Cucurbitacin glycosides from Citrullus colocynthis

Hatam, Natiq A.R.; Whiting, Donald A.; Yousif, Nahia J.

doi:10.1016/0031-9422(89)80230-4

Cited by 69 publications

(45 citation statements)

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“…The fruit of C. colocynthis have been commonly used as an catharsis and antidiabetic agents in traditional Egyptian and Indian Ayurvedic medicines. [2][3][4][5][6][7][8][9] Previously, several triterpene, [3][4][5] flavonoid 7) and aliphatic compounds 6) have been isolated from the fruit and roots of this medicinal plant and the pharmacological activities such as anti-cancer 1) and insulinotropic effects 9) were reported. In the course of our characterization studies on Egyptian herbal medicines such as Cyperus longus, 10,11) Anastatica hierochuntica, 12,13) Nigella sativa, 14,15) Crinum yemense, 16) and Dichrocephala integrifolia, 17) the methanolic extract from the fruit of C. colocynthis was found to show an antiallergic effect on ear passive cutaneous anaphylaxis (PCA) reaction as a type I allergic model in mice.…”

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“…In the course of our characterization studies on Egyptian herbal medicines such as Cyperus longus, 10,11) Anastatica hierochuntica, 12,13) Nigella sativa, 14,15) Crinum yemense, 16) and Dichrocephala integrifolia, 17) the methanolic extract from the fruit of C. colocynthis was found to show an antiallergic effect on ear passive cutaneous anaphylaxis (PCA) reaction as a type I allergic model in mice. From the methanolic extract, two new cucurbitanetype triterpene glycosides, colocynthosides A (1) and B (2), were isolated from this herbal medicine together with 17 known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). This paper deals with the structure elucidation of new compounds (1, 2) from the fruit of C. colocynthis as well as the antiallergic activities of the methanolic extract and the principal constituent, cucurbitacin E 2-O-b-D-glucopyranoside (3), and the aglycon, cucurbitacin E (3a), on ear PCA reaction in mice as type I allergic model.…”

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confidence: 99%

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Bioactive Saponins and Glycosides. XXVII. Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis

et al. 2007

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The methanolic extract from the fruit of Citrullus colocynthis showed an inhibitory effect on ear passive cutaneous anaphylaxis reactions as a type I allergic model in mice. From the methanolic extract, two new cucurbitane-type triterpene glycosides, colocynthosides A and B, were isolated together with 17 known constituents. The structures of colocynthosides A and B were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal cucurbitane-type triterpene glycoside, cucurbitacin E 2-O-b b-D-glucopyranoside, and its aglycon, cucurbitacin E, exhibited the antiallergic activity at a dose of 100 and 1.25 mg/kg, p.o., respectively.

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confidence: 99%

Bioactive Saponins and Glycosides. XXVII. Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis

et al. 2007

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“…Phytochemical investigations of its bitter principles 'cucurbitacins' were numerous. From the pulp of C. colocynthis, ·-elaterin, ·-elaterin-2-D-glucopyranoside, and citrullol [4] and from defatted plants 2-O-ß-D-glucopyranosyl cucurbitacin and 2-O-ß-D-glucopyranozyl cucurbitacin were isolated [5]. Fruits contain hentriacontane, n-octacosanol, and 1,2,6-hexa-cosanediol [6], while in the shoots malonic acid was detected [7].…”

Section: Introductionmentioning

confidence: 99%

Induction of Reversible Antifertility with a Crude Ethanol Extract of <i>Citrullus colocynthis</i> Schrad Fruit in Male Rats

Chaturvedi¹,

Mali

Ansari

2003

Pharmacology

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A crude 50% ethanol extract of Citrullus colocynthis Schrad was administered orally to male albino rats for evaluation of antifertility effects. The animals were divided into five groups: group A was a vehicle-treated control group; treatment groups B, C, and D received 100 mg/kg/day C. colocynthis extract for periods of 20, 40, and 60 days, respectively, and group E animals received the extract at 100 mg/kg/day for 60 days followed by 60 days of recovery. For androgenicity evaluation of the extract, the animals were divided into four groups: group F animals were castrated 30 days before the experiment to serve as controls, and group G, H, and I were subjected to castration 30 days before the experiments, followed by administration of fruit extract (100 mg/kg/day p.o.), testosterone propionate (0.01 mg/rat/alternate day s.c.), and fruit extract along with testosterone propionate, respectively, for 30 days. Significantly reduced cauda epididymis sperm motility and density, number of pups, fertility, and circulatory levels of testosterone were observed in all treatment groups. The weights of testes, epididymis, seminal vesicle, and prostate were significantly decreased in groups B, C, and D. The weights of all organs in the different groups of the androgenicity study were markedly decreased in group F when compared with group A, in group G when compared with group F, and in group I when compared with group H, and increased in group H when compared with group F. The serum testosterone levels also showed a similar pattern. The concentration of testicular cholesterol was significantly elevated, while protein, sialic acid, acid and alkaline phosphatase concentrations were decreased. The histoarchitecture of the testes showed degenerative changes in the seminiferous epithelium, arrest of spermatogenesis at the secondary spermatocyte stage, cytolysis, and the lumen filled with eosinophilic material. Histometric parameters except Sertoli cell nuclear area and number of round spermatids showed marked alterations. All altered parameters restored to normal in group E. No changes were observed in body weight, litter size, hematology, and serum biochemistry. In conclusion, a 50% ethanol extract of C. colocynthis showed an antiandrogenic nature, thereby reduced reversible infertility in male albino rats.

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“…The ethnobotanical use efficiency of this plant was consolidated by a number of studies which demonstrated that C. colocynthis Schrad has a potent anti-tumour (Tannin-Spitz et al, 2007), anti-microbial (Marzouk et al, 2009(Marzouk et al, , 2010a and antioxidant activity (Marzouk et al, 2010b). Many secondary metabolites from C. colocynthis, including cucurbitacins, flavonoids, caffeic acid derivatives and terpenoids, have been previously reported (Yankov and Hussein, 1975;Hatam et al, 1989;Maatooq et al, 1997) and could explain the biological activity of this plant.…”

Section: Introductionmentioning

confidence: 99%

An aqueous Citrillus colocynthis peel extract inhibits neutrophil reactive oxygen species production and attenuates lung inflammation in mice

Zioud¹,

Mahmoud²,

Boussetta³

et al. 2015

J. Med. Plants Res.

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Citrillus colocynthis peel aqueous extract (CCPAE) is widely used to treat disorders such as inflammation, ulcers and infections, but its pharmacological target is not known. The objectives of this work were to study the effect of C. colocynthis peel aqueous extract, on human neutrophil reactive oxygen species (ROS) production in vitro, and to evaluate its protective effect on lipopolysaccharide (LPS)-induced lung inflammation in vivo in mice. Neutrophils were isolated from blood of healthy volunteers. ROS generation was measured by luminol-amplified chemiluminescence. Superoxide anion generation was detected by the cytochrome c reduction assay. H 2 O 2 was detected by horseradish peroxidase (HRP)-amplified chemiluminescence assay. Myeloperoxidase (MPO) activity was measured by the tetramethylbenzidine oxidation method. Lung inflammation was induced in mice by LPS instillation. CCPAE inhibited luminol-amplified chemiluminescence of resting neutrophils and N-formylmethionyl-leucyl-phenylalanine (fMLF)-or phorbolmyristate acetate (PMA)-stimulated neutrophils, in a concentration-dependent manner. CCPAE also inhibited superoxide anion generation; and did not scavenge H 2 O 2 and superoxide anions nor inhibited MPO activity in vitro suggesting that it inhibits nicotinamide adenine dinucleotide phosphate (NADPH) oxidase activation. In vivo studies showed that CCPAE attenuated LPS-induced lung inflammation in mice. This study shows that CCPAE inhibits neutrophil ROS production and attenuates LPS-induced lung inflammation in mice. Inhibition of NADPH oxidase activation by CCPAE could explain its anti-inflammatory action.

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Cucurbitacin glycosides from Citrullus colocynthis

Cited by 69 publications

References 11 publications

Bioactive Saponins and Glycosides. XXVII. Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis

Bioactive Saponins and Glycosides. XXVII. Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis

Induction of Reversible Antifertility with a Crude Ethanol Extract of <i>Citrullus colocynthis</i> Schrad Fruit in Male Rats

An aqueous Citrillus colocynthis peel extract inhibits neutrophil reactive oxygen species production and attenuates lung inflammation in mice

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