Trikendiol, an unusual red pigment from the sponge Trikentrion loeve, anti-HIV-1 metabolite

Loukaci, Ali; Guyot, Michèle

doi:10.1016/0040-4039(94)85027-5

Cited by 13 publications

(12 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…LC-MS analysis of the semi-purified extracts revealed ions that did not correspond to any of the known Trikentrion alkaloids, which prompted further investigations. [3][4][5] A large-scale MeOH extraction of T. flabelliforme (voucher specimen: G303344) followed by C 18 flash column chromatography (MeOH/H 2 O/1.0% TFA) and C 18 HPLC (MeOH/H 2 O/1.0% TFA), resulted in the isolation of two new metabolites, which we have named trikentramides A and B (9 and 10). Chemical investigations of an additional specimen of T. flabelliforme (voucher specimen: G306125) using similar chromatographic methods resulted in the identification of two additional alkaloids, trikentramides C (11) and D (12).…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR data (Table 1) This was supported by the NMR data for 12 that showed only one carbonyl signal (δ C 177. 4) and an extra methylene resonance (δ H 3.31/ δ C 34.5). HMBC correlations were observed from the methylene protons (δ H 3.31) to the amide carbonyl (δ C 177.4, C-2) as well as the aromatic carbons C-3a (δ C 122.5), C-4 (δ C 131.4) and C-8b (δ C 146.0).…”

Section: Resultsmentioning

confidence: 99%

“…1 Sponges belonging to the genus Trikentrion have been the source of several novel indole alkaloids. These include the antibacterial trikentrins 1-5 from the Australian T. flabelliforme, 3 as well as trikendiol 4 and trikentramine 5 from the West African sponge T. leave. Although the trikentrins were the first report of cyclopenta[g]indoles from the marine environment, the related compounds, herbindoles A-C (6-8) from an Axinella sp.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Trikentramides A–D, Indole Alkaloids from the Australian Sponge Trikentrion flabelliforme

et al. 2013

View full text Add to dashboard Cite

Chemical investigations of two specimens of Trikentrion flabelliforme collected from Australian waters have resulted in the identification of four new indole alkaloids, trikentramides A-D (9-12). The planar chemical structures for 9-12 were established following analysis of 1D/2D NMR and MS data. The relative configurations for 9-12 were determined following the comparison of (1)H NMR data with data previously reported for related natural products. The application of a quantum mechanical modeling method, density functional theory, confirmed the relative configurations and also validated the downfield carbon chemical shift observed for one of the quaternary carbons (C-5a) in the cyclopenta[g]indole series. The indole-2,3-dione motif present in trikentramides A-C is rare in nature, and this is the first report of these oxidized indole derivatives from a marine sponge.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Trikentramides A–D, Indole Alkaloids from the Australian Sponge Trikentrion flabelliforme

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Compound 57 was found to be active in a CEM-4 HIV-1 infection assay with an IC 50 value of 2µg/ml as measured by inhibition of cytopathogenic effect of the virus, but caused no inhibition of the HIV-1 aspartyl protease at 10 -5 M [80]. Fig.…”

Section: Alkaloidsmentioning

confidence: 97%

Recent Studies on Natural Products as Anti-HIV Agents

Jung¹,

Lee²,

Kim³

et al. 2000

CMC

View full text Add to dashboard Cite

The discovery of medicinal agents capable of specifically inhibiting human immunodeficiency virus (HIV) is urgently needed due to its globally widespread infection. Most of clinically useful anti-HIV agents are nucleosides but their use is limited due to their severe toxicity and emerging drug resistance. More than 50% of world marketed drugs have their origin of the nature. Natural products, of which structural diversity is so broad, are good sources for the effective discovery of anti-HIV agents with decreased toxicity. Over the past decade, substantial progress has been made in research on the natural products for the anti-HIV agents. New natural products that have potent anti-HIV activities with novel structures were reviewed in this article. These compounds, isolated mainly from medicinal plants, in this review have been classified as secondary metabolites such as terpenes, phenolics, and naturally scarce peptides and sugars. Especially, terpenes and phenol substances have gained much interest due to their significant anti-HIV activities along with their structural diversity. Recent studies also showed that several polysaccharides are effective inhibitors of HIV replication. Most of chemotherapeutic targets reviewed in this article are found to be HIV reverse transcriptase (RT).

show abstract

“…For all data entries reported in this chapter, formaldehyde was never observed, presumably due to evaporation during the removal of solvents. Subsequent to the isolation of the trikentrins, the related trikendiol, 31 trikentramine, 32 and trikentramides 33 have all been isolated from sponges belonging to the genus Trikentrion. The structurally similar herbindoles were isolated from Axinella sp., an Australian sponge, by Scheuer et al 34 Alder reaction of quinoid imines.…”

Section: Resultsmentioning

confidence: 99%

Base-mediated formation of N-hydroxy- and N-alkoxyindoles, synthesis of dilemmaones A and B, and novel efforts in indole methodology and total synthesis

Lambson¹

View full text Add to dashboard Cite

Base-mediated formation of N-hydroxy-and N-alkoxyindoles, synthesis of dilemmaones A and B, and novel efforts in indole methodology and total synthesis Katharine E. Lambson A novel and facile base-mediated formation of N-hydroxy-and N-alkoxyindoles from 2-(2-nitrophenyl)butenoates has been developed. Either potassium tert-butoxide in tertbutanol or sodium tert-pentoxide in toluene, with or without the subsequent addition of an

show abstract

Trikendiol, an unusual red pigment from the sponge Trikentrion loeve, anti-HIV-1 metabolite

Cited by 13 publications

References 6 publications

Trikentramides A–D, Indole Alkaloids from the Australian Sponge Trikentrion flabelliforme

Trikentramides A–D, Indole Alkaloids from the Australian Sponge Trikentrion flabelliforme

Recent Studies on Natural Products as Anti-HIV Agents

Base-mediated formation of N-hydroxy- and N-alkoxyindoles, synthesis of dilemmaones A and B, and novel efforts in indole methodology and total synthesis

Contact Info

Product

Resources

About