| Identification | Back Directory | [Name]
Andrographolide | [CAS]
5508-58-7 | [Synonyms]
ANDRO
ANDROGRAPHIS
Andrographolid
ANDROGRAPHOLIDE
Andrographalide
Rhizoma Sparganii
ANDROGRAPHOLIDE(P)
Andrographolide (50 mg)
5-alpha,6-alpha,8a-alpha))-t
Andrographolide, froM Andrographis paniculata
3A,14,15,18-TETRAHYDROXY-5B,9B,H,10A-LAMBDA-8,20-DIENE
ent-(3β,12E,14R)-3,14,19-Trihydroxy-8(17),12-labdadien-16,15-olide
3α,14,15,18-Tetrahydroxy-5β,9βH,10α-labda-8(20),12-dien-16-oic Acid γ-Lactone
hylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-,(1r-(1-alpha(e(s*)),4a-be
2(3h)-furanone,3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-met
5.beta.,9.beta.h,10.alpha.-labda-8(20),12-dien-16-oic acid, 3.alpha.,14,15,18-tetrahydroxy-, .gamma.-lactone (8ci)
3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl]ethylidene]dihydro-4-hydroxyfuran-2(3H)-one
3-[2-[Decahydro-6-hydroyx-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenylethylidene]dihydro-4-hydroxy-2(3H)-furanone
(3E,4S)-3-[2-[(1S,4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decalin-1-yl]ethylidene]-4-hydroxy-oxolan-2-one
(S)-3-[(E)-2-[[(1R,4aα)-Decahydro-6β-hydroxy-5β-hydroxymethyl-5,8aβ-dimethyl-2-methylenenaphthalen]-1β-yl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
(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
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxyMethyl)-5,8a-diMethyl-2-Methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
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)-
2(3H)-FURANONE,3-[2-[(1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL]ETHYLIDENE]DIHYDRO-4-HYDROXY-, (3E,4S)-
[1R-[1α[E(S*)],4aβ,5α,6α,8aα]]-3-[2-[Decahydro-6-hydroxy-5-(hydroxyMethyl)-5,8a-diMethyl-2-Methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
ANDROGRAPHOLIDE:2(3H)-FURANONE,3-[2-[(1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL]ETHYLIDENE]DIHYDRO-4-HYDROXY-, (3E,4S)-,
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthalene-1-yl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-2(3H)-furanone | [EINECS(EC#)]
226-852-5 | [Molecular Formula]
C20H30O5 | [MDL Number]
MFCD07778082 | [MOL File]
5508-58-7.mol | [Molecular Weight]
350.45 |
| Chemical Properties | Back Directory | [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 temp. ]
2-8°C | [solubility ]
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 8 mg/ml). | [form ]
Off-white solid | [pka]
12.36±0.20(Predicted) | [color ]
Off-white | [optical activity]
[α]20/D 126°, c = 1.5 in acetic acid | [λmax]
223nm(MeOH)(lit.) | [Merck ]
13,638 | [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. | [InChIKey]
BOJKULTULYSRAS-QPSYGYIJSA-N | [LogP]
0.424 (est) | [CAS DataBase Reference]
5508-58-7 |
| Hazard Information | Back Directory | [Chemical Properties]
colorless Plates | [Usage]
Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. 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. | [Usage]
antineoplastic | [Physical properties]
Appearance: white square prism or flaky crystals (ethanol or methanol) and odorless, with a bitter taste. Solubility: dissolved in boiling ethanol, slightly soluble in
methanol or ethanol, very slightly soluble in chloroform, and almost insoluble in
water. Since andrographolide has an ester structure, it is easy to hydrolysis, open
loop and isomerization in the aqueous solution to affect the drug stability. At lower
temperature, the stability of andrographolide is better; it is unstable in alkaline conditions, and its instability increased with the increase in alkaline strength. The most
stable pH value is 3–5. Andrographolide is more stable in chloroform | [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. 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. | [Uses]
antineoplastic | [Application]
Andrographolide may be used as a reference standard for the determination of andrographolide in:
Leaves of Andrographis paniculata by soxhlet extraction-recrystallization-column chromatography purification followed by analyses using reversed phase high performance liquid chromatography (RP-HPLC) as well as gas chromatography-mass spectrometry (GC-MS).
Roots of Andrographis paniculata by HPLC with diode array detection (DAD), gas chromatography-mass spectrometry (GC-MS) and LC coupled to tandem mass spectrometry (MS/MS) equipped with electrospray ionization (ESI) and multiple reaction monitoring (MRM) mode of detection.
Stems of Andrographis paniculata by ultra-HPLC combined coupled to triple quadrupole-linear ion trap mass spectrometry (QqQLIT-ESI-MS/MS) with MRM detection.
Rat plasma samples by protein precipitation and subsequent ESI-LC-MS/MS determination using MRM detection. | [Definition]
ChEBI: A labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. | [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. | [Biochem/physiol Actions]
Diterpenoid lactone with anti-inflammatory properties. It blocks T-cell proliferation to allogenic stimuli and the chemotactic migration of macrophages induced by complement. Blocks the proliferation of several cancer cell lines in vitro. | [Pharmacology]
Modern pharmacological studies have shown that andrographolide has effects of
anti-inflammatory, antibacterial, antivirus, antitumor, and immune regulation and
can be used in treatment of cardiovascular-cerebrovascular diseases and protectionof the liver and gallbladder. Andrographolide can treat the fever caused by pneumococcus and hemolytic Streptococcus mutans, mainly by inhibiting the hypothalamus PGE2 and cAMP content to exert its antipyretic, nonetheless reducing the
chemotaxis (fMLP) CD11b + and CD18
+ may be the main mechanism of its antiinflammatory effect. Andrographolide has antagonistic effects on Hong Kong virus
(HKV), Ebola virus (EBOV), and respiratory syncytial virus (RSV) and has been
shown to inhibit HIV, SARS, and viral myocarditis ST2 in?vitro
Andrographolide can also ameliorate myocardial ischemia and serve as protection from ischemia-reperfusion injury. It also has protection effect of vascular endothelial cells as well as can regulate lipid disorder, lower blood pressure, and exert
effect of anti-atherosclerosis. It can also prevent angiogenesis after restenosis and
improve blood rheology. Its mechanisms are mainly due to its free radical scavenging and antiplatelet aggregation properties. Andrographolide can increase the bile
flow, bile salt, bile acid, and deoxycholic acid in experimental rats and guinea pigs
and can reverse the reduction of bile and cholic acid and other secretions caused by
paracetamol and improve liver function . | [Anticancer Research]
It is a labdane diterpenoid, which shows cytotoxic effect against different cancercell lines like human epidermoid cancer cells (KB), lymphocytic leukemia cells(P388), breast cancer cells (MCF-7), and colon cancer cells (HCT-116). It inhibitsthe proliferation of colon cancer cells (HT-29) and exerts pro-differentiative effecton mouse myeloid leukemia M1 cell line (Desai et al. 2008). | [Clinical Use]
This product is commonly used clinically for dysentery, leptospirosis, meningitis,
pneumonia, upper respiratory tract infection, and enhancing adrenal cortical function. In view of the requirement for clinical viral infection emergency, it is important to introduce the hydrophilic group in different lactone structure, enhance its
water solubility, and improve efficacy. There are a variety kinds of andrographolide
injection, including potassium dehydroandrograpolide succinate needle, potassium
sodium dehydroandrographolide succinate needle. Lianbizhi is the representative of
this class of drugs in current clinical application. Oral administration of andrographolide may induce bitter vomiting. Oral administration of this product and other
preparations in large doses can cause epigastric discomfort and loss of appetite. It
had been reported of drug eruption, upper abdominal pain, and anaphylactic shock
caused by intramuscular injection. Severe symptom response emerged such as chest
tightness, shortness of breath, pallor, lip bruising, cold sweats, weak pulse, decreased
blood pressure, etc. Light reactions include abdominal pain, vomiting, asthma, urticaria, pimples, dizziness, head swelling, sneezing, chest pain, etc. The reaction is
real time and also 5–20?min after injection and gradually improves 5–45?min after
rescue and individual recovered by 24?h. There are also reports of acute amniotic
fluid blockage caused by weaning lotion exchange. In addition, taking into account
the adverse effects of andrographolide on reproduction, it is recommended to be
used cautiously by fertility couples and pregnant women. | [in vitro]
andrographolide was found to suppress the expression of inducible nitric oxide synthase in a concentration-dependent manner. in the andrographolide-treated group, a reduction of akt, c-jun n-terminal kinase and p65 phosphorylation was observed. andrographolide also caused a decrease in bcl-2/nf-κb expression and a dose-dependent increase in the expression of cleaved-caspase3/bax protein [1]. | [in vivo]
rats were dosed with andrographolide intragastrically for 5 consecutive days in a hepatoprotection study. results indicated that andrographolide could up-regulate glutamate cysteine ligase catalytic and modifier subunits, heme oxygenase-1, superoxide dismutase-1, glutathione s-transferase protein and mrna expression in the heart, liver, and kidney [2]. | [IC 50]
11.0 ± 0.28 μg/ml for α-glucosidase; 11.3 ± 0.29 μg/ml for α-amylase | [storage]
Store at -20°C |
| Questions And Answer | Back Directory | [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.
| [References]
[1] Mari?a A. Hidalgo, Juan L. Hancke, Juan C. Bertoglio and Rafael A. Burgos (2013) Andrographolide a New Potential Drug for the Long Term Treatment of Rheumatoid Arthritis Disease in book “Innovative Rheumatology”
[2] https://www.drugs.com/npp/andrographis.html
[3] Mitchell Low, Cheang S Khoo, Gerald Münch, Suresh Govindaraghavan, Nikolaus J Sucher (2014) An in vitro study of anti-inflammatory activity of standardised Andrographis paniculata extracts and pure andrographolide, BMC Complementary and Alternative Medicine, 15:18
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