Nitrogenous bisabolene sesquiterpenes from marine invertebrates

Chemotaxonomy of Agelas (Porifera: Demospongiae)

“…[Marcus et aL (1989)] --Axlnyssa sp.t [Sullivan et al (1986)] --Axmyssa sp. [Molinski et al (1987)] "Eplpolasls" kushlmotoensls [Tada and Yasuda (1985)] Ciocalypta sp..l: ; Gulavita et al (1986); Hagadone et aZ (1979); Karuso et aL (1989); Tada and Yasuda (1985)} "Stylotella" sp. § [Pais et al (19~7)] = Axlnyssa aplysinoldes 7rachyops~s aplyslholdes [He et aL (1989)] Halichondrla sp.…”

New Biologically Active Marine Sesquiterpenoid and Steroid from the Okinawan Sponge of the Genus Axinyssa.

“…The distortionless enhancement by polarization transfer (DEPT) spectrum indicated four methyls, five sp 3 methylenes, one sp 3 methine, two sp 2 methines, one sp 3 quaternary carbon, and three sp 2 quaternary carbons. Two of the quaternary carbon signals at d 56.3 (J NC ϭ5.5 Hz) and 156.1 (J NC ϭ5.5 Hz) ppm in C 6 D 6 were both observed as a triplet due to the coupling with 14 N. 8) These findings together with the IR absorption at 2130 cm Ϫ1 strongly suggest the presence of an isonitrile group (-NC) in 1. The 1 H-NMR analysis showed the presence of three olefinic methyls at d 1.45 (s), 1.61 (s), and 1.71 (s) ppm, one methyl group connected to quaternary carbon at d 1.00 (t, Jϭ2.0 Hz) ppm, and two olefinic protons at d 5.14 (t, Jϭ7.1 Hz) and 5.27 (t, Jϭ 7.1 Hz) ppm ( (Fig.…”

“…These spectroscopic findings together with the unsaturation number (Uϭ5) disclosed that compound 1 had the structure of a bisabolane-type sesquiterpenoid with an isonitrile moiety at C-3. [8][9][10] This gross structure of 1 indicated that the molecule of 1 has a plane of symmetry across the C-3 and C-6 positions on the cyclohexane ring, and thus 1 is achiral and optically inactive; [a] D 25 0.0°(CHCl 3 ). However, the stereochemistry of the olefin moiety and the relative configuration between C-3 and C-6 must be determined.…”

Isocyanates in marine sponges: Axisocyanate-3, a new sesquiterpene from Acanthella cavernosa

“…Much less commonly encountered are terpenes functionalized by thiocyanato, dichloroimine or isocyanato functional groups. 1,2 Examples of the isocyanate functionality in the marine terpene literature include the bisabolene (1) 3 and aromadendrane (2) 4 sesquiterpenes, the amphilectane diterpenes 3-5, 5,6 and the kalihinol A derivative 6. 7 Novel biological activites have been described for these metabolites; compounds 3-5 are cytotoxic with 5 also showing potent and selective antiplasmodial activity, 8 while 6 inhibits the metamorphosis of barnacle larvae.…”