Art. -Nr.: HY-N2217

Rotundic acid

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Rotundic acid is an orally effective triterpenoid with a K_d value of 51.3 µM for PTP1B. Rotundic acid downregulates the AKT/mTOR pro-survival pathway and modulates the MAPK pathway. Rotundic acid induces cell cycle S-phase arrest, DNA damage and apoptosis; it inhibits migration, invasion, angiogenesis and proliferation of cancer cells. Rotundic acid improves leptin sensitivity, regulates gut microbiota and reduces cellular senescence. Rotundic acid can be used in research related to hepatocellular carcinoma, obesity, aging, acute lung injury and type 2 diabetes.

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Reinheit: 98.41%
CAS. Nr.: 20137-37-5
Formel: C₃₀H₄₈O₅
Molecular Weight:488.70

Speicherung:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Rotundic acid Chemical Structure

CAS. Nr.: 20137-37-5

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

mTOR

p38 MAPK

Alle Akt Isoform-spezifische Produkte anzeigen :

Alle mTOR Isoform-spezifische Produkte anzeigen :

Alle p38 MAPK Isoform-spezifische Produkte anzeigen :

Alle Interleukin Related Isoform-spezifische Produkte anzeigen :

Alle NF-κB Isoform-spezifische Produkte anzeigen :

Alle PI3K Isoform-spezifische Produkte anzeigen :

Alle Heme Oxygenase (HO) Isoform-spezifische Produkte anzeigen :

HO-1
HO-2

Alle Toll-like Receptor (TLR) Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A-375	IC₅₀	16.58 μM Compound: 1, RA, Rotundic acid	Cytotoxicity against human A375 cells after 24 hrs by MTT assay Cytotoxicity against human A375 cells after 24 hrs by MTT assay	[PMID: 23558236]
HeLa	IC₅₀	31.92 μM Compound: 1, RA, Rotundic acid	Cytotoxicity against human HeLa cells after 24 hrs by MTT assay Cytotoxicity against human HeLa cells after 24 hrs by MTT assay	[PMID: 23558236]
HepG2	IC₅₀	7.33 μM Compound: 1, RA, Rotundic acid	Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay	[PMID: 23558236]
NCI-H446	IC₅₀	11.4 μM Compound: 1, RA, Rotundic acid	Cytotoxicity against human NCI-H446 cells after 24 hrs by MTT assay Cytotoxicity against human NCI-H446 cells after 24 hrs by MTT assay	[PMID: 23558236]

In Vitro

Rotundic acid (10-30 μM) dose-dependently inhibits the migration of HUVEC cells^[1].
Rotundic acid (0-1000 μM) is a non-competitive inhibitor of human PTP1B, whose optimal inhibitory effect depends on the C-terminus of this protein. The IC₅₀ values against PTP1B_1-298, PTP1B_1-321 and PTP1B_1-393 are 2 mM, 481.8 μM and 443.7 μM, respectively^[2].
Rotundic acid (3.125-100 μM; 48 h) significantly extends the replicative lifespan of BY4741 yeast cells, with a maximum extension of up to 135% at the concentration of 12.5 μM^[2].
Rotundic acid (5-20 μM; 24 h) reduces cellular senescence levels in senescent WI-38 human embryonic lung fibroblasts, as evidenced by a decrease in SA-β-gal-positive cells; it also promotes cell proliferation at a concentration of 12.5 μM^[2].
Rotundic acid (15-60 μM; 24 h) shows no cytotoxicity against RAW264.7 mouse macrophages, and its concentration can reach up to 60 μM after 24 h of incubation^[3].
Rotundic acid (15-60 μM; 1 h pretreatment) dose-dependently reduces nitrite production in LPS (HY-D1056)-stimulated RAW264.7 murine macrophages^[3].
Rotundic acid (15-60 μM; 1 h pretreatment) inhibits LPS-induced release of TNF-α and IL-6 in RAW264.7 mouse macrophages^[3].
Rotundic acid (15-60 μM; 1 h pretreatment) regulates multiple inflammatory signaling pathways in LPS-stimulated RAW264.7 murine macrophages, including inhibiting the activation of NF-κB, MAPK and PI3K/Akt/mTOR, upregulating the Keap-1/Nrf2/HO-1 signaling pathway and reducing the expression of TLR4^[3].
Rotundic acid (15-60 μM; 1 h pretreatment) reduces LPS-induced NO release, ROS production and intracellular Ca²⁺ levels in RAW264.7 murine macrophages^[3].
Rotundic acid exhibits significant cytotoxic activity against Daoy, Hep-2 and MCF-7 human tumor cell lines^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[3]

Cell Line:

RAW264.7 murine macrophages
Concentration:

15, 30, 60 μM
Incubation Time:

24 h
Result:

Showed no cytotoxic effect on RAW264.7 macrophages at all tested concentrations, with cell viability remaining above 80% relative to the control group.

ELISA Assay^[3]

Cell Line:

LPS-stimulated RAW264.7 murine macrophages
Concentration:

15-60 μM
Incubation Time:

1 h pretreatment, followed by 18 h LPS stimulation
Result:

Significantly decreased the release of TNF-α and IL-6 at all tested concentrations, with consistent, significant inhibition across doses.
Increased TNF-α and IL-6 release strongly when LPS was applied alone.

In Vivo

Rotundic acid (50 mg/kg; i.p.; once every 2 days; for 60 consecutive days) achieves a 75.6% tumor growth inhibition rate in a Balb/c nude mouse model with human hepatocellular carcinoma HepG2 cell xenografts. It also reduces tumor weight, inhibits proliferation and angiogenesis, induces cell apoptosis, and causes no significant body weight loss^[1].
Rotundic acid (40 mg/kg; i.p.; 1 week per month for 6 consecutive months) extends the average lifespan of naturally aged male C57BL/6J mice by 16.2% and improves their aging-related functional indicators^[2].
Rotundic acid (40 mg/kg; i.p.; once daily; for 14 consecutive days) reduces the body weight of high-fat diet-induced obese mice by up to 26.3% and decreases their food intake in a dose-dependent manner^[2].
Rotundic acid (i.p.; 40 mg/kg; once daily for 14 consecutive days) reduces body weight by 25.1% in high-fat diet-induced obese mice with an average body weight of approximately 58 g, while also decreasing their food intake, reducing adipose tissue weight, and downregulating plasma leptin levels^[2].
Rotundic acid (40 mg/kg; i.p.; once daily for 14 consecutive days) exerts no effect on body weight, food intake, or adipose tissue mass in normal lean male C57BL/6N mice^[2].
Rotundic acid (40 mg/kg; i.p.; once daily for 14 consecutive days) improves glucose homeostasis and insulin sensitivity in high-fat diet-induced obese mice^[2].
Rotundic acid (20-40 mg/kg; i.p.) reduces xylene-induced ear swelling in mice by more than 80% and ameliorates associated pathological tissue damage^[3].
Rotundic acid (20-40 mg/kg; i.p.) increases the 144-hour survival rate of LPS-induced endotoxic shock mice to 30%^[3].
Rotundic acid (10-40 mg/kg; i.p.) reduces LPS-induced levels of inflammatory markers, ameliorates pulmonary function impairment, and alleviates lung pathological damage in a mouse model of acute lung injury^[3].
Rotundic acid (40 mg/kg; oral gavage; daily; 8 weeks) improves glucose and lipid metabolism, reduces blood pressure, protects against cardiovascular, hepatic and renal damage, alleviates oxidative stress and inflammatory responses, and restores gut microbiota dysbiosis induced by a high-fat diet combined with low-dose streptozotocin in type 2 diabetic rats^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Balb/c nude (male, 5 weeks old, subcutaneous HepG2 cell xenograft)^[1]
Dosage:

50 mg/kg
Administration:

i.p.; every 2 days; 60 days
Result:

Reduced mean tumor volume to 78.95 mm³ (vs. 323.64 mm³ in controls), achieving 75.6% tumor growth inhibition.
Reduced tumor weights significantly compared to controls.
Showed no significant body weight loss.
Reduced expression of proliferation marker Ki-67, angiogenesis marker CD-31, phosphorylated AKT, and phosphorylated mTOR in tumor tissue.
Increased expression of phosphorylated p38 MAPK in tumor tissue.
Induced apoptosis via increased cleaved PARP and cleaved caspase-3 in tumor tissue.

Animal Model:

C57BL/6N (male, 8 weeks old, high-fat diet-induced obese)^[2]
Dosage:

40 mg/kg
Administration:

i.p.; daily; 14 days
Result:

Reduced body weight in a dose-dependent manner, with the 40 mg/kg dose causing a 26.3% decrease.
Reduced daily food intake by 62.3% in the first week of 40 mg/kg treatment.

Animal Model:

BALB/c (male, 18-20 g, LPS-induced acute lung injury model)^[3]
Dosage:

10 mg/kg; 20 mg/kg; 40 mg/kg
Administration:

i.p.; two doses: 2 hours before LPS, 4 hours after LPS
Result:

Decreased LPS-induced increases in blood lymphocytes, neutrophils, and white blood cells.
Reduced levels of TNF-α, IL-6, and IL-1β in serum, bronchoalveolar lavage fluid, and lung tissue homogenate.
Reduced myeloperoxidase activity in lung tissue.
Significantly recovered mouse lung function including peak expiratory flow, dynamic lung compliance, inspiratory resistance, expiratory resistance, and minute ventilation volume.
Ameliorated LPS-induced alveolar interstitial exudation, alveolar structural destruction, and inflammatory cell infiltration observed via H&E staining.

Animal Model:

Sprague-Dawley (5-week-old male, weight 180-220 g, type 2 diabetes induced by high-fat diet + low-dose streptozotocin)^[4]
Dosage:

40 mg/kg
Administration:

i.g.; daily; 8 weeks
Result:

Increased body weight compared to T2D model rats.
Decreased water intake and increased food intake compared to T2D model rats.
Reduced fasting glucose, glycated hemoglobin A1c (HbA1c), and insulin levels compared to T2D model rats.
Reduced glucose area under the curve (AUC) for OGTT and ITT, and reduced HOMA-IR index compared to T2D model rats.
Significantly reduced serum total glyceride (TG), total cholesterol (TC), low-density lipoprotein cholesterol (LDL-C), and free fatty acid (FFA) levels, and increased high-density lipoprotein cholesterol (HDL-C) levels compared to T2D model rats.
Reduced systolic blood pressure (SYS), diastolic blood pressure (DIA), mean arterial pressure (MAP), and serum angiotensin-2 (ANG-2) levels compared to T2D model rats.
Significantly reduced serum myocardial enzymes (α-HBDH: 151.9 U/L, CK: 0.418 U/L, CK-MB: 191.7 U/L, LDH: 1854.0 U/L), C-reactive protein (CRP: 422.7 pg/mL), endothelin-1 (ET-1: 48.9 pg/mL), alanine aminotransferase (ALT: 44.6 IU/L), aspartate aminotransferase (AST: 99.32 IU/L), alkaline phosphatase (ALP: 15.1 KU/100 mL), uric acid (UA: 131.0 μmol/L), and urea nitrogen (BUN: 5.3 mmol/L) compared to T2D model rats.
Increased serum superoxide dismutase (SOD: 246.7 U/L) and interleukin-4 (IL-4: 55.2 pg/mL) levels compared to T2D model rats.
Decreased serum malondialdehyde (MDA: 4.73 nmol/mL), tumor necrosis factor-α (TNF-α: 259.1 pg/mL), interferon-γ (INF-γ: 16.6 pg/mL), interleukin-1β (IL-1β: 11.0 pg/mL), and interleukin-6 (IL-6: 8.7 pg/mL) levels compared to T2D model rats.
Increased Chao1 and Shannon α-diversity indices compared to T2D model rats.
Reversed the elevated Firmicutes-to-Bacteroidetes ratio seen in T2D model rats.
Increased relative abundances of beneficial/commensal genera Prevotella, Ruminococcus, Leuconostoc, and Streptococcus compared to T2D model rats.
Decreased relative abundances of opportunistic pathogen genera Klebsiella and Proteus compared to T2D model rats.

Chemical Information

CAS. Nr. 20137-37-5
Appearance Solid
Molecular Weight 488.70
Formel C₃₀H₄₈O₅
Color White to off-white
SMILES

C[C@@]1(CO)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H]
Structure Classification
- Terpenoids
- Triterpenes
Initial Source
- Plants
- Aquifoliaceae
- Plants
- other families
- Microorganisms
I. rotunda
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (204.62 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.0462 mL

10.2312 mL

20.4625 mL

5 mM

0.4092 mL

2.0462 mL

4.0925 mL

10 mM

0.2046 mL

1.0231 mL

2.0462 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: 2.5 mg/mL (5.12 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: 2.5 mg/mL (5.12 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (5.12 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (293 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Roy G, et al. Rotundic Acid Induces DNA Damage and Cell Death in Hepatocellular Carcinoma Through AKT/mTOR and MAPK Pathways. Front Oncol. 2019;9:545. Published 2019 Jun 26. [Content Brief]

[2]. Zhu J, et al. The natural product rotundic acid treats both aging and obesity by inhibiting PTP1B. Life Med. 2022;1(3):372-386. Published 2022 Oct 26. [Content Brief]

[3]. Li XX, et al. Rotundic acid reduces LPS-induced acute lung injury in vitro and in vivo through regulating TLR4 dimer. Phytother Res. 2021;35(8):4485-4498. [Content Brief]

[4]. Yan Z, et al. Rotundic Acid Protects against Metabolic Disturbance and Improves Gut Microbiota in Type 2 Diabetes Rats. Nutrients. 2019;12(1):67. Published 2019 Dec 26. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.0462 mL	10.2312 mL	20.4625 mL	51.1561 mL
	5 mM	0.4092 mL	2.0462 mL	4.0925 mL	10.2312 mL
	10 mM	0.2046 mL	1.0231 mL	2.0462 mL	5.1156 mL
	15 mM	0.1364 mL	0.6821 mL	1.3642 mL	3.4104 mL
	20 mM	0.1023 mL	0.5116 mL	1.0231 mL	2.5578 mL
	25 mM	0.0818 mL	0.4092 mL	0.8185 mL	2.0462 mL
	30 mM	0.0682 mL	0.3410 mL	0.6821 mL	1.7052 mL
	40 mM	0.0512 mL	0.2558 mL	0.5116 mL	1.2789 mL
	50 mM	0.0409 mL	0.2046 mL	0.4092 mL	1.0231 mL
	60 mM	0.0341 mL	0.1705 mL	0.3410 mL	0.8526 mL
	80 mM	0.0256 mL	0.1279 mL	0.2558 mL	0.6395 mL
	100 mM	0.0205 mL	0.1023 mL	0.2046 mL	0.5116 mL

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Rotundic acid

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