz FJ, Kelly-Borges M (1999) Six new spongian diterpenes from the sponge Spongia matamata. J Nat Prod 62:287–290CrossRef

Mitchell SS, Harper MK, Faulkner DJ (1999) Spongiabutenolides A–D: minor γ-hydroxybutenolide diterpenoids from a Philippines Spongia sp. Tetrahedron 55:10887–10892CrossRef

Reverdy C, Conrath S, Lopez R, Planquette C, Atmanene C, Collura V, Harpon J, Battaglia V, Vivat V, Sippl W, Colland F (2012) Discovery of specific inhibitors of human USP7/HAUSP deubiquitinating enzyme. Chem Biol 19:467–477CrossRef

Colland F, Formstecher E, Jacq X, Reverdy C, Planquette C, Conrath S, Trouplin V, Bianchi J, Aushev VN, Camonis J, Calabrese A, Borg-Capra C, Sippl W, Collura V, Boissy G, Rain JC, Guedat P, Delansorne R, Daviet L (2009) Small-molecule inhibitor of USP7/HAUSP ubiquitin protease stabilizes and activates p53 in cells. Mol Cancer Ther 8:2286–2295CrossRef

Altun M, Kramer HB, Willems LI, McDermott JL, Leach CA, Goldenberg SJ, Kumar KG, Konietzny R, Fischer R, Kogan E, Mackeen MM, McGouran J, Khoronenkova SV, Parsons JL, Dianov GL, Nicholson B, Kessler BM (2011) Activity-based chemical proteomics accelerates inhibitor development for deubiquitylating enzymes. Chem Biol 18:1401–1412CrossRef

10.

Yamaguchi M, Miyazaki M, Kodrasov MP, Rotinsulu H, Losung F, Mangindaan REP, de Voogd NJ, Yokosawa H, Nicholson B, Tsukamoto S (2013) Spongiacidin C, a bromopyrrole alkaloid from the marine sponge Stylissa massa, functions as a USP7 inhibitor. Bioorg Med Chem Lett 23:3884–3886CrossRef

11.

Tanokashira N, Kukita S, Kato H, Nehira T, Angkouw ED, Mangindaan REP, de Voogd NJ, Tsukamoto S (2016) Petroquinones: trimeric and dimeric xestoquinone derivatives isolated from the marine sponge Petrosia alfiani. Tetrahedron 72:5530–5540CrossRef

12.

Kagiyama I, Kato H, Nehira T, Frisvad JC, Sherman DH, Williams RM, Tsukamoto S (2016) Angew Chem Int Ed 55:1128–1132CrossRef

Titel: Ceylonins G–I: spongian diterpenes from the marine sponge Spongia ceylonensis
verfasst von: Ahmed H. El-Desoky
Hikaru Kato
Sachiko Tsukamoto
Publikationsdatum: 01.10.2017
Verlag: Springer Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 4/2017
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-017-1087-4

Die Highlights vom Kongress des American College of Cardiology 2024

Springer Medizin

Ceylonins G–I: spongian diterpenes from the marine sponge Spongia ceylonensis

Abstract

Die Highlights vom Kongress des American College of Cardiology 2024

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 4/2017

Erratum to: Naturally occurring Vpr inhibitors from medicinal plants of Myanmar

Shikonin changes the lipopolysaccharide-induced expression of inflammation-related genes in macrophages

Phytochemical profile and angiotensin I converting enzyme (ACE) inhibitory activity of Limonium michelsonii Lincz

A new biphenyl ether derivative produced by Indonesian ascidian-derived Penicillium albobiverticillium

Nine pairs of megastigmane enantiomers from the leaves of Eucommia ulmoides Oliver

Comparison of the ameliorative effects of Qingfei Tongluo formula and azithromycin on Mycoplasma pneumoniae pneumonia