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

doi:10.1016/j.tet.2014.12.035

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

Chemistry

Research output: Contribution to journal › Article › peer-review

19 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 language	English
Pages (from-to)	577-583
Number of pages	7
Journal	Tetrahedron
Volume	71
Issue number	4
Early online date	13 Dec 2014
DOIs	https://doi.org/10.1016/j.tet.2014.12.035
Publication status	Published - 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellose",

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.",

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",

author = "Hassan, {Marwa H. A.} and Mostafa Rateb and Mona Hetta and Abdelaziz, {Tarek A.} and Sleim, {Mohamed A.} and Marcel Jaspars and Rabab Mohammed",

note = "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.",

year = "2015",

month = jan,

day = "28",

doi = "10.1016/j.tet.2014.12.035",

language = "English",

volume = "71",

pages = "577--583",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

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TY - JOUR

T1 - Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellose

AU - Hassan, Marwa H. A.

AU - Rateb, Mostafa

AU - Hetta, Mona

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.

PY - 2015/1/28

Y1 - 2015/1/28

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.

KW - scalarane sesterterpenes

KW - phyllospongia lamellosa

KW - phyllospongin

KW - cytotoxic

KW - antibacterial

KW - marine sponge

KW - carteriospongia-foliascens

KW - Indonesian sponge

KW - natural-products

KW - bishomoscalarane sesterterpenes

KW - homoscalarane sesterpenes

KW - strepsichordaia-aliena

KW - cacospongia-scalaris

KW - dereplication

KW - metabolites

U2 - 10.1016/j.tet.2014.12.035

DO - 10.1016/j.tet.2014.12.035

M3 - Article

VL - 71

SP - 577

EP - 583

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 4

ER -

Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellose

Abstract

Keywords

UN SDGs

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