Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia

Mohamed Ashour, RuAngelie Edrada, Rainer Ebel, Victor Wray, Wim Wätjen, K Padmakumar, Werner E G Müller, Wen Han Lin, Peter Proksch, Ruangelie Edrada-Ebel

Research output: Contribution to journalArticle

90 Citations (Scopus)

Abstract

Two new cyclic depsipeptide derivatives, kahalalides R (1) and S (2), together with two known congeners, kahalalides F (3) and D (4), were isolated from the Indian sacoglossan mollusk Elysia grandifolia. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, HMBC) and mass spectrometric (FABMS, ESIMS, MALDI-TOF/PSD) data, which also included Marfey amino acid analyses. The new derivative kahalalide R was found to exert comparable or even higher cytotoxicity than the potential drug candidate kahalalide F toward the MCF7 human mammary carcinoma cell line.

LanguageEnglish
Pages1547-1553
Number of pages7
JournalJournal of Natural Products
Volume69
Issue number11
DOIs
Publication statusPublished - Nov 2006

Fingerprint

Depsipeptides
Mollusca
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Breast Neoplasms
Derivatives
Amino Acids
Cell Line
Cytotoxicity
Pharmaceutical Preparations
Cells
Nuclear magnetic resonance
kahalalide F
kahalalide R
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • animals
  • antineoplastic agents
  • cell line, tumor
  • depsipeptides
  • drug screening assays, antitumor
  • Indian Ocean
  • mammary neoplasms
  • molecular structure
  • mollusca
  • nuclear magnetic resonance, Biomolecular

Cite this

Ashour, Mohamed ; Edrada, RuAngelie ; Ebel, Rainer ; Wray, Victor ; Wätjen, Wim ; Padmakumar, K ; Müller, Werner E G ; Lin, Wen Han ; Proksch, Peter ; Edrada-Ebel, Ruangelie. / Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia. In: Journal of Natural Products. 2006 ; Vol. 69, No. 11. pp. 1547-1553.
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abstract = "Two new cyclic depsipeptide derivatives, kahalalides R (1) and S (2), together with two known congeners, kahalalides F (3) and D (4), were isolated from the Indian sacoglossan mollusk Elysia grandifolia. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, HMBC) and mass spectrometric (FABMS, ESIMS, MALDI-TOF/PSD) data, which also included Marfey amino acid analyses. The new derivative kahalalide R was found to exert comparable or even higher cytotoxicity than the potential drug candidate kahalalide F toward the MCF7 human mammary carcinoma cell line.",
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Ashour, M, Edrada, R, Ebel, R, Wray, V, Wätjen, W, Padmakumar, K, Müller, WEG, Lin, WH, Proksch, P & Edrada-Ebel, R 2006, 'Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia' Journal of Natural Products, vol. 69, no. 11, pp. 1547-1553. https://doi.org/10.1021/np060172v

Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia. / Ashour, Mohamed; Edrada, RuAngelie; Ebel, Rainer; Wray, Victor; Wätjen, Wim; Padmakumar, K; Müller, Werner E G; Lin, Wen Han; Proksch, Peter; Edrada-Ebel, Ruangelie.

In: Journal of Natural Products, Vol. 69, No. 11, 11.2006, p. 1547-1553.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia

AU - Ashour, Mohamed

AU - Edrada, RuAngelie

AU - Ebel, Rainer

AU - Wray, Victor

AU - Wätjen, Wim

AU - Padmakumar, K

AU - Müller, Werner E G

AU - Lin, Wen Han

AU - Proksch, Peter

AU - Edrada-Ebel, Ruangelie

PY - 2006/11

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N2 - Two new cyclic depsipeptide derivatives, kahalalides R (1) and S (2), together with two known congeners, kahalalides F (3) and D (4), were isolated from the Indian sacoglossan mollusk Elysia grandifolia. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, HMBC) and mass spectrometric (FABMS, ESIMS, MALDI-TOF/PSD) data, which also included Marfey amino acid analyses. The new derivative kahalalide R was found to exert comparable or even higher cytotoxicity than the potential drug candidate kahalalide F toward the MCF7 human mammary carcinoma cell line.

AB - Two new cyclic depsipeptide derivatives, kahalalides R (1) and S (2), together with two known congeners, kahalalides F (3) and D (4), were isolated from the Indian sacoglossan mollusk Elysia grandifolia. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, HMBC) and mass spectrometric (FABMS, ESIMS, MALDI-TOF/PSD) data, which also included Marfey amino acid analyses. The new derivative kahalalide R was found to exert comparable or even higher cytotoxicity than the potential drug candidate kahalalide F toward the MCF7 human mammary carcinoma cell line.

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KW - mammary neoplasms

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Ashour M, Edrada R, Ebel R, Wray V, Wätjen W, Padmakumar K et al. Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia. Journal of Natural Products. 2006 Nov;69(11):1547-1553. https://doi.org/10.1021/np060172v