Jasplakinolide, a cyclodepsipeptide from the marine sponge, SP.

Crews, Phillip; Manes, L.; Boehler, Mark A.

doi:10.1016/s0040-4039(00)84645-6

Cited by 316 publications

(199 citation statements)

References 10 publications

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“…yielded the cyclodepsipeptide jasplakinolide (9) as the major bioactive compound. Jasplakinolide (9) is normally isolated from sponges, rather than form soft corals [51], suggesting that the Sinularia sp. extract included in our study was probably contaminated with spongean material on which the soft coral had been encrusted.…”

Section: Fatty Acid Composition Of the Microalgae Screened For Nf-b-mentioning

confidence: 99%

The inhibition of TNF-α-induced NF-κB activation by marine natural products

Folmer

Jaspars

Solano

et al. 2009

Biochemical Pharmacology

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, et al.. The inhibition of TNF-α induced NF-κB activation by marine natural products. Biochemical Pharmacology, Elsevier, 2009, 78 (6) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A c c e p t e d M a n u s c r i p t 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 AbstractThe deregulated activation of NF-B is associated with cancer development and inflammatory diseases. With the aim to find new NF-B inhibitors, we purified and characterized compounds from extracts of the Fijian sponge Rhabdastrella globostellata, the crinoid Comanthus parvicirrus, the soft corals Sarcophyton sp. nov. and Sinularia sp., and the gorgonian Subergorgia sp. after an initial screening of 266 extracts from different marine origins.Results obtained show that selected purified compounds had a cytotoxic effect on the human leukaemia cell line K562, inhibited both TNF--induced NF-B-DNA binding as well as TNF- induced IB degradation and nuclear translocation of p50/p65. Furthermore, we observed inhibition of NF-B activation induced by an overexpression of TNFR1, TRAF2, TRADD, or IKK Interestingly, natural products inhibited IKK kinase as well as the 26S proteasome proteolytic activity.

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Section: Fatty Acid Composition Of the Microalgae Screened For Nf-b-mentioning

confidence: 99%

The inhibition of TNF-α-induced NF-κB activation by marine natural products

Folmer

Jaspars

Solano

et al. 2009

Biochemical Pharmacology

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“…This unique cyclodepsipeptide exhibited cytotoxicity against HeLa-S 3 cells with an IC 50 of 0.005 g͞ml (14). Structurally, doliculide is related to a family of cyclodepsipeptides known as geodiamolides (26,27) and jaspamide (28,29). It is distinct in many respects, particularly by the presence of three alternating syn-related C-methyl groups as part of the 11-carbon dihydroxy branched carboxylic acid subunit (Fig.…”

mentioning

confidence: 99%

Total synthesis of the cytotoxic cyclodepsipeptide (-)-doliculide: The “ester” effect in acyclic 1,3-induction of deoxypropionates

Hanessian

Mascitti

Giroux

2004

Proc. Natl. Acad. Sci. U.S.A.

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The total synthesis of the marine cyclodepsipeptide (؊)-doliculide is described. An acyclic (2S,4S,6R)-trimethyl alkanoic acid precursor to the ''hydrocarbon'' portion of doliculide was synthesized starting with L-ascorbic acid based on a stereocontrolled iterative conjugate addition of lithium dimethylcuprate to acyclic ␦-Cmethyl ␣,␤-unsaturated ester derivatives. syn͞syn selectivity was achieved by relying on 1,3-induction in preferred folded conformations that avoid 1,5-syn-pentane interactions in the transition states. The nature of the ester moiety seems to play an important role in determining the syn͞anti ratios of C-methyl adducts. The 1-methyl-1-cyclopentyl ester group was found to confer the best syn selectivity to the cuprate addition products, especially in seven-carbon enoates.

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“…sponge. [48]. It was later reisolated as a tumor cell cytotoxic component in a Papua New Guinea sponge (Auletta cf.…”

Section: Apoptosismentioning

confidence: 99%

Mechanism Targeted Discovery of Antitumor Marine Natural Products

Nagle¹,

Zhou²,

Mora³

et al. 2004

Current Medicinal Chemistry

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Antitumor drug discovery programs aim to identify chemical entities for use in the treatment of cancer. Many strategies have been used to achieve this objective. Natural products have always played a major role in anticancer medicine and the unique metabolites produced by marine organisms have increasingly become major players in antitumor drug discovery. Rapid advances have occurred in the understanding of tumor biology and molecular medicine. New insights into mechanisms responsible for neoplastic disease are significantly changing the general philosophical approach towards cancer treatment. Recently identified molecular targets have created exciting new means for disrupting tumor-specific cell signaling, cell division, energy metabolism, gene expression, drug resistance, and blood supply. Such tumor-specific treatments could someday decrease our reliance on traditional cytotoxicity-based chemotherapy and provide new less toxic treatment options with significantly fewer side effects. Novel molecular targets and state-of-the-art molecular mechanism-based screening methods have revitalized antitumor research and these changes are becoming an ever-increasing component of modern antitumor marine natural products research. This review describes marine natural products identified using tumor-specific mechanism-based assays for regulators of angiogenesis, apoptosis, cell cycle, macromolecule synthesis, mitochondrial respiration, mitosis, multidrug efflux, and signal transduction. Special emphasis is placed on natural products directly discovered using molecular mechanism-based screening.

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Jasplakinolide, a cyclodepsipeptide from the marine sponge, SP.

Cited by 316 publications

References 10 publications

The inhibition of TNF-α-induced NF-κB activation by marine natural products

The inhibition of TNF-α-induced NF-κB activation by marine natural products

Total synthesis of the cytotoxic cyclodepsipeptide (-)-doliculide: The “ester” effect in acyclic 1,3-induction of deoxypropionates

Mechanism Targeted Discovery of Antitumor Marine Natural Products

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