C-p-hydroxybenzoylglycoflavones from Citrullus colocynthis

Maatooq, Galal T.; El-Sharkawy, Saleh; Afifi, Mohamed; Rosazza, Jack P.N.

doi:10.1016/s0031-9422(96)00465-7

Cited by 52 publications

(28 citation statements)

References 5 publications

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“…Such cucurbitacins are relevant to the bitterness and toxicity of the plants, as well as their anti-inflammatory, purgative and anti-cancer activities, such as the inhibition of cell adhesion resulting from the cytoskeleton destabilizing in cancer cells exposed to cucurbitacin E [27] . As far as flavonoids are concerned, isovitexin, iso-orientin and iso-orientin-3'-methylether were isolated from the hydromethanolic extract of C. colocynthis fruits, whilst the leaves and stems contains other flavonoids such as C-p-hydroxybenzyl derivatives, 8-Cp-hydroxybenzoylisovitexin, 6-C-phydroxybenzoylvitexin, 8-C-p-hydroxybenzoyl isovitexin-4'-O-glucoside [28,29] . Another flavonoid, quercetin, was identified in different parts of the plant (fruit, stem, leave and root) in ethyl acetate and diethyl ether fractions recovered from water-methanol (80%) extract [30] .…”

Section: Discussionmentioning

confidence: 99%

Phytochemical screening and free radical scavenging activity of Citrullus colocynthis seeds extracts

Benariba

Djaziri

Bellakhdar

et al. 2013

Asian Pacific Journal of Tropical Biomedicine

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Objective: To study the phytochemical screening of different extracts from Citrullus colocynthis (C. colocynthis ) seeds extracts and to assess their antioxidant activity on the DPPH free radical scavenging. Methods: Phytochemical screening, total content of polyphenols and flavonoids of C. colocynthis seeds extracts, including a crude aqueous extract (E1), a defatted aqueous extract (E2), a hydromethanolic extract (HM), an ethyl acetate extract (EA) and a n-butanol extract (n-B) was carried out according to the standard methods and to assess their corresponding effect on the antioxidant activity of this plant. Results: None of these extracts contained detectable amount of alkaloid, quinone, antraquinone, or reducing sugar. Catechic tannins and flavonoids were abundant in E1, HM and EA, whilst terpenoids were abundantly present in E1 and n-B but only weekly in HM. Coumarins were found in E2, EA and n-B. Polyphenols, expressed as gallic acid equivalent, amounted, per 100 g plant matter, to 329, 1002 and 150 mg in EA, HM an E1 respectively. Flavonoids, expressed as catechin equivalent, amounted, per 100 g plant matter to 620, 241 and 94 mg in EA, HM and E1 respectively. Comparable values were found in n-B and E1, with lower values in E2. Quercetin, myricetin and gallic acid were found in the EA and HM extracts by thin layer chromatography, The antioxidative effect of these extracts yielded, when tested at a concentration of 2 000 μg/mL in a 1,1-diphenyl-2-picrylhydrazyl assay, a reducing percentage of 88.8% with EA, 74.5% with HM and 66.2% with E1, and corresponding IC 50 of 350, 580 and 500 μg/mL as compared to 1.1 μg/mL for ascorbic acid. Conclusions: These qualitative and quantitative analytical data document the presence in C. colocynthis extracts of such chemical compounds as flavonoids responsible for the antioxidant activity, as well as other biological activities of this plant. Contents lists available at ScienceDirectPeer reviewer C h e r i t i A b d e l k r i m , P r o f e s s o r , D e p a r t m e n t o f C h e m i s t r y ,

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Section: Discussionmentioning

confidence: 99%

Phytochemical screening and free radical scavenging activity of Citrullus colocynthis seeds extracts

Benariba

Djaziri

Bellakhdar

et al. 2013

Asian Pacific Journal of Tropical Biomedicine

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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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confidence: 99%

“…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%

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

Yoshikawa

Morikawa

Kobayashi

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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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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“…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: 90%

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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C-p-hydroxybenzoylglycoflavones from Citrullus colocynthis

Cited by 52 publications

References 5 publications

Phytochemical screening and free radical scavenging activity of Citrullus colocynthis seeds extracts

Phytochemical screening and free radical scavenging activity of Citrullus colocynthis seeds extracts

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

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

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