Triptergium glycosides
triptolide
CAS: 38748-32-2
Molecular Formula: C20H24O6
Triptergium glycosides - Names and Identifiers
| Name | triptolide |
| Synonyms | PG490 triptolid triptolide TRIPTOLIDE Triptolide ,7as,7bs,8as,8bs)- Triptergium glycosides TRIPTOLIDE, TRIPTERYGIUM WILFORDII 8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-,(3bs,4as,5as,6r,6ar |
| CAS | 38748-32-2 |
| EINECS | 683-214-2 |
| InChI | InChI=1/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1 |
| InChIKey | DFBIRQPKNDILPW-CIVMWXNOSA-N |
Triptergium glycosides - Physico-chemical Properties
| Molecular Formula | C20H24O6 |
| Molar Mass | 360.4 |
| Density | 1.1656 (rough estimate) |
| Melting Point | 226-227°C |
| Boling Point | 412.43°C (rough estimate) |
| Specific Rotation(α) | D25 -154° |
| Flash Point | 220.7°C |
| Solubility | Insoluble in water, soluble in methanol, ethyl acetate, chloroform, etc. |
| Vapor Presure | 5.51E-17mmHg at 25°C |
| Appearance | White or yellowish crystals |
| Color | white to off-white |
| Merck | 14,9747 |
| pKa | 14.25±0.60(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Refractive Index | 1.4450 (estimate) |
| MDL | MFCD00210565 |
| Physical and Chemical Properties | Soluble in methanol, ethyl acetate, chloroform, etc. Derived from the whole plant or peeled woody part of the Celastraceae plant Tripterygium wilfordii. |
| Use | Immunosuppressive agents for the treatment of rheumatoid arthritis, Dermatomyositis, glomerulonephritis and other diseases |
Triptergium glycosides - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | 2811 |
| WGK Germany | 3 |
| RTECS | YK7751000 |
| HS Code | 29321900 |
| Hazard Class | 6.1 |
| Packing Group | I |
| Toxicity | LD50 i.p. in mice: 1.93 mg/kg (Chen) |
Triptergium glycosides - Nature
Open Data Verified Data
- melting point 227 to 228 °c. Soluble in 5% ethanol chloroform solution, almost insoluble in water.
- dosage form 0. 25 mg/kg triptolide granules; 01% parent drug.
Last Update：2024-01-02 23:10:35
Triptergium glycosides - Hair-making
Open Data Verified Data
Tripterygium wilfordii root a extraction a concentration extraction a refinement a concentration a drying a crushing a sieving a finished product
Last Update：2022-01-01 11:19:10
Triptergium glycosides - Use
Open Data Verified Data
plant-derived rodenticide, by inhibiting the fertility of rodents, reduce the density of rodents, reduce all kinds of harm caused by rodents. Farmland voles can be controlled by feeding.
Last Update：2022-01-01 11:19:11
Triptergium glycosides - Safety
Open Data Verified Data
- is a moderately toxic pesticide. Mouse acute oral LD50 (male) 190. 9 mg/kg, (female) 185. 97 mg/kg, acute percutaneous LD50 >5000mg/kg.
- sealed with double-layer polyethylene plastic bag, each bag for 1kg, external carton packaging, each box of 10kg. Packages should be stored in a ventilated, dry warehouse, protected from moisture and light, sealed and stored. Storage and transportation should be strictly protected against moisture and sun exposure, and should not be mixed with food, seeds and feed, avoid contact with skin and eyes, and prevent inhalation from mouth and nose.
Last Update：2022-01-01 11:19:12
Triptergium glycosides - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | triptolide (triptolide) is the most active epoxidized diterpene lactone compound isolated from tripterygium wilfordii. it is one of the main effective components of tripterygium wilfordii, and its related titer is 100-200 times higher than that of tripterygium wilfordii total glycosides. Pharmacological and clinical tests show that it has exact biological activities such as immunosuppression, anti-inflammatory, anti-fertility and anti-tumor. |
| uses | triptolide has the effects of treating rheumatoid arthritis, anti-tumor, anti-inflammatory, immunosuppressive, antiviral, etc. Triptolide is a diterpenoid tricyclic oxide with immunosuppressive and antitumor properties. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: anti-oxidation, anti-rheumatoid, anti-senile dementia and other effects, as well as anti-cancer effects. |
| Plant source | Tripterygium wilfordii is also known as yellow vine root, water mango grass, vegetable insect medicine, mountain arsenic, broken intestine grass, red purple root, southern snake root, dry grass Flower, red medicine. It is the root, leaf, flower and fruit of Tripterygium wilfordii, a plant of the Euonymus family Tripterygium wilfordii, and wilfovdii Hook. f., a Tripterygium of Tripterygium wilfordii and Tripterygium wilfordii in the northeast. There are 4 species of Tripterygium wilfordii in the world, 4 species in China and 3 species in medicine. Climbing rattan wood, 2~3 meters high. Branchlets reddish brown with angular, with oblong tuberculate protrusions and iron-brown tomentose. The flowering period is from May to June. Fruit ripening period is from August to September. Born in shady, wet and fat hillsides, valleys, brook shrubs and secondary mixed woods. Distributed in the south of the Yangtze River, Anhui, Zhejiang, Fujian, Taiwan, Jiangxi, Hunan, Guangdong and even the southwestern provinces. Summer, autumn harvest. Bitter, big poison. Insecticidal, anti-inflammatory, detoxification. This product is poisonous, so it should be taken with caution. ① Treatment of rheumatoid arthritis: Tripterygium wilfordii root, leaves, mash and apply externally, go after half an hour, otherwise it will blisters (Jiangxi Herbal Manual). ② Treatment of itchy skin: Tripterygium wilfordii leaves, mash and apply (Hunan Medicine Journal). (3) Treatment of belt sores: Tripterygium wilfordii flower, black medicine, research and wipe the affected area ("Hunan Medicine History"). |
| Anti-inflammatory and immunosuppressive | Triptolide, also known as triptolide and triptolide, is an epoxy diterpene lactone compound extracted from the roots, leaves, flowers and fruits of Tripterygium wilfordii, a plant of Euonymus family, with Tripterygium, Tripterygium, Tripterygium, Tripterygium, Tripterygium, Tripterygium, Tripterygium and other alkaloids constitute the main active ingredients of Tripterygium extract, which are insoluble in water and easily soluble in methanol, Dimethyl sulfoxide, absolute ethanol, ethyl acetate, chloroform, etc. It has anti-inflammatory and immunosuppressive effects, 10 μg/kg SC for 10 days, which can reduce the auricle swelling of mice induced by croton oil. 0.05~1 μg/ml in vitro test has a stabilizing effect on amniotic erythrocyte membrane. 75,150mg/kgsc, for 7 days, significantly increased the total complement content in rat serum and inhibited the formation of hemolysin antibody in rat initial immune response, there was no obvious inhibition on the formation of hemolysin antibody in the re-immune response. 150 μg/kg ig for 7 days. It has a certain degree of inhibition on the phagocytic function of mouse peritoneal phagocytes. 300 μg/kg SC for 15 days has inhibitory effect on auricle swelling induced by croton oil in mice. 75,150 μg/kgsc for 14 days has inhibitory effect on carrageenan-induced foot plantar swelling in rats. The hemolysis test results of 0.22~4.44 μg/ml concentration in the alcohol extract of polygala showed that it has protective effect on erythrocyte membrane of rats. 0.25,1 mg/kg ip, significantly inhibited the production and secretion of mouse antibodies (QHS method),50,500ng/ml concentration, significantly inhibited the proliferation of T and B cells, in vitro tests, 5,50,500ng/ml and in vivo administration of 0.5,0.75,1 mg/kg ip, all significantly inhibited the production of mouse spleen cell IL-2. 0.1~1 μg/ml in vitro test can inhibit Con A- induced lymphocyte proliferation in mice. The concentration of 0.5~10 μg/L can inhibit unidirectional mixed lymphocyte culture (MLC). The mixed lymphocytes induced by the concentration of 5,10 μg/L can inhibit the second MLC after 60Co irradiation, indicating that triptolide can induce inhibitory T cells (Ts);0.12~0.5 mg/kg ip can significantly inhibit DTH,0.25,0.5 mg/kg in mice induced by DNFB, the IL-2 secretion activity of spleen cells in mice was inhibited, which also increased DTH response induced by large dose of cyclophosphamide. 0.25 mg/kg can reduce the ratio of Th/Ts cells in thymus of mice. The experimental results show that triptolide has immunosuppressive effect, and its mechanism may be related to inhibiting the secretion activity of Th cells and IL-2 and inducing Ts cells. |
| anticancer effect | in recent years, a large number of in vivo and in vitro studies have proved that this product has good antitumor activity against various cancers such as leukemia, breast cancer, pancreatic cancer and lung cancer. Recent studies have found that triptolide not only specifically affects certain proteins and signaling pathways, but also inhibits a wide range of gene transcription, but its mechanism of action needs to be further clarified. Yu Qiang's research group from Shanghai Institute of Materia Medica, Chinese Academy of Sciences conducted in-depth research on the molecular mechanism of triptolide inhibiting a wide range of gene transcription. It has been found that it inhibits gene transcription by promoting phosphorylation of Rpb1, the largest and most important functional subunit of RNA polymerase II, and subsequent ubiquitination degradation of Rpb1. Rpb1 upstream kinase PTEF-b plays a positive regulatory role in Triptolide-induced phosphorylation of Rpb1. The study also found that triptolide can induce DNA damage. These studies suggest that it activates P-TEFb by causing DNA damage to cells, phosphorylating Rpb1 and degrading Rpb1, thus inhibiting broad-spectrum gene transcription. |
| TLCS method for determination of triptolide content | (1) chromatographic conditions: silica gel G-CMCNa plate; Chloroform-ether (2:1) is the developing agent; 2% 3,5-dinitrobenzoic acid ethanol solution and 2mol/L sodium hydroxide ethanol solution. Before use, press 1:3 to mix as a developer, spray color, and inspect under natural light. (2) preparation of reference substance solution: accurately weigh the appropriate amount of triptolide reference substance, and add chloroform to prepare a solution containing 1.528mg per milliliter as the reference substance solution. (3) preparation of sample solution: accurately weigh the appropriate amount of dried medicinal materials, add ethanol for reflux extraction for 3 times, each time for 3 hours, combine the extracts, recover the ethanol to dryness, dissolve and extract the extract with ethyl acetate, check that there is no triptolide in the thin layer of the extract, recover ethyl acetate to obtain the extract, accurately weigh 0.4g of the extract powder dried to constant weight at 90 ℃, and dissolve with 5ml of dichloromethane, add 8g of neutral alumina and mix well, evaporate dichloromethane, transfer it into Soxhlet extractor, reflux with petroleum ether (60~90 ℃) for 3h, discard petroleum ether, take out filter paper cartridge, swing solvent, then place it in extractor and reflux with chloroform 70ml for 5h, recover chloroform until dry, cool it, accurately add chloroform 3ml to dissolve as sample solution. (4) determination: accurately absorb 10 μl of sample solution, 2,7 μl of reference solution, and point on the same thin-layer plate. Expand according to the above chromatographic conditions, take out, dry, and develop color. Cover the same size glass plate, seal with adhesive tape for 4 weeks, 10min later, scan by thin layer scanning method. λS = 535nm,λR = 650nm; Double wavelength reflection sawtooth scanning; Slit: 1.25mm × 1.25mm; Sensitivity × 5. The absorption integral value of the sample and the reference substance was measured, and the content was calculated by the external standard two-point method. (5) determination results: according to the above conditions, the contents of triptolide in root bark, root heart and whole root of triptolide were 0.001%, 0.0004% and 0.0018% respectively. |
| prepare | 300kg of triptolide (after testing, the content of triptolide is 0.0043%), pulverize to 20-30 mesh, put into extraction tank, add 3 tons of ethyl acetate, add 360g of ascorbic acid, heat reflux extraction for 3 times, each time for 5 hours, the extracted solution is filtered and concentrated under reduced pressure to obtain 8.3kg of extract. Dissolve the extract with 360 liters of dichloromethane, drive it into the extraction tank, weigh 17.28 kg of NaOH, prepare 720 liters of 0.6moL/LNaOH solution, drive it into the extraction tank twice, perform alkaline washing on the dichloromethane solution twice, concentrate the dichloromethane phase to obtain 2kg of extract after alkaline washing; take 10kg of 200~300 mesh Qingdao ocean column chromatography normal phase silica gel, wet loading 35cm diameter column, alkali washing after the extract sample first with dichloromethane elution, after the eluent color becomes lighter with dichloromethane: methanol = 50:1 mixed solvent to elute 2 column volumes, and then elute with methanol, concentrate the methanol eluent to obtain a alcohol eluate 427g; take 20kg of normal silica gel for 200~300 mesh Qingdao ocean column chromatography, wet-pack 50cm diameter column, methanol eluate sample, then use petroleum ether: ethyl acetate = 10:1, 6:1, 4:1, 2:1, 1:1 (volume ratio) mixed solvent for gradient elution, and elute about 8 column volumes in each ratio, the eluent containing triptolide was collected, concentrated to about 1/8 volume, and then standing for crystallization at 4 ℃ to obtain 13.8g of triptolide crude product. The crude product was recrystallized with isopropyl ether as crystallization solvent at room temperature. After crystallization, 12.3g of triptolide pure product was obtained by filtration, and its purity was 99.4% by HPLC. |
Last Update：2024-04-09 20:02:46
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