Two New Oxodolastane Diterpenes from the Jamaican Macroalga Canistrocarpus cervicornis

Campbell, Sanjay; Murray, JeAnn; Delgoda, Rupika; Gallimore, Winklet A.

doi:10.3390/md15060150

Cited by 6 publications

(5 citation statements)

References 21 publications

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“…349 Two dolastane diterpenes 879, 880 were isolated from the Jamaican alga Canistrocarpus cervicornis. 350 A 3R/3S diasteromeric mixture of the meroditerpene, tetraprenyltoluquinone 881, 882 was isolated from Cystoseira baccata, 351 and a carotenoid metabolite, an isololiolide derivative, schiffnerilolide 883 has been reported from a Tunisian collection of Cystoseira schiffneri. 352 An Indian collection of Sargassum wightii was claimed to contain two unusual polyketide lactones, 884, 885.…”

Section: Brown Algaementioning

confidence: 99%

Marine natural products

et al. 2019

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Section: Brown Algaementioning

confidence: 99%

Marine natural products

et al. 2019

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“…Jamaica has a wide array of selfmedicated herbs and medicinal plants in use against illnesses [7], with some displaying anti-cancer properties. Petiveria alliacea and key phytochemical, dibenzyl trisulfide [8] and the Jamaican ball moss (Tillandsia recurvata L.) [9] exemplifies use in prostate cancer, among other biodiversity with disparate cytotoxic properties [10]. A recent survey among cancer patients in the country [11] helped identify common ethnomedical practices in the island nation and Annona muricata L. emerged as a popular ingredient, in line with findings emerging from Indonesia, [12] and Trinidad [13].…”

Section: Introductionmentioning

confidence: 71%

Selective cytotoxic and anti-metastatic activity in DU-145 prostate cancer cells induced by Annona muricata L. bark extract and phytochemical, annonacin

Foster

Oyenihi

Rademan

et al. 2020

BMC Complement Med Ther

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Background Annona muricata L. was identified as a popular medicinal plant in treatment regimens among cancer patients in Jamaica by a previously conducted structured questionnaire. Ethnomedically used plant parts, were examined in this study against human prostate cancer cells for the first time and mechanisms of action elucidated for the most potent of them, along with the active phytochemical, annonacin. Methods Nine extracts of varying polarity from the leaves and bark of A. muricata were assessed initially for cytotoxicity using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay on PC-3 prostate cancer cells and the ethyl acetate bark (EAB) extract was identified as the most potent. EAB extract was then standardized for annonacin content using High-performance Liquid Chromatography - Mass Spectrometry (HPLC-MS) and shown to be effective against a second prostate cancer cell line (DU-145) also. The mode of cell death in DU-145 cells were assessed via several apoptotic assays including induction of increased reactive oxygen species (ROS) production, reduction of mitochondrial membrane potential, activation of caspases and annexin V externalization combined with morphological observations using confocal microscopy. In addition, the potential to prevent metastasis was examined via inhibition of cell migration, vascular endothelial growth factor (VEGF) and angiogenesis using the chorioallantoic membrane assay (CAM). Results Annonacin and EAB extract displayed selective and potent cytotoxicity against the DU-145 prostate carcinoma cells with IC50 values of 0.1 ± 0.07 μM and 55.501 ± 0.55 μg/mL respectively, without impacting RWPE-1 normal prostate cells, in stark contrast to chemotherapeutic docetaxel which lacked such selectivity. Docetaxel’s impact on the cancerous DU-145 was improved by 50% when used in combination with EAB extract. Insignificant levels of intracellular ROS content, depolarization of mitochondrial membrane, Caspase 3/7 activation, annexin V content, along with stained morphological evaluations, pointed to a non-apoptotic mode of cell death. The extract at 50 μg/mL deterred cell migration in the wound-healing assay, while inhibition of angiogenesis was displayed in the CAM and VEGF inhibition assays for both EAB (100 μg /mL) and annonacin (0.5 μM). Conclusions Taken together, the standardized EAB extract and annonacin appear to induce selective and potent cell death via a necrotic pathway in DU-145 cells, while also preventing cell migration and angiogenesis, which warrant further examinations for mechanistic insights and validity in-vivo.

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“…Fraction 11 was crystallized in methylene chloride to yield white orthorhombic crystals of (4 R,9S,14S)-4,9,14-trihydroxydolast-1(15),7diene (20) while fraction 12 was further fractionated on silica gel to yield 4R-hydroxy-8S,9S-epoxy-14S-hydroxy-7oxodolastane (21). Moderate, concentration-dependent cytotoxicity against human tumour cell lines PC3 and HT29 was observed with the compounds isolated [48]. Work conducted on the Brazilian C. cervicornis led to the isolation of a dolastane exhibiting antileishmanial activity [49], thereby confirming the diverse utility of compounds from marine sources.…”

Section: Canistrocarpus Cervicornismentioning

confidence: 80%

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

Gallimore

2018

JAC

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Research efforts to examine the chemistry of marine organisms collected from the Ramsar site of Port Royal, Jamaica, has led to the isolation of a range of compounds as diverse as the species from which they were derived. Six sponges, two algal species, one ascidian and one soft coral collected from the mangrove area and the shallow coastal reefs were studied to yield compounds including steroids, aromatic compounds and terpenoids.

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Two New Oxodolastane Diterpenes from the Jamaican Macroalga Canistrocarpus cervicornis

Cited by 6 publications

References 21 publications

Marine natural products

Marine natural products

Selective cytotoxic and anti-metastatic activity in DU-145 prostate cancer cells induced by Annona muricata L. bark extract and phytochemical, annonacin

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

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