Determination of bioactive diterpenoids from Andrographis paniculata by micellar electrokinetic chromatography

The intracellular level of glutathione (GSH) was significantly decreased after the addition of andrographolide (1) to cell cultures of HepG2. When the molecular interaction between andrographolide and GSH was investigated under a condition mimicking the in vivo environment, we observed that the level of GSH dropped in the presence of andrographolide. Stoichiometric analysis indicates that the reaction between these two reactants was 1 to 1 at pH 7 and followed second order kinetics. The activation energy of the overall reaction was 41.9؎10 kJ · mol ؊1 according to the Arrhenius equation. Using a micro-liquid-liquid extraction method followed by micellar electrokinetic chromatographic separation, two major products were isolated and identified, and their chemical structures were determined as 14-deoxy-12-(glutathione-amino)-andrographolide (2) and 14-deoxy-12-(glutathione-S-yl)-andrographolide (3). Based on these structural findings, a hypothetical mechanism of reaction between glutathione and andrographolide was proposed. It is concluded that the a a,b b-unsaturated lactone moiety of andrographolide reacts with GSH through a Michael addition followed by dehydration of the adduct.

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“…5 s. The buffers 23,24) used in CE separation were composed of 15 mM SDS, 20 mM borate buffer (pHϭ9.5) and 5% (v/v) methanol.…”

Section: Methodsmentioning

confidence: 99%

Molecular Interaction between Andrographolide and Glutathione Follows Second Order Kinetics

Zhang

Chan

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Many of them are still quite popular even today. For example, the plant Andrographis (Andrographis paniculate), which is a rich source for andrographolide (Andro) 4 (7)(8)(9), has long been used as a folk remedy for alleviation of inflammatory disorders in China, India, Japan, and Korea. It currently is a prescribed medicine for treatment of laryngitis, diarrhea, and rheumatoid arthritis in China.…”

mentioning

confidence: 99%

Andrographolide Attenuates Inflammation by Inhibition of NF-κB Activation through Covalent Modification of Reduced Cysteine 62 of p50

Xia

et al. 2004

The Journal of Immunology

340

285

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NF-κB is a central transcriptional factor and a pleiotropic regulator of many genes involved in immunological responses. During the screening of a plant extract library of traditional Chinese herbal medicines, we found that NF-κB activity was potently inhibited by andrographolide (Andro), an abundant component of the plant Andrographis that has been commonly used as a folk remedy for alleviation of inflammatory disorders in Asia for millennia. Mechanistically, it formed a covalent adduct with reduced cysteine (62) of p50, thus blocking the binding of NF-κB oligonucleotide to nuclear proteins. Andro suppressed the activation of NF-κB in stimulated endothelial cells, which reduced the expression of cell adhesion molecule E-selectin and prevented E-selectin-mediated leukocyte adhesion under flow. It also abrogated the cytokine- and endotoxin-induced peritoneal deposition of neutrophils, attenuated septic shock, and prevented allergic lung inflammation in vivo. Notably, it had no suppressive effect on IκBα degradation, p50 and p65 nuclear translocation, or cell growth rates. Our results thus reveal a unique pharmacological mechanism of Andro’s protective anti-inflammatory actions.

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“…The system and the method of data analysis were the same as previously described [11]. The CE system was operated in a normal mode with the cathode at the detector end.…”

Section: Apparatusmentioning

confidence: 99%

Simultaneous determination of key bioactive components in Hedyotis diffusa by capillary electrophoresis

Cheung

Law

et al. 2006

Journal of Chromatography B

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Determination of bioactive diterpenoids from Andrographis paniculata by micellar electrokinetic chromatography

Cited by 81 publications

References 5 publications

Molecular Interaction between Andrographolide and Glutathione Follows Second Order Kinetics

Molecular Interaction between Andrographolide and Glutathione Follows Second Order Kinetics

Andrographolide Attenuates Inflammation by Inhibition of NF-κB Activation through Covalent Modification of Reduced Cysteine 62 of p50

Simultaneous determination of key bioactive components in Hedyotis diffusa by capillary electrophoresis

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