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THE CHEMISTRY OF JUGLONE A DETECTIVE STORY OF UNSOLVED

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Title: THE CHEMISTRY OF JUGLONE A DETECTIVE STORY OF UNSOLVED


1
  • THE CHEMISTRY OF JUGLONE
  • A DETECTIVE STORY
  • OF
  • UNSOLVED MYSTERY

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Juglone A Natural Herbicide(Allelopath)
  • Historical Profile/Toxicity?
  • Isolation
  • Synthesis
  • Mechanism
  • Characterization
  • Recent Studies
  • Future plans
  • Acknowledgement

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JUGLONEC10H6O3
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1,4-Naphthalenedione, 5-hydroxy- Formula
C10H6O3 Molecular Weight 174.15 CAS
Registry Number 481-39-0 Chemical
Structure
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Other Names 1,4-Naphthoquinone, 5-hydroxy-
Akhnot C.I. Natural Brown 7 C.I. 75500
Iuglon Juglane Juglon Juglone Nucin
Regianin Walnut Extract Yuglon
5-Hydroxy-1,4-naphthoquinone 5-Hydroxy-1,4-naphth
osemiquinone 5-Hydroxynaphthoquinone
8-Hydroxy-1,4-naphthoquinone Jugnlon NCI 2323
Oil Red BS 1,4-Naphthoquinone, 8-hydroxy-
5-Hydroxy-1,4-naftochinon Lawsone
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Historical Profile of JugloneThe Birth of
Allelopathy (1950)
  • Toxicity of Juglone has been and continues to
    be an unsolved Problem!

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  • 1925 - Massey reported experiments showing a
    toxic effect of walnut bark on tomato plants.
  • 1927 - Schneiderhan reported killing of apple
    trees near walnuts.
  • 1950 - Davis reported that isolated Juglone
    was highly toxic when injected into alfalfa and
    tomato plants.

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  • 1940 - MacDaniels and Muenscher reported a
    3-year greenhouse study showing no toxicity by
    Juglone on tomato plants, alfalfa, and apple
    trees.
  • 1950 - USDA published a press release under the
    title Test Clears Walnut Reputation. claiming
    no evidence of any toxic effect by Juglone
    on Tomatoes. Birth of Allelopathy!

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  • 1951 - Brooks studied the controversy for 12
    years on 218 species. He confirmed Masseys
    earlier work suggesting that the toxicity
    appeared only when the roots were in
    contact with each other.
  • NOTE Dow Chemical reported that UV light was
    essential for the secretion of Juglone, which
    explained the negative toxicity reported by
    MacDaniels and Muenscher in 1940.

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  • 1975 - An extensive study at Ithaca, New York
    confirmed the toxicity of Juglone with the
    following assertions
  • Antagonism between walnut and other plants has
    been observed.
  • The substance responsible for this antagonism is
    Juglone.
  • Root to root contact must exist for toxicity to
    occur.

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  • 1999 Recent studies by Boyer at Cornell found
    the following
  • Juglone extract from unripe walnuts can cause a
    sedative effect in different species of animals.
    In one study , goldfish, mice, rats, and rabbits
    all experienced a depressant effect from the
    juglone.
  • Rabbits also experienced a rise in ear
    temperature due to vasodilation.
  • It also dilated the coronary arteries of rabbits
    heart. However, juglone does not appear to have
    any effect on the blood pressure and heart rate
    of dogs.

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  • When rats were fed juglone, an accumulation of
    abdominal fluid accompanied by proteins, a loss
    of fluid from lung tissues, and a decrease in
    plasma proteins occurred.
  • There was also an increase in plasma potassium,
    but not in plasma sodium. These findings suggest
    that juglone may increase capillary permeability.

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  • Dogs administered juglone intravenously also
    experienced fluid loss in the lungs. In addition,
    experimental dogs had an increased hematocrit and
    blood specific gravity, but a lower plasma
    specific gravity.
  • This also gives evidence that juglone is toxic to
    cell membranes, increasing capillary
    permeability.
  • Several studies have been done on horses in an
    attempt to determine whether or not juglone is
    the toxic compound in black walnuts that causes
    laminitis in horses.

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  • A juglone-ethanol solution administered to ponies
    via a stomach tube resulted in symptoms of mild
    laminitis in two of four ponies.
  • Juglone applied topically to horses' forelimbs
    resulted in increased digital pulses after 3
    hours and in increased skin temperatures after
    five hours. Laminitis and increased hoof
    temperature were not noticed.

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  • Horses receiving juglone intravenously had an
    anaphylactic type of response. Respiratory rates
    increased, fluid accumulated in the lungs, but
    the ponies did not show any signs of laminitis.
  • An anaphylactic response only occurred in ponies
    that had previously been exposed to juglone.

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  • In Summary
  • The physiological action of juglone and its
    allelopathic effects are not well understood.
  • Research has shown that juglone may alter the
    normal oxygen uptake of mitochondria and may also
    impair photosynthesis which would lead to
    decreased growth rates of the effected plants.

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Our ResearchI Isolation of Juglone
  • Isolation was done by extracting crushed hull
    with petroleum ether. Recrystallization produced
    orange needles with MP of 153-159 C

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II Synthesis of Juglone
  • Sodium dichromate in water is carefully added to
    conc. sulfuric acid. To this slurry, add
    1,5-dihydroxynaphthalene. The mixture is then
    heated to no more than 50C for thirty min. Crude
    product is recrystallized from hexane.
    Yellow-orange needles were produced with MP
    148-153C.

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III Spectral Characterization
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H-NMR Parameter
Parts Per Million Hz D (A) 7.579 D
(B) 7.601 D (C) 7.243 D (D)
11.834 J (A,B) 7.56 J (A,C) 1.19
J (A,D) 0.0 J
(B,C) 8.44 J (B,D) 0.37 J (C,D) 0.0
D (E) 6.917
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C-13 NMR Carbon Assignment Integration Parts Per
Million 1 309 190.26 2 258
184.19 3 608 161.45 4
845 139.57 5 1000
138.62 6 938 136.54 7 454
131.78 8 814 124.48 9
969 119.13 10 381
114.97
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Juglone
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Molecular Mass Fragments
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Current Goals Summer 2003
  • - Examine the allelopathy of Juglone on Tomato
    Plants
  • Decide most effective solvent
  • Decide range of effective concentrations of
    Juglone
  • Design and set-up experiment
  • Collect data
  • Test allelopathy on Space and Earth Tomatoes

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Progress
  • 1. That ethanol is the ideal solvent of choice.
  • 2. That Juglone concentrations of 5, 10, 50,
    100, and 250, 500, and 1000 µM were adequate.
  • 3. Our team of four students tried to duplicate
    their data with inconclusive results.
  • 4. Work on these goals shall resume Spring and
    Summer 2005 (any interested students?)
  • (Dr. Angie Hejl working with Mr. Sebastian Ribi,
    a graduate student from Switzerland

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Recent Studies
  • Krajci, W. M., and Lynch, D. L. (1978). The
    inhibition of various micro-organisms by crude
    walnut hull extracts and Juglone. Microbios
    Letters. 4, 175-181

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  • Craton, D. W., and Williams, R. D. (1980).
    Juglone Dermatitis Allergy or Irritant? Indiana
    Academy of Science. 90 98-102

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  • Clark, A. M., Jurgens, T. A., and Hufford, C. D.
    (1990). Antimicrobial Activity of Juglone.
    Phytotherapy Research. 4, 11-14.

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  • Galey, F. D., Whiteley, H. E., Goetz, T. E.,
    Kuenstler, A. R. Davis, C. A., and Beasley V. R.
    (1991). Black walnut (Juglans nigra) Toxicosis A
    Model for Equine Laminitis. J. Comp. Path. 104,
    313-326.

43
Acknowledgements
  • University of St. Francis (USF)
  • Kelly Wentz-Hunter (Ph.D.)
  • Sherry Litko (BS, USF)
  • Kerri Banser (BS, USF)
  • Kristina Taylor (BS, USF)
  • Brian Herbst (Senior at USF)
  • Hadyn Hollister (Senior at USF)
  • NASA Tomato Space Program

44
  • Thank you
  • Dr. Salim M. Diab
  • Professor of Chemistry
  • University of St. Francis
  • Lewis University
  • Joliet, Illinois 60435
  • sdiab_at_stfrancis.edu
  • 815-740-3855
  • 2004
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