Two New Jaspamide Derivatives from the Marine Sponge Jaspis splendens

Ebada, Sherif S.; Wray, Victor; Voogd, Nicole J. de; Deng, Zhiwei; Lin, Wenhan; Proksch, Peter

doi:10.3390/md7030435

Cited by 45 publications

(40 citation statements)

References 45 publications

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“…(2) While oxidation of the Trp is ruinous to nM activity8,10 this does not apply to the β-Tyr residue as activity is retained in 13 in spite of further aryl hydroxylation. (3) Removal or addition of halogens to the Trp is also tolerated as shown by the data of 7 and 8 in comparison to that of 1 9,40. (4) A conformation change in the macrolide ring induced by the Δ2,3 double bond ( 13 vs. 14 ) obliterates nM activity.…”

Section: Resultsmentioning

confidence: 98%

Biostructural Features of Additional Jasplakinolide (Jaspamide) Analogues

et al. 2011

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The cyclodepsipeptide jasplakinolide (1) (a.k.a. jaspamide), isolated previously from the marine sponge Jaspis splendens, is a unique cytotoxin and molecular probe that operates through stabilization of filamentous actin (F-actin). We have recently disclosed that two analogues of 1, jasplakinolides B (3) and E, were referred to the National Cancer Institute's (NCI) Biological Evaluation Committee and the objective of this study was to re-investigate a Fijian collection of J. splendens in an effort to find jasplakinolide congeners with similar biological properties. The current efforts have afforded six known jasplakinolide analogues (4 -7, 9 -10), two structures requiring revision (8 and 14) and four new congeners of 1 (11 -13, 15) including open chain derivatives and structures with modified β-tyrosine residues. Compounds were evaluated for biological activity in the NCI's 60 cell line screen and in a microfilament disruption assay in both HCT-116 and HeLa cells. These two phenotypic screens provide evidence that each cytotoxic analogue, including jasplakinolide B (3), operates by modification of microfilaments. The new structure jasplakinolide V (13) has also been selected for study by the NCI's Biological Evaluation Committee. In addition, the results of a clonogenic dose response study on jasplakinolide are presented.The unique cyclodepsipeptide jasplakinolide (1) (a.k.a. jaspamide) has been a seed for continuous chemical and biological investigations since its discovery in 1986. 1,2 This mixed polyketide-peptide compound (often referred to as a PKS-NRPS hybrid) 3 was first isolated from Jaspis (syn: Doryplores) splendens 4 (order Astrophorida, family Ancorinidae) sponges collected in Fiji and Palau, and subsequent investigations [5][6][7][8][9][10] have shown that 1 can be obtained from Jaspis sponges collected throughout the Indo-Pacific. We recently disclosed seven new analogues of 1 ,10 and included an account of the 15 additional natural derivatives divided into two frameworks along with a bio-geographical outline of the two sponge orders that are the source of these metabolites. Other marine sponge genera are also the source of related cyclodepsipeptides named the geodiamolides (Geodia, and Cymbastela) [11][12][13][14][15][16] and the seragamides (Suberites). 17 Similar to the jasplakinolide family, the members of these two classes occur in taxonomically distant groups of sponges. The discovery of yet another † Dedicated to Dr. Koji Nakanishi of Columbia University for his pioneering work on bioactive natural products.* Corresponding author. Tel: 831-459-2603. Fax: 831-459-2935. phil@chemistry.ucsc.edu. ‡ Department of Chemistry and Biochemistry § UCSC Chemical Screening Center ⊥ Henry Ford Hospital Supporting Information Available: 1 H, 13 C, gHMQC and gHMBC NMR spectra for compounds 6-15, a sponge picture of 00101, NCI 60 cell line results, and microfilament effects of 10. This material is available free of charge via the Internet at http://pubs.acs.org. The push to understand the biological ...

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Section: Resultsmentioning

confidence: 98%

Biostructural Features of Additional Jasplakinolide (Jaspamide) Analogues

et al. 2011

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“…The complete structure of JDC3 was elucidated based on 1 H and 13 C‐NMR, total correlation spectroscopy (TOCSY), heteronuclear multiple‐quantum correlation spectroscopy (HMQC) and heteronuclear multiple‐bond correlation (HMBC) spectral data and were found to be Jaspamide. Jaspamide is a 19‐membered ring made up of four moieties, namely an alanine moiety, an abrine ( N ‐methyl tryptophan) moiety, a β‐tyrosine moiety and a polypropionate moiety (11‐carbon hydroxyl acid containing four methyl groups on alternating carbons) [5,7,26,27]. The presence of each of the four moieties in JDC3 was confirmed by 1D and 2D NMR as follows: (1) The alanine moiety showed 1 H‐NMR signals at δ H 4.71 (quin, 6.7) for H‐15, 0.75 δ H (d, 6.7) for Me‐16 and δ H 6.59 (1H, d , 6.7 Hz) for the N H ‐Ala.…”

Section: Resultsmentioning

confidence: 97%

Evaluation of hexane and ethyl acetate extracts of the sponge Jaspis diastra collected from Mauritius Waters on HeLa cells

Beedessee

Ramanjooloo

Tiscornia

et al. 2014

Journal of Pharmacy and Pharmacology

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“…This bioactive substance can exert a pronounced antitumour effect in breast and prostate cancer patients by inducing polymerization of the actin filaments of tumour cells. Recently, two new jaspamide derivatives have been isolated from the marine sponge Jaspis splendens . In vitro experimental results demonstrated that these compounds could effectively suppress rat lymphoma cell L5178Y.…”

Section: Drugs Containing Antitumour Bioactive Peptides With Differenmentioning

confidence: 99%

Antitumour bioactive peptides isolated from marine organisms

Xing

Tong

Jiang

et al. 2017

Clin Exp Pharma Physio

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SummaryMarine organisms are an important source of antitumour active substances. Thus, pharmaceutical research in recent years has focused on exploring new antitumour drugs derived from marine organisms, and, many peptide drugs with strong antitumour activities have been successfully extracted. Based on different mechanisms, this paper reviews the research on several typical antitumour bioactive peptides in marine drugs and the latest progress therein. Additionally, the development prospects for these antitumour bioactive peptide-based drugs are discussed so as to provide a reference for future research in this field. K E Y W O R D Santitumour, bioactive peptides, marine organisms

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Two New Jaspamide Derivatives from the Marine Sponge Jaspis splendens

Cited by 45 publications

References 45 publications

Biostructural Features of Additional Jasplakinolide (Jaspamide) Analogues

Biostructural Features of Additional Jasplakinolide (Jaspamide) Analogues

Evaluation of hexane and ethyl acetate extracts of the sponge Jaspis diastra collected from Mauritius Waters on HeLa cells

Antitumour bioactive peptides isolated from marine organisms

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