Mass spectrometric analysis of ptaquiloside, the toxic sesquiterpene from bracken fern

Bonadies, F.; Borzacchiello, Giuseppe; Dezzi, Sandro; Nicoletti, Rosario; Roperto, Sante

doi:10.1002/rcm.1410

Cited by 21 publications

(17 citation statements)

References 15 publications

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“…It possesses the structure of an illudane and is quite unstable in mildly acidic or basic conditions, decomposing into an illudane-dienone. Additionally, the ptaquiloside aglycone ptaquilosin is also very unstable and decomposes into the same dienone [3,15]. The dienone has been shown to alkylate DNA via a reactive cyclopropyl ring to form a number of different DNA adducts at N3 of adenines, which can lead to point mutations.…”

Section: Bracken Fern As a Cofactor For Carcinogenesismentioning

confidence: 99%

“…Moreover, bracken eating cattle with BEH and/or suffering from bladder cancer develop chromosomal abnormalities [67,80,88,101,129] due to a clastogenic activity of compounds from fern. Metabolites from ptaquiloside and quercetin along with other chemicals from bracken are also found in the blood, urine and milk of cows naturally exposed to bracken and suffering from bladder cancer [15,80]. Exposure to ptaquiloside indirectly through milk from bracken-grazing cows has a big impact on human health, since it has been correlated with human oesophageal and gastric cancer [3,122,139].…”

Section: Bracken Fern As a Cofactor For Carcinogenesismentioning

confidence: 99%

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Bovine papillomaviruses, papillomas and cancer in cattle

Borzacchiello¹,

Roperto²

2008

Vet. Res.

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173

149

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-Bovine papillomaviruses (BPV) are DNA oncogenic viruses inducing hyperplastic benign lesions of both cutaneous and mucosal epithelia in cattle. Ten (BPV 1-10) different viral genotypes have been characterised so far. BPV 1-10 are all strictly species-specific but BPV 1/2 may also infect equids inducing fibroblastic tumours. These benign lesions generally regress but may also occasionally persist, leading to a high risk of evolving into cancer, particularly in the presence of environmental carcinogenic co-factors. Among these, bracken fern is the most extensively studied. The synergism between immunosuppressants and carcinogenic principles from bracken fern and the virus has been experimentally demonstrated for both urinary bladder and alimentary canal cancer in cows whose diets were based on this plant. BPV associated tumours have veterinary and agricultural relevance in their own right, although they have also been studied as a relevant model of Human papillomavirus (HPV). Recent insights into BPV biology have paved the way to new fields of speculation on the role of these viruses in neoplastic transformation of cells other than epithelial ones. This review will briefly summarise BPV genome organization, will describe in greater detail the functions of viral oncoproteins, the interaction between the virus and co-carcinogens in tumour development; relevant aspects of immunity and vaccines will also be discussed.

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Section: Bracken Fern As a Cofactor For Carcinogenesismentioning

confidence: 99%

Section: Bracken Fern As a Cofactor For Carcinogenesismentioning

confidence: 99%

Bovine papillomaviruses, papillomas and cancer in cattle

Borzacchiello¹,

Roperto²

2008

Vet. Res.

Self Cite

173

149

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“…In table 6, the activation of the Tanzanian medicinal plants on PXR is shown. Significant PXR activation with an induction factor >2.00 was found for A. salicifolia (5.44), C. hildebrandtii (2.41), E. buchannanii (4.49), J. multifida (5.9), P. aquillinum (3.58), S. birrea (3.33), Ster.…”

Section: Pxr Assaymentioning

confidence: 99%

“…Some of them were found to contain compounds that can be potentially cytotoxic or genotoxic. For example, Pteridium aquillinum contains the carcinogenic compound ptaquiloside [6][7][8][9][10]. A case of Agaura salicifolia intoxication, with vomiting, arterial hypotension and bradycardia was reported in a 28-year-old woman due to ingestion of tea made of the leaves [11].…”

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confidence: 99%

Evaluation of Cytotoxic, Genotoxic and CYP450 Enzymatic Competition Effects of Tanzanian Plant Extracts Traditionally Used for Treatment of Fungal Infections

Beukel

Hamza

Moshi

et al. 2008

Basic Clin Pharma Tox

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HIV-infected patients in sub-Saharan countries highly depend on traditional medicines for the treatment of opportunistic oral infections as candidiasis. Previous investigations on antifungal activity of medicinal plant extracts utilized by traditional healers in Tanzania have revealed 12 extracts with potent antifungal activity. Although the plants may be good candidates for new treatment opportunities, they can be toxic or genotoxic and could cause pharmacokinetic interactions when used concomitantly with antiretroviral agents. Therefore, we investigated the cytotoxicity, genotoxicity and cytochrome P450 interaction potential of these medicinal plants. Cytotoxicity was tested by Hoechst 33342, Alamar Blue, calcein-AM, glutathione depletion and O 2 -consumption assays and genotoxicity by a Vitotox assay. Competition of the 12 extracts on substrate metabolism by CYP3A4, 2C9, 2C19 and 2D6 was tested with high-throughput CYP inhibition screening. Pregnane X receptor (PXR) activation was tested using Chinese hamster ovary cell lines expressing human PXR. Herbal extracts inducing high human PXR activation were tested for enhanced CYP3A4 mRNA levels with quantitative polymerase chain reaction. Genotoxicity was found for Jatropha multifida , Sterculia africana and Spirostachys africana . All plant extracts showed high cytotoxic effects in almost all tests. Potent competition with CYP3A4, 2D6, 2C9 and 2C19 was found for 75% of the herbal extracts. Spirostachys africana did not affect CYP2D6 and for S. africana and Turraea holstii no effect on CYP2D6 and CYP3A4 (DBF) was found. Nine plant extracts showed significant activation of human PXR, but only Agaura salicifolia , Turraea holstii and S. africana significantly induced CYP3A4 mRNA levels. These results indicate the possibility of potential medicinal plant-antiretroviral interactions.Traditional medicines are commonly used in sub-Saharan countries like Tanzania, with up to 80% of the population depending on traditional medicines for their primary health care [1]. In Tanzania, up to 21% of the people who seeked care from public health care facilities first consult a traditional healer [2]. Especially, HIV-infected persons who often encounter opportunistic infections during their disease course highly depend on this form of health care. According to Medicine du Monde , a French non-governmental organization, in Kagera region, five out of every six HIV-infected patients receive their medical attention from a traditional healer rather than from a hospital or primary health care facility [3]. A survey among 532 HIV patients visiting the HIV clinic of Muhimbili National Hospital, Dar es Salaam, Tanzania, reported use of traditional medicines by 62 patients (11.7%). Focusing on HIV patients with oral lesions, mostly oral Candida infections, a prevalence of traditional medicine use of 40.3% was found [4].Fungal infections, like oral candidiasis, are commonly seen among HIV-infected patients in sub-Saharan Africa. The problems with effective management of these infec...

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“…A mass spectrometric approach was recently successfully applied. It is based on the transformation of ptaquiloside to bromopterosin (BrPt, 1c; Figure 1) or methoxypterosin followed by a GC-MS and stable isotope dilution assays using d 2 -bromopterosin as internal standard [11,12]. More recently, a sensitive LC-MS/MS method for quantifying Pta in soil and groundwater based on the transformation of ptaquiloside to pterosin B has been published [13].…”

Section: Introductionmentioning

confidence: 99%

A New Facile Synthesis of D4-Pterosin B and D4-Bromopterosin, Deuterated Analogues of Ptaquiloside

et al. 2012

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Ptaquiloside (Pta) is a potent carcinogen present in bracken fern and in soil matrices, that can potentially leach to the aquatic environment. More recently its presence in the milk of different farm animals has been reported. Pterosin B (Ptb) and bromopterosin (BrPt) represent the most convenient analogues in the detection of ptaquiloside by mass spectrometry. Pterosin sesquiterpenes are also involved in many patented biomedical protocols. In this work we introduce a new and convenient approach to the synthesis in three steps and more than 80% yield of d 4 -pterosin B (d 4 -Ptb) and d 4 -bromopterosin (d 4 -BrPt), useful as internal standards in the quantification of ptaquiloside.

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Mass spectrometric analysis of ptaquiloside, the toxic sesquiterpene from bracken fern

Cited by 21 publications

References 15 publications

Bovine papillomaviruses, papillomas and cancer in cattle

Bovine papillomaviruses, papillomas and cancer in cattle

Evaluation of Cytotoxic, Genotoxic and CYP450 Enzymatic Competition Effects of Tanzanian Plant Extracts Traditionally Used for Treatment of Fungal Infections

A New Facile Synthesis of D4-Pterosin B and D4-Bromopterosin, Deuterated Analogues of Ptaquiloside

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