Sponge-Derived 24-Homoscalaranes as Potent Anti-Inflammatory Agents

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 Lendenfeldia sp., resulting in the isolation of six new 24-homoscalaranes, lendenfeldaranes E–J (1–6). The structures of the new metabolites were determined by extensive spectroscopic analyses, and the absolute configuration of 1 was established by electronic circular dichroism (ECD) calculations. Compounds 2 and 3 were discovered to individually reduce the generation of superoxide anions, and compound 1 displayed an inhibitor effect on the release of elastase. These three compounds were proven to be the first anti-neutrophilic scalaranes.

[1]  P. Sung,et al.  Probing Anti-Proliferative 24-Homoscalaranes from a Sponge Lendenfeldia sp. , 2020, Marine drugs.

[2]  J. Heo,et al.  Deacetylphylloketal, a New Phylloketal Derivative from a Marine Sponge, Genus Phyllospongia, with Potent Anti-Inflammatory Activity in In Vitro Co-Culture Model of Intestine , 2019, Marine drugs.

[3]  C. Tzeng,et al.  A novel NOX2 inhibitor attenuates human neutrophil oxidative stress and ameliorates inflammatory arthritis in mice , 2019, Redox biology.

[4]  Y. Wu,et al.  Targeting allosteric site of AKT by 5,7-dimethoxy-1,4-phenanthrenequinone suppresses neutrophilic inflammation , 2019, EBioMedicine.

[5]  R. Sakai,et al.  Two New Mycosporine-like Amino Acids LC-343 and Mycosporine-ethanolamine from the Micronesian Marine Sponge Lendenfeldia chondrodes , 2017 .

[6]  Chia-Hua Chou,et al.  Antileukemic Scalarane Sesterterpenoids and Meroditerpenoid from Carteriospongia (Phyllospongia) sp., Induce Apoptosis via Dual Inhibitory Effects on Topoisomerase II and Hsp90 , 2016, Scientific Reports.

[7]  W. Alarif,et al.  Cytotoxic scalarane-type sesterterpenes from the Saudi Red Sea sponge Hyrtios erectus , 2016, Journal of Asian natural products research.

[8]  Z. Wen,et al.  New Cytotoxic 24-Homoscalarane Sesterterpenoids from the Sponge Ircinia felix , 2015, International journal of molecular sciences.

[9]  M. Jacob,et al.  Polybrominated diphenyl ethers from the marine organisms Lendenfeldia dendyi and Sinularia dura with anti-MRSa activity , 2015, Medicinal Chemistry Research.

[10]  Li-Hsueh Wang,et al.  New Scalarane Sesterterpenoids from the Formosan Sponge Ircinia felix , 2015, Marine drugs.

[11]  S. Nam,et al.  Cytotoxic scalarane sesterterpenes from a Korean marine sponge Psammocinia sp. , 2013, Bioorganic & medicinal chemistry letters.

[12]  Li-lian Liu,et al.  Cytotoxic Sesterterpenoids from a Sponge Hippospongia sp. , 2012, Marine drugs.

[13]  Miguel A. González.  Scalarane Sesterterpenoids , 2010 .

[14]  Yang Liu,et al.  Molecular-targeted antitumor agents. 19. Furospongolide from a marine Lendenfeldia sp. sponge inhibits hypoxia-inducible factor-1 activation in breast tumor cells. , 2008, Journal of natural products.

[15]  D. Nagle,et al.  Cytotoxic metabolites from an Indonesian sponge Lendenfeldia sp. , 2007, Journal of natural products.

[16]  S. Ross,et al.  Two New Sulfated Sterols from the Marine Sponge Lendenfeldia dendyi , 2007 .

[17]  R. Sakai,et al.  1-Deoxynojirimycin Derivatives from the Marine Sponge Lendenfeldia chondrodes , 2006, The Journal of Antibiotics.

[18]  A. Hizi,et al.  New sesterterpenes from Madagascan Lendenfeldia sponges , 2004 .

[19]  R. Ebel,et al.  Employing dereplication and gradient 1D NMR methods to rapidly characterize sponge-derived sesterterpenes. , 2002, Journal of natural products.

[20]  Sera,et al.  A new epidioxy sterol as an antifouling substance from a palauan marine sponge, lendenfeldia chondrodes , 1999, Journal of natural products.

[21]  P. Potier,et al.  Scalarane-type bishomosester terpenes from the sponge Phyllospongia foliascens. , 1992, Journal of natural products.

[22]  P. Crews,et al.  Homoscalarane sesterterpenes from Lendenfeldia frondosa. , 1992, Journal of natural products.

[23]  P. Pratt,et al.  Neutrophil elastase activity and superoxide production are diminished in neutrophils of alcoholics. , 1990, The American review of respiratory disease.

[24]  R. Wells,et al.  Five new C26 tetracyclic terpenes from a sponge (Lendenfeldia sp.) , 1982 .