New steroidal saponins from the sponge Erylus lendenfeldi

Mostafa Fouad; Khaled Al-Trabeen; Mohammad Badran; Victor Wray; Ruangelie Edrada-Ebel; Peter Proksch; Rainer Ebel

New steroidal saponins from the sponge Erylus lendenfeldi

Mostafa Fouad, Khaled Al-Trabeen, Mohammad Badran, Victor Wray, Ruangelie Edrada-Ebel, Peter Proksch, Rainer Ebel

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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20 Citations (Scopus)

Abstract

Our search for biologically active marine natural products has led to the isolation of two new steroidal saponins, eryloside K (2) and eryloside L (3) together with the known antitumor and antifungal glycoside eryloside A (1) from the organic extract of the sponge Erylus lendenfeldi (Geodiidae) collected in the Red Sea. The structures of the new compounds were elucidated on the basis of comprehensive spectral analyses ( ¹H, ¹³C, COSY, HMQC, HMBC and TOCSY NMR) as well as GC/MS analysis to infer the absolute stereochemistry of the sugar moieties. Eryloside K (2) is the 24,25-didehydro congener of 1, while eryloside L (3) features an unusual 8α,9α- epoxy-4α-methyl-8,9-secocholesta-7,9(11),14-triene skeleton which appears to be unprecedented in nature. Eryloside A (1) displayed antibacterial activity against Bacillus subtilis and Escherichia coli together with antifungal activity against Candida albicans.

Original language	English
Pages (from-to)	17-27
Number of pages	11
Journal	Arkivoc
Volume	2004
Issue number	13
Publication status	Published - 23 Aug 2004

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Keywords

antibacterial
antifungal
marine sponge
saponin
steroidal saponin

Cite this

Fouad, M., Al-Trabeen, K., Badran, M., Wray, V., Edrada-Ebel, R., Proksch, P., & Ebel, R. (2004). New steroidal saponins from the sponge Erylus lendenfeldi. Arkivoc, 2004(13), 17-27.

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abstract = "Our search for biologically active marine natural products has led to the isolation of two new steroidal saponins, eryloside K (2) and eryloside L (3) together with the known antitumor and antifungal glycoside eryloside A (1) from the organic extract of the sponge Erylus lendenfeldi (Geodiidae) collected in the Red Sea. The structures of the new compounds were elucidated on the basis of comprehensive spectral analyses ( 1H, 13C, COSY, HMQC, HMBC and TOCSY NMR) as well as GC/MS analysis to infer the absolute stereochemistry of the sugar moieties. Eryloside K (2) is the 24,25-didehydro congener of 1, while eryloside L (3) features an unusual 8α,9α- epoxy-4α-methyl-8,9-secocholesta-7,9(11),14-triene skeleton which appears to be unprecedented in nature. Eryloside A (1) displayed antibacterial activity against Bacillus subtilis and Escherichia coli together with antifungal activity against Candida albicans.",

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author = "Mostafa Fouad and Khaled Al-Trabeen and Mohammad Badran and Victor Wray and Ruangelie Edrada-Ebel and Peter Proksch and Rainer Ebel",

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T1 - New steroidal saponins from the sponge Erylus lendenfeldi

AU - Fouad, Mostafa

AU - Al-Trabeen, Khaled

AU - Badran, Mohammad

AU - Wray, Victor

AU - Edrada-Ebel, Ruangelie

AU - Proksch, Peter

AU - Ebel, Rainer

PY - 2004/8/23

Y1 - 2004/8/23

N2 - Our search for biologically active marine natural products has led to the isolation of two new steroidal saponins, eryloside K (2) and eryloside L (3) together with the known antitumor and antifungal glycoside eryloside A (1) from the organic extract of the sponge Erylus lendenfeldi (Geodiidae) collected in the Red Sea. The structures of the new compounds were elucidated on the basis of comprehensive spectral analyses ( 1H, 13C, COSY, HMQC, HMBC and TOCSY NMR) as well as GC/MS analysis to infer the absolute stereochemistry of the sugar moieties. Eryloside K (2) is the 24,25-didehydro congener of 1, while eryloside L (3) features an unusual 8α,9α- epoxy-4α-methyl-8,9-secocholesta-7,9(11),14-triene skeleton which appears to be unprecedented in nature. Eryloside A (1) displayed antibacterial activity against Bacillus subtilis and Escherichia coli together with antifungal activity against Candida albicans.

AB - Our search for biologically active marine natural products has led to the isolation of two new steroidal saponins, eryloside K (2) and eryloside L (3) together with the known antitumor and antifungal glycoside eryloside A (1) from the organic extract of the sponge Erylus lendenfeldi (Geodiidae) collected in the Red Sea. The structures of the new compounds were elucidated on the basis of comprehensive spectral analyses ( 1H, 13C, COSY, HMQC, HMBC and TOCSY NMR) as well as GC/MS analysis to infer the absolute stereochemistry of the sugar moieties. Eryloside K (2) is the 24,25-didehydro congener of 1, while eryloside L (3) features an unusual 8α,9α- epoxy-4α-methyl-8,9-secocholesta-7,9(11),14-triene skeleton which appears to be unprecedented in nature. Eryloside A (1) displayed antibacterial activity against Bacillus subtilis and Escherichia coli together with antifungal activity against Candida albicans.

KW - antibacterial

KW - antifungal

KW - marine sponge

KW - saponin

KW - steroidal saponin

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M3 - Article

AN - SCOPUS:5044231245

VL - 2004

SP - 17

EP - 27

JO - Arkivoc

JF - Arkivoc

SN - 1551-7012

IS - 13

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