Deoxyandrographolide - CAS 79233-15-1
Catalog number:
79233-15-1
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H30O4
Molecular Weight:
334.45
COA:
Inquire
Targets:
Others
Description:
Deoxyandrographolide is a natural compound extracted from the herbs of Andrographis paniculata (Burm. f.) Nees. It could potently inhibit the growth of liver (HepG2 and SK-Hep1) and bile duct (HuCCA-1 and RMCCA-1) cancer cells. It controlled ethanol-induced hepatosteatosis by interfering with dysregulation of lipid metabolism. It was capable of preventing the development of fatty liver through AMPK-mediated regulation of lipid metabolism. It reduced the extracellular acidification rate and the intracellular alkalinization in a dose-dependent manner in concentrations between 10-100 microM. It reduced PAF-induced calcium flux in the presence of extracellular calcium. It mediated activation of adenylate cyclase-cAMP signaling leading to up-regulation of cNOS may provide a promising approach in the prevention of liver diseases during chronic alcoholism.
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Purity:
>98%
Appearance:
Solid powder
Synonyms:
4-[2-[(4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one;2(5H)-Furanone, 3-[2-[(4aS,5R,6R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-1-naphthalenyl]ethyl]-
Solubility:
10 mM in DMSO
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Deoxyandrographolide could potently inhibit the growth of liver (HepG2 and SK-Hep1) and bile duct (HuCCA-1 and RMCCA-1) cancer cells. It controlled ethanol-induced hepatosteatosis by interfering with dysregulation of lipid metabolism. It reduced the extracellular acidification rate and the intracellular alkalinization in a dose-dependent manner in concentrations between 10-100 microM. It reduced PAF-induced calcium flux in the presence of extracellular calcium.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
Boiling Point:
511.7±50.0 °C | Condition: Press: 760 Torr
Density:
1.123±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
DAXSYTVXDSOSIE-HNJRGHQBSA-N
InChI:
InChI=1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,16-17,21-22H,4-8,10-12H2,1-3H3/t16-,17+,19-,20-/m0/s1
Canonical SMILES:
CC1=C(C2(CCC(C(C2CC1)(C)CO)O)C)CCC3=CCOC3=O
1.[HPLC Specific Fingerprint of Alcohol Extract of Andrographis paniculata].
Liu FF, Fan CL, Huang XJ, Wang GY, Wang Y, Ye WC. Zhong Yao Cai. 2015 Jul;38(7):1505-8.
OBJECTIVE: To establish the specific fingerprint of alcohol extract of Andrographis paniculata by HPLC.
2.Determination of six components of Andrographis paniculata extract and one major metabolite of andrographolide in rat plasma by liquid chromatography-tandem mass spectrometry.
Wang J1, Yang W1, Wang G1, Tang P1, Sai Y2. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 1;951-952:78-88. doi: 10.1016/j.jchromb.2014.01.028. Epub 2014 Jan 28.
Andrographis paniculata (AP) has been widely used in Asian countries to treat many kinds of diseases for several decades. Hutchison Medipharma Ltd. developed an aqueous ethanol extract of A. paniculata (APE) named as HMPL-004 to treat inflammatory bowel diseases. The representative chemical components of HMPL-004 include andrographolide (AND), neoandrographolide (NAND), 14-deoxyandrographolide (DAND), 14-deoxy-11,12-didehydro-andrographolide (DDAND), apigenin-7-O-β-d-glucuronopyranoside (AODG) and chlorogenic acid (CLA). HM5013620 is the major circulating metabolite of AND. The purpose of this study was to develop a bioanalytical method to determine all seven compounds in rat plasma using liquid chromatography coupled to electrospray tandem mass spectrometry (LC-MS/MS). The assay was fully validated according to FDA guidelines. The LC-MS/MS detection was operated in the negative mode, and the multiple reaction monitoring (MRM) mode was used for the quantification.
3.A Simple and Sensitive LC-MS/MS Method for Determination of Four Major Active Diterpenoids from Andrographis paniculata in Human Plasma and Its Application to a Pilot Study.
Pholphana N1, Panomvana D2, Rangkadilok N1, Suriyo T1, Ungtrakul T3, Pongpun W3, Thaeopattha S2, Satayavivad J1. Planta Med. 2016 Jan;82(1-02):113-20. doi: 10.1055/s-0035-1558115. Epub 2015 Nov 17.
Andrographis paniculata contains four major active diterpenoids, including andrographolide (1), 14-deoxy-11, 12-didehydroandrographolide (2), neoandrographolide (3), and 14-deoxyandrographolide (4), which exhibit differences in types and/or degrees of their pharmacological activity. Previous pharmacokinetic studies in humans reported only the parameters of compound 1 and its analytical method in human plasma. The purpose of this study was to develop a simple, sensitive, and selective liquid chromatography tandem-mass spectrometry technique for the simultaneous determination of all four major active diterpenoids in the A. paniculata product in human plasma. These four diterpenoids in plasma samples were extracted by a simple protein precipitation method with methanol and separated on a Kinetex C18 column using a gradient system with a mobile phase of acetonitrile and water. The liquid chromatography tandem-mass spectrometry was performed in the negative mode, and the multiple reaction monitoring mode was used for the quantitation.
4.Regioselective glucuronidation of andrographolide and its major derivatives: metabolite identification, isozyme contribution, and species differences.
Tian X1, Liang S, Wang C, Wu B, Ge G, Deng S, Liu K, Yang L, Ma X. AAPS J. 2015 Jan;17(1):156-66. doi: 10.1208/s12248-014-9658-8. Epub 2014 Sep 10.
Andrographolide (AND) and two of its derivatives, deoxyandrographolide (DEO) and dehydroandrographolide (DEH), are widely used in clinical practice as anti-inflammatory agents. However, UDP-glucuronosyltransferase (UGT)-mediated phase II metabolism of these compounds is not fully understood. In this study, glucuronidation of AND, DEO, and DEH was characterized using liver microsomes and recombinant UGT enzymes. We isolated six glucuronides and identified them using 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. We also systematically analyzed various kinetic parameters (K m, V max, and CLint) for glucuronidation of AND, DEO, and DEH. Among 12 commercially available UGT enzymes, UGT1A3, 1A4, 2B4, and 2B7 exhibited metabolic activities toward AND, DEO, and DEH. Further, UGT2B7 made the greatest contribution to glucuronidation of all three anti-inflammatory agents. Regioselective glucuronidation showed considerable species differences.
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CAS 79233-15-1 Deoxyandrographolide

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