Bioactive 12-Oleanene Triterpene and Secotriterpene Acids from Maytenus undata

Muhammad, Ilias; Sayed, Khalid A. El; Mossa, Jaber S.; Alsaid, Mansour S.; El‐Feraly, Farouk S.; Clark, Alice M.; Hufford, Charles D.; Oh, and Stephen; Mayer, Alejandro M. S.

doi:10.1021/np990456y

Cited by 52 publications

(45 citation statements)

References 26 publications

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“…Triterpenes are well represented in the literature (Muhammad et al, 2000) with a report of a seco-A-ring oleanene, koetjapic acid (25), from Maytenus undata (Celastraceae) (MIC; 50 and 12.5 lg/ml; SA). The seco compound is probably related to other oleananes present in the plant via a Baeyer-Villiger type oxidation (Figure 12).…”

Section: Anti-infective Natural Productsmentioning

confidence: 97%

Plants as a Source of Bacterial Resistance Modulators and Anti-Infective Agents

2005

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The spread of multidrug-resistant (MDR) strains of bacteria necessitates the discovery of new classes of antibacterials and compounds that inhibit these resistance mechanisms. At present, there are no single chemical entity plant-derived antibacterials used clinically, and this chemically diverse group deserves consideration as a source for two major reasons. First, plants have exceptional ability to produce cytotoxic agents and second there is an ecological rationale that antimicrobial natural products should be present or synthesised de novo in plants following microbial attack to protect the producer from pathogenic microbes in its environment. We have been characterising plant-derived products that are either antibacterial in their own right, or modulators of resistance in bacterial strains possessing multidrug efflux mechanisms. These efflux transporters are responsible for resistance to certain antibiotics and antiseptics and occur in strains of methicillin-resistant Staphylococcus aureus (MRSA), a major clinical problem at present. We are also investigating plant sources for compounds with activity against mycobacteria with a view to discovering drug leads with potential activity toward tuberculosis (TB) producing species. This paper will briefly review the literature on plant derived bacterial resistance modifying agents and antibacterials. Examples in this area from our own work will be given. The activities of plant-derived antibacterials show that there are many potential new classes of antibacterial agents which should undergo further cytotoxicity, microbial specificity and preclinical studies.

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Section: Anti-infective Natural Productsmentioning

confidence: 97%

Plants as a Source of Bacterial Resistance Modulators and Anti-Infective Agents

2005

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“…Koetjapic acid (KA) is a seco-A-ring oleanene triterpene isolated from S. koetjape and was found to have mild cytotoxicity on a number of human cancer cell lines and murine lymphocytic leukemia (7,9). KA has been found to have anti-bacterial, anti-inflammatory, anti-tumor promoting activity and DNA polymerase inhibition properties (10)(11)(12)(13). In this study, an attempt has been made to understand the cellular and molecular mechanisms involved in cytotoxic effects of KA towards colon cancer.…”

Section: Introductionmentioning

confidence: 99%

Koetjapic acid, a natural triterpenoid, induces apoptosis in colon cancer cells

et al. 2011

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Abstract. Deregulated cell signaling pathways result in cancer development. More than one signal transduction pathway is involved in colorectal cancer pathogenesis and progression. Koetjapic acid (KA) is a naturally occurring seco-A-ring oleanene triterpene isolated from the Sandoricum koetjape stem bark. We report the cellular and molecular mechanisms of anticancer activity of KA towards human colorectal cancer. The results showed that KA induces apoptosis in HCT 116 colorectal carcinoma cells by inducing the activation of extrinsic and intrinsic caspases. We confirmed that KA-induced apoptosis was mediated by DNA fragmentation, nuclear condensation and disruption in the mitochondrial membrane potential. Further studies on the effect of KA on cancer pathways show that the compound causes down-regulation of Wnt, HIF-1α, MAP/ERK/JNK and Myc/Max signaling pathways and up-regulates the NF-κB signaling pathway. The result of this study highlights the anticancer potential of KA against colorectal cancer.

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“…[12][13][14] Since the n-hexane extract showed potential anti-proliferative activity against a breast cancer cell line, 15) it has been suggested that KA may have potential value as an anti-breast cancer agent. Accordingly, this study has been performed in order to examine the growth inhibitory effect of KA on human breast cancer cells (MCF 7), and to elucidate the mechanism(s) involved in the action of KA.…”

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confidence: 99%

In Vitro Antimetastatic Activity of Koetjapic Acid against Breast Cancer Cells

Nassar

Aisha

Al‐Suede

et al. 2012

Biological & Pharmaceutical Bulletin

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Breast cancer is the most common cancer in women, and it can metastasize very rapidly. Tumor metastasis is the primary cause of cancer deaths. In the present study, we investigated the capability of koetjapic acid, a natural triterpene, in the induction of apoptosis and the inhibition of metastasis in the breast cancer cell line (MCF 7). The effects of koetjapic acid against 4 steps of metastasis have been assessed, including cell survival, clonogenicity, migration and invasion. Koetjapic acid exhibited cytotoxic activity against MCF 7 cells with an IC 50 of 68.88 6.075 μg/mL. The mechanism of cell death was confirmed due to the induction of apoptosis machineries; early and late apoptosis-related changes were detected, including the stimulation of caspase 3/7 activities, apoptosis-related morphological changes such as membrane blebbing, chromatin condensation and DNA fragmentation. A mitochondrial apoptosis pathway was found to be involved in koetjapic acid-induced cell death induction. Moreover, at a sub-toxic dose (15 μg/mL), Koetjapic acid inhibited cell migration and invasion significantly. Finally, koetjapic acid inhibited the colony formation properties of MCF 7 significantly. These results indicate that koetjapic acid possesses significant antitumor and antimetastatic effects, and warrants further investigation.

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Bioactive 12-Oleanene Triterpene and Secotriterpene Acids from Maytenus undata

Cited by 52 publications

References 26 publications

Plants as a Source of Bacterial Resistance Modulators and Anti-Infective Agents

Plants as a Source of Bacterial Resistance Modulators and Anti-Infective Agents

Koetjapic acid, a natural triterpenoid, induces apoptosis in colon cancer cells

<i>In Vitro</i> Antimetastatic Activity of Koetjapic Acid against Breast Cancer Cells

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