New Scalarane Sesterterpenoids from the Formosan Sponge Ircinia felix

Abstract

Five new scalarane sesterterpenoids, felixins A–E (1–5), were isolated from the Formosan sponge Ircinia felix. The structures of scalaranes 1–5 were elucidated on the basis of spectroscopic analysis. Cytotoxicity of scalaranes 1–5 against the proliferation of a limited panel of tumor cell lines was evaluated.

Marine natural products

“…Two suvanine sesterterpenoid salts 1045 and 1046 were found from Coscinoderma sp. 668 A large number of scalaranes 1047-1051, 669 1052 and 1053, 670 1054-1058, 671 1059 and 1060, 672 1061-1071, 673 1072 and 1073 (ref. 674) were reported from ve different sponge genera, Carteriospongia, Hyattella, Ircinia, Phyllospongia and Spongia respectively.…”

Antileukemic Scalarane Sesterterpenoids and Meroditerpenoid from Carteriospongia (Phyllospongia) sp., Induce Apoptosis via Dual Inhibitory Effects on Topoisomerase II and Hsp90

“…Scalarane sesterterpenoids displayed a wide spectrum of interesting biological properties, such as antifeedant, antimicrobial, antifungal, ichthyotoxicity, antitubercular, antitumor, cytotoxicity, anti-HIV, antifouling, inhibition of platelet-aggregation, inhibition of transactivation for the nuclear hormone receptor (FXR, farnesoid X-activated receptor), stimulation of nerve growth factor synthesis, as well as anti-inflammatory activity28. Recent reports from our group revealed the potent cytotoxic potential of scalarane-type sesterterpenoids2930. Carteriospongia ( Phyllospongia ) sp.…”

New Cytotoxic 24-Homoscalarane Sesterterpenoids from the Sponge Ircinia felix

“…Compound 1 was found to show cytotoxicity toward the leukemia K562, MOLT-4, and SUP-T1 cells (IC 50 ≤ 5.0 μM). By comparing the cytotoxic data of 1 with those of 2 and the relative scalarane derivatives, flexins A−E, that we isolated previously [ 13 ], we find that 1 is more cytotoxic toward most tumor cells.…”

“…The sponge Ircinia felix (Duchassaing and Michelotti, 1864) (family Irciniidae, order Dictyoceratida, class Demospongiae, phylum Porifera) ( Figure 1 ) has been proven to be an important source of interesting natural substances [ 1 , 2 , 3 , 4 , 5 ], and the extract from this organism has also played interesting roles in marine ecology [ 6 , 7 , 8 , 9 , 10 ] and medicinal use [ 11 , 12 ]. In our previous study, five new scalarane analogues, felixins A–E, were isolated from I. felix [ 13 ], and several compounds showed cytotoxicity. Scalarane-type sesterterpenoids were proven to be active in a number of bioassays, particularly in cytotoxic activity, and played important roles in chemical markers and chemical ecology [ 14 ].…”