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Getting Good Stuff from Wasted Stuff The Cole-Fort Research Group 1.

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Presentation on theme: "Getting Good Stuff from Wasted Stuff The Cole-Fort Research Group 1."— Presentation transcript:

1 Getting Good Stuff from Wasted Stuff The Cole-Fort Research Group 1

2 Want to Avoid the Flu? Southeast Asian Cooking Shikimic acid Tamiflu  An H1N1 inhibitor Star Anise 2

3 3

4 Shikimic Acid is Made by All Plants and Some Bacteria 4 More:

5 Well, trees are plants…… Pinus strobus (White Pine) Pinus strobus in front of Aubert Hall …. And Maine has a bunch of ‘em 5

6 6 So we went needle collecting in the University Forest north of campus

7 We made conifer needle tea, and analyzed it Soxhlet extractor Agilent GC-MS System 7

8 Some of Our Analytical Results 8

9 Conifers Compared to Other Sources of Shikimate 9

10 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 11 Now, scale it up Rotating Digester Giant tea bag Filter Chromatograph Will it work on kg scale?

12 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 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:

14 14 Resveratrol is Made by Many Plants

15 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 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

17 17

18 18 Source Resveratrol,  g/g Norway spruce567 Black Spruce439 White spruce382 Eastern White Pine7.1 Japanese knotweed523 Grape skins32.5 Low bush blueberries12.8 Heirloom tomatoes1.8 Unsweetened chocolate1.24 Quantitation by HPLC-MS, GC-MS, SIM

19 19 Tons of bark are burned by mills every day!

20 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

21 21 Extra: How does Resveratrol Work?

22 22 Extra: How Does Resveratrol Work?

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