Irciformonins E – K, C22‐Trinorsesterterpenoids from the Sponge Ircinia formosana

Chemical investigation of the sponge Ircinia formosana resulted in the isolation of seven new linear C22-sesterterpenoids, irciformonins E–K (1–7) in addition to irciformonin A (8), a previously isolated furanosesterterpenoid (=a furan-moiety-containing sesterterpenoid) from the same species. The structures were determined by interpretation of HR-ESI-MS and 2D-NMR spectra. The structure of irciformonin A (8) was revised. Compound 5 exhibited significant inhibition of peripheral blood mononuclear cell proliferation induced by phytohemaglutinin.

[1]  J. Blunt,et al.  Marine natural products. , 2012, Natural product reports.

[2]  P. Abreu,et al.  Heterocyclic terpenes: linear furano- and pyrroloterpenoids. , 2006, Natural product reports.

[3]  Yu-Chi Lin,et al.  Novel linear C22-sesterterpenoids from sponge Ircinia formosana , 2006 .

[4]  Y. Kuo,et al.  Inhibitory effects of acylated kaempferol glycosides from the leaves of Cinnamomum kotoense on the proliferation of human peripheral blood mononuclear cells. , 2005, Planta Medica.

[5]  X. Yao,et al.  Two New Ceramides from the Marine Sponge Ircinia fasciculata , 2005 .

[6]  A. Kijjoa,et al.  Cytotoxicity and Inhibition of Lymphocyte Proliferation of Fasciculatin, a Linear Furanosesterterpene Isolated from Ircinia variabilis Collected from the Atlantic Coast of Morocco , 2005, Marine Drugs.

[7]  Jongki Hong,et al.  Cytotoxic furanosesterterpenes from a marine sponge Psammocinia sp. , 2004, Journal of natural products.

[8]  Jongki Hong,et al.  New cytotoxic sesterterpenoids and norsesterterpenoids from two sponges of the genus Sarcotragus. , 2003, Journal of natural products.

[9]  V. Roussis,et al.  New sesterterpene metabolites from the Mediterranean sponge Cacospongia scalaris. , 2003, Journal of natural products.

[10]  Lie-Chwen Lin,et al.  Samarangenin B from Limonium sinense Suppresses Herpes Simplex Virus Type 1 Replication in Vero Cells by Regulation of Viral Macromolecular Synthesis , 2002, Antimicrobial Agents and Chemotherapy.

[11]  S. Zea,et al.  Does the Odor from Sponges of the Genus Ircinia Protect Them from Fish Predators? , 2002, Journal of Chemical Ecology.

[12]  B. H. Bae,et al.  New cytotoxic sesterterpenes from the sponge Sarcotragus species. , 2001, Journal of natural products.

[13]  Y C Kuo,et al.  Regulation of cell proliferation, gene expression, production of cytokines, and cell cycle progression in primary human T lymphocytes by piperlactam S isolated from Piper kadsura. , 2000, Molecular pharmacology.

[14]  K. Ang,et al.  In Vivo Antimalarial Activity of the Beta-Carboline Alkaloid Manzamine A , 2000, Antimicrobial Agents and Chemotherapy.

[15]  M. Hamann,et al.  THE BIOCATALYTIC TRANSFORMATION OF FURAN TO AMIDE IN THE BIOACTIVE MARINE NATURAL PRODUCT PALINURIN , 1999 .

[16]  W. Fenical,et al.  ANTIMICROBIAL ACTIVITY OF CARIBBEAN SPONGE EXTRACTS , 1999 .

[17]  Y. Venkateswarlu,et al.  A new epoxy sterol from the sponge Ircinia fasciculata , 1996 .

[18]  M. Kelly-Borges,et al.  Waiakeamide, a Cyclic Hexapeptide from the Sponge Ircinia dendroides(1). , 1996, Journal of Organic Chemistry.

[19]  Y. Venkateswarlu,et al.  Three New Heptaprenylhydroquinone Derivatives from the Sponge Ircinia fasciculata , 1994 .

[20]  Takuma Sasaki,et al.  Ircinals A and B from the Okinawan marine sponge Ircinia sp.: plausible biogenetic precursors of manzamine alkaloids , 1992 .

[21]  R. Capon,et al.  A New Sesterterpene Tetronic Acid From An Australian Sponge, Ircinia Sp , 1987 .