Cylindradines A and B: Novel Bromopyrrole Alkaloids from the Marine Sponge Axinella cylindratus

Abstract

The novel alkaloids cylindradines A and B were isolated from Axinella cylindratus, and their structures were elucidated by spectroscopic analyses. Stereochemistries of these compounds were determined by X-ray analysis. Cylindradines showed moderate inhibitory activity against the murine leukemia cell line P388.

Pyrrolactams from Marine Sponge <i>Stylissa massa</i> Collected from Myanmar and Their Anti-Vpr Activities

“…The absolute configuration at C-10 was determined on the basis of the comparison of the experimental and calculated electronic circular dichroism (ECD) data. The experimental ECD spectrum of 1 exhibited the negative Cotton effects (CE) at 280 nm and positive CE at 272 nm, which were in accordance with the calculated ECD data for the model compound of 1 with 10R configuration, using the time-dependent density functional theory (TDDFT) method 19) (Fig. 3).…”

Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids

“…Recently, cylindradine A ( 33A ) and B ( 33B ) isolated from Axinella cylindratus showed moderate inhibitory activity against the murine leukemia cell lines P388 with IC 50 values of 20 and 77 μM, respectively. 31 In the original isolation of palau’amine ( 10 ), it was reported to be active against P-388 (IC 50 0.1 μgmL −1 ), A549 (0.2μg/mL), HT-29 (2μg/mL) and KB (10 μg/mL) cell lines. 7 …”

Structure of debromo-carteramine A, a novel bromopyrrole alkaloid from the Mediterranean sponge Axinella verrucosa

“…[1][2][3][4][5][6][7] Historically, these compounds, which have been found only in the marine environment to date, have attracted the attention of natural product chemists because of their structural complexity. Today, the interest is sparked not only by the wide structural diversity, ranging from simple molecules like oroidin 8,9 to complex structures like palau'amine 10,11 and stylissadine A and B, 12 but also by their organic synthesis, 13 bio-synthesis, 14 and pharmacological activities.…”

“…Today, the interest is sparked not only by the wide structural diversity, ranging from simple molecules like oroidin 8,9 to complex structures like palau'amine 10,11 and stylissadine A and B, 12 but also by their organic synthesis, 13 bio-synthesis, 14 and pharmacological activities. 6,7,15 Furthermore, these compounds have a chemo-ecological interest due to their role in chemically mediated interactions such as in the chemical defense against predators 16,17 and fouling organisms. [18][19][20] The crude extracts of different Axinella species have also been reported to inhibit the growth of several environmental bacteria.…”