Anticancer Activity Evaluation of Kuanoniamines A and C Isolated from the Marine Sponge Oceanapia sagittaria, Collected from the Gulf of Thailand

Kijjoa, Anake; Wattanadilok, Rawiwan; Campos, Nair; Nascimento, María Säo José; Pinto, Madalena; Herz, Werner

doi:10.3390/md502006

Cited by 41 publications

(21 citation statements)

References 22 publications

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“…27 Similarly, kuanoniamine A and C isolated from sponges has been found to inhibit the growth of tumour and non-tumour cell lines, as well as an oestrogen-dependent breast cancer cell line. 28 Smith et al revealed that hymenialdisine has anti-cancer properties against human colorectal carcinomas. 29 Furthermore, gallic acid has been shown as a potent compound with antimicrobial, antioxidant, quorum-sensing inhibitory and anti-cancer properties.…”

Section: Discussionmentioning

confidence: 99%

Screening for Anti-Cancer Compounds in Marine Organisms in Oman

Dobretsov

Tamimi

Al-Kindi

et al. 2016

SQUMJ

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Objectives: Marine organisms are a rich source of bioactive molecules with potential applications in medicine, biotechnology and industry; however, few bioactive compounds have been isolated from organisms inhabiting the Arabian Gulf and the Gulf of Oman. This study aimed to isolate and screen the anti-cancer activity of compounds and extracts from 40 natural products of marine organisms collected from the Gulf of Oman. Methods: This study was carried out between January 2012 and December 2014 at the Sultan Qaboos University, Muscat, Oman. Fungi, bacteria, sponges, algae, soft corals, tunicates, bryozoans, mangrove tree samples and sea cucumbers were collected from seawater at Marina Bandar Al-Rowdha and Bandar Al-Khayran in Oman. Bacteria and fungi were isolated using a marine broth and organisms were extracted with methanol and ethyl acetate. Compounds were identified from spectroscopic data. The anti-cancer activity of the compounds and extracts was tested in a Michigan Cancer Foundation (MCF)-7 cell line breast adenocarcinoma model. Results: Eight pure compounds and 32 extracts were investigated. Of these, 22.5% showed strong or medium anti-cancer activity, with malformin A, kuanoniamine D, hymenialdisine and gallic acid showing the greatest activity, as well as the soft coral Sarcophyton sp. extract. Treatment of MCF-7 cells at different concentrations of Sarcophyton sp. extracts indicated the induction of concentration-dependent cell death. Ultrastructural analysis highlighted the presence of nuclear fragmentation, membrane protrusion, blebbing and chromatic segregation at the nuclear membrane, which are typical characteristics of cell death by apoptosis induction. Conclusion: Some Omani marine organisms showed high anti-cancer potential. The efficacy, specificity and molecular mechanisms of anti-cancer compounds from Omani marine organisms on various cancer models should be investigated in future in vitro and in vivo studies.

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Section: Discussionmentioning

confidence: 99%

Screening for Anti-Cancer Compounds in Marine Organisms in Oman

Dobretsov

Tamimi

Al-Kindi

et al. 2016

SQUMJ

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“…Kuanoniamine A proved to be a potent growth inhibitor of all the human tumor cell lines as well as the nontumour cell line. Though kuanoniamine C was found to be much less potent than kuanoniamine A, it was found to possess a high selectivity toward the estrogen dependent breast cancer cell line . Kuanoniamine E (R = i‐ Pr) and kuanoniamine F (R = CH(Me)Et) (Figure ) were isolated from a Singaporean ascidian along with other pyridoacridines, including ascididemine (Figure ) and the “ring‐opened” variant 87 drawn to suggest its structural relationship to other pyridoacridine alkaloids .…”

Section: Pyrido[234‐kl]acridinementioning

confidence: 99%

“…A simple synthesis of subarine from a Singapore ascidian employs a cross‐coupling as a key step (Scheme ) . The structure is drawn in such a way as to suggest its relationship to the pentacyclic alkaloids of the ascididemine group, but with one ring “missing” – hence its inclusion, though tricyclic, in this Section.…”

Section: Pyrido[234‐kl]acridinementioning

confidence: 99%

Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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This minireview summarizes the work developed during this century with compounds containing the pyridoacridine scaffold in its different isomeric forms. The isolation of natural products, syntheses, bioactivities, chelation capacity, and other properties of compounds containing this framework are discussed. For reasons of length, only compounds containing a maximum of seven condensed rings have been considered, with a few exceptions.

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“…Although most of the current natural product-derived therapeutic drugs originated from terrestrial plant extracts marine-based natural products are recently considered to be an important resource for procurement of new chemical entities [2]. In particular, many compounds derived from marine sponges have exhibited anticancer activities with diverse mechanisms of action [3,4,5]. Eribulin mesylate, a structurally simplified macrolactone derivative of halichondrin B, which was originally isolated from the marine sponge Halichondria okadai , is an example of recently approved anticancer drug for metastatic breast cancer [6].…”

Section: Introductionmentioning

confidence: 99%

Antimetastatic Effect of Halichondramide, a Trisoxazole Macrolide from the Marine Sponge Chondrosia corticata, on Human Prostate Cancer Cells via Modulation of Epithelial-to-Mesenchymal Transition

et al. 2013

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Halichondramide (HCA), a trisoxazole-containing macrolide isolated from the marine sponge Chondrosia corticata has been shown to exhibit cytotoxicity and antifungal activities. In our previous study, HCA was also found to exhibit antiproliferative activity against a variety of cancer cells. However, the precise mechanism of action of HCA in the antitumor activity remains to be elucidated. In the present study, we identified the antimetastatic activity of HCA in the highly metastatic PC3 human prostate cancer cells. HCA showed potent growth inhibitory activity of the PC3 cells with an IC50 value of 0.81 µM. Further analysis revealed that HCA suppressed the expression of a potential metastatic biomarker, phosphatase of regenerating liver-3 (PRL-3), in PC3 cells. The suppression of PRL-3 by HCA sequentially down-regulates the expression of phosphoinositide 3-kinase (PI3K) subunits p85 and p110. The antimetastatic effect of HCA was also correlated with the down-regulation of matrix metalloproteases (MMPs) and the modulation of cadherin switches N-cadherin and E-cadherin. In addition, HCA also effectively suppressed the migration and invasion of PC3 cells. These findings suggest that halichondramide might serve as a potential inhibitor of tumor cell metastasis with the modulation of PRL-3.

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Anticancer Activity Evaluation of Kuanoniamines A and C Isolated from the Marine Sponge Oceanapia sagittaria, Collected from the Gulf of Thailand

Cited by 41 publications

References 22 publications

Screening for Anti-Cancer Compounds in Marine Organisms in Oman

Screening for Anti-Cancer Compounds in Marine Organisms in Oman

Pyridoacridines in the 21st Century

Antimetastatic Effect of Halichondramide, a Trisoxazole Macrolide from the Marine Sponge Chondrosia corticata, on Human Prostate Cancer Cells via Modulation of Epithelial-to-Mesenchymal Transition

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