Conifers Compared to Other Sources of Shikimate 9
10 OK, we know it’s in there, now let’s get it out! Step one: Chromatograph on ion exchange resin Step two: Chromatograph on special silica gel Step three: recrystallize ~ 3% isolated yield
11 Now, scale it up Rotating Digester Giant tea bag Filter Chromatograph Will it work on kg scale?
12 Want to Live to Be 140? Start with calorie restriction (CR): Calorie restriction means a low calorie diet containing all necessary nutrients CR extends the life of C. elegans, Drosophila, mice, and some primates Good health is maintained Resveratrol Found in red wine (ng/mL) Claimed to be responsible for the “French paradox” Mimics the effect of calorie restriction
13 OK, you’re a fat mouse, and we feed you resveratrol: Insulin sensitivity increases Insulin-like growth factor (IGF-1) decreases Peroxisome proliferator increases Motor function improves Alzheimer’s peptide decreases Result: No type II diabetes Reduced risk of cancer Lower blood lipids You make the mouse Olympics More: http://chemistry.umeche.maine.edu/CHY431/Resveratrol.html
15 So, we went out in the woods again, and cut down a bunch of trees, stripped the bark, and extracted it with acetone/water
16 Why the bark? Conifers store antioxidants in the bark to guard against fungi and bark beetles Fungi use oxidative enzymes (laccase, peroxidase) to degrade bark; beetles attack partially degraded bark
20 Shikimic AcidResveratrol Nilmini Vithanage (PhD)Regan LeBlanc (MS) Alex Schaffer (REU)Melody Rhine (REU) Mark Rowe (OHS)Dustin Neidt (BS) Jess Richards (OHS)Sorel Edes (OHS) Zach Caron (OHS) Sorel Edes (OHS) Chi Truong Joe Dumont Francis and Robin Avery, Brian Perkins $$ USDA, NSF-EPSCoR, FBRI Prof. Barbara Cole Prof. Joe GencoProf. Ray Fort