Cristaxenicin A, an Antiprotozoal Xenicane Diterpenoid from the Deep Sea Gorgonian Acanthoprimnoa cristata

Abstract

A new xenicane diterpenoid, cristaxenicin A (1), has been isolated from the deep sea gorgonian Acanthoprimnoa cristata. The structure of 1 was elucidated on the basis of spectral analysis including NMR and MS. The absolute configuration of 1 was determined on the basis of quantum chemical calculation of CD spectra. Cristaxenicin A (1) showed antiprotozoal activities against Leishmania amazonensis and Trypanosoma congolense with IC(50) values of 0.088 and 0.25 μM, respectively.

Marine Pharmacology in 2012–2013: 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

“…Balunas and colleagues isolated the polyketide coibacin A ( 83 ) from a Panamanian marine cyanobacterium Oscillatoria sp., and observed potent activity against L. donovani axenic amastigotes [88]. Ishigami and colleagues isolated a new xenicane diterpenoid cristaxenicin A ( 84 ) from the deep-sea gorgonian Acanthoprimnoa cristata , which showed potent activity against L. amazonensis and T. congolense [89]. Chianese and colleagues completed structure-activity relationship studies with several natural and semisynthetic manadoperoxide B analogues ( 85 , 86 ), isolated from the Indonesian sponge Plakortis sfr.…”

Diterpenoids of Gorgonian Corals: Chemistry and Bioactivity

“…In 2012, a new xenicane diterpenoid, cristaxenicin A ( 225 ) , was obtained from a specimen of gorgonian A. cristata , collected around Yakushima‐Shinsone, Kagoshima prefecture, Japan. Cristaxenicin A ( 225 ) was found to have a novel skeleton with an enol acetate, an α , β ‐unsaturated aldehyde, a ketone conjugated with a dihydropyran ring, and an acetylated acetal.…”

“…In bioactivity testing, briacavatolides C ( 155 ) and F ( 158 ) were found to display antiviral activity against HCMV (human cytomegalovirus). Cristaxenicin A ( 225 ) displayed antiprotozoal activities against Leishmania amazonensis and Trypanosoma congolense with IC 50 values of 0.088 and 0.25 μ m , respectively. Aberrarone ( 242 ) displayed inhibitory activity against the protozoan parasite Plasmodium falciparum ( IC 50 = 10 μg/ml).…”

Recent advances in deep-sea natural products

“…In 2010, the stinging venoms of the Mediterranean scyphozoan jellysh were reviewed by Mariottini et al 83 In 2012, the chemical constituents and biological properties of the marine so coral Nephthea were reviewed by Amir et al including deep-sea species. 85 Two new dolabellane diterpenoids (6 and 7) were also reported from the cnidarian Convexella magelhaenica collected from the South Atlantic by dredging at a depth of 93 m. Both 5 and 6 exhibited signicant cytotoxic activities against a human pancreatic adenocarcinoma cell line at micromolar concentrations. Since 2008, of the four cnidarian classes, only a small handful of reports on novel secondary metabolites have appeared, all from deep-sea anthozoans, from the order Alcyonacea (so corals).…”