Momordicine II

CAS# 91590-75-9

Momordicine II

2D Structure

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3D structure

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Momordicine II

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Chemical Properties of Momordicine II

Cas No. 91590-75-9 SDF Download SDF
PubChem ID 131751889 Appearance Powder
Formula C36H58O9 M.Wt 634.9
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Momordicin II
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3,7-dihydroxy-4,4,13,14-tetramethyl-17-[6-methyl-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-9-carbaldehyde
SMILES CC(CC(C=C(C)C)OC1C(C(C(C(O1)CO)O)O)O)C2CCC3(C2(CCC4(C3C(C=C5C4CCC(C5(C)C)O)O)C=O)C)C
Standard InChIKey WCYLDCDQWJYEPO-UHFFFAOYSA-N
Standard InChI InChI=1S/C36H58O9/c1-19(2)14-21(44-32-30(43)29(42)28(41)26(17-37)45-32)15-20(3)22-10-11-35(7)31-25(39)16-24-23(8-9-27(40)33(24,4)5)36(31,18-38)13-12-34(22,35)6/h14,16,18,20-23,25-32,37,39-43H,8-13,15,17H2,1-7H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Momordicine II

The herbs of Mormodica charantia L.

Biological Activity of Momordicine II

DescriptionMomordicine II may have antidiabetic activity, it significantly stimulated insulin secretion. It also can deter oviposition by L. trifolii significantly.
In vitro

Saponins from the traditional medicinal plant Momordica charantia stimulate insulin secretion in vitro.[Pubmed: 22133295 ]

Phytomedicine. 2011 Dec 15;19(1):32-7.

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

Cucurbitane glucosides from Momordica charantia leaves as oviposition deterrents to the leafminer, Liriomyza trifolii.[Pubmed: 16610222 ]

Z Naturforsch C. 2006 Jan-Feb;61(1-2):81-6.


METHODS AND RESULTS:
The American serpentine leaf mining fly, Liriomyza trifolii, whose larva feeds on more than 120 plant species is well characterized by its high degree of polyphagy. Observations on the oviposition behavior by L. trifolii demonstrated that among cucurbitaceous plants, Momordica charantia is rarely attacked by L. trifolii. The methanol extract of M. charantia leaves strongly deterred the females from ovipositing on kidney bean leaves treated at a concentration of 1 g leaf equivalent extract/ml. Analysis of the polar fraction of the methanol extract of M. charantia leaves resulted in the isolation of a novel cucurbitane glucoside, 7-O-beta-D-glucopyranosyl-3,23-dihydroxycucurbita-5,24-dien-19-al, named momordicine IV, along with another known compound, Momordicine II.
CONCLUSIONS:
Momordicine II and IV deterred oviposition by L. trifolii significantly when bioassays were carried out on kidney bean leaves treated at 75.6 and 20.3 microg/cm2 leaf surface, respectively. There was no synergistic effect on oviposition deterrent when the two compounds were combined in their natural abundance.

Protocol of Momordicine II

Cell Research

Transport in Caco-2 cell monolayers of antidiabetic cucurbitane triterpenoids from Momordica charantia fruits.[Pubmed: 25116119 ]

Planta Med. 2014 Jul;80(11):907-11.

Bitter melon, the fruit of Momordica charantia L. (Cucurbitaceae), is a widely-used treatment for diabetes in traditional medicine systems throughout the world. Various compounds have been shown to be responsible for this reputed activity, and, in particular, cucurbitane triterpenoids are thought to play a significant role. The objective of this study was to investigate the gastrointestinal transport of a triterpenoid-enriched n-butanol extract of M. charantia using a two-compartment transwell human intestinal epithelial cell Caco-2 monolayer system, simulating the intestinal barrier.
METHODS AND RESULTS:
Eleven triterpenoids in this extract were transported from the apical to basolateral direction across Caco-2 cell monolayers, and were identified or tentatively identified by HPLC-TOF-MS. Cucurbitane triterpenoids permeated to the basolateral side with apparent permeability coefficient (P app) values for 3-β-7-β,25-trihydroxycucurbita-5,23(E)-dien-19-al and momordicine I and Momordicine II at 9.02 × 10(-6), 8.12 × 10(-6), and 1.68 × 10(-6)cm/s, respectively. Also, small amounts of these triterpenoids were absorbed inside the Caco-2 cells.
CONCLUSIONS:
This is the first report of the transport of the reputed antidiabetic cucurbitane triterpenoids in human intestinal epithelial cell monolayers. Our findings, therefore, further support the hypothesis that cucurbitane triterpenoids from bitter melon may explain, at least in part, the antidiabetic activity of this plant in vivo.

Momordicine II Dilution Calculator

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Momordicine II Molarity Calculator

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Preparing Stock Solutions of Momordicine II

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5751 mL 7.8753 mL 15.7505 mL 31.501 mL 39.3763 mL
5 mM 0.315 mL 1.5751 mL 3.1501 mL 6.3002 mL 7.8753 mL
10 mM 0.1575 mL 0.7875 mL 1.5751 mL 3.1501 mL 3.9376 mL
50 mM 0.0315 mL 0.1575 mL 0.315 mL 0.63 mL 0.7875 mL
100 mM 0.0158 mL 0.0788 mL 0.1575 mL 0.315 mL 0.3938 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Momordicine II

Saponins from the traditional medicinal plant Momordica charantia stimulate insulin secretion in vitro.[Pubmed:22133295]

Phytomedicine. 2011 Dec 15;19(1):32-7.

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 beta-cells incubated with an ethanol extract, saponin-rich fraction, and five purified saponins and cucurbitane triterpenoids from M. charantia, 3beta,7beta,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-beta-glucopyranoside (4), and kuguaglycoside G (5). Treatments were compared to incubation with high glucose (27 mM) and the insulin secretagogue, glipizide (50 muM). At 125 mug/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 mug/ml, compounds 3 and 5 also significantly stimulated insulin secretion as compared to the vehicle, p

Cucurbitane-type triterpenoids from Momordica charantia.[Pubmed:20379957]

Planta Med. 2010 Oct;76(15):1758-61.

One new cucurbitane-type triterpenoid glycoside, momordicoside U (1), together with five known cucurbitane-type triterpenoids and related glycosides, 3beta,7 beta,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-beta-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.

A new oviposition deterrent to the leafminer, Liriomyza trifolii: cucurbitane glucoside from Momordica charantia.[Pubmed:17913080]

Z Naturforsch C J Biosci. 2007 Jul-Aug;62(7-8):603-7.

A new cucurbitane glucoside, 23-O-beta-D-glucopyranosyl-7-hydroxy-3-O-malonylcucurbita-5,24-dien-19-al, named momordicine V, has been isolated from Momordica charantia leaves, along with the previously reported compounds, momordicines I, II, IV and 3-O-malonylmomordicine I. The structure of the new compound was established on the basis of spectral analysis, as well as by its conversion to Momordicine II by alkaline catalyzed hydrolysis. Momordicine V deterred significantly the oviposition by L. trifolii on host plant leaves treated at 26.16 microg/cm2 leaf surface.

Cucurbitane glucosides from Momordica charantia leaves as oviposition deterrents to the leafminer, Liriomyza trifolii.[Pubmed:16610222]

Z Naturforsch C J Biosci. 2006 Jan-Feb;61(1-2):81-6.

The American serpentine leaf mining fly, Liriomyza trifolii, whose larva feeds on more than 120 plant species is well characterized by its high degree of polyphagy. Observations on the oviposition behavior by L. trifolii demonstrated that among cucurbitaceous plants, Momordica charantia is rarely attacked by L. trifolii. The methanol extract of M. charantia leaves strongly deterred the females from ovipositing on kidney bean leaves treated at a concentration of 1 g leaf equivalent extract/ml. Analysis of the polar fraction of the methanol extract of M. charantia leaves resulted in the isolation of a novel cucurbitane glucoside, 7-O-beta-D-glucopyranosyl-3,23-dihydroxycucurbita-5,24-dien-19-al, named momordicine IV, along with another known compound, Momordicine II. Momordicine II and IV deterred oviposition by L. trifolii significantly when bioassays were carried out on kidney bean leaves treated at 75.6 and 20.3 microg/cm2 leaf surface, respectively. There was no synergistic effect on oviposition deterrent when the two compounds were combined in their natural abundance.

Identification of triterpenoid feeding deterrent of red pumpkin beetles (Aulacophora foveicollis) fromMomordica charantia.[Pubmed:24302337]

J Chem Ecol. 1987 Jul;13(7):1689-94.

The triterpenoids isolated from the leaves ofMomordica charantia Linn (bitter gourd) were found to elicit feeding-deterrent activity against red pumpkin beetles (Aulacophora foveicollis Lucas). The most abundant triterpenoid which deterred feeding was identified as Momordicine II, 23-O-beta-glucopyranoside of 3,7,23-trihydroxycucurbita-5,24-dien-19-al. A concentration of 3200mug/ml and above of the triterpenoids caused significant reduction of feeding by red pumpkin beetles in in vitro bioassay experiments, which compared favorably with the levels of triterpenoids inM. charantia leaves found in nature.

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