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
Identifiers & Physical Properties
| CAS No. | 5508-58-7 |
|---|---|
| Molecular formula | C20H30O5 |
| Average molar mass | 350.4 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 2.2 |
|---|---|
| Topological polar surface area | 87 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 3 |
| Heavy atoms | 25 |
| Formal charge | 0 |
| Complexity | 597 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Dietary Ingredients | Andrographis |
| Melting point | 229-232 °C (lit.) |
| alpha | -126 º (c=1.5,HAc) |
| Boiling point | 557.3±50.0 °C(Predicted) |
| Density | d421 1.2317 |
| Storage conditions | 2-8°C |
| Solubility | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 8 mg/ml). |
| pKa (acidity coefficient) | 12.36±0.20(Predicted) |
| Physical state | Off-white solid |
| Color | Off-white |
| optical activity | [α]20/D 126°, c = 1.5 in acetic acid |
| λmax | 223nm(MeOH)(lit.) |
| Merck | 14,633 |
| BRN | 42762 |
| Stability | 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. |
| Cosmetics Ingredients Functions | 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 (partition coefficient) | 0.424 (est) |
| CAS DataBase Reference | 5508-58-7 |
| EWG's Food Scores | 1 |
| FDA UNII | 410105JHGR |
| UNSPSC Code | 85151701 |
| NACRES | NA.77 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H332-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xn |
| Risk statements (R) | 20/21/22-36/37/38 |
| Safety statements (S) | 22-24/25-36-26 |
| Water hazard class (WGK) | 3 |
| RTECS number | LU3490750 |
| Customs code | 29322980 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | 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. |
|---|---|
| Regulatory information | 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%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| RTECS number | LU3490750 |
| Customs code | 29322980 |
| Risk statements (R) | 20/21/22-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 22-24/25-36-26 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302-H315-H319-H332-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
Applications & Uses
Description
Andrographolide is the bitter principle, a colorless and neutral crystalline substance. It is the major labdane diterpenoid isolated from Andrographis paniculate. It exhibits antiviral, anti-inflammatory, and anticancer activities. The underlying mechanism is the inhibition of the mitogen-activated protein kinase/extracellular signal-regulated kinase (MAPK/ERK) signaling (specifically p38 MAPK/ERK1/2) pathway and downstream transcription factors such as nuclear factor kappa B (NF-κB) and nuclear factor of activated T cells (NFAT). Andrographolide is also confirmed with chemopreventive effects against and the inhibitory effects on cancer cell growth in breast, colon, epidermoid, gastric, liver, leukemia, myeloma, peripheral blood lymphocytes, and prostate cancers. Andrographolide has been used for liver complaints and fever, and as an anti-inflammatory and immunostimulant. Andrographolide exerts anti-growth and pro-apoptotic effects on human rheumatoid arthritis fibroblast- like synoviocytes, the main cellular constituent of pannus, that combined with a massive infiltration of lymphocytes and macrophages, invades and destroys the local articular structure. Thereby, andrographolide is proposed to be used in Rheumatoid Arthritis and other autoimmune diseases.
Description
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 .
Uses
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.
General Description
Andrographolide, a bioactive diterpene lactone, is the main constituent of Andrographis paniculata, a plant used in traditional medicines. It is known to have different biological activities such as anti-inflammatory, anti-malarial, anti-cancer and hepatoprotective activity. It also shows potent anti-viral effect against dengue virus.