Debromocymopolone from the Green Alga, <i>Cymopolia Barbata</i>

Gallimore, Winklet A.; Sambo, Tandose; Campbell, T. H.

doi:10.3184/030823409x416901

Cited by 6 publications

(6 citation statements)

References 5 publications

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“…325 Biosynthetic studies of curacin A, a metabolite of mixed polyketide-peptideorigin from the cyanobacterium Lyngbya majuscula, 326 revealed an unprecedented decarboxylative chain termination mechanism involving a module containing adjacent sulfotransferase (ST) and thioesterase (TE) catalytic domains. 334 A significant find was the discovery of two new cyclic depsipeptides from Bryopsis pennata (Kahala Bay, Ohau, Hawaii). from the Okinawan brown alga Stypopodium zonale, 329 indicated that the former fungus converted aplysistatin into 5a-hydroxyaplysistatin, 5a-hydroxyisoaplysistatin and 9b-hydroxyaplysistatin, whilst the latter fungus, transformed aplysistatin, palisadin A and 12-hydroxypalisadin B to 3,4-dihydroaplysistatin and 9,10-dehydrobromopalisadin A.…”

Section: Marine Microorganisms and Phytoplanktonmentioning

confidence: 99%

“…333 Debromocymopolone, 296 was isolated from Cymopolia barbata (Fairy Hill Beach, Jamaica), and is the first non-halogenated cymopol isolated. 334 A significant find was the discovery of two new cyclic depsipeptides from Bryopsis pennata (Kahala Bay, Ohau, Hawaii). These were 5-OHKF 297 and norKA 298, and join the other seventeen congeners of the kahalide family that have to date been isolated from B. pennata or molluscs of the genus Elysia.…”

Section: Green Algaementioning

confidence: 99%

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Marine natural products

et al. 2011

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Section: Marine Microorganisms and Phytoplanktonmentioning

confidence: 99%

Section: Green Algaementioning

confidence: 99%

Marine natural products

et al. 2011

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“…Fraction 23–28 was found to contain 7-hydroxycymopolone (PBQ2). Both PBQs were identified by comparison of their 1 H and 13 C NMR data with the literature [1,34]. …”

Section: Resultsmentioning

confidence: 99%

Cytotoxic and potent CYP1 inhibitors from the marine algae Cymopolia barbata

et al. 2012

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BackgroundExtracts from the marine algae Cymopolia barbata have previously shown promising pharmacological activity including antifungal, antitumor, antimicrobial, and antimutagenic properties. Even though extracts have demonstrated such bioactivity, isolated ingredients responsible for such bioactivity remain unspecified. In this study, we describe chemical characterization and evaluations of biological activity of prenylated bromohydroquinones (PBQ) isolated from the marine algae C. barbata for their cytotoxic and chemopreventive potential.MethodsThe impact of PBQs on the viability of cell lines (MCF-7, HT29, HepG, and CCD18 Co) was evaluated using the MTS assay. In addition, their inhibitory impact on the activities of heterologously expressed cytochrome P450 (CYP) enzymes (CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2D6, and CYP3A4) was evaluated using a fluorescent assay.Results7-Hydroxycymopochromanone (PBQ1) and 7-hydroxycymopolone (PBQ2) were isolated using liquid and column chromatography, identified using 1 H and 13 C NMR spectra and compared with the spectra of previously isolated PBQs. PBQ2 selectively impacted the viability of HT29, colon cancer cells with similar potency to the known chemotherapeutic drug, fluorouracil (IC50, 19.82 ± 0.46 μM compared to 23.50 ± 1.12 μM, respectively) with impact toward normal colon cells also being comparable (55.65 ± 3.28 compared to 55.51 ± 3.71 μM, respectively), while PBQ1 had no impact on these cells. Both PBQs had potent inhibition against the activities of CYP1A1 and CYP1B1, the latter which is known to be a universal marker for cancer and a target for drug discovery. Inhibitors of CYP1 enzymes by virtue of the prevention of activation of carcinogens such as benzo-a-pyrene have drawn attention as potential chemopreventors. PBQ2 potently inhibited the activity of CYP1B1 (IC50 0.14 ± 0.04 μM), while both PBQ1 and PBQ2 potently inhibited the activity of CYP1A1 (IC50s of 0.39 ± 0.05 μM and 0.93 ± 0.26 μM, respectively). Further characterizations showed partial noncompetitive enzyme kinetics for PBQ2 with CYP1B1 with a Ki of 4.7 × 10–3 ± 5.1 × 10–4 μM and uncompetitive kinetics with CYP1A1 (Ki = 0.84 ± 0.07 μM); while PBQ1 displayed partial non competitive enzyme kinetics with CYP1A1 (Ki of 3.07 ± 0.69 μM), noncompetitive kinetics with CYP1A2 (Ki = 9.16 ± 4.68 μM) and uncompetitive kinetics with CYP1B1 (Ki = 0.26 ± 0.03 μM) .ConclusionsWe report for the first time, two isolated ingredients from C. barbata, PBQ1 and PBQ2, that show potential as valuable chemotherapeutic compounds. A hydroxyl moiety resident in PBQ2 appears to be critical for selectivity and potency against the cancer colon cells, HT29, in comparison to the three other malignant cell lines studied. PBQs also show potency against the activities of CYP1 enzyme which may be a lead in chemoprevention. This study, the first on isolates from these marine algae, exemplifies the value of searching within nature for unique structural motifs that can display multiple biological activities.

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“…Both (PBQI) and (PBQ2) are reported to be chemotherapeutic compounds but make residue of the hydroxyl moiety (PB2) to act selectively against cancer colon cells. Crude extracts of Cymopolia barbata blocked progesterone-stimulated gene expression in human progesterone receptor cells and purified cyclic epimeric bromo-hydro-quinones (cymobarbatol and 4-isocymobarbatol), showing antimutagenic activity against Salmonella typhimurium [ 41 , 42 ].…”

Section: Green Algae a Source Of Bioactive Secondary Metabolitesmentioning

confidence: 99%

Chemically Diverse and Biologically Active Secondary Metabolites from Marine Phylum chlorophyta

et al. 2020

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For a long time, algal chemistry from terrestrial to marine or freshwater bodies, especially chlorophytes, has fascinated numerous investigators to develop new drugs in the nutraceutical and pharmaceutical industries. As such, chlorophytes comprise a diverse structural class of secondary metabolites, having functional groups that are specific to a particular source. All bioactive compounds of chlorophyte are of great interest due to their supplemental/nutritional/pharmacological activities. In this review, a detailed description of the chemical diversity of compounds encompassing alkaloids, terpenes, steroids, fatty acids and glycerides, their subclasses and their structures are discussed. These promising natural products have efficiency in developing new drugs necessary in the treatment of various deadly pathologies (cancer, HIV, SARS-CoV-2, several inflammations, etc.). Marine chlorophyte, therefore, is portrayed as a pivotal treasure in the case of drugs having marine provenience. It is a domain of research expected to probe novel pharmaceutically or nutraceutically important secondary metabolites resulting from marine Chlorophyta. In this regard, our review aims to compile the isolated secondary metabolites having diverse chemical structures from chlorophytes (like Caulerpa ssp., Ulva ssp., Tydemania ssp., Penicillus ssp., Codium ssp., Capsosiphon ssp., Avrainvillea ssp.), their biological properties, applications and possible mode of action.

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Debromocymopolone from the Green Alga, Cymopolia Barbata

Abstract: Investigation of a Jamaican green alga, Cymopolia barbata led tothe isolation of a new geranyl-1,4-dihydroxybenzene, debromocymopolone, the structure of which was elucidated by spectroscopic techniques.

Cited by 6 publications

References 5 publications

Marine natural products

Marine natural products

Cytotoxic and potent CYP1 inhibitors from the marine algae Cymopolia barbata

Chemically Diverse and Biologically Active Secondary Metabolites from Marine Phylum chlorophyta

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