Cucurbitacins and Cucurbitane Glycosides: Structures and Biological Activities

Chen, Jian Chao; Chiu, Ming; Nie, Rui Lin; Cordell, Geoffrey A.; Qiu, Samuel X.

doi:10.1002/chin.200539234

Cited by 94 publications

(163 citation statements)

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“…Due to the selection of non-bitter plants for food use made by our ancestors and later by plant breeders, the cucurbits currently consumed generally do not synthesize these compounds. Structurally, cucurbitacins are tetracyclic triterpenes with a cucurbitane skeleton and differ from most other tetracyclic triterpenes because they are highly unsaturated and contain many keto, hydroxy and acetoxy groups (Chen et al, 2005;Gry et al, 2006). A chronic exposure to these compounds is not expected in humans given their extremely bitter and disagreeable taste and the accidental occurrence in plant foods (Gry et al, 2006).…”

Section: Brydiofin and Cucurbitacinsmentioning

confidence: 99%

“…For example, S. hispanicum is already cultivated and commercialized in some regions of Spain and its shoots are sold as gourmet food product (Łuczaj et al, 2012). The agricultural interest for non-food crops for obtaining high-added value products is also attractive, namely n-3 fatty acids from seeds of B. officinalis (GuilGuerrero et al, 2013), tocopherols from G. hederacea (Barros et al, 2010d) and C. ambrosioides , phenolic compounds from R. ulmifolius (Barros et al, 2010e), inulin from C. intybus (Amaducci and Pritoni, 1998), cucurbitacins from B. dioica roots (Chen et al, 2005;Gry et al, 2006;Hylands and Mansour, 1982;Hylands and Salama, 1976;Oobayashi et al, 1992;Pohlmann, 1975), and prenylflavonoids from H. lupulus inflorescences (Kristanc and Kreft, 2016b). -Breeding and genetic characterization of crop wild relatives: The genetic improvement of crop wild relatives is a scientific challenge that should be pursued.…”

Section: Valorisation Strategies Challenges and Trendsmentioning

confidence: 99%

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Wild edible plants: Nutritional and toxicological characteristics, retrieval strategies and importance for today's society

Pinela

Ferreira

2017

Food and Chemical Toxicology

137

111

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A B S T R A C TWild edible plants (WEPs) are part of the cultural and genetic heritage of different regions of the world. In times of famine and scarcity, these sources of nutrients and health-promoting compounds have received high importance mainly in rural and suburban areas. Although currently underutilized, WEPs are still consumed traditionally by different communities and are gaining relevance in today's society. However, these foods lack recognition as significant contributors to the human diet in developed areas. This review describes the nutritional value of WEPs from the North-eastern region of Portugal and points out those containing potentially toxic compounds. Several retrieval strategies are presented with the aim of promoting the (re)use, production, commercialization and conservation of WEPs (wild harvested plants and crop wild relatives), and their importance for social, economic and agro-ecological development is highlighted.

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Section: Brydiofin and Cucurbitacinsmentioning

confidence: 99%

Section: Valorisation Strategies Challenges and Trendsmentioning

confidence: 99%

Wild edible plants: Nutritional and toxicological characteristics, retrieval strategies and importance for today's society

Pinela

Ferreira

2017

Food and Chemical Toxicology

137

111

View full text Add to dashboard Cite

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“…Cucurbitacin B (CuB) is a natural triterpenoid isolated from Cucurbitaceae plants, and it has been shown to have anti-plasmodial, immunomodulatory, free-radical scavenging, hepato-protective, cardiovascular, anti-inflammatory, anti-helminthic, and anti-fertility activities (9)(10)(11)(12). Recently, there has been growing interest in CuB-mediated anticancer activities, mainly mediated through induction of G 2 -M phase cell-cycle arrest, inhibition of the JAK/STAT pathway, and induction of apoptosis (13)(14)(15)(16)(17)(18)(19).…”

Section: Introductionmentioning

confidence: 99%

Cucurbitacin B Alters the Expression of Tumor-Related Genes by Epigenetic Modifications in NSCLC and Inhibits NNK-Induced Lung Tumorigenesis

Shukla

Khan

Kumar

et al. 2015

Cancer Prevention Research

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Non-small cell lung cancer (NSCLC) represents almost 85% of total diagnosed lung cancer. Studies have shown that combination of DNA methyltransferase (DNMT) and histone deacetylase (HDAC) inhibitors is effective against various cancers, including lung cancer. However, optimizing the synergistic dose regime is very difficult and involves adverse side effects. Therefore, in this study, we have shown that cucurbitacin B (CuB), a single bioactive triterpenoid compound, inhibits both DNMTs and HDACs starting at a very low dose of 60 nmol/L in NSCLC H1299 cells. The CuB-mediated inhibition of DNMTs and HDACs in H1299 cells leads to the reactivation of key tumor suppressor genes (TSG) such as CDKN1A and CDKN2A, as well as downregulation of oncogenes c-MYC and K-RAS and key tumor promoter gene (TPG), human telomerase reverse transcriptase (hTERT). The upregulation of TSGs and downregulation of TPG were consistently correlated with the alterations in their promoter methylation and histone modifications. This altered expression of TPG and TSGs is, at least in part, responsible for the inhibition of cellular proliferation and induction of cellular apoptosis in NSCLC. Furthermore, CuB treatment significantly inhibited the tumor incidence and multiplicity in 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis in A/J mice, which was associated with the induction of apoptosis and inhibition of hyperproliferation in the lung tissues. Together, our study provides new insight into the CuB-mediated epigenetic alterations and its chemotherapeutic effects on lung cancer. Cancer Prev Res; 8(6); 552-62. Ó2015 AACR.

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“…Cucurbitacins are tetracyclic triterpens isolated from plant families such as the Cucurbitaceae and Cruciferae that have been used for centuries as folk medicines [1]. Indeed, cucurbitacins have been shown to have anti-inflammatory, analgesic as well as cytotoxic activity in vitro and in vivo [2,3].…”

Section: Introductionmentioning

confidence: 99%

Activated kRas protects colon cancer cells from cucurbitacin-induced apoptosis: The role of p53 and p21

Escandell

Kaler

Recio

et al. 2008

Biochemical Pharmacology

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Cucurbitacins have been shown to inhibit proliferation in a variety of cancer cell lines. The aim of this study was to determine their biological activity in colon cancer cell lines that do not harbor activated STAT3, the key target of cucurbitacin. In order to establish the role of activated kRas in the responsiveness of cells to cucurbitacins, we performed experiments in isogenic colon cancer cell lines, HCT116 and Hke-3, which differ only by the presence of an activated kRas allele. We compared the activity of 23, 24-dihydrocucurbitacin B (DHCB) and cucurbitacin R (CCR), two cucurbitacins that we recently isolated, with cucurbitacin I (CCI), a cucurbitacin with established antitumorigenic activity. We showed that cucurbitacins induced dramatic changes in the cytoskeleton (collapse of actin and bundling of tubulin microfilaments), inhibited proliferation and finally induced apoptosis of both HCT116 and Hke3 cells. However, the presence of oncogenic k-Ras significantly decreased the sensitivity of cells to the three cucurbitacins tested, CCR, DHCB and CCI. We confirmed that mutational activation of kRas protects cells from cucurbitacin-induced apoptosis using nontransfromed intestinal epithelial cells with inducible expression of k-RasV12. Cucurbitacins induced the expression of p53 and p21 predominantly in HCT116 cells that harbor mutant Ras. Using HCT116 cells with targeted deletion of p53 or p21 we confirmed that p53 and p21 protect cells from apoptosis induced by cucurbitacins. These results demonstrated that sensitivity of human colon cancer cell lines to cucurbitacins depends on the kRas and p53/p21 status, and established that cucurbitacins can exert antitumorigenic activity in the absence of activated STAT3.

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Cucurbitacins and Cucurbitane Glycosides: Structures and Biological Activities

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 94 publications

References 1 publication

Wild edible plants: Nutritional and toxicological characteristics, retrieval strategies and importance for today's society

Wild edible plants: Nutritional and toxicological characteristics, retrieval strategies and importance for today's society

Cucurbitacin B Alters the Expression of Tumor-Related Genes by Epigenetic Modifications in NSCLC and Inhibits NNK-Induced Lung Tumorigenesis

Activated kRas protects colon cancer cells from cucurbitacin-induced apoptosis: The role of p53 and p21

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