The marine natural product 16-deacetoxy-12-epi-scalarafuranacetate, isolated from Spongua officinalis , was synthesized in 18 linear steps, starting from (-)-sclareol, with high stereoselectivity and an overall yield of 6.1%. The intermediate 16-deacetoxy-12-epi-scalarafuran could be easily transformed into a series of natural scalarane sesterterpenoids in a few steps.
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http://dx.doi.org/10.1021/jo2008127 | DOI Listing |
Mar Drugs
November 2021
Laboratory of Chemistry of Natural and Biologically Active Compounds, Institute of Chemistry, 3 Academiei Str., MD 2028 Chişinău, Moldova.
Scalarane sesterterpenoids emerged as interesting bioactive natural products which were isolated extensively from marine sponges and shell-less mollusks. Some representatives were also reported recently from superior plants. Many scalarane sesterterpenoids displayed a wide spectrum of valuable properties, such as antifeedant, antimicrobial, antifungal, antitubercular, antitumor, anti-HIV properties, cytotoxicity and stimulation of nerve growth factor synthesis, as well as anti-inflammatory activity.
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August 2020
National Museum of Marine Biology and Aquarium, Pingtung 944401, Taiwan.
Scalarane-type sesterterpenoids are known for their therapeutic potential in cancer treatments. However, the anti-inflammatory properties of this class of metabolites remain elusive. Our current work aimed to investigate the anti-inflammatory scalaranes from marine sponge sp.
View Article and Find Full Text PDFNat Prod Res
December 2021
Central Marine Fisheries Research Institute, Ernakulam North P.O, Cochin, India.
Two new scalarane-type sesterterpenes, hyrtioscalaranes A and B, were isolated from the organic extract of the Demosponge through extensive chromatographic purification. Hyrtioscalarane A exhibited significantly greater attenuation property against cyclooxygense-2 (IC 0.83 mM) than that displayed by hyrtioscalarane B (IC 0.
View Article and Find Full Text PDFMar Drugs
July 2020
Fujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361005, China..
12-Deacetyl-12--scalaradial, a scalarane sesterterpenoid from a marine sponge , has been reported to possess cytotoxic activity on HepG2, MCF-7, and HCT-116 cells. However, there is no research to indicate that 12-deacetyl-12--scalaradial exhibited anticancer effect on cervical cancer HeLa cells. The aim of this study was to investigate the anticancer activity of 12-deacetyl-12--scalaradial against HeLa cells and to explore the mechanism.
View Article and Find Full Text PDFSci Rep
October 2016
Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung, 944, Taiwan.
Two new scalarane sesterterpenoids, 12β-(3'β-hydroxybutanoyloxy)-20,24-dimethyl-24-oxo-scalara-16-en-25-al (1) and 12β-(3'β-hydroxypentanoyloxy)-20,24-dimethyl-24-oxo-scalara-16-en-25-al (2), along with one known tetraprenyltoluquinol-related metabolite (3), were isolated from the sponge Carteriospongia sp. In leukemia Molt 4 cells, 1 at 0.0625 μg/mL (125 nM) triggered mitochondrial membrane potential (MMP) disruption and apoptosis showing more potent effect than 2 and 3.
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