Cucurbitane-Type Triterpenoids from the Stems of <i>Cucumis melo</i>

Chen, Chuan; Qiang, Shigao; Lou, Liguang; Zhao, Weimin

doi:10.1021/np800692t

Cited by 50 publications

(34 citation statements)

References 31 publications

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“…36) In addition, Chen et al recently reported the importance of an a,b-unsaturated ketone in the side chains and the 25-acetoxy group in a preliminary analysis of structure-activity relationships. 38) Consistent with the results of these studies, 36,38) 15) was not effective less than 30 mM (inhibition: Ϫ7.7Ϯ1.3% at 30 mM after 72 h). Our results also demonstrate that an a,b-conjugated ketone moiety at the 22-24 positions and an acetoxy group at the 25 position are essential for the greater activity [3 (9.2 nM)Ͼ6 (0.22 mM); 5 (16 nM)Ͼ7 (3.3 mM); 3 (9.2 nM)Ͼ4 (0.33 mM)].…”

Section: Structures Of Bryoniaosides a (1) And B (2)supporting

confidence: 85%

Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B

et al. 2010

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NoteBryonia cretica L., is a Cucurbitaceae plant growing widely in the western Mediterranean coastal region and in Egypt.1) This plant has been used in folk medicine as a drastic purgative, emetic, bitter tonic and anti-diabetic agent. 2)Previous chemical study of B. cretica revealed the presence of cucurbitacins B (3), E (5), I, and L.3) In the course of our studies on bioactive constituents from Egyptian natural medicines, 4-15) the 90% aqueous ethanolic (90% EtOH) extract from the roots of B. cretica showed strong inhibition of the proliferation of human leukemia U937 cells (IC 50 value at 72 hϭ0.035 mg/ml).Here we describe the chemical elucidation of two new cucurbitane-type triterpene glycosides, bryoniaosides A (1) and B (2), and anti-proliferative effects of several cucurbitanetype triterpenes (3-9) on U937 cells together with several structural requirements for the activity. Results and DiscussionThe 90% EtOH extract of the roots of B. cretica (11.5% from the dried roots) was partitioned into an ethyl acetate (EtOAc)-H 2 O (1 : 1, v/v) mixture to furnish the EtOAc-soluble fraction and an aqueous layer. The aqueous layer was extracted with n-butanol (n-BuOH) to give n-BuOH and H 2 Osoluble fractions. As shown in Table 1, the EtOAc-soluble fraction exhibited marked activity (IC 50 value at 72 hϭ 0.050 mg/ml), but the n-BuOH-and H 2 O-soluble fraction lacked the activity (IC 50 values at 72 hϾ1 mg/ml).The EtOAc-soluble fraction was subjected to normalphase and reversed-phase silica gel column chromatography and repeated HPLC to give two new cucurbitane-type triter-

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Section: Structures Of Bryoniaosides a (1) And B (2)supporting

confidence: 85%

Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B

et al. 2010

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“…Another representative of the triterpenoids with anticancer activity is cucurbitacin B (Fig. 1), which can be found in many cucurbitacaea species [21], for example, also in the stems of Cucumis melo (melon) [22]. Cucurbitacin B was found to have antiproliferative activity on glioblastoma multiforme cells [23], breast cancer [24], myeloid leukemia [25], pancreatic cancer [26], laryngeal squamous cell carcinoma, and other tumor cells [27].…”

Section: Triterpenoidsmentioning

confidence: 99%

Betulinic acid, a natural compound with potent anticancer effects

Mullauer

Kessler²,

Medema³

2010

Anti-Cancer Drugs

177

105

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New therapies using novel mechanisms to induce tumor cell death are needed with plants playing a crucial role as a source for potential anticancer compounds. One highly promising class of natural compounds are the triterpenoids with betulinic acid (BetA) as the most prominent representative. In-vitro studies have identified this agent as potently effective against a wide variety of cancer cells, also those derived from therapy-resistant and refractory tumors, whereas it has been found to be relatively nontoxic for healthy cells. In-vivo preclinically applied BetA showed some remarkable anticancer effects and a complete absence of systemic toxicity in rodents. BetA also cooperated with other therapies to induce tumor cell death and several potent derivatives have been discovered. Its antitumor activity has been related to its direct effects on mitochondria where it induces Bax/Bak-independent cytochrome-c release.

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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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Cucurbitane-Type Triterpenoids from the Stems of Cucumis melo

Cited by 50 publications

References 31 publications

Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B

Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B

Betulinic acid, a natural compound with potent anticancer effects

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

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