Role of chlorogenic acid in the toxicity induced by Chinese herbal injections

Bao-qiu, LI; Dong, Xin; Yang, Guiqin; Fang, Shi-hong; Gao, Ji-you; Zhang, Jianxin; Gu, Fang-min; Miao, Xiuming; Zhao, Hua

doi:10.3109/01480540903580055

Cited by 20 publications

(9 citation statements)

References 20 publications

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“…5-CQA is one of the major bioactive ingredients of these injections, and its daily intravenous dosage is from 1 to 45 mg (Zhang et al, 2008(Zhang et al, , 2009. Several studies have shown that 5-CQA can induce allergic response in humans and rats, as well as liver and kidney injuries in dogs (Freedman et al, 1961;Bariana et al, 1965;Li et al, 2010;Zhang et al, 2010). The potential risks to human health posed by herbal injections containing 5-CQA need to be evaluated further.…”

Section: Introductionmentioning

confidence: 99%

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Xie¹,

Zhong²,

Chen³

2012

Drug Metab Dispos

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ABSTRACT:5-O-Caffeoylquinic acid (5-CQA) is one of the major bioactive ingredients in some Chinese herbal injections. Occasional anaphylaxis has been reported for these injections during their clinical use, possibly caused by reactive metabolites of 5-CQA. This study aimed at characterizing the bioactivation pathway(s) of 5-CQA and the metabolic enzyme(s) involved. After incubating 5-CQA with GSH and NADPH-supplemented human liver microsomes, two types of GSH conjugates were characterized: one was M1-1 from the 1,4-addition of GSH to ortho-benzoquinone intermediate; the other was M2-1 and M2-2 from the 1,4-addition of GSH directly to the ␣,␤-unsaturated carbonyl group of the parent. The formation of M1-1 was cytochrome P450 (P450)-mediated, with 3A4 and 2E1 as the principal catalyzing enzymes, whereas the formation of M2-1 and M2-2 was independent of NADPH and could be accelerated by cytosolic glutathione transferase. In the presence of cumene hydroperoxide, M1-1 formation increased 6-fold, indicating that 5-CQA can also be bioactivated by P450 peroxidase under oxidizing conditions. Furthermore, M1-1 could be formed by myeloperoxidase in activated human leukocytes, implying that 5-CQA bioactivation is more likely to occur under inflammatory conditions. This finding was supported by experiments on lipopolysaccharideinduced inflammatory rats, where a greater amount of M1-1 was detected. In S-adenosyl methionine-and GSH-supplemented human S9 incubations, M1-1 formation decreased by 80% but increased after tolcapone-inhibited catechol-O-methyltransferase (COMT) activity. In summary, the high reactivities of the orthobenzoquinone metabolite and ␣,␤-unsaturated carbonyl group of 5-CQA to nucleophiles have been demonstrated. Different pathological situations and COMT activities in patients may alter the bioactivation extent of 5-CQA.

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Section: Introductionmentioning

confidence: 99%

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Xie¹,

Zhong²,

Chen³

2012

Drug Metab Dispos

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“…This agent is used for the treatment of chronic jaundice and hepatitis [24,25]. The main constituents of YZHI are coumarin from Herba Artemisiae Scopariae (Yinchen), chlorogenic from Flos Lonicerae (Jinyinhua), gardenoside from Fructus Gardeniae (Zhizi) and baicalin from Radix Scutellariae (Huangqin), and they have detoxification and antimicrobial properties [26,27]. However, only the content of baicalin has been adopted for the QC of YZHI (http://baike.baidu.com/view/564926.htm#sub564926).…”

Section: Introductionmentioning

confidence: 99%

A strategy for the detection of quality fluctuation of a Chinese herbal injection based on chemical fingerprinting combined with biological fingerprinting

Ren

Zhang

Yan

et al. 2011

Journal of Pharmaceutical and Biomedical Analysis

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“…Perhaps the change in the traditional drug-delivery way (p.o.) brings increasing rapidly cases of adverse drug reaction (ADR) (Li et al, 2010), and an alarm over QKLI-caused potential risks in patients was released by the Chinese National Center for Adverse Drug Reaction Monitoring in June 2008and April 2009, respectively (National Center for ADR Monitoring, 2008National Center for ADR Monitoring, 2009). In fact, QKLI is the second leading cause of ADRs induced by traditional Chinese medicine injections (Zhang et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Qing-Kai-Ling Injection Induces Immediate Hypersensitivity Reaction via the Activation of Anaphylatoxin C3

Gao

Zhang

et al. 2020

Front. Pharmacol.

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Background and Objective: Qing-Kai-Ling (QKL) is derived from a famous ancient Chinese patent medicine Angong Niuhuang pills (ANP) which has been used across Asia, especially in China, for the treatment of "febrile disease," such as stroke, encephalitis and meningitis for hundreds of years. As an extract of ANP without heavy metal, the clinical applicability of QKL is more intensive, of which its injection is commonly used in acute and serious diseases. This study aims to clarify the potential mechanisms of immediate hypersensitivity reaction (IHR) induced by QKL injection (QKLI). Methods: b-hexosaminidase release assay was performed on the human mast cell line LAD2 and mouse peritoneal mast cells. T helper 2 (Th2) immunity-amplified mice were prepared by aluminum adjuvant. Anaphylactic shock was detected by measuring rectal thermometry in propranolol-pretreated mice. For evaluating microvascular permeability, Evans Blue extravasation assay was used. Serum total IgE (tIgE) and the activated complement-derived anaphylatoxin C3 (C3a) levels were measured by ELISA. Results: QKLI was unable to elevate serum tIgE level in the Th2 immunity-amplified mice, but can increase vasopermeability and trigger anaphylaxis after the first injection. By screening seven fractions of QKLI, only the extract of Isatidis Radix (Isatis tinctoria L.) induced hindpaw Evans Blue extravasation, which was disappeared in Isatidis Radix-free QKLI. Mechanism study indicated that QKLI or Isatidis Radix-caused IHR could be blocked by the antagonists for histamine or C3a, rather than PAF or C5a. Consistently, QKLI and Isatidis Radix could also directly activate human serum complement-derived anaphylatoxin 3 (C3) in vitro with the half effective concentration values of 0.69% and 218.6 mg/ml, respectively. Conclusion: QKLI-IHR is complement activation-related pseudoallergy, rather than an IgE-mediated allergy. QKLI activates C3 and might consequently provoke mast cells to release histamine, which is a principal effector of its IHR. The pseudoallergic reaction induced by QKLI was attributed to the extract of Isatidis Radix. This study suggests a potential therapeutic strategy for the prophylaxis and treatment of QKLI-IHR.

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Role of chlorogenic acid in the toxicity induced by Chinese herbal injections

Cited by 20 publications

References 20 publications

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

A strategy for the detection of quality fluctuation of a Chinese herbal injection based on chemical fingerprinting combined with biological fingerprinting

Qing-Kai-Ling Injection Induces Immediate Hypersensitivity Reaction via the Activation of Anaphylatoxin C3

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