Studies on the constituents of Momordica charantia L. I. Isolation and characterization of momordicosides A and B, glycosides of a pentahydroxy-cucurbitane triterpene.

Okabe, Hikaru; Miyahara, Yumi; Yamauchi, Tatsuo; Miyahara, Kazumoto; Kawasaki, Toshio

doi:10.1248/cpb.28.2753

Cited by 80 publications

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“…Previous pharmacological studies have showed that the extracts or compounds of tissues of M. charantia possess anti-diabetic and anti-inflammatory activities. [1][2][3] Chemical investigations of M. charantia also revealed that more than seventy cucurbitane-type triterpenes have been isolated form the fruits, [3][4][5][6][7][8][9][10][11][12] seeds, 13,14 root, 15 and leaves and vines 16,17 of M. charantia. As part of our program aimed at the discovery of bioactive secondary metabolites from Taiwanese M. charantia, we had reported the isolation and structure elucidation of twenty-five cucurbitane-type triterpenoids from the MeOH extract of the stems of this plant.…”

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confidence: 99%

Sterols from the Stems of Momordica charantia

Liao

Chen

Hsu

et al. 2011

J Chinese Chemical Soc

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A new sterol, 5a,6a-epoxy-3b-hydroxy-(22E,24R)-ergosta-8,22-dien-7-one (1), together with eight known sterols, 5a,6a-epoxy-(22E,24R)-ergosta-8,22-diene-3b,7a-diol (2), 5a,6a-epoxy-(22E,24R)-ergosta-8,22-diene-3b,7b-diol (3), 5a,6a-epoxy-(22E,24R)-ergosta-8(14),22-diene-3b,7a-diol (4), 3b-hydroxy-(22E,24R)-ergosta-5,8,22-trien-7-one (5), ergosterol peroxide (6), clerosterol (7), decortinol (8), and decortinone (9), were isolated from the stems of Momordica charantia. Their structures were elucidated by mean of extensive spectroscopic methods, including 1 H, 13 C, 2D-NMR and HR-EI-MS, as well as comparison with the literature data. Compounds 1, 4, 5, 8, and 9 were not cytotoxic against the SK-Hep 1 cell line.

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Section: Introductionmentioning

confidence: 99%

Sterols from the Stems of Momordica charantia

Liao

Chen

Hsu

et al. 2011

J Chinese Chemical Soc

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“…Bitter and non-bitter cucurbitane triterpene aglycones and/or glycosides have been isolated from the plant. [4][5][6][7][8][9][10][11] The bitter principles so far reported have been characterized as momordicosides K and L, and momordicines I and II. 5,8) Interestingly, the four compounds have C-9 formyl, 7-OH or O-b-D-glucopyranosyl groups and are unsaturated at C-5, C-6.…”

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“…12,13) In the course of our phytochemical screening of medicinal plants aimed at finding the active principles for antidiabetic activities, eleven compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11) were isolated from the Indian bitter gourd sample. The structural elucidation of compounds 1-3 is reported and the major compounds (4 and 5) have been tested against the antidiabetic strain of male ddY mice.…”

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Momordica charantia Constituents and Antidiabetic Screening of the Isolated Major Compounds

et al. 2006

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Diabetes mellitus is one of the most common chronic diseases and a major contributor to the development of cardiovascular diseases. It is due to a deficiency or a failure of normal action of insulin, which is responsible of the use of the sugar from the diet. The number of cases of non-insulin dependent diabetes mellitus has increased dramatically due to the changes in lifestyle, increasing prevalence of obesity, and ageing of populations. 1) In the year 2000, the number of diabetic patients was 151 million and is estimated to rise to 300 million by 2025. 2,3)The uses of natural drugs, such as plants and herbal remedies to treat diseases is very common in Asia and developing countries, where the population is linked with the use of traditional medicines, due to their efficiency or due the costs of the synthetic drugs and/or pharmaceuticals. One of the aims of phytochemists is to find the application of ethnomedicine in drug discovery. Moreover, WHO study groups emphasize strongly the optimal, rational uses of traditional and natural indigenous medicines (http://www.who.int/mediacentre/factsheets/fs134/en/). The leprosy gourd (bitter gourd, ayurveda name: karela), Momordica charantia L., a well known plant for its antidiabetic properties in Asia and some African countries, is among the candidates. Bitter and non-bitter cucurbitane triterpene aglycones and/or glycosides have been isolated from the plant. [4][5][6][7][8][9][10][11] The bitter principles so far reported have been characterized as momordicosides K and L, and momordicines I and II. 5,8) Interestingly, the four compounds have C-9 formyl, 7-OH or O-b-D-glucopyranosyl groups and are unsaturated at C-5, C-6. These features might be the structural requirement for the bitter taste and undoubtedly, the high content of saponins in the plant can be related to its taste.The constituents responsible for the glucose lowering activity are not yet well known even though over hundred scientific articles have described the phytochemical and pharmacological properties of the plant. 12,13) In the course of our phytochemical screening of medicinal plants aimed at finding the active principles for antidiabetic activities, eleven compounds (1-11) were isolated from the Indian bitter gourd sample. The structural elucidation of compounds 1-3 is reported and the major compounds (4 and 5) have been tested against the antidiabetic strain of male ddY mice. The objective of the present study is to find the relationship between Momordica charantia constituents and the antidiabetic properties of the plant. Results and DiscussionEffect of the Extracts on Diabetes Induced Mice The ether and ethyl acetate fractions of the water suspension of the bitter gourds methanol extract were tested for antidiabetic assay in mice. Oral administration of each fraction at 500 mg/kg (Figs. 3, 4, respectively) resulted marked hypoglycaemic effects comparable to glibenclamide (at 200 mg/kg).Isolation and Characterization of Constituents from the Active Extracts A combination of size exclusion and sil...

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“…In the EI-MS of 1, a molecular ion peak was observed at m/z 486 [M ϩ ], and the molecular formula C 32 H 54 O 3 was determined by high-resolution MS measurement. The 1 H-NMR (pyridine-d 5 ) and 13 C-NMR (Table 1) spectra of 1, which was assigned by various NMR experiments, 24) showed signals due to eight methyls [ (Table 1) (Fig. 1).…”

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Structures of New Cucurbitane-Type Triterpenes and Glycosides, Karavilagenins and Karavilosides, from the Dried Fruit of Momordica charantia L. in Sri Lanka

et al. 2006

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The Cucurbitaceae plant Momordica (M.) charantia L. is cultivated in Asian countries and the fruit of this plant has been used as a bitter stomachic, a laxative, an antidiabetic, and an anthelmintic for children in Chinese, Indian Ayurvedic, and Indonesian Jamu traditional medicines. The alcoholic extract from the fruit of M. charantia originated in Sri Lanka was reported to inhibit the increase in serum glucose levels after glucose-loaded rats.1) In addition, Several cucurbitane-type triterpene glycosides were reported as chemical constituents of the fruit.5-10) However, chemical and pharmacological studies [1][2][3][4] on the fruit of M. charantia were yet left uncharacterised. During the course of characterization studies on the bioactive constituents of medicinal foodstuffs, [11][12][13][14][15][16][17][18][19][20][21] we reported the isolation and structure elucidation of eight cucurbitane-type triterpene glycosides, goyaglycosides-a, -b, -c, -d, -e, -f, -g, and -h, and three oleanane-type triterpene glycosides, goyasaponins I, II, and III, from the fresh fruit of Japanese M. charantia.

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Studies on the constituents of Momordica charantia L. I. Isolation and characterization of momordicosides A and B, glycosides of a pentahydroxy-cucurbitane triterpene.

Cited by 80 publications

References 1 publication

Sterols from the Stems of Momordica charantia

Sterols from the Stems of Momordica charantia

Momordica charantia Constituents and Antidiabetic Screening of the Isolated Major Compounds

Structures of New Cucurbitane-Type Triterpenes and Glycosides, Karavilagenins and Karavilosides, from the Dried Fruit of Momordica charantia L. in Sri Lanka

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