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Getting Good Stuff from Wasted Stuff The Cole-Fort Research Group. Want to Avoid the Flu?. Southeast Asian Cooking. Star Anise. Tamiflu â An H1N1 inhibitor. Shikimic acid. Shikimic Acid is Made by All Plants and Some Bacteria.

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slide1

Getting Good Stuff from Wasted Stuff

The Cole-Fort Research Group

slide2

Want to Avoid the Flu?

Southeast

Asian

Cooking

Star Anise

Tamifluâ

An H1N1

inhibitor

Shikimic acid

slide4

Shikimic Acid is Made by All Plants and Some Bacteria

More: http://chemistry.umeche.maine.edu/CHY431/Shikimate.html

slide5

Well, trees are plants……

Pinusstrobusin front of Aubert Hall

Pinusstrobus(White Pine)

…. And Maine has a bunch of ‘em

slide7

We made conifer needle tea, and analyzed it

Agilent GC-MS System

Soxhlet extractor

slide10

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

slide11

Now, scale it up

Rotating

Digester

Filter

Chromatograph

Will it work

on kg scale?

Giant tea bag

slide12

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
slide13

OK, you’re a fat mouse, and we feed you resveratrol:

  • Insulin sensitivity increases
  • Insulin-like growth factor (IGF-1) decreases
  • Peroxisomeproliferator 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

slide15

So, we went out in the woods again, and cut down a bunch of trees, stripped the bark, and extracted it with acetone/water

slide16

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

slide20

Shikimic AcidResveratrol

NilminiVithanage (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 Genco Prof. Ray Fort

slide21

Extra:

How does

Resveratrol

Work?