Monday, September 16, 2013

And now for something completely different: Chris McCandless, lathyrism and HPLC

If you've ever read Jon Krakauer's book Into the Wild (I have not), you may be interested in this story. Even if you haven't, it's probably worth your time. Krakauer's book is about Chris McCandless, a young man who became a bit of a wanderer in the American West. He ultimately died in Alaska of what was, until recently, believed to be starvation. But Krakauer recently published a blog post noting a fascinating story of chemistry and chemists that might explain why he actually died:
After Hamilton read “Into the Wild” and became convinced that ODAP (CJ's note: beta-N-oxalyl-L-alpha-beta diaminoproprionic acid) was responsible for McCandless’s sad end, he approached Dr. Jonathan Southard, the assistant chair of the chemistry department at Indiana University of Pennsylvania, and persuaded Southard to have one of his students, Wendy Gruber, test the seeds of both Hedysarum alpinum and Hedysarum mackenzii for ODAP. Upon completion of her tests, in 2004, Gruber determined that ODAP appeared to be present in both species of Hedysarum, but her results were less than conclusive. “To be able to say that ODAP is definitely present in the seeds,” she reported, “we would need to use another dimension of analysis, probably by H.P.L.C.-M.S.”—high-pressure liquid chromatography. But Gruber possessed neither the expertise nor the resources to analyze the seeds with H.P.L.C., so Hamilton’s hypothesis remained unproven.
Read the whole thing, for a fascinating story of 3 different teams of chemists (academic and industrial!), TLC, natural products, botany and HPLC.

12 comments:

  1. the comment section on that page is full of some really strong opinions. i guess the author of Into The Wild has presented a few wrong hypotheses before this about what killed the book's subject, and some people are displeased with what they perceived to be a positive depiction of the kid's life choices.

    in any case finding ODAP in those seeds and linking to the concentration camp case makes for an interesting enough read

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  2. I was reading another thrilling book from Krakauer - "Into the wild", about two doomed Mt. Everest commercial summit parties. (Lots of people did not make it back including the guides). He was a paying member of one of the team. His account is apparently less than accurate - some other survivors never spoke to him again after he published it because he was rather too quick to assign blame to everyone but himself.

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    1. The name of Krakauer book should have been "Into thin air", sorry for the typo

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    2. But the ODAP poisoning theory sounds very plausible. There are nasty related toxic aminoacids as plant toxins: beta-methylaminoalanin (BMAA) and mimosine (aka leucenol)

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    3. Into Thin Air is a great read. No matter who gets the blame (another guide published an account of the same Everest trip) but it does give compelling evidence that there are probably too many people with too little experience climbing Everest.

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    4. yeah into thin air is a very good book. I think you get the sense of the tunnel vision, isolation and consequent subjective experience of climbing everest, which turns into a disaster of course. Krakauer is accused mainly in this book of changing the facts to defend his position of letting another party member descend unaided, ultimately to his death. He claims he mistook the identity of the individual due to his extreme exhaustion - as i recall he mistook him for a guide, and let him go, assuming he was returning to base camp. The widow took great exception to this part of the book and claimed krakauer made up the mistaken identity story to defend his actions.

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  3. One thing I love about the article by Krakauer is it is probably the first time I've seen an account of how chemists actually do work. As CJ said, it was 3 different teams of chemists + serendipity of finding the account of the Holocaust experimentation.

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  4. Fans really go to great lengths to prove that McCandless was some messianic hero thwarted by an insidious plot or cosmic conspiracy instead of a naive kid who had no business going "into the wild" and died because of his poor choices. Around here people die in the wilderness on a regular basis because they were unprepared. However, their unfortunate exploits don't have the romance, poetry or the Eddie Vedder soundtrack to glamorize it. They just meet an ignominious end without much fanfare and serve as reminders for the rest of us to be prepared.

    That said, Krakauer can sure spin a good yarn.

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    1. Tim Treadwell aka grizzly man got himself and his girlfriend eaten by a bear; the old bear had to be shot afterwards because it got used to eating people. Treadwell turned on a camera as he was attacked at night and left behind a gruesome sound recording, the sounds of the two of them getting eaten by a bear. So McCandless demise is not so terrible by comparison.

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    2. I think Krakauer makes it pretty clear that McCandless died because of poor choices. After all, he was 3 miles from a fully functioning bridge that would have saved him in the spring. He also very clearly raises the question of Krakauers suicidal actions - but leaves the question hanging. What Krakauer has been trying to do is to elicit the truth of his death, and if it changes botanical knowledge of poisonous plants, then so be it for the better. Maybe he has glamorized his death somewhat, but I dont think you are left feeling like McCandless is some kind of robin hood. Clearly the guy had issues - like tim treadwell.

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    3. "Krakauers suicidal actions " - I meant "McCandless' suicidal actions" of course

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  5. Even before he ate the seeds, he was starving. The seeds had never been known to poison anyone before. But McCandless was starving and vulnerable. Perhaps the ODAP pushed him over the edge, in the absence of other food. Didn't Paracelsus say something about dose and poison once? It's pretty well argued here that he died of starvation. He consistently failed to eat enough to survive, every day, for 4 months. Check out the argument here, which I find reasonably convincing:

    http://foragersharvest.com/into-the-wild-and-other-poisonous-plant-fables/

    It sure seems reasonable to me.

    The crux of the argument is that life in Alaska is HARD. It's not the jungle. There's not that much energy available for photosynthesis, and hence high-energy plants are not found. And even the food that nearly all humans eat today is not 'natural' - we eat crops that have been carefully bred to produce dense, high-calorie seeds, fruits, and tubers. We eat meat, some of us, from animals that have been bred to store lots of fat in their tissues. Even a poor starving Irish laborer back in the day, with nothing to eat but potatoes, would need to eat a couple pounds of them a day. And the potato is something people invented and bred, for the purpose of having lots of calories (and even healthy vitamin C!) on hand. There's nothing like the humble potato just hanging around in the taiga.

    So poor Chris McCandless didn't need to eat a few berries and a (lean, nondomesticated) small animal every day. He needed to eat pounds of berries and roots every day, or eat 10 or 15 small critters. And he couldn't just sit down and much, say, 5 pounds of blueberries or else he'd find the mass indigestable - he'd need a variety every day. It would be HARD to survive by foraging in the Alaskan taiga. It's not the Edenic jungle we evolved in.

    Every animal there is either capable of digesting cellulose, or it's largely carnivorous. Even people - the native Alaskans lived mostly off of fish and game. But Chris McCandless doesn't seem to have been that great of a hunter.

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