ChemInform Abstract: Alkaloids from the Antarctic Sponge Kirkpatrickia varialosa. Part 1. Variolin B, a New Antitumor and Antiviral Compound.

Abstract

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Alkaloids from Marine Invertebrates as Important Leads for Anticancer Drugs Discovery and Development

“…Variolins constitute a new family of inhibitors of CDKs. They are marine alkaloids possessing an uncommon pyrido [3',2':4,5]pyrrolo [1,2-c]pyrimidine skeleton, which were first isolated in 1994 from Kirkpatrickia variolosa, a rare Antarctic sponge [1,2]. Five variolins have been isolated: variolin A (1), variolin B (2), deoxyvariolin B (3), N(3')-methyl tetrahydrovariolin B (4), and variolin D (5) (Figure 1).…”

“…It was found to be cytotoxic against L-1210 murine leukemia cells in vitro with IC50 value of 0.39 μg/mL. Delfourne et al, synthesized an isomer of ascididemin, named as 9H-quino[4,3,2-de] [1,7]phenanthroline-9-one (124) [124]. These compounds were tested in vitro at six different concentrations on 12 different human cancer cell lines such as glioblastomas, breast, colon, lung, prostate, and bladder cancers.…”

Racemosins A and B, two novel bisindole alkaloids from the green alga Caulerpa racemosa

“…Within the marine environment, numerous unique bisindole alkaloids such as meridianins [1], topsentins [2], nortopsentins [3], dragmacidins [4], variolins [5], and rhopaladins [6] have been reported from sponges [2][3][4][5], actinomycetes [7], tunicates [6] and green algae [8,9]. In addition, some of these marine bisindole compounds were found to be responsible for potent and diverse bioactive properties, e.g., antifungal [8,10], antibacterial [11], antiviral [12], cytotoxic [7], anti-inflammatory [13], and noteworthy antitumor [12,14] activities.…”

“…Up to now, more than 120 naturally occuring or chemo(bio)syhthetic marine bisindole alkaloids have been discovered, and some of them possessed new carbon skeletons. Recently, four cytotoxic bisindole alkaloids, spiroindimicins A-D, containing unusual [5,6] or [5,5] spiro-ring skeletons, were isolated from a deep-sea-derived Streptomyces sp. SCSIO 03032 through a-PCR-based screening approach [7], indicating that marine habitats can contiguously provide structurally intriguing bisindole alkaloids.…”

Intercalative DNA binding of the marine anticancer drug variolin B

“…1a)1. It exerts pro-apoptotic activity, causes cell-cycle perturbations on several human cancer cell lines, and is active against Herpes simplex type I virus23. Variolin B and some derivatives, such as the more soluble deoxyvariolin B analogue (Fig.…”