Two epimeric aliphatic amino alcohols from a sponge. Xestospongia sp

New Polyunsaturated Amino Ketones from a Guangxi Sponge Haliclona sp.

“…The 13 C-NMR (Table), DEPT, and HMQC experiments revealed the presence of two quaternary C-atoms, 13 sp 2 CH and ten CH 2 groups, and one Me group. The low-field signals between 7.19 and 7.29 in the 1 H-NMR spectrum of 1 were indicative of a Ph moiety that was confirmed by 13 C-NMR resonances at d(C) 139.6 (C(3')), 128.7 (C(4') and C(4'')), 128.5 (C(5') and C(5'')), and 126.2 (C(6')). The remaining five degrees of unsaturation were accounted for by a ketone CO group (d(C) 209.8 (C(3))) and four disubstituted C¼C bonds.…”

“…After a detailed examination of 1D-and 2D-NMR data of 2, we observed that the only difference between 2 and 1 was the substituents at the N-atom, where the H-atom and 2-phenylethyl group in 1 were replaced by two Et groups in 2. The presence of a Et 2 N moiety in 2 was supported by 13 C-NMR (d(C) 46.8 (C(1')) and 11.6 (C(2'))) and 1 H-NMR data (d(H) 2.51 (q, J ¼ 6.9, CH 2 (1')) and 1.00 (t, J ¼ 6.9, Me(2'))). Detailed anlysis of the 2D-NMR spectra allowed the unambiguous elucidation of the structure of 2.…”

“…Finally, the (Z)-geometries of the four C¼C bonds of polyunsaturated ketone part were assigned by 13 C-NMR, since the resonances observed for the olefinic C-atoms (C(6) (d(C) 129.0), C(7) (128.6), C(9) (128.3), C(10) (128.1), C(12) (128.0), C(13) (127.0), C(15) (127.8), and C(16) (132.0)), as well as those of the allylic CH 2 groups (C(8) (d(C) 25.6), C(11) (25.6), and C(14) (25.6)) showed the typical d(C) values for a CH 2 -interrupted (Z)-C¼C bond system [8 -10]. The (Z)-geometries of these C¼C bonds were further confirmed by comparing the 13 C chemical shifts of C(3) -C(18) of 1 with those of the corresponding part of the model compound 3 (Fig. 1), which is a metabolite of a marine sponge of the genus Callyspongia [11].…”

General synthetic strategy for clavaminols A, C and H

“…These molecules are mostly long chain amino alcohols and their potent biological activity which ranges from antimicrobial activity to inhibition of cell proliferation through prevention of the formation of actin stress fibers in cultured cells, [21][22][23][24][25][26][27][28][29] attracted many natural products chemists.…”

Chemical and Biological Aspects of Marine Sponges of the Genus Xestospongia

“…from Fiji [78]. In addition, five amino alcohols, 264 -268, were isolated from marine sponges of the genus Xestospongia [79] [80].…”