Larrea nitida is a plant that belongs to the Zygophyllaceae family and is widely used in South America to treat inflammatory diseases, tumors and menstrual pain. However, its pharmacological activity remains unclear. In this study we evaluated the property of selective estrogen receptor modulator (SERM) of Larrea nitida extracts (LNE) as a phytoestrogen that can mimic, modulate or disrupt the actions of endogenous estrogens, depending on the tissue and relative amount of other SERMs. To investigate the property of SERM of LNE, we performed MCF-7 cell proliferation assays, estrogen response element (ERE)-luciferase reporter gene assay, human estrogen receptor (hER) binding assays and in vivo uterotrophic assay. To gain insight into the active principles, we performed a bioassay-guided analysis of LNE employing solvents of various polarities and using classical column chromatography, which yielded 16 fractions (LNs). LNE showed high binding affinities for hERalpha and hERbeta with IC50 values of 1.20x10(-7) g/ml and 1.00x10(-7) g/ml, respectively. LNE induced 17beta-estradiol (E2)-induced MCF-7 cell proliferation, however, it reduced the proliferation in the presence of E2. Furthermore, LNE had an atrophic effect in the uterus of immature rats through reducing the expression level of progesterone receptor (PR) proteins. LN08 and LN10 had more potent affinities for binding on hER alpha and beta than other fractions. Our results indicate that LNE had higher binding affinities for hERbeta than hERalpha, and showed SERM properties in MCF-7 breast cancer cells and the rat uterus. LNE may be useful for the treatment of estrogen-related conditions, such as female cancers and menopause.
Animals ; Breast Neoplasms ; Chromatography ; Dysmenorrhea ; Estrogens* ; Female ; Genes, Reporter ; Humans ; Inhibitory Concentration 50 ; Larrea* ; MCF-7 Cells* ; Menopause ; Phytoestrogens ; Plants ; Rats* ; Receptors, Progesterone ; Response Elements ; Selective Estrogen Receptor Modulators ; Solvents ; South America ; Uterus* ; Zygophyllaceae

To study chemical constituents contained in Tetraena mongolica. Chemical constituents were separated and purified by using such methods as silica gel, Toyopearl HW-40C and HPLC preparative chromatography. Their structures were identified by organic spectral method. One new compound was separated from T. mongolica and identified olean-11-oxo-12-en-28-ol-3beta-yl-caffeate.
Drugs, Chinese Herbal ; chemistry ; standards ; Organic Chemicals ; analysis ; chemistry ; isolation & purification ; Quality Control ; Zygophyllaceae ; chemistry

The contents of terrestrosin D and hecogenin from Tribuli Fructus were determined before and after stir-frying. The results showed that the content of terrestrosin D was decreased significantly,and the content of hecogenin was increased significantly after such processing. In order to verify the inference that terrestrosin D was converted to hecogenin by stir-frying,the quantitative variation rules of terrestrosin D and hecogenin were studied by simulated processing technology,and the simulated processing product of terrestrosin D was qualitatively characterized by ultra performance liquid chromatography/time of flight mass spectrometry( UPLC-TOF/MS) to clarify its transformation process during stir-frying. The results showed that the content of terrestrosin D was decreased significantly at first and then a platform stage appeared with the prolongation of processing time at a certain temperature. Raising the stir-frying temperature could further decrease the content of terrestrosin D and delay the time that the platform stage appeared. When the processing was simulated at higher temperatures( 220 ℃ and 240 ℃),the content of hecogenin was increased gradually with the increase of processing temperature and the prolongation of processing time. In the process of stir-frying,the deglycosylation reaction of terrestrosin D to hecogenin was not completed in one step. The deglycosylation reaction occurred first at the end of the sugar chain,and then other glycosyl units in the sugar chain were sequentially removed from the outside to the inside to finally form the hecogenin. This study provides a basis for further revealing the detoxification mechanism of stir-fried Tribuli Fructus.
Chromatography, Liquid ; Fruit ; chemistry ; Hot Temperature ; Phytochemicals ; analysis ; Sapogenins ; analysis ; Tandem Mass Spectrometry ; Zygophyllaceae ; chemistry

OBJECTIVETo study the immunosuppressive constituents from Tetraena mongolica.

METHODChemical constituents were isolated and purified by repeated column chromatography( silica gel, Toyopearl HW40C and preparative HPLC). Their structures were elucidated on the basis of spectral data analysis. The MTT assay was applied to evaluate the isolated compounds on the inhibition effect of lymphocyte transformation.

RESULTSix triterpenes were isolated and their structures were identified as follows: 3beta-hydroxy-11alpha, 12alpha:13beta,28-diepoxyoleanane(1), 3beta-(3, 4-dihydroxycinnamoyl)-erythrodi-ol(2), olean-28-al-3beta-yl-caffeate(3), erythrodiol (4), 12-oleanaen-3beta-caffeate(5), 3-O-(E) -coumaroylerythrodiol(6). Compound 24 exhibited the inhibition effects on lymphocyte transformation.

CONCLUSIONCompounds 1-6 were isolated from this plant for the first time, and compound 1 was a new nature product. Compound 2-4 showed significant immunosuppressive activity.

Animals ; Cells, Cultured ; Immunosuppressive Agents ; chemistry ; isolation & purification ; pharmacology ; Lymphocyte Activation ; drug effects ; Magnetic Resonance Spectroscopy ; Male ; Mice ; Mice, Inbred BALB C ; Triterpenes ; chemistry ; isolation & purification ; pharmacology ; Zygophyllaceae ; chemistry

OBJECTIVETo study the suitable growth density and the optimal harvest time of Tribulus terrestris.

METHODFour growth densities were set with 60 cm breadth ridge and individual distance of 10, 20, 30 and 50 cm. The yield per individual and per unit area under the different growth densities were determined. Using yam saponin as a standard substance, the total saponin of T. terrestris was determined by UV spectrophotometry.

RESULTThe individual yield decreased with the density increase, but the difference between 30 cm and 50 cm individual distance was not substantial. The yield per unit area increased with density increase, and the difference between all densities was significant. The yield peak was in the last ten-day of August. The best leaves area index was 1.4 at the growth peak time. The total saponins content reached peaks respectively in the last ten-day of June and August, but the peak in last ten-day of August was consistent with the one of yield per unit area, and the total ashes content was the lowest at the same time.

CONCLUSIONThe suitable growth density is 10 cm individual distance on the 60 cm breadth ridge. The optimal harvest time is in the last ten-day of August. The yield per unit area is 1 400 - 2 000 kg x hm(-2).

Drugs, Chinese Herbal ; chemistry ; Saponins ; analysis ; Seasons ; Time Factors ; Tribulus ; chemistry ; growth & development

PURPOSE: Tribulus terrestris has been used as an aphrodisiac. However, little is known about the effects and mechanism of action of T. terrestris on penile erection. Therefore, the effect of a T. terrestris extract and the mechanism of action of the extract on relaxation of the corpus cavernosum (CC) were investigated. The erectogenic effects of an oral preparation of the extract were also assessed. MATERIALS AND METHODS: The relaxation effects and mechanism of action of the T. terrestris extract on rabbit CC were investigated in an organ bath. The intracavernous pressure (ICP) was calculated after oral administration of the extract for 1 month to evaluate whether the relaxation response of the CC shown in the organ bath occurred in vivo. Additionally, cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) were measured in the CC by immunoassay. Smooth muscle relaxation was expressed as the percentage decrease in precontraction induced by phenylephrine. The ICP was also assessed in rats after oral administration of the extract for 1 month, and changes in concentrations of cGMP and cAMP were monitored. RESULTS: Concentration-dependent relaxation effects of the extract on the CC were detected in the organ bath study. Relaxation of the CC by the T. terrestris extract was inhibited in both an endothelium-removed group and an L-arginen methyl ester pretreatment group. The ICP measured after oral administration of the T. terrestris extract for 1 month was higher than that measured in the control group, and a significant increase in cAMP was observed in the T. terrestris extract group. CONCLUSIONS: The T. terrestris extract induced concentration-dependent relaxation of the CC in an organ bath. The mechanism included a reaction involving the nitric oxide/nitric oxide synthase pathway and endothelium of the CC. Moreover, in an in vivo study, the T. terrestris extract showed a significant concentration-dependent increase in ICP. Accordingly, the T. terrestris extract may improve erectile function.
Adenosine Monophosphate ; Administration, Oral ; Animals ; Baths ; Endothelium ; Guanosine Monophosphate ; Immunoassay ; Male ; Muscle, Smooth ; Penile Erection ; Phenylephrine ; Rats ; Relaxation ; Tribulus

OBJECTIVEThe content differences of leaf, plant and fruit of Tribulus terrestris was compared to study the feasibility of whole plant medicinal use.

METHODThe samples were collected in three typical habitats and six different production areas of T. terrestris. The main medicinal ingredients saponins and flavonoids were determined in root, stem, leaf and fruit during the harvest time.

RESULTThe two ingredients were abounded in leaf and more than 2.61 times as in other parts of the plant. The results showed that there were no differences between the whole plant and the fruit.

CONCLUSIONIt should pay more attentions on the collection, preservation and utilization of the leaf of T. terrestris in the harvesting and processing stage. The whole plant for medical use was feasibility based on the content of the ingredients.

Flavonoids ; analysis ; Fruit ; chemistry ; Plant Roots ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Saponins ; analysis ; Tribulus ; chemistry

Anti-coccidial effects of the fruits of Tribulus terrestris (Tribuli fructus) ethanol extract (TTE) were studied with animal experiment following per oral administration with Eimeria (E.) tenella. This experiment was performed on the 3-day-old chicks (n=30). The animals were divided with 3 groups; TFE 15mg per animal+infected (n=10), TTE untreated+infected (n=10) and non-infected control (n=10). Animals were administrated with or without TTE during 1 week, and then inoculated with E. tenella. The anti-coccidial activity were evaluated with oocysts shedding numbers in stools, body weights changes and food intake changes. The TTE-inoclated animals revealed significantly decreased stool oocysts numbers (P < 0.05) when compared to the TTE untreated animals. Also, TTE-treated animals showed more increased body weight gains (P < 0.05) than the TTE untreated animals. These results demonstrate that TTE produce anticoccidial activities against E. tenella. TTE could be a promising treatment for the coccidiosis.
Administration, Oral ; Animal Experimentation ; Animals ; Body Weight ; Coccidiosis ; Eating ; Eimeria tenella* ; Eimeria* ; Ethanol* ; Fruit* ; Oocysts ; Polytetrafluoroethylene ; Tribulus*

The contents of terrestroside B and terrestrosin K in Tribuli Fructus with different degree of stir-frying were determined by high performance liquid chromatography with evaporative light-scattering detector( HPLC-ELSD). The results showed that the contents of terrestroside B and terrestrosin K were increased at first and then decreased,and both of them had the highest content at the best time of heating. The results of simulated processing of Tribulus Terrestris saponins showed that when the processing time kept constant,the contents of terrestroside B and terrestrosin K were decreased gradually with the increase of processing temperature from 180 ℃ to240 ℃. At a certain temperature,the content of terrestrosin K was increased first and then decreased with the prolongation of processing time,and reached the highest level at 5 min. However,the content of terrestroside B was increased first and then decreased with the increase of processing time only at 180 ℃,and reached the highest level at 10 min. When the processing temperature was controlled at200,220 and 240 ℃ respectively,the content of terrestroside B was decreased gradually with the increase of processing time. The simulated processing products of tribuluside A,terrestroside B and terrestrosin K were qualitatively characterized by ultra-performance liquid chromatography-time of flight mass spectrometry( UPLC-TOF/MS). It was proved that tribuluside A and terrestrosin Ⅰ containing C-22-OH were dehydroxylated in the processing of Tribuli Fructus and transformed respectively into terrestroside B and terrestrosin K containing C-20-C-22 double bond. As a result,the contents of terrestroside B and terrestrosin K were increased. The sugar chains at C-3 and C-26 positions of terrestroside B and terrestrosin K could be deglycosylated and converted into monosaccharide chain saponins and short sugar chain saponins,so the contents of terrestroside B and terrestrosin K were reduced. The study provides reference for further revealing the processing principle of Tribuli Fructus.
Chemistry, Pharmaceutical ; Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; analysis ; Fruit ; chemistry ; Saponins ; analysis ; Tandem Mass Spectrometry ; Tribulus ; chemistry

OBJECTIVE: The present study investigated antiglycation and antioxidant activities of crude dry extract and saponin fraction of Tribulus terrestris. It also developed a method of microencapsulation and evaluated antiglycation and antioxidant activities of crude dry extract and saponin fraction before and after microcapsule release. METHODS: Antiglycation activity was determined by relative electrophoretic mobility (REM), free amino groups and inhibition of advanced glycation end-product (AGE) formation. Antioxidant activity was determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH), ferric ion-reducing antioxidant power (FRAP), nitric oxide (NO) and thiobarbituric acid reactive species (TBARS) tests. Microcapsules were prepared using maltodextrin as wall material and freeze-drying as encapsulation technique. Morphological characterization of microcapsules was evaluated by scanning electron microscopy, and encapsulation efficiency and microcapsule release were determined by total saponins released. Antiglycation and antioxidant assays were performed using crude dry extract and saponin fraction of T. terrestris before and after release. RESULTS: Saponin fraction showed an increase of 32.8% total saponins. High-performance liquid chromatography-mass spectrometry analysis showed the presence of saponins in the obtained fraction. Antiglycation evaluation by REM demonstrated that samples before and after release presented antiglycation activity similar to bovine serum albumin treated with aminoguanidine. Additionally, samples inhibited AGE formation, highlighting treatment with saponin fraction after release (89.89%). Antioxidant tests demonstrated antioxidant activity of the samples. Crude dry extract before encapsulation presented the highest activities in DPPH (92.00%) and TBARS (32.49%) assays. Saponin fraction before encapsulation in FRAP test (499 μmol Trolox equivalent per gram of dry sample) and NO test (15.13 μmol nitrite formed per gram of extract) presented the highest activities. CONCLUSION This study presented antiglycation activity of crude dry extract and saponin fraction of T. terrestris, besides it demonstrated promising antioxidant properties. It also showed that the encapsulation method was efficient and maintained biological activity of bioactive compounds after microcapsule release. These results provide information for further studies on antidiabetic and antiaging potential, and data for new herbal medicine and food supplement formulations containing microcapsules with crude extract and/or saponin fraction of T. terrestris.
Antioxidants/chemistry* ; Capsules ; Complex Mixtures ; Glycation End Products, Advanced ; Plant Extracts/pharmacology* ; Saponins/pharmacology* ; Thiobarbituric Acid Reactive Substances ; Tribulus