Mogrol

CAS# 88930-15-8

Mogrol

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Chemical structure

Mogrol

3D structure

Chemical Properties of Mogrol

Cas No. 88930-15-8 SDF Download SDF
PubChem ID 14525327 Appearance White powder
Formula C30H52O4 M.Wt 476.73
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in methan
Chemical Name (3S,8S,9R,10R,11R,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-diol
SMILES CC(CCC(C(C)(C)O)O)C1CCC2(C1(CC(C3(C2CC=C4C3CCC(C4(C)C)O)C)O)C)C
Standard InChIKey JLYBBRAAICDTIS-AYEHCKLZSA-N
Standard InChI InChI=1S/C30H52O4/c1-18(9-13-24(32)27(4,5)34)19-15-16-28(6)22-12-10-20-21(11-14-23(31)26(20,2)3)30(22,8)25(33)17-29(19,28)7/h10,18-19,21-25,31-34H,9,11-17H2,1-8H3/t18-,19-,21-,22+,23+,24-,25-,28+,29-,30+/m1/s1
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 Mogrol

The fruit of Siraitia grosvenorii Swingle.

Biological Activity of Mogrol

DescriptionMogrol has exhibited anti-cancer activities, it suppressed leukemia cell growth via inhibition of the ERK1/2 and STAT3 pathways, in particular, through the suppression of p-ERK1/2 and p-STAT3. Mogrol significantly improved LPS-induced memory impairment in mice. It also suppressed adipogenesis by reducing CREB activation in the initial stage of cell differentiation and by activating AMPK signaling in both the early and late stages of this process.
TargetsAMPK | ERK | STAT3 | CREB

Protocol of Mogrol

Kinase Assay

Mogrol Derived from Siraitia grosvenorii Mogrosides Suppresses 3T3-L1 Adipocyte Differentiation by Reducing cAMP-Response Element-Binding Protein Phosphorylation and Increasing AMP-Activated Protein Kinase Phosphorylation.[Pubmed: 27583359]

Mogrol represents a novel leukemia therapeutic, via ERK and STAT3 inhibition.[Pubmed: 26101699]

American Journal of Cancer Research,2015,5(4):1308-1318.

Unlike solid tumors, the primary strategy for leukemia treatment is chemotherapy. However, leukemia chemotherapy is associated with adverse drug effects and drug resistance. Therefore, it is imperative to identify novel agents that effectively treat leukemia while minimizing adverse effects.
METHODS AND RESULTS:
The Raf/MEK/extracellular regulated kinase (ERK) and signal transducer and activator of transcription 3 (STAT3) pathways have been implicated in leukemia carcinogenesis, and provide novel molecular targets for therapeutic intervention in cancer. Mogrol, a biometabolite of mogrosides found in Siraitia grosvenorii, has exhibited anti-cancer activities; however, the underlying mechanism of this effect remains unclear. To clarify its anti-cancer activity and mechanism of action, we treated K562 leukemia cells with Mogrol. Mogrol suppressed leukemia cell growth via inhibition of the ERK1/2 and STAT3 pathways, in particular, through the suppression of p-ERK1/2 and p-STAT3. Inhibition of these pathways suppressed Bcl-2 expression, thereby inducing K562 cell apoptosis. Furthermore, Mogrol enhanced p21 expression, resulting in G0/G1 cell cycle arrest.
CONCLUSIONS:
The findings provide new perspectives regarding the role of Mogrol in leukemia treatment.

PLoS ONE, 2016, 11(9):e0162252.

This study investigated the effects of Mogrol, an aglycone of mogrosides from Siraitia grosvenorii, on adipogenesis in 3T3-L1 preadipocytes.
METHODS AND RESULTS:
Mogrol, but not mogrosides, suppressed triglyceride accumulation by affecting early (days 0–2) and late (days 4–8), but not middle (days 2–4), differentiation stages. At the late stage, Mogrol increased AMP-activated protein kinase (AMPK) phosphorylation and reduced glycerol-3-phosphate dehydrogenase activity. At the early stage, Mogrol promoted AMPK phosphorylation, inhibited the induction of CCAAT/enhancer-binding protein β (C/EBPβ; a master regulator of adipogenesis), and reduced 3T3-L1 cell contents (e.g., clonal expansion). In addition, Mogrol, but not the AMPK activator AICAR, suppressed the phosphorylation and activity of the cAMP response element-binding protein (CREB), which regulates C/EBPβ expression.
CONCLUSIONS:
These results indicated that Mogrol suppressed adipogenesis by reducing CREB activation in the initial stage of cell differentiation and by activating AMPK signaling in both the early and late stages of this process.

Animal Research

Mogrol attenuates lipopolysaccharide (LPS)-induced memory impairment and neuroinflammatory responses in mice.[Reference: WebLink]

Journal of Asian Natural Products Research, 2019:1-15.

This study aimed to evaluate whether Mogrol, a main bioactive ingredient of Siraitia grosvenorii, could attenuate LPS-induced memory impairment in mice.
METHODS AND RESULTS:
The behavioral tests and immunohistochemical analysis and Western blot were performed.
CONCLUSIONS:
The present results showed that oral administration of Mogrol (20, 40, 80 mg/kg) significantly improved LPS-induced memory impairment in mice. The results also indicated that Mogrol treatment significantly reduced the number of Iba1-positive cells, the nuclear NF-κB p65 and levels of TNF-α, IL-1β and IL-6 both in the hippocampus and frontal cortex of LPS-challenged mice.

Mogrol Dilution Calculator

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Preparing Stock Solutions of Mogrol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0976 mL 10.4881 mL 20.9762 mL 41.9525 mL 52.4406 mL
5 mM 0.4195 mL 2.0976 mL 4.1952 mL 8.3905 mL 10.4881 mL
10 mM 0.2098 mL 1.0488 mL 2.0976 mL 4.1952 mL 5.2441 mL
50 mM 0.042 mL 0.2098 mL 0.4195 mL 0.839 mL 1.0488 mL
100 mM 0.021 mL 0.1049 mL 0.2098 mL 0.4195 mL 0.5244 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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Background on Mogrol

Mogrol is a biometabolite of mogrosides, and acts via inhibition of the ERK1/2 and STAT3 pathways, or reducing CREB activation and activating AMPK signaling.

In Vitro:Mogrol (0-250 µM) significantly and dose- and time-dependently inhibits K562 cell growth and increases the number of apoptotic cells. Mogrol (0, 10, 100, and 250 µM) induces G1 phase cell cycle arrest in K562 cells. Treatment with mogrol significantly decreases ERK phosphorylation as compared to control cells, whereas total ERK protein is not affected. Mogrol dose-dependently induces growth arrest in G0/G1 phase of the cell cycle. Mogrol significantly and dose-dependently enhances p21 protein expression in K562 cells[1]. Mogrol significantly represses the increase in cellular TG levels induced by differentiation stimuli, and suppresses TG accumulation at micromolar levels, with a statistically significant suppression observed above 10 μM. Mogrol suppresses adipogenesis in 3T3-L1 cells at concentrations that does not affect cell viability. Mogrol suppresses adipogenesis through at least two different mechanisms, increasing AMPK phosphorylation and repressing the activation of CREB[2].

References:
[1]. Liu C, et al. Mogrol represents a novel leukemia therapeutic, via ERK and STAT3 inhibition. Am J Cancer Res. 2015 Mar 15;5(4):1308-18. [2]. Naoki Harada, et al. Mogrol Derived from Siraitia grosvenorii Mogrosides Suppresses 3T3-L1 Adipocyte Differentiation by Reducing cAMP-Response Element-Binding Protein Phosphorylation and Increasing AMP-Activated Protein Kinase Phosphorylation. PLoS One. 2

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References on Mogrol

Functional Characterization of Cucurbitadienol Synthase and Triterpene Glycosyltransferase Involved in Biosynthesis of Mogrosides from Siraitia grosvenorii.[Pubmed:25759326]

Plant Cell Physiol. 2015 Jun;56(6):1172-82.

Mogrosides, the major bioactive components isolated from the fruits of Siraitia grosvenorii, are a family of cucurbitane-type tetracyclic triterpenoid saponins that are used worldwide as high-potency sweeteners and possess a variety of notable pharmacological activities. Mogrosides are synthesized from 2,3-oxidosqualene via a series of reactions catalyzed by cucurbitadienol synthase (CbQ), Cyt P450s (P450s) and UDP glycosyltransferases (UGTs) in vivo. However, the relevant genes have not been characterized to date. In this study, we report successful identification of SgCbQ and UGT74AC1, which were previously predicted via RNA-sequencing (RNA-seq) and digital gene expression (DGE) profile analysis of the fruits of S. grosvenorii. SgCbQ was functionally characterized by expression in the lanosterol synthase-deficient yeast strain GIL77 and was found to accumulate cucurbitadienol as the sole product. UGT74AC1 was heterologously expressed in Escherichia coli as a His-tag protein and it showed specificity for Mogrol by transfer of a glucose moiety to the C-3 hydroxyl to form mogroside IE by in vitro enzymatic activity assays. This study reports the identification of CbQ and glycosyltransferase from S. grosvenorii for the first time. The results also suggest that RNA-seq, combined with DGE profile analysis, is a promising approach for discovery of candidate genes involved in biosynthesis of triterpene saponins.

Mogrol represents a novel leukemia therapeutic, via ERK and STAT3 inhibition.[Pubmed:26101699]

Am J Cancer Res. 2015 Mar 15;5(4):1308-18. eCollection 2015.

Unlike solid tumors, the primary strategy for leukemia treatment is chemotherapy. However, leukemia chemotherapy is associated with adverse drug effects and drug resistance. Therefore, it is imperative to identify novel agents that effectively treat leukemia while minimizing adverse effects. The Raf/MEK/extracellular regulated kinase (ERK) and signal transducer and activator of transcription 3 (STAT3) pathways have been implicated in leukemia carcinogenesis, and provide novel molecular targets for therapeutic intervention in cancer. Mogrol, a biometabolite of mogrosides found in Siraitia grosvenorii, has exhibited anti-cancer activities; however, the underlying mechanism of this effect remains unclear. To clarify its anti-cancer activity and mechanism of action, we treated K562 leukemia cells with Mogrol. Mogrol suppressed leukemia cell growth via inhibition of the ERK1/2 and STAT3 pathways, in particular, through the suppression of p-ERK1/2 and p-STAT3. Inhibition of these pathways suppressed Bcl-2 expression, thereby inducing K562 cell apoptosis. Furthermore, Mogrol enhanced p21 expression, resulting in G0/G1 cell cycle arrest. The findings provide new perspectives regarding the role of Mogrol in leukemia treatment.

Oxidation of Cucurbitadienol Catalyzed by CYP87D18 in the Biosynthesis of Mogrosides from Siraitia grosvenorii.[Pubmed:26903528]

Plant Cell Physiol. 2016 May;57(5):1000-7.

Mogrosides, the principally bioactive compounds extracted from the fruits of Siraitia grosvenorii, are a group of glycosylated cucurbitane-type tetracyclic triterpenoid saponins that exhibit a wide range of notable biological activities and are commercially available worldwide as natural sweeteners. The biosynthesis of mogrosides involves initial cyclization of 2,3-oxidosqualene to the triterpenoid skeleton of cucurbitadienol, followed by a series of oxidation reactions catalyzed by Cyt P450s (P450s) and then glycosylation reactions catalyzed by UDP glycosyltransferases (UGTs). We previously reported the identification of a cucurbitadienol synthase (SgCbQ) and a Mogrol C-3 hydroxyl glycosyltransferase (UGT74AC1). However, molecular characterization of further transformation of cucurbitadienol to Mogrol by P450s remains unavailable. In this study, we report the successful identification of a multifunctional P450 (CYP87D18) as being involved in C-11 oxidation of cucurbitadienol. In vitro enzymatic activity assays showed that CYP87D18 catalyzed the oxidation of cucurbitadienol at C-11 to produce 11-oxo cucurbitadienol and 11-hydroxy cucurbitadienol. Furthermore, 11-oxo-24,25-epoxy cucurbitadienol as well as 11-oxo cucurbitadienol and 11-hydroxy cucurbitadienol were produced when CYP87D18 was co-expressed with SgCbQ in genetic yeast, and their structures were confirmed by liquid chromatography-solid-phase extraction-nuclear magnetic resonance-mass spectrometry coupling (LC-SPE-NMR-MS). Taken together, these results suggest a role for CYP87D18 as a multifunctional cucurbitadienol oxidase in the mogrosides pathway.

Mogrol Derived from Siraitia grosvenorii Mogrosides Suppresses 3T3-L1 Adipocyte Differentiation by Reducing cAMP-Response Element-Binding Protein Phosphorylation and Increasing AMP-Activated Protein Kinase Phosphorylation.[Pubmed:27583359]

PLoS One. 2016 Sep 1;11(9):e0162252.

This study investigated the effects of Mogrol, an aglycone of mogrosides from Siraitia grosvenorii, on adipogenesis in 3T3-L1 preadipocytes. Mogrol, but not mogrosides, suppressed triglyceride accumulation by affecting early (days 0-2) and late (days 4-8), but not middle (days 2-4), differentiation stages. At the late stage, Mogrol increased AMP-activated protein kinase (AMPK) phosphorylation and reduced glycerol-3-phosphate dehydrogenase activity. At the early stage, Mogrol promoted AMPK phosphorylation, inhibited the induction of CCAAT/enhancer-binding protein beta (C/EBPbeta; a master regulator of adipogenesis), and reduced 3T3-L1 cell contents (e.g., clonal expansion). In addition, Mogrol, but not the AMPK activator AICAR, suppressed the phosphorylation and activity of the cAMP response element-binding protein (CREB), which regulates C/EBPbeta expression. These results indicated that Mogrol suppressed adipogenesis by reducing CREB activation in the initial stage of cell differentiation and by activating AMPK signaling in both the early and late stages of this process.

Biotransformation of mogrosides from Siraitia grosvenorii Swingle by Saccharomyces cerevisiae.[Pubmed:23796186]

J Agric Food Chem. 2013 Jul 24;61(29):7127-34.

Mogrosides are a group of triterpenoidal saponins from the fruit of Siraitia grosvenorii Swingle; they are intensely sweet and have consequently been used as a substitute for sugar by the food industry. The lack of efficient methods to produce specific mogrosides has hindered investigation of the relationship between their structure and bioactivity, e.g., down-regulation of blood glucose levels, anti-inflammation, and antiviral infection. Here, we attempt to selectively convert the major saponin mogroside V, a Mogrol pentaglucoside, into mogroside III E, a triglucoside, via the beta-glucosidases of the budding yeast Saccharomyces cerevisiae. We report that the beta-glucopyranosyl and beta-glucopyranosyl-(1-->2)-beta-d-glucopyranosyl attached on C-3 and -24 of Mogrol, respectively, were resistant to hydrolysis by yeast beta-d-glucosidases. We further screened 16 mutants bearing single defective glucanase or glucosidase genes, thereby demonstrating that Exg1 is a major enzyme of the initiation of mogroside V conversion. Deletion of the KRE6 gene unexpectedly facilitated the production of mogroside III E in yeast culture. This paper demonstrates that yeast knockout mutants are a valuable tool for saponin modification and for studying the specificity of glucosidase function.

Potential AMPK activators of cucurbitane triterpenoids from Siraitia grosvenorii Swingle.[Pubmed:21893415]

Bioorg Med Chem. 2011 Oct 1;19(19):5776-81.

AMP-activated kinase (AMPK) as a key controller in the regulation of whole-body energy homeostasis, plays an important role in protecting the body from metabolic diseases. Recently, improved glucose, lipid utility and increased insulin sensitivity were observed on several diabetic rodent models treated with crude mogrosides isolated from the fruit of Siraitia grosvenorii Swingle, but the precise active compounds responsible for the anti-diabetic activity of this plant have not been clearly identified. In our current work, acid hydrolysis of crude mogrosides provided five new cucurbitane triterpenoids (1-4, 8), along with three known ones (5-7). The main aglycone Mogrol (7) and compounds 4 and 8 were found to be potent AMPK activators in the HepG2 cell line. This result suggested AMPK activation by the mogroside aglycones 7 and 8 was proved to contribute at least partially to the anti-hyperglycemic and anti-lipidemic properties in vivo of S. grosvenorii.

Development and Validation of a Sensitive LC-MS-MS Method for Quantification of Mogrol in Rat Plasma and Application to Pharmacokinetic Study.[Pubmed:27884874]

J Chromatogr Sci. 2017 Mar 1;55(3):284-290.

Mogrol, the aglycone of mogrosides, is a potential pharmacologically active ingredient isolated from the fruits of Siraitia grosvenorii. The aim of this study was to develop and validate an LC-MS-MS method for the quantification of Mogrol in rat plasma. Protein precipitation extraction procedure using methanol/water (1:1, v/v) was employed to extract Mogrol from rat plasma. Chromatographic separation was performed on a reverse-phase Agilent Zorbax XDB C18 column (50 mm x 2.1 mm, 3.5 mum) with gradient elution using a mobile phase containing methanol and water, both of which contained 0.1% formic acid at a flow rate of 0.50 mL/min. The analyte was monitored by tandem-mass spectrometry with positive electrospray ionization mode. The precursor/product transitions (m/z) in the positive ion mode were 459.3-->423.3 and 386.2-->122.3 for Mogrol and internal standard, respectively. The method was validated over the concentration range of 10.0-10,000 ng/mL with a lower limit of quantification of 10.0 ng/mL in rat plasma. Validation experiments included tests for specificity, precision, accuracy, matrix effect, and stability under different storage and handling conditions. This method was successfully utilized to pharmacokinetic evaluation of Mogrol after intravenous and oral administration of a single dose in rats at 2.0 and 5.0 mg/kg, respectively. The oral absolute bioavailability (F) of Mogrol was estimated to be 10.3 +/- 2.15% with an elimination half-life (t1/2) value of 2.41 +/- 0.11 h.

Description

Mogrol is a biometabolite of mogrosides, and acts via inhibition of the ERK1/2 and STAT3 pathways, or reducing CREB activation and activating AMPK signaling.

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