Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellose

Marwa H. A. Hassan, Mostafa Rateb, Mona Hetta, Tarek A. Abdelaziz, Mohamed A. Sleim, Marcel Jaspars*, Rabab Mohammed

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Biology and HRESIMS-guided screening of the dichloromethane fraction of the marine sponge Phyllospongia lamellosa collected from the Red Sea resulted in the isolation and characterization of five new scalarane sesterterpenes; phyllospongins A–E (1–5), in addition to four known derivatives, 12α-acetoxy-20,24-dimethyl-25-norscalar-16-en-24-one (6), 12α-acetoxy-13β,18β-cyclobutan-20,24-dimethyl-24-oxoscalar-16-en-25β-ol (7), 12α-acetoxy-24,25-epoxy-24-hydroxy-20,24-dimethylscalarane (8), and scalardysin-A (9) that were previously isolated from Carteriospongia sp. and Dysidea sp. The structures of the isolated compounds were fully characterized using NMR spectroscopic techniques and mass spectrometric analysis. All the isolated compounds were tested for their cytotoxic activity against human cancer cell lines (HePG-2, MCF-7, and HCT-116) and antibacterial activity against some Gram-positive and Gram-negative strains.
Original languageEnglish
Pages (from-to)577-583
Number of pages7
JournalTetrahedron
Volume71
Issue number4
Early online date13 Dec 2014
DOIs
Publication statusPublished - 28 Jan 2015

Keywords

  • scalarane sesterterpenes
  • phyllospongia lamellosa
  • phyllospongin
  • cytotoxic
  • antibacterial
  • marine sponge
  • carteriospongia-foliascens
  • Indonesian sponge
  • natural-products
  • bishomoscalarane sesterterpenes
  • homoscalarane sesterpenes
  • strepsichordaia-aliena
  • cacospongia-scalaris
  • dereplication
  • metabolites

Cite this

Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellose. / Hassan, Marwa H. A.; Rateb, Mostafa; Hetta, Mona; Abdelaziz, Tarek A.; Sleim, Mohamed A.; Jaspars, Marcel; Mohammed, Rabab.

In: Tetrahedron, Vol. 71, No. 4, 28.01.2015, p. 577-583.

Research output: Contribution to journalArticle

Hassan, Marwa H. A. ; Rateb, Mostafa ; Hetta, Mona ; Abdelaziz, Tarek A. ; Sleim, Mohamed A. ; Jaspars, Marcel ; Mohammed, Rabab. / Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellose. In: Tetrahedron. 2015 ; Vol. 71, No. 4. pp. 577-583.
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AU - Abdelaziz, Tarek A.

AU - Sleim, Mohamed A.

AU - Jaspars, Marcel

AU - Mohammed, Rabab

N1 - Acknowledgements The authors would like to thank the Bioassay-Cell Culture Laboratory, National Research Centre, El-Tahrir St., Dokki, Cairo, Egypt for performing cytotoxic activity testing on different human cancer cell lines, Michelle Kelly, Department of Pharmacognosy, Pharmacology, Chemistry and Biochemistry and National Center for Natural Products Research, The University of Mississipi for primary identification of Phyllospongia lamellosa and the Finance and Development Unit of research projects, University of Beni-Suef for supporting our project No. 12/11.

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N2 - Biology and HRESIMS-guided screening of the dichloromethane fraction of the marine sponge Phyllospongia lamellosa collected from the Red Sea resulted in the isolation and characterization of five new scalarane sesterterpenes; phyllospongins A–E (1–5), in addition to four known derivatives, 12α-acetoxy-20,24-dimethyl-25-norscalar-16-en-24-one (6), 12α-acetoxy-13β,18β-cyclobutan-20,24-dimethyl-24-oxoscalar-16-en-25β-ol (7), 12α-acetoxy-24,25-epoxy-24-hydroxy-20,24-dimethylscalarane (8), and scalardysin-A (9) that were previously isolated from Carteriospongia sp. and Dysidea sp. The structures of the isolated compounds were fully characterized using NMR spectroscopic techniques and mass spectrometric analysis. All the isolated compounds were tested for their cytotoxic activity against human cancer cell lines (HePG-2, MCF-7, and HCT-116) and antibacterial activity against some Gram-positive and Gram-negative strains.

AB - Biology and HRESIMS-guided screening of the dichloromethane fraction of the marine sponge Phyllospongia lamellosa collected from the Red Sea resulted in the isolation and characterization of five new scalarane sesterterpenes; phyllospongins A–E (1–5), in addition to four known derivatives, 12α-acetoxy-20,24-dimethyl-25-norscalar-16-en-24-one (6), 12α-acetoxy-13β,18β-cyclobutan-20,24-dimethyl-24-oxoscalar-16-en-25β-ol (7), 12α-acetoxy-24,25-epoxy-24-hydroxy-20,24-dimethylscalarane (8), and scalardysin-A (9) that were previously isolated from Carteriospongia sp. and Dysidea sp. The structures of the isolated compounds were fully characterized using NMR spectroscopic techniques and mass spectrometric analysis. All the isolated compounds were tested for their cytotoxic activity against human cancer cell lines (HePG-2, MCF-7, and HCT-116) and antibacterial activity against some Gram-positive and Gram-negative strains.

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KW - Indonesian sponge

KW - natural-products

KW - bishomoscalarane sesterterpenes

KW - homoscalarane sesterpenes

KW - strepsichordaia-aliena

KW - cacospongia-scalaris

KW - dereplication

KW - metabolites

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JO - Tetrahedron

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SN - 0040-4020

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ER -