Novel pyrroloquinoline ribosides from the South African latrunculid sponge Strongylodesma aliwaliensis

Keyzers, Robert A.; Samaai, Toufiek; Davies‐Coleman, Michael T.

doi:10.1016/j.tetlet.2004.10.106

Cited by 24 publications

(47 citation statements)

References 16 publications

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“…3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays were done using the MTT kit from Roche according to manufacturer's instructions and as previously described (10,12).…”

Section: Chemicalsmentioning

confidence: 99%

Reactive oxygen species mediated apoptosis of esophageal cancer cells induced by marine triprenyl toluquinones and toluhydroquinones

Whibley

McPhail

Keyzers

et al. 2007

Molecular Cancer Therapeutics

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Section: Chemicalsmentioning

confidence: 99%

Reactive oxygen species mediated apoptosis of esophageal cancer cells induced by marine triprenyl toluquinones and toluhydroquinones

Whibley

McPhail

Keyzers

et al. 2007

Molecular Cancer Therapeutics

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“…A portion of this extract was fractionated on HP‐20. Two polar fractions were then further purified using a C18 Sep‐Pak® followed by separation using C18 RP‐HPLC to give the three known compounds, damirone C ( 5 ) and makaluvamines I ( 6 ) and M ( 7 ),17 and two new compounds, N ‐1‐β‐d‐ribofuranosyldamirone C ( 8 ) and N ‐1‐β‐d‐ribofuranosylmakalu‐vamine I ( 9 )18 (Fig. 3).…”

Section: Resultsmentioning

confidence: 99%

“…3). The eluent from the HP‐20 column was then evaporated to dryness in vaccuo and separated using both C18 Sep‐Pak and C18 RP‐HPLC to yield the two new compounds makaluvic acid C ( 10 ) and N ‐1‐β‐d‐ribofuranosylmakaluvic acid C ( 11 )19 (Fig. 3).…”

Section: Resultsmentioning

confidence: 99%

Antiesophageal Cancer Activity from Southern African Marine Organisms

Whibley¹

2005

Annals of the New York Academy of Sciences

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Squamous cell esophageal cancer presents a significant health burden in many developing countries around the world. In South Africa, this disease is one of the most common causes of cancer-related deaths in black males. Because this cancer is only modestly responsive to available chemotherapeutic agents, there is a need to develop more effective therapeutic agents for this cancer. Marine organisms are currently regarded as a promising source of unique bioactive molecules because they display a rich diversity of secondary metabolites. Some of these compounds have significant anticancer activity, with a few of these currently in phase I and II clinical trials. We report here an ongoing program to screen marine organisms collected from subtidal benthic communities off the coast of southern Africa for activity against cultured esophageal cancer cells. Of the 137 extracts tested, 2.2% displayed high activity (score = 3) and 11.7% displayed moderate activity (score = 2) against cultured esophageal cancer cells. Our results suggest that sponges had a higher hit rate (21.9%) than ascidians (7.1%). Using activity-directed purification, seven previously described compounds and four novel compounds, with varying activity against esophageal cancer cell lines, were isolated from the sponges Axinella weltneri, Aplysilla sulphurea, and Strongylodesma aliwaliensis. The results of this study suggest that subtidal benthic marine organisms collected off the coast of southern Africa hold potential for identifying possible drug leads for the development of agents with activity against esophageal cancer.

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“…Over 100 marine pyrroloiminquinone natural products have been isolated from marine organisms collected from across the globe and the chemistry and bioactivities of this group of compounds have been regularly reviewed in the chemistry literature. 21,[26][27][28] Of the pyrroloiminoquinones isolated thus far from marine sponges, 30 (of which 16 were new compounds) have been isolated from five South African latrunculid sponge species: T. favus 12,29 , T. pedunculata 12 , C. bellae (formerly L. bellae) 12 , S. algoaensis 12 and S. aliwalensis 30,31 (Figures 1 and 5), and the names of these compounds are presented in Tables 2 and 3. Selected compounds from Tables 2 and 3, with novel chemical structural features observed for the first time in this group of compounds, are presented in Figure 4 and the significance of their discovery will be briefly discussed here.…”

Section: Figurementioning

confidence: 99%

“…N-β-D-ribofuranosylmakaluvamine I (Figure 4). 30,31 The sugar moiety in the latter three compounds was identified by chiral gas chromatography comparison of the peracetylated aldononitrile derivative of the acid hydrosylate derived from each compound with a similarly peracetylated aldononitrile derivative of D-ribose. The three ribofuranosyl-containing metabolites from S. alwaliensis remain the only known pyrroloiminoquinone glycosides isolated thus far from marine organisms.…”

Section: Figurementioning

confidence: 99%

The colourful chemistry of South African latrunculid sponges

2019

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Marine sponges – in common with many other sessile marine invertebrates seemingly devoid of obvious physical forms of defence against predators, e.g. spines or shells – are the sources of a diverse array of organic chemical compounds known as marine natural products or secondary metabolites. Recent research has indicated that the production of natural products via cellular secondary metabolic pathways in some sponge species may not occur within the sponge cells themselves, but rather in microbial endosymbionts which inhabit the surface and interstitial spaces within the sponge tissue. Regardless of their biosynthetic origin, the bioactivity, e.g. toxicity, of many of these marine natural products may be utilised by sponges as chemical feeding deterrents to discourage predation or to provide a chemical anti-fouling competitive edge in the intense competition for living space amongst filter-feeders on space-limited benthic reefs. Paradoxically, a small number of sponge natural products have serendipitously shown potential as new pharmaceuticals, e.g. novel anti-cancer drugs. Marine biodiscovery (or bioprospecting) is the search for new pharmaceuticals from marine organisms. Exploration of the taxonomy, natural products chemistry and biomedicinal potential of the rich diversity of South African latrunculid sponges (family Latrunculiidae), at Rhodes University, the South African Department of Environmental Affairs and the University of the Western Cape has continued unabated for over a quarter of a century as part of a collaborative marine biodiscovery programme. A short review of this multidisciplinary latrunculid sponge research is presented here.

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Novel pyrroloquinoline ribosides from the South African latrunculid sponge Strongylodesma aliwaliensis

Cited by 24 publications

References 16 publications

Reactive oxygen species mediated apoptosis of esophageal cancer cells induced by marine triprenyl toluquinones and toluhydroquinones

Reactive oxygen species mediated apoptosis of esophageal cancer cells induced by marine triprenyl toluquinones and toluhydroquinones

Antiesophageal Cancer Activity from Southern African Marine Organisms

The colourful chemistry of South African latrunculid sponges

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