Cucurbitane-Type Triterpenoids from Momordica charantia

Office of Regulatory Science, Center for Food Safety and Applied Nutrition, U. S. Food and Drug Administration, College Park, MD 20740, USA.
Planta Medica (Impact Factor: 2.15). 04/2010; 76(15):1758-61. DOI: 10.1055/s-0030-1249807
Source: PubMed


One new cucurbitane-type triterpenoid glycoside, momordicoside U (1), together with five known cucurbitane-type triterpenoids and related glycosides, 3β,7 β,25-trihydroxycucurbita-5,23 (E)-dien-19-al (2), momordicine I (3), momordicine II (4), 3-hydroxycucurbita-5,24-dien-19-al-7,23-di-O-β-glucopyranoside (5), and kuguaglycoside G (6), were isolated from the whole plant of Momordica charantia. Their structures were determined by chemical and spectroscopic methods. Momordicoside U (1) was evaluated for insulin secretion activity in an in vitro insulin secretion assay and displayed moderate activity.

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    • "A review of the existing scientific literature indicated that all the plants used for treatment of diabetes by the Garo practitioners are validated in their uses, based on reported relevant bio-activity. In oral glucose tolerance test, antihyperglycemic activity has been observed with leaves and stems of L. coromandelica in mice (Mannan et al., 2010). It is to be noted that either barks or roots of this plant was observed to be used by the Garo practitioners for treatment of diabetes. "
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    ABSTRACT: Diabetes mellitus is an endocrinological disorder arising from insulin deficiency or due to ineffectiveness of the insulin produced by the body. This results in high blood glucose and with time, to neurological, cardiovascular, retinal and renal complications. It is a debilitating disease and affects the population of every country of the world. Around 200 million people of the world suffer from this disease and this figure is projected to rise to 300 million in the coming years. The disease cannot be cured with allopathic medicine as the drugs used do not restore normal glucose homeostasis and moreover have side-effects. On the other hand, traditional medicinal practitioners of various countries claim to cure diabetes or at least alleviate the major symptoms and progression of this disease through administration of medicinal plants. The Garos are an indigenous community of Bangladesh, who still follow their traditional medicinal practices. Their traditional medicinal formulations contain a number of plants, which they claim to be active antidiabetic agents. Since observation of indigenous practices have led to discovery of many modern drugs, it was the objective of the present study to conduct a survey among the Marakh sect of the Garos residing in Mymensingh district of Bangladesh to find out the medicinal plants that they use for treatment of diabetes. It was found that the tribal practitioners of the Marakh sect of the Garos use twelve medicinal plants for treatment of diabetes. These plants were Lannea coromandelica, Alstonia scholaris, Catharanthus roseus, Enhydra fluctuans, Terminalia chebula, Coccinia grandis, Momordica charantia, Cuscuta reflexa, Phyllanthus emblica, Syzygium aqueum, Drynaria quercifolia, and Clerodendrum viscosum. A review of the scientific literature demonstrated that almost all the plants used by the Garo tribal practitioners have reported antidiabetic and/or antioxidant properties and have enormous potential for possible development of new and efficacious antidiabetic drugs.
    African Journal of Traditional, Complementary and Alternative Medicines 09/2012; 9(3):380-5. DOI:10.4314/ajtcam.v9i3.12 · 0.56 Impact Factor
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    • "D-(+)-trehalose isolated from BG was shown to inhibit α-glucosidase [26] and delayed the digestion and absorption of dietary carbohydrates. Recently, cucurbitane-type triterpenoids isolated from BG were shown to increase glucose transporter 4 translocation through activation of AMPK [27], inhibit α-glucosidase [28], and modulate insulin secretion activity [29]. 9c,11t,13t-conjugated linolenic acid [30] and momordin [31] from BG were noted to activate PPAR α, γ and PPAR β/δ respectively. "
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    ABSTRACT: Bitter gourd (Momordica charantia L.) is a common tropical vegetable that has been used in traditional or folk medicine to treat diabetes. Wild bitter gourd (WBG) ameliorated metabolic syndrome (MetS) in animal models. We aimed to preliminarily evaluate the effect of WBG supplementation on MetS in Taiwanese adults. A preliminary open-label uncontrolled supplementation trial was conducted in eligible fulfilled the diagnosis of MetS from May 2008 to April 2009. A total of 42 eligible (21 men and 21 women) with a mean age of 45.7 ± 11.4 years (23 to 63 years) were supplemented with 4.8 gram lyophilized WBG powder in capsules daily for three months and were checked for MetS at enrollment and follow-up monthly. After supplementation was ceased, the participants were continually checked for MetS monthly over an additional three-month period. MetS incidence rate were analyzed using repeated-measures generalized linear mixed models according to the intention-to-treat principle. After adjusting for sex and age, the MetS incidence rate (standard error, p value) decreased by 7.1% (3.7%, 0.920), 9.5% (4.3%, 0.451), 19.0% (5.7%, 0.021), 16.7% (5.4%, 0.047), 11.9% (4.7%, 0.229) and 11.9% (4.7%, 0.229) at visit 2, 3, 4, 5, 6, and 7 compared to that at baseline (visit 1), respectively. The decrease in incidence rate was highest at the end of the three-month supplementation period and it was significantly different from that at baseline (p = 0.021). The difference remained significant at end of the 4th month (one month after the cessation of supplementation) (p = 0.047) but the effect diminished at the 5th and 6th months after baseline. The waist circumference also significantly decreased after the supplementation (p < 0.05). The WBG supplementation was generally well-tolerated. This is the first report to show that WBG improved MetS in human which provides a firm base for further randomized controlled trials to evaluate the efficacy of WBG supplementation.
    Nutrition Journal 01/2012; 11(1):4. DOI:10.1186/1475-2891-11-4 · 2.60 Impact Factor
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    • "The ranges in bioactivity of compounds 1-5 may be due to their differences in structure. The previously tested compound, momordicoside U (Ma et al., 2010), along with the active compound 3, are monodesmoside cucurbitanes as opposed to their aglycones, inactive compounds 2 and 4, respectively (Fig. 1). Although compound 4 is a bidesmoside and is inactive, it also contains an aldehyde group whereas the bidesmoside compound 5 does not, and is the only compound tested to contain both of these moieties (Fig. 1). "
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    ABSTRACT: The antidiabetic activity of Momordica charantia (L.), Cucurbitaceae, a widely-used treatment for diabetes in a number of traditional medicine systems, was investigated in vitro. Antidiabetic activity has been reported for certain saponins isolated from M. charantia. In this study insulin secretion was measured in MIN6 β-cells incubated with an ethanol extract, saponin-rich fraction, and five purified saponins and cucurbitane triterpenoids from M. charantia, 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al (1), momordicine I (2), momordicine II (3), 3-hydroxycucurbita-5,24-dien-19-al-7,23-di-O-β-glucopyranoside (4), and kuguaglycoside G (5). Treatments were compared to incubation with high glucose (27 mM) and the insulin secretagogue, glipizide (50 μM). At 125 μg/ml, an LC-ToF-MS characterized saponin-rich fraction stimulated insulin secretion significantly more than the DMSO vehicle, p=0.02. At concentrations 10 and 25 μg/ml, compounds 3 and 5 also significantly stimulated insulin secretion as compared to the vehicle, p≤0.007, and p=0.002, respectively. This is the first report of a saponin-rich fraction, and isolated compounds from M. charantia, stimulating insulin secretion in an in vitro, static incubation assay.
    Phytomedicine: international journal of phytotherapy and phytopharmacology 12/2011; 19(1):32-7. DOI:10.1016/j.phymed.2011.06.019 · 3.13 Impact Factor
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