Chem 298 - ARC Bottlebrush Project
(Callistemon citrinus)

Leptospermone: http://www.manukaoil.com/manuka_oil_low_aroma.htm
http://en.wikipedia.org/wiki/Leptospermone
flavesone, leptospermone and iso-leptospermone
: ....successfully isolated triketone (enol  form) from the leaves of a Melaleuca cajeputi species; practically odourless, this substance has a UV absorbing power comparable to any synthetic products  used in sunscreens also "presents the advantage of significantly absorbing both UVA and UVB radiations"-
US Patent 5,411,728

U.S. Pat. 4,202,840 (1980)
U.S. Pat. 4,202,685 (1980)

http://ip.com/patent/US7820209
_____________________________________________
There are 37 species of bottle brush.: http://www.anbg.gov.au/callistemon/
The photos of the bottlebrush is along Dr. R.'s driveway. They show the right species to collect, extract and chromatograph.
Bio 131 students provided verification of the taxonomic classification.

Preparative TLC and Bioassay



 

Callisto: callisto_technical_en.pdf

Common Bleaching Biochemistry / But different than triketones


____________________________________________

Tyrosine anemia, Infants and Newborn Disease
: A group of disorders which have in common elevations of tyrosine in the blood and urine secondary to an enzyme deficiency. Type I tyrosinemia features episodic weakness, self-mutilation, hepatic necrosis, renal tubular injury, and seizures and is caused by a deficiency of the enzyme fumarylacetoacetase. Type II tyrosinemia features mental retardation, painful corneal ulcers, and keratoses of the palms and plantar surfaces and is caused by a deficiency of the enzyme TYROSINE TRANSAMINASE. Type III tyrosinemia features mental retardation and is caused by a deficiency of the enzyme 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE. (Menkes, Textbook of Child Neurology, 5th ed, pp. 42-3)
( 4 Hydroxyphenylpyruvate Dioxygenase Deficiency Disease)


 
*
Christopher G. Knudsen, David L. Lee, William J. Michaely, Hsiao-Ling Chin, Nhan H, Nguyen, Ronald J. Rusay, Thomas H. Cromartie, Reed Gray, Byron H. Lake, Torquil E. M. Fraser and David Cartwright, "Discovery of the Triketone Class of HPPD Inhibiting Herbicides and Their Relationship to Naturally Occurring beta-Triketones"; Allelopathy in Ecological Agriculture and Forestry, Chapter 7, p. 101-112.  S. S. Narwal, R. E. Hoagland, R. H. Dilday and M. J. Reigosa eds.   Kluwer Academic Publishers, Dordrecht, The Netherlands, 2000.  ISBN 0-7923-6348-5

http://en.wikipedia.org/wiki/P-hydroxyphenylpyruvate_dioxygenase_inhibitor
_____________________________________________

Chemical & Engineering News
Phytochemicals: The discovery and development of the triketones