Ginkgotoxin

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Ginkgotoxin
Names
Preferred IUPAC name
5-(Hydroxymethyl)-4-(methoxymethyl)-2-methylpyridin-3-ol
Other names
4'-O-methylpyridoxine; 4-O-methylpyridoxine
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C9H13NO3/c1-6-9(12)8(5-13-2)7(4-11)3-10-6/h3,11-12H,4-5H2,1-2H3 checkY
    Key: SVINQHQHARVZFF-UHFFFAOYSA-N checkY
  • Oc1c(c(cnc1C)CO)COC
Properties
C9H13NO3
Molar mass 183.207 g·mol−1
Hazards
GHS labelling:
GHS06: Toxic
Danger
H300, H330
P260, P264, P270, P271, P284, P301+P310, P304+P340, P310, P320, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Ginkgotoxin (4'-O-methylpyridoxine) is a

epileptic seizures
.

Occurrence

Seeds and phytopharmaceuticals derived from the plant Ginkgo biloba are

alcohol use disorder.[1]

Ginkgotoxin is found in the seeds and, in lesser amounts, in the leaves of Ginkgo biloba. The seeds can be consumed as is and the leaves can be used to prepare the dietary supplements. Analyses of raw seeds from eight different location in Japan by

seasonal variation of ginkgotoxin concentration in the seeds. The maximum has been observed in August.[3] Analyses of the powder of Ginkgo biloba capsules revealed the presence of ginkgotoxin. However, as most supplements are made from the leaves, which contain only small amounts of ginkgotoxin, below the level of toxicological relevance, no threat is thought to be posed to consumers.[citation needed
]

Ginkgotoxin-5'-glucoside is a derivative of ginkgotoxin that possesses a

glycosidic linkage is possible. Nevertheless, the toxicity
of the mechanism of action glucoside form is not fully understood.

Ginkgotoxin can also be found in other plants of the genus Albizia.[3] However, these plants have no known dietary use for humans, so their production of ginkgotoxin is of lesser concern.

Biosynthesis

Ginkgotoxin is the 4'-O-methyl derivative of vitamin B6 (

Pdx1 and Pdx2, and form pyridoxal phosphate. The second step is hypothetical and consists of the removal of a hydride in the presence of a dehydrogenase to produce pyridoxine. The last step involves the O-methylation of pyridoxine to form 4'-O-methylpyridoxine (ginkgotoxin).[1]

Toxicity

A few cases reported poisoning from commercially available products. The consumption of seeds represent a greater concern. Overconsumption of Ginkgo biloba seeds, especially by children, can result in

convulsions, and death.[4]

Ginkgotoxin is structurally related to vitamin B6. It is suspected that ginkgotoxin interferes with the synthesis of the vitamin by decreasing the activity of

epileptic seizures.[6]
The toxicity of ginkgotoxin consequently can be relieved by taking vitamin B6 supplements.

References

  1. ^
    PMID 20041670
    .
  2. PMID 19195661
    .
  3. ^
    PMID 11128132
    .
  4. ^
    doi:10.1080/10826070500531466
    .
  5. PMID 10691705
    .
  6. ^
    PMID 17250738
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Ginkgotoxin&oldid=1183908424"