The identification of salicylates as normal constituents of serum: a link between diet and health?

Paterson, John R.; Blacklock, Claire; Campbell, Graham; Wiles, D. H.; Lawrence, J. R.

doi:10.1136/jcp.51.7.502

Cited by 41 publications

(44 citation statements)

References 19 publications

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“…Although there is some uncertainty concerning the quantitative estimation of the salicylate content of plant-based foods, evidence for dietary as opposed to pharmaceutical sources is suggested by the detection of salicylic acid and associated metabolites in plasma and urine of individuals not taking aspirin or related preparations (Paterson et al 1998;Blacklock et al 2001;Baxter et al 2002). Moreover, serum ( Red wine 3 .…”

Section: Evidence For Dietary Uptake Of Salicylic Acidmentioning

confidence: 99%

Is there a role for dietary salicylates in health?

et al. 2006

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Acetylsalicylic acid (aspirinTM; 2-acetoxybenzoic acid) has been used for >100 years for pain relief and to treat inflammatory conditions and fevers. More recently, regular intake has been associated with decreased incidence of certain cancers, particularly colon cancer. After absorption aspirin is very rapidly hydrolysed to salicylic acid (2-hydroxybenzoic acid). The anti-cancer effects of aspirin may be a result of salicylic acid reducing the transcription of prostaglandin H2-synthase and thereby the synthesis of pro-inflammatory and potentially-neoplastic prostaglandins. Salicylic acid is widely present in plants and functions as a hormonal mediator of the systemic acquired resistance response to pathogen attack and environmental stress. Thus, it is present in a large range of fruit, vegetables, herbs and spices of dietary relevance. Consequently, the recognised effect of consuming fruit and vegetables on lowering risk of colon cancer may be partly attributable to salicylates in plant-based foods. The present review discusses which types of fruit and vegetables are the richest source of salicylates and whether they are sufficiently released from the food matrix to modify the key cellular events associated with the pathogenesis of colon cancer.

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Section: Evidence For Dietary Uptake Of Salicylic Acidmentioning

confidence: 99%

Is there a role for dietary salicylates in health?

et al. 2006

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“…After administration, aspirin undergoes rapid hydrolysis to generate salicylic acid (SA), and it is this phenolic acid that may be responsible for the persistence of the anti-in£ammatory e¡ect of aspirin. 2 Paterson et al, 3 using high-performance liquid chromatography (HPLC), gas chromatography^mass spectrometry (GCMS) and salicylate hydroxylase, demonstrated that SA and two of its hydroxylated metabolites were present in the serum of people who had not taken salicylate drugs, and they suggested that these phenolic acids may have had a dietary origin. Swain et al 4 determined SA in foodstu¡s using HPLC with UV detection and estimated that the dietary intake of SA was in the range 70^1100 mol per person per 24 h. Janssen et al 5 examined acid-treated urine using HPLC with £uorescence detection, and suggested that the dietary intake of SA was about 10 mol per person per 24 h. However, neither Swain et al nor Janssen et al had characterized the compound(s) they had determined.…”

Section: Introductionmentioning

confidence: 99%

Identification and determination of salicylic acid and salicyluric acid in urine of people not taking salicylate drugs

Baxter¹,

Lawrence

Graham³

et al. 2002

Ann Clin Biochem

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“…Salicylates may be found as constituents of a normal diet (fruit and vegetables) and, notwithstanding our ignorance of the molecular pathways they activate in the gut epithelium, one can reasonably infer that ingestion of such dietary salicylates may contribute to the health of an individual by reducing colorectal cancer incidence (39,44). In an effort to understand the molecular basis of the growth inhibitory effect of ASA against cancer cells we examined a number of derivatives of salicylic acid.…”

Section: Discussionmentioning

confidence: 99%

Activity of aspirin analogues and vanillin in a human colorectal cancer cell line

Nicholl¹

2011

Oncol Rep

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Abstract. Colorectal cancer is the third most common cancer and is associated with significant morbidity and mortality. epidemiological and animal studies indicate that regular acetylsalicylic acid (aspirin) intake is associated with a reduction in the incidence of colorectal cancer. Acetylsalicylic acid (ASA) has also been shown to inhibit colorectal cancer cell proliferation in vitro. The molecular basis for this specific cytotoxicity is an area of considerable debate. To investigate the toxicity of salicylates, the sensitivity of the DNA mismatch repair proficient SW480 human colorectal cancer cell line to four categories of compounds with varying degrees of structural similarity to acetylsalicylic acid was tested. These compounds were: i) salicylic acid analogues with substituents at the 5-position; ii) ASA analogues with extended chain lengths in the acyl group; iii) vanillin (4-hydroxy-3-methoxybenzaldehyde; and iv) bis(2-carboxyphenyl) succinate (BCS) and structurally similar derivatives thereof. It was found that compounds with amino and acetamido substituents at the salicylate 5-position were less toxic than ASA itself. Modifications to the length of the hydrocarbon chain in the acyl groups of ASA analogues also marginally reduced toxicity. Vanillin exhibited relatively limited toxicity against the SW480 colorectal cancer cell line. Commercially available and in-house synthesised BCS (diaspirin) were notably more inhibitory to cell growth than ASA itself, yet retained substantial specificity against colorectal cancer cell lines vs. non-colorectal cancer cell lines. BCS and ASA were toxic to SW480 cells through initiation of necrotic and apoptotic pathways. Fumaroyldiaspirin and benzoylaspirin exhibited greater toxicity than ASA against the SW480 cell line. A novel method for synthesis of BCS, a compound that has erratic commercial availability, is described. We propose that the anti-inflammatory and anticancer capacity of BCS and the other analogues described herein is worthy of investigation.

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The identification of salicylates as normal constituents of serum: a link between diet and health?

Cited by 41 publications

References 19 publications

Is there a role for dietary salicylates in health?

Is there a role for dietary salicylates in health?

Identification and determination of salicylic acid and salicyluric acid in urine of people not taking salicylate drugs

Activity of aspirin analogues and vanillin in a human colorectal cancer cell line

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