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Juglon
Synonym(s)
DefinitionThis section has been translated automatically.
Phylloquinone, which is found as a 1,4-naphthoquinone derivative (see also vitamin K) mainly in the green shells and in the green leaves and nut shells of the walnut. It is present there in glycosidic form (hydrojuglon glycoside). The substance is sparingly soluble in water, but is highly soluble in ether and benzene.
OccurrenceThis section has been translated automatically.
The nut kernel of the walnut contains no juglone. In the green nut shells and in the leaves the hydrojuglon glycoside is found. Hydrojuglon glycoside is the reduced and glucose-bound form of juglon and is less reactive, non-toxic, and colorless.
The actual juglon is formed by the oxidation of hydrojuglon glycoside. The oxidized form is reactive, relatively toxic and polymerizes to a brown dye. This dye combines strongly with proteins and is difficult to remove (brownish discoloration of the hands when handling green walnuts). Juglon is also used to dye textiles.
EffectsThis section has been translated automatically.
Juglon has antibacterial, antimycotic and antiproliferative effects. Furthermore, juglon inhibits angiogenesis and, experimentally, tumor growth of various tumor types. tumor cell lines. Juglon promotes wound healing (see below chronic wound).
Note(s)This section has been translated automatically.
Name "Juglon" is composed of the generic name "Juglans" and naphthoquinone). Juglon is isomer to Lawson, the dye of the henna leaves.
LiteratureThis section has been translated automatically.
- Avcı E et al. (2016) Investigation of juglone effects on metastasis and angiogenesis in pancreatic cancer cells. Genes 588:74-78.
- Fang F et al (2015) Juglone exerts antitumor effect in ovarian cancer cells. Iran J Basic Med Sci 18:544-548.
- Wahedi HM et al. (2016) Juglone ameliorates skin wound healing by promoting skin cell migration through Rac1/Cdc42/PAK pathway. Wound Repair Rain 24:786-794.
- Wang J et al (2016) Antibacterial Activity of Juglone against Staphylococcus aureus: From Apparent to Proteomic. Int J Mol Sci 17(6). doi: 10.3390/ijms17060965.
- Meskelevicius D et al (2016) Juglone Exerts Cytotoxic, Anti-proliferative and Anti-invasive Effects on Glioblastoma Multiforme in a Cell Culture Model. Anticancer Agents Med Chem.16:1190-1197.