Spongian Diterpenoids from the SpongeSpongia(Heterofibria) sp.

Abstract

Five new (1, 2, 4-6) and one known (3) diterpenoid were isolated from the keratose sponge Spongia (Heterofibria) sp. Structures of these compounds and their absolute configurations were proposed on the basis of X-ray analysis of 1, its CD spectrum, and NMR and MS spectroscopic studies of 1-6. One of the new diterpenoids was shown to be 2(R),3(S),4(S)-3,18-methylene-2-acetoxyspongia-13(16),14-diene (6), possessing a novel carbon skeleton system.

Terpenoid Metabolites from Spongia spp. and Their Effects on Nucleic Acid Biosynthesis in Sea Urchin Eggs

“…The sponge Spongia sp.I (subgenus Heterofibria, family Spongiidae, order Dictyoceratida) was collected by SCUBA near Suwarrow atoll (Northern Cook Islands, Pacific ocean) at a depth at 5 m in February 1998 and identified by Dr. V. B. Krasokhin [2]. The sponge has a solid base from which arise upright distinct conical fistules (up to 60 mm high) of varying development.…”

“…The ethanol-chloroform extract of Spongia sp.I contains appreciable amount of spongian diterpenes. The 19norspongia-13(16),14-dien-3-one (1) and nine previously known spongian diterpenes, namely 3,18-methylene-2acetoxyspongia-13(16),14-diene (2) [2], spongia-13(16),14-dien-3-one (4) [3], 3-acetoxyspongia-13(16),14-diene (5) [2], 3-acetoxyspongia-13(16),14diene (6) [2], 19-acetoxyspongia-13(16),14-diene (7) [2], 19-acetoxyspongia-13(16),14-dien-3-one (8) [2], 3,19diacetoxyspongia-13(16),14-diene (9) [2], 19hydroxyspongia-13(16),14-dien-3-one (10) [4a], 3,17,19triacetoxyspongia-13(16),14-dien-2-one (11) The compounds 8, 10, 11 are major components in ethanol-chloroform extract of Spongia sp.I. In contrast,  5,7 sterols dominated in ethanol-chloroform extract of Spongia sp.II.…”

“…In contrast,  5,7 sterols dominated in ethanol-chloroform extract of Spongia sp.II. Minor amounts of the spongia-13(16),14-diene (3) [5b] and 3-acetoxyspongia-13(16),14-diene (5) [2] were isolated from Spongia sp.II. We should note that metabolites 1-11 from both species belong to the same group of furanospongian diterpenes.…”

Spongian Diterpenes from the Sponge <i>Hyattella</i> aff. <i>intestinalis</i>

“…General Experimental Procedures NMR spectra were recorded on a Bruker AVANCE III spectrometer either at 500 or 400 MHz for 1 H and 125 or 100 MHz for 13 C. All ESI mass spectra were measured on a Jeol JMS-T100LP mass spectrometer. HPLC was performed on a unit composed of a Hitachi L-6000 pump, a Hitachi L-4000 UV detector, Shodex RI-101 detector with a column (Cosmosil 5C 8 -MS, 10×250 mm or Cosmosil 5C 18 -ARII, 4.6×250 mm).…”

“…Spongian diterpenes were first reported in 1979 as unique metabolites of a sponge, 8) and since then a number of spongians have been reported. [9][10][11][12][13][14] Recent reports include new cyototoxic spongians 15) and rediscovery of spongiatriol (1) as a moderate apoptosis inducer and an inhibitor of nuclear factor-kappaB (NF-κB) activation. 16,17) In this report we describe the structures of three new spongians and their biological activities.…”