Baculiferins A–O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera

Marine Pharmacology in 2009–2011: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and other Miscellaneous Mechanisms of Action

“…GT2002/1503 bacterium and demonstrated selective inhibition against macrophage and T cell β-chemokine receptor CCR5 (5) tropic HIV-infection (estimated IC 50 = 7.2 μg/mL), with no effect against α-chemokine receptor CXCR4 (X4) tropic HIV [89]. Fan and colleagues isolated several DOPA-derived pyrrole alkaloids, baculiferins I, J, L and M ( 97 – 100 ), from the Chinese marine sponge Iotrochota baculifera , which were found to be potent inhibitors of HIV-1 IIIB (IC 50 = 0.2–7.0 μM) by binding to the HIV target proteins Vif, APOBEC3G, and gp41 in an as yet undetermined mechanism [90]. Plaza and colleagues isolated several new cyclic depsipeptides from the Indonesian marine sponge Siliquariaspongia mirabilis including celebesides A and C ( 101 – 102 ), which inhibited HIV-1 in an infectivity assay (IC 50 = 1.9 ± 0.4 μg/mL), thus correlating the anti-HIV activity of these compounds with the presence of phosphoserine [57].…”

Bioactive Dehydrotyrosyl and Dehydrodopyl Compounds of Marine Origin

“…In addition, they also exhibited significant MDR reversal activity at non-cytotoxic concentrations [94,95]. Recently a group of about five different compounds that are derivatives of purpurone and ningalins were isolated from the Chinese marine sponge, Iotrochota baculifera and shown to possess anti HIV-1 activity [96]. Since ningalins resemble a number of lamellarins, it was proposed that ningalins might serve as the biosynthetic precursor for a number of lamellarins [93].…”

The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones

“…1) as being present as a core structure in a variety of naturally occurring alkaloids and most recently are represented in the ningalin1 (2–4) and baculiferin2 (5–6) family of marine natural products. Several of the ningalins have been shown to possess very good cytotoxic activity3 against a variety of cancer cell lines and very significant multidrug resistance reversal4 activity.…”

“…Several of the ningalins have been shown to possess very good cytotoxic activity3 against a variety of cancer cell lines and very significant multidrug resistance reversal4 activity. Other members of the family have exhibited ATP-citrate lyase inhibitory properties5 and the recently isolated baculiferins have been found to be significant inhibitors2 of the HIV-IIIB virus in MT4 and MAGI cells. Since the ylidenepyrrol-2(5H)-one motif is a key structural element of such bioactive alkaloids, efficient synthetic methods for construction of this heterocyclic framework is of some importance.…”