Juglone

Juglone
Names
IUPAC name
5-Hydroxy-1,4-naphthalenedione
Other names
5-Hydroxy-1,4-naphthoquinone
5-Hydroxy-p-naphthoquinone
Regianin, 5-hydroxynaphthoquinone, Nucin, NCI 2323, Oil Red BS
Identifiers
481-39-0 YesY
ChemSpider 3674 N
Jmol interactive 3D Image
PubChem 3806
RTECS number QJ5775000
UNII W6Q80SK9L6 YesY
Properties
C10H6O3
Molar mass 174.16 g·mol−1
Appearance Yellow solid
Melting point 162 to 163 °C (324 to 325 °F; 435 to 436 K)
Slightly sol.
Hazards
R-phrases R25
S-phrases S28 S45
Related compounds
Related compounds
 quinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is an organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble in dioxane, from which it crystallizes as yellow needles.[1] It is an isomer of lawsone, which is the staining compound in the henna leaf.

Juglone occurs naturally in the leaves, roots, husks, fruit (the epicarp), and bark of plants in the Juglandaceae family, particularly the black walnut (Juglans nigra), and is toxic or growth-stunting to many types of plants.[2] It is sometimes used as a herbicide, as a dye for cloth and inks, and as a coloring agent for foods and cosmetics.

History

The harmful effects of walnut trees on other plants have been observed for at least two millennia. The ancient civilizations of Greece and Rome used the walnut for its cytotoxic properties as did residents of the American South for easily gathering fish when they threw cut husks into the water with the fish.[3] However, juglone was not isolated until the 1850s. Two men, A. Vogel Jr. and C. Reischauer, were able to isolate the compound from the walnut tree in 1851. The compound was known as nucin at that time. Juglone was then synthesized and characterized for the first time in 1887 by A. Bernthsen and A. Semper. It was not until 1928 the compound was identified and confirmed to be toxic to other plants by E.F. Davis.

The use of walnut tree has historically been used within the field of traditional medicine. In America during the early 1900s, doctors prescribed juglone for the treatment of various skin diseases.[4]

Chemistry and synthesis

Juglone is derived by oxidation of 1,5-dihydroxynaphthalene.[5] It can be also be obtained by oxidations of 5,8-dihydroxy-1-tetralone with silver oxide (Ag2O), manganese dioxide (MnO2), or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).[1]

The spectral data for juglone confirms its bicylic structure which contains a hydroxyl group as well as two carbonyl groups. The IR for juglone shows peaks at 3400 cm-1, 1662 cm-1, and 1641 cm-1 which are characteristic of the hydroxyl and carbonyl groups.[6] The 13C NMR shows 10 peaks indicating the correct number of unique carbon atoms in the molecule as well as peaks at 160.6 ppm, 183.2 ppm, and 189.3 ppm for the carbon attached to the hydroxyl group and the two carbons part of the two carbonyl groups.[6]

Biological effects

Juglone is an example of allelopathic compound, a substance that is produced by a plant to stunt the growth of another. Landscapers have long known that gardening underneath or near black walnut trees can be difficult. Juglone exerts its effect by inhibiting certain enzymes needed for metabolic function. A number of plants and trees are resistant to juglone including some species of maple (Acer), birch (Betula), and beech (Fagus).

It is highly toxic to many insect herbivores. Some of them, however, are capable of detoxification of juglone (and related naphthoquinones) to non-toxic 1,4,5-trihydroxynaphthalene. It has also shown anthelmintic (expelling parasitic worms) activity on mature and immature Hymenolepis nana in mice.[7] Napthoquinonic compounds also exhibit antimicrobial activity.[8][9][10]

Uses

Juglone is occasionally used as a herbicide. Traditionally, juglone has been used as a natural dye for clothing and fabrics, particularly wool, and as ink. Because of its tendency to create dark orange-brown stains, juglone has also found use as a coloring agent for foods and cosmetics, such as hair dyes.

Juglone is currently being studied for its anticancer properties. http://en.cnki.com.cn/Article_en/CJFDTOTAL-SLYY200902008.htm "[Effect of juglone on the ultrastructure of human liver cancer BEL-7402 cells].". Nan Fang Yi Ke Da Xue Xue Bao 29 (6): 1208–11. Jun 2009. PMID 19726363.  http://xuebao.jlu.edu.cn/yxb/EN/abstract/abstract4445.shtml One of the potential pathways through which juglone achieves its anticancer properties is through the formation of the semiquinone radical; the semiquinone radical causes superoxide anion radicals to form which can lead to apoptosis when present in large concentrations.[11] This conversion from juglone to semiquinone radical that causes the superoxide anion radical to form takes place in the mitochondria as well as the cystol.[12]

References

  1. 1 2 J. Khalafy and J.M. Bruce (2002). "Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones". Journal of Sciences, Islamic Republic of Iran 13 (2): 131–139.
  2. ↑ Juglone toxicity
  3. ↑ Soderquist, C.J. Juglone and Allelopathy. J. Chem. Educ. 1973, 50, 782-783. doi:10.1021/ed050p782
  4. ↑ M. Strugstad (2012). "A Summary of Extraction, Synthesis, Properties, and Potential Uses of Juglone: A Literature Review". Journal of Ecosystems and Management 13 (3): 72–82.
  5. ↑ Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.
  6. 1 2 Suchard, O.; Kane, R.; Roe, B. J.; Zimmermann, E.; Jung, C.; Waske, P. A.; Mattay, J.; Oelgemöller, M. Photooxygenations of 1-naphthols: an environmentally friendly access to 1, 4 naphthoquinones. Tetrahedron. 2006, 62, 1467-1473. doi:10.1016/j.tet.2005.11.021
  7. ↑ Dama L.B. and Jadhav B.V. (1997). "Anthelmintic effect of Juglone on mature and Immature Hymenolepis nana in mice". Riv. Di Parassitol. 2: 301–302.
  8. ↑ Dama L.B., Poul B.N. and Jadhav B.V. (1998). "Antimicrobial activity of Napthoquinonic compounds". J. Ecotoxicol.Environ. Monit. 8: 213–215.
  9. ↑ Dama L.B., Poul B.N., Jadhav B.V and Hafeez MD. (1999). "Effect of "Juglone" on Development of the plant parasitic nematode (Meloidogyne Spp.) on Arachis hypogaea L.". J. Ecotoxicol. Environ. Monit. 9: 73–75.
  10. ↑ Dama L.B. (2002). "Effect of naturally occurring napthoquinones on root- knot nematode Meloidogyne spp.". Indian Phytopathology 55 (1): 67–69.
  11. ↑ Ji Yu-Bin, Y.B.; Qu, Z.Y.; Zou, X. Juglone-induced apoptosis in human gastric cancer SGC-7901 cells via the mitochondrial pathway. Exp. Toxicol. Pathol. 2011, 63, 69-78. doi:10.1016/j.etp.2009.09.010
  12. ↑ Inbaraj, J.J.; Chignell, C.F. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem. Res. Toxicol. 2004, 17, 55-62. doi:10.1021/tx034132s
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