High Performance Liquid Chromatographic Determination of Ginkgotoxin and Ginkgotoxin‐5′‐Glucoside in<i>Ginkgo Biloba</i>Seeds

Yoshimura, Teizo; Udaka, Nobuyoshi; Morita, Junsuke; Zhang, Jinyu; Sasaki, Keiko; Kobayashi, Daisuke; Wada, Keiji; Hori, Yasushi

doi:10.1080/10826070500531466

Cited by 29 publications

(19 citation statements)

References 10 publications

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“…The MPN content showed a significant decrease in the 60 min heat treatment group at 150°C, the 45 min heat treatment group at 180°C, and the 30 min heat treatment group at 210°C (p \ 0.05), thus revealing that the MPN content decreased rapidly with increases in the heat treatment temperature. The MPN content of the control group before heat treatment reported in this study was similar to that reported by Yosimura et al [36], whose study determined the MPN content of raw GBS to be 936 nmol/g (approximately 171.4 lg/g) and 1177 nmol/g (approximately 215.6 lg/g) using HPLC. In addition, Kobayasi et al [37] reported that the MPN content of raw GBS significantly decreased in a 5 min boiled heat treatment group at 100°C and the 45 s microwave heat treatment group, respectively.…”

Section: Antioxidant Capacitiessupporting

confidence: 90%

Effects of roasting conditions on physicochemical properties and antioxidant activities in Ginkgo biloba seeds

Lim

Kim

2018

Food Sci Biotechnol

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The roasting treatment has been used to extend the shelf life of food and improves its quality, and eliminate or reduce toxic. In this study, we investigate the changes in the physicochemical properties and antioxidant activities of seeds (GBS) according to the roasting temperature and duration. As the roasting temperature and duration increased, the pH (from 7.32 to 6.31) and total cyanide content (from 1.49 to 0.70 µg/g) decreased, whereas the titratable acidity (from 0.39 to 0.84%) increased. The antioxidant activities increased rapidly at 210 °C according to the increase in the roasting temperature and duration. The 4'--methylpyridoxine (MPN) content in the 210 °C heat treatment group decreased by more than 70% compared to the MPN content in the control group. These results suggest that heat-treated GBS could be used in food materials and medicines for decreasing cyanide and MPN contents as well as for increasing antioxidant compound contents.

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Section: Antioxidant Capacitiessupporting

confidence: 90%

Effects of roasting conditions on physicochemical properties and antioxidant activities in Ginkgo biloba seeds

Lim

Kim

2018

Food Sci Biotechnol

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“…In negative ion, example is [Mg+3Fm] - . Isotope pattern consistent with Mg.2Choline (67-48-1)C 5 H 14 N 1 O 1 RT, UV and MS/MS spectra consistent with authentic standard.3Trigonelline (6138-41-6)C 7 H 7 N 1 O 2 RT, UV and MS/MS spectra consistent with authentic standard.L-Proline (147-85-3)C 5 H 9 N 1 O 2 RT, UV and MS/MS spectra consistent with authentic standard.L-Valine (72-18-4)C 5 H 11 N 1 O 2 RT, UV and MS/MS spectra consistent with authentic standard.Mannitol (69-65-8)C 6 H 14 O 6 RT, UV and MS/MS spectra consistent with authentic standard.Quinic Acid (77-95-2)C 7 H 12 O 6 RT, UV and MS/MS spectra consistent with authentic standard.4Ginkgotoxin-5-O-glucoside (323579-25-5)C 15 H 23 N 1 O 8 MS/MS indicates hexose and is consistent with structure [20]. UnknownC 7 H 12 O 5 Unknown, but probably similar to Quinic acid (less oxygen).5Protocatechuic Acid (99-50-3)C 7 H 6 O 4 RT, UV and MS/MS spectra consistent with authentic standard.6Xanthurenic Acid (59-00-7)C 10 H 7 N 1 O 4 RT, UV and MS/MS spectra consistent with authentic standard.7UnknownC 16 H 24 O 9 Observed as [M+NH 4 ] + in positive ion mode and [M+ Formate] - in negative ion mode.L-Tryptophan (73-22-3)C 11 H 12 N 2 O 2 RT, UV and MS/MS spectra consistent with authentic standard.8Caffeine (58-08-2)C 8 H 10 N 4 O 2 RT, UV and MS/MS spectra consistent with authentic standard.9Gallocatechin (3371-27-5)C 15 H 14 O 7 RT, UV and MS/MS spectra consistent with authentic standard.Hydroxy-benzaldehydeC 7 H 6 O 2 MS/MS spectrum suggests Hydroxybenzaldehyde10Vanillic Acid (121-34-6)C 8 H 8 O 4 RT, UV and MS/MS spectra consistent with authentic standard.Esculetin (305-01-1)C 9 H 6 O 4 RT, UV and MS/MS spectra consistent with authentic standard.Catechin (7295-85-4)C 15 H 14 O 6 RT, UV and MS/MS spectra consistent with authentic standard.Salicylic Acid (69-72-7)C 7 H 6 O 3 RT, UV and MS/MS spectra consistent with authentic standard.Quercetin with 2 glucose and 1 rhamnoseC 39 H 50 O 25 MS/MS shows losses of glucose and rhamnose.11UnknownC 19 H 28 O 11 Observed as [M+NH 4 ] + in positive ion mode and [M+ Formate] - in ...…”

Section: Resultsmentioning

confidence: 73%

“… Quinic Acid (77-95-2) C 7 H 12 O 6 RT, UV and MS/MS spectra consistent with authentic standard. 4 Ginkgotoxin-5-O-glucoside (323579-25-5) C 15 H 23 N 1 O 8 MS/MS indicates hexose and is consistent with structure [ 20 ]. Unknown C 7 H 12 O 5 Unknown, but probably similar to Quinic acid (less oxygen).…”

Section: Resultsmentioning

confidence: 99%

A multi-detector chromatographic approach for characterization and quantitation of botanical constituents to enable in silico safety assessments

Baker

Regg

2018

Anal Bioanal Chem

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An approach has been developed to characterize the individual chemical constituents of botanicals. The challenge was to identify and quantitate the significant analytes in these complex mixtures, largely in the absence of authentic standards. The data-rich information content generated by this three-detector configuration was specifically intended to be used to conduct safety and/or quality evaluations for complex botanical mixtures, on a chemical constituent basis. The approach utilized a broad gradient UHPLC chromatographic separation. Following the chromatographic separation and UV detection, the eluent was split and sent into a charged aerosol detector (CAD), for quantitation, and a quadrupole/time-of-flight high-resolution mass spectrometer for component identification. The known bias of the otherwise universal CAD response, for organic solvent composition of the mobile phase, was compensated by the addition of an inverse gradient make-up stream. This approach and the orthogonal information content from the chromatography and three different detectors was specifically designed to enable in-silico safety assessments. These guide, minimize, or even eliminate the need for in vivo and in vitro safety assessments. The methodology was developed and demonstrated using standardized extracts of Ginkgo biloba. Results from the development of this novel approach and the characterization example reported here demonstrate the suitability of this instrumental configuration for enabling in-silico safety assessments and proving general quality assessments of botanicals.Electronic supplementary materialThe online version of this article (10.1007/s00216-018-1163-y) contains supplementary material, which is available to authorized users.

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“…MPN 並びにその配糖体に関する検討， 11,12) 2)MPN による生体内ビタミン B 6 濃度への影響， 13) 3)銀杏中毒の症例に関する情報を報告した． 14 18) 本稿では，これらの報告に加えて，現在までの銀杏中毒研究について海外での研究も含めて，紹介する． 2. 銀杏中に含まれる MPN 並びにその配糖体の毒性当初銀杏中毒の原因物質は，青酸配糖体であるとみなされていたが，銀杏中に青酸配糖体が存在しないという報告も存在した． 19,20) 1985 年に Wada らは，モルモットを使ったけいれん誘発試験により，中毒成分の分離を行い，銀杏中毒原因物質 MPN の単離に成功した． 7,8) Inserted numbers mean onset time (min) of convulsions after administration of MPN.…”

Section: 筆者らの研究グループは，1)銀杏中に含まれるunclassified

Food Poisoning by Ginkgo Seeds through Vitamin B<sub>6</sub> Depletion

Kobayashi

2019

YAKUGAKU ZASSHI

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Overconsumption of Ginkgo biloba seeds induces food poisoning characterized by tonic-clonic convulsions and vomiting. The primary toxic component, 4′-O-methylpyridoxine (MPN), was puriˆed from the seeds in 1985. This review includes the following aspects of ginkgo seed poisoning: 1) toxicity related to the content of MPN and MPN glucoside in G. biloba seeds; 2) the eŠect of MPN on vitamin B 6 analogs, including an increase in pyridoxal and pyridoxic acid and decrease in pyridoxal-5′-phosphate plasma concentrations; 3) case reports of ginkgo seed poisoning in Asia, North America, and Europe, and their eŠective treatment via vitamin B 6 administration. Considering the increase in the use of G. biloba seeds, it is essential to raise global awareness of their potential toxicity.

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High Performance Liquid Chromatographic Determination of Ginkgotoxin and Ginkgotoxin‐5′‐Glucoside inGinkgo BilobaSeeds

Cited by 29 publications

References 10 publications

Effects of roasting conditions on physicochemical properties and antioxidant activities in Ginkgo biloba seeds

Effects of roasting conditions on physicochemical properties and antioxidant activities in Ginkgo biloba seeds

A multi-detector chromatographic approach for characterization and quantitation of botanical constituents to enable in silico safety assessments

Food Poisoning by Ginkgo Seeds through Vitamin B<sub>6</sub> Depletion

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