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.

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)

Biological Activity

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	Tribuloside is a glycosyloxyflavone that is kaempferol attached to a 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite. It is a glycosyloxyflavone, a cinnamate ester, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol and a trans-4-coumaric acid. Tiliroside has been reported in Daphne genkwa, Leonurus japonicus, and other organisms with data available. Tribuloside is a natural glycoflavonoid isolated from plants such as Tribulus terrestris L. (tribulus) and Heritiera littoralis Dryand. (looking-glass tree) [1,2] Its estrogen-like mechanism is proposed to involve binding to estrogen receptors (ERα/ERβ), thereby regulating estrogen-responsive genes and exerting protective effects on reproductive organs and bones in estrogen-deficient animals [1] Tribuloside exhibits potential application in the treatment of menopause syndrome due to its estrogen-like activity, and may be developed as an antimicrobial and antioxidant agent for related infections or oxidative stress-related diseases [1,2] The antimycobacterial activity of Tribuloside suggests its potential in combating Mycobacterium tuberculosis infections, while its antioxidant property is attributed to the ability to scavenge free radicals and reduce oxidative damage [2]

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.