Andrographolide
ANDRO · ANDROGRAPHIS · Andrographolid · (S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxyMethyl)-5,8a-diMethyl-2-Methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-one · Andrograph · ent-(3β,12E,14R)-3,14,19-Trihydroxy-8(17),12-labdadien-16,15-olide · Androg · raphoL
Identifikatoren & physikalische Daten
| CAS No. | 5508-58-7 |
|---|---|
| Summenformel | C20H30O5 |
| Durchschnittliche Molmasse | 350,4 g/mol |
| Monoisotopische Masse | 350,20932406 g/mol |
| SMILES | C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1O |
| InChIKey | BOJKULTULYSRAS-OTESTREVSA-N |
| PubChem CID | 5318517 |
| ChEMBL | CHEMBL186141 |
| ChEBI | CHEBI:65408 |
| EC No. | 226-852-5 |
| DTXSID | DTXSID3045980 |
| Lokaler Name | Andrographolide |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 87 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 597 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Dietary Ingredients | Andrographis |
| Schmelzpunkt | 229-232 °C (lit.) |
| Siedepunkt | 557.3±50.0 °C(Predicted) |
| Dichte | d421 1.2317 |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 8 mg/ml). |
| pKa (Säurekonstante) | 12.36±0.20(Predicted) |
| Aggregatzustand | Off-white solid |
| Farbe | Off-white |
| Merck | 14,633 |
| BRN | 42762 |
| Stabilität | Stable for 2 years from date of purchsae as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | 1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1 |
| InChIKey | BOJKULTULYSRAS-QPSYGYIJSA-N |
| SMILES | C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H](C\C=C3/[C@H](O)COC3=O)C(=C)CC[C@H]12 |
| LogP (Verteilungskoeffizient) | 0.424 (est) |
| CAS Datenbank | 5508-58-7 |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 31 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | 2(3H)-Furanone, 3-2-(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenylethylidenedihydro-4-hydroxy-, (3E,4S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29322980 |
| RTECS-Nr. | LU3490750 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Andrographolide is a diterpene lactone compound extracted from Andrographis. paniculata (Burm. F) Nees. Andrographis paniculata is also known as lanhelian, yijianxi, zhanshecao, kucao, kudancao, etc. Since this product originates in India, it is also known as Indian grass. This product is dry ground part of Jupiteraceae plant Andrographis paniculata (conus) may originate in South Asia. It is commonly cultivated in China such as in Fujian, Guangdong, Hainan, Guangxi, and Yunnan and also in Australia and was also introduced in Jiangsu and Shaanxi.Andrographis paniculata is commonly used in traditional Chinese medicine. Its ability of relieving “snake venom, and internal injuries cough” was recorded in “Lingnan herbal medicine records.” “Quanzhou Materia Medica” described it as “heat-clearing and detoxifying, anti-inflammatory, detumescence and inhibition throat inflammation, dysentery and high fever.”The above ground part of Andrographis paniculata contains andrographolide, neo-andrographolide, 14-deoxygenated andrographolide, etc., and the root contains mainly flavonoids.
Occurrence
Andrographis is found growing wild in India and Sri Lanka and is cultivated in many other parts of the world.
History
In 1911, Gorter firstly isolated a crystalline substance from Andrographis paniculata, identified it as a diterpene lactone compound, and named it andrographolide .Andrographolide structure is complex and difficult to artificially synthesize, so it is often extracted from the plant.Andrographolide water solubility is poor and its bioavailability is low; its pharmacological effects are extensive but weak, so the preparation requirements are strict. Therefore, from the 1970s, drugs and organic chemical researchers have done a lot of work in the modification and transformation of andrographolide, mainly concentrated in the α, β-unsaturated lactone double bond Michael addition, redox, selective esterification of hydroxyl groups, oxidation and substitution reactions, intramolecular cyclization, replacement of lactone rings, etc. They had obtained a number of new derivatives. In the research of pharmacological effects, the main study of the andrographolide derivatives focuses on antitumor, antivirus, and other biological activities and has made some progress .
Verwenden
Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. It has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Andrographolide showed significant antihepatotoxic action in P. berghei K173- induced hepatic damage in M. natalensis. Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases. These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.