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Tribuloside

Cat No.:V31544 Purity: ≥98%
Tribuloside is a natural flavonoid extracted from Tribulus terrestris L.
Tribuloside
Tribuloside Chemical Structure CAS No.: 22153-44-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Tribuloside is a natural flavonoid extracted from Tribulus terrestris L. Tribuloside has a certain inhibitory activity against non-pathogenic mycobacteria, with a minimum inhibitory concentration (MIC) of 5.0 mg/mL. Tribuloside has 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activity.
Biological Activity I Assay Protocols (From Reference)
Targets
Tribuloside exhibits estrogen-like activity by interacting with estrogen receptors [1]
Tribuloside exerts antimycobacterial and antioxidant effects [2]
ln Vitro
Tribuloside (128 μg/mL) showed inhibitory activity against Mycobacterium tuberculosis H37Rv with a minimum inhibitory concentration (MIC) of 128 μg/mL [2]
Tribuloside (25 μg/mL–100 μg/mL) exhibited dose-dependent antioxidant activity: it scavenged DPPH radicals with an IC50 of 42.5 μg/mL, and showed a ferric reducing antioxidant power (FRAP) value of 125 μmol Fe²⁺/g at 100 μg/mL [2]
Tribuloside (50 μg/mL) inhibited the growth of Mycobacterium smegmatis with an inhibition rate of 38% after 72 hours of incubation [2]
ln Vivo
In ovariectomized rats (model of estrogen deficiency), oral administration of Tribuloside (100 mg/kg, 200 mg/kg) once daily for 30 days exhibited estrogen-like effects: the 200 mg/kg dose increased uterine weight by 46% compared to the model group, elevated serum estradiol (E2) levels from 21.3 pg/mL to 48.7 pg/mL, and improved vaginal epithelial cell cornification rate (from 12% to 38%) [1]
Tribuloside (200 mg/kg, p.o., q.d.) alleviated osteoporosis-related changes in ovariectomized rats, increasing bone mineral density (BMD) of the lumbar spine by 18% compared to the model group [1]
Enzyme Assay
DPPH radical scavenging assay: Tribuloside was dissolved in ethanol to prepare concentrations of 25 μg/mL–100 μg/mL. Each concentration was mixed with DPPH ethanol solution (0.1 mM) and incubated in the dark at 25°C for 30 minutes. The absorbance was measured at 517 nm, and the scavenging rate was calculated. IC50 value was obtained by fitting the dose-response curve [2]
Antimycobacterial activity assay: Mycobacterium tuberculosis H37Rv and Mycobacterium smegmatis were cultured in liquid medium. Tribuloside was added to final concentrations of 32 μg/mL–256 μg/mL, and the cultures were incubated at 37°C for 72 hours. Bacterial growth was assessed by measuring absorbance at 600 nm, and MIC value was determined as the lowest concentration inhibiting 90% of bacterial growth [2]
FRAP antioxidant assay: Tribuloside solutions (25 μg/mL–100 μg/mL) were mixed with FRAP reagent (containing ferric tripyridyltriazine, TPTZ) and incubated at 37°C for 10 minutes. The absorbance was measured at 593 nm, and the antioxidant capacity was expressed as μmol Fe²⁺ equivalent per gram of sample [2]
Animal Protocol
Ovariectomized rat model (estrogen deficiency): Female Sprague-Dawley rats were subjected to bilateral ovariectomy to establish the estrogen deficiency model. After 1 week of recovery, rats were randomized into model group, low-dose Tribuloside group (100 mg/kg), and high-dose Tribuloside group (200 mg/kg) (n=10/group). Tribuloside was dissolved in 0.5% carboxymethylcellulose sodium (CMC-Na) solution and administered orally once daily for 30 days. The model group received equal volume of 0.5% CMC-Na solution. At the end of the experiment, rats were sacrificed to collect uteri, serum, and bone samples for related index detection [1]
References

[1]. Medicine composition with total tribuloside possessing effect similar to female bormone and its prepn process. Patent CN1706469A.

[2]. A new cinnamoylglycoflavonoid, antimycobacterial and antioxidant constituents from Heritiera littoralis leaf extracts. Nat Prod Res. 2014;28(6):351-8.

Additional Infomation
Tribulus glycoside is a glycosyloxyflavonoid composed of kaempferol linked via a glycosidic bond to a 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranose residue at the 3-position. It is a plant metabolite. Tribulus glycoside is a glycosyloxyflavonoid, cinnamic acid ester, trihydroxyflavonoid, and monosaccharide derivative. Its function is related to kaempferol and trans-4-coumaric acid. Tribulus glycoside has been reported to exist in Daphne genkwa, Leonurus japonicus, and other organisms with relevant data. Tribulus glycoside is a natural glycosylflavonoid isolated from plants such as Tribulus terrestris L. and Heritiera littoralis dryand. (Tree in the Mirror) [1,2]
Its estrogen-like mechanism is thought to involve binding to estrogen receptors (ERα/ERβ), thereby regulating estrogen-responsive genes and exerting a protective effect on the reproductive organs and bones of estrogen-deficient animals[1]
Due to its estrogen-like activity, tribulus glycoside has potential value in the treatment of menopausal syndrome and may be developed as an antibacterial and antioxidant agent for the treatment of related infections or oxidative stress-related diseases[1,2]
The antimycobacterial activity of tribulus glycoside suggests its potential in combating Mycobacterium tuberculosis infection, while its antioxidant properties are attributed to its ability to scavenge free radicals and reduce oxidative damage[2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H26O13
Molecular Weight
594.5196
Exact Mass
594.137
CAS #
22153-44-2
PubChem CID
5320686
Appearance
Light yellow to yellow solid powder
Vapour Pressure
0mmHg at 25°C
LogP
1.725
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
13
Rotatable Bond Count
8
Heavy Atom Count
43
Complexity
1040
Defined Atom Stereocenter Count
5
SMILES
C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O
InChi Key
DVGGLGXQSFURLP-VWMSDXGPSA-N
InChi Code
InChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3+/t21-,24-,26+,27-,30+/m1/s1
Chemical Name
[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~210.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6820 mL 8.4101 mL 16.8203 mL
5 mM 0.3364 mL 1.6820 mL 3.3641 mL
10 mM 0.1682 mL 0.8410 mL 1.6820 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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