Ready for some #PenAndInkPoison?
For some reason, I like the poisons in our food. I should clarify: I like the poisons *nature* puts in our food. We all gotta eat, right?
So buckle up for a 🧵, for today I present you with something new: BONGKREKIC ACID Chemical structure of bongkrekic acid and a purple Narwhal f
Have you ever had tempeh? It's an Indonesian food made from fermented soybeans. Tempeh is sold as a very firm cake and has a wonderful nutty, earthy flavor. It's common in vegetarian and vegan cooking. I like it a lot. [FoodCraftLab (CC BY-SA-2.0)] stacked cakes of tempeh
So tempeh is a common, staple food, made from soybeans. On the island of Java, however, is a type of tempeh made from coconut called tempeh bongkrek. And it can be toxic. Toxic tempeh. A pile of tempeh bonkrek on a plate. It does not look appeti
To make it, coconut is fermented with the fungus Rhizopus oligosporus. The fungus forms fluffy white mycelia strands that bind everything together to make the cake firm. The more mycelia, the better the tempeh. The fungus is the white stuff on the tempeh - don't tell my kids.
So far, so good. The problem with tempeh bongkrek is that the concoction is susceptible to Burkholderia cocovenenans, an aerobic gram-negative bacteria. In plants, it can cause rot, and in humans, it can severely sicken.
Illness in humans is due to bongkrekic acid, a chemical produced by the bacteria. Eating tempeh bongrek infected with B. cocovenenans can cause gastrointestinal pain, fatigue, coma, and in severe cases, death. Symptoms start within hours, and death can occur within 24 hours.
Clinically, there is an initial HYPERglycemia as your body uses all of its glycogen stores, followed by HYPOglycemia when it's all used up. In short, glycogen is a long-term storage of energy (along with fat), and our body is now running on empty.
How does this happen? You've heard of adenosine triphosphate (ATP), our "energy currency" made in the mitochondria of our cells? Bongkrekic acid is an adenine nucleotide translocase inhibitor and an inhibitor of oxidative phosphorylation in the mitochondria. In English, please?
When our cells use ATP energy, the byproduct is adenosine diphosphate (ADP). Bonkgrekic acid blocks the transport of ADP back into the mitochondria so it can be transformed (phosphorylated) back into ATP. Now our cells have no fuel, which is why we went with the backup, glycogen.
Even simpler: Think of the mitochondria as a gas station. Bongkrekic acid isn't blowing up the gas station, rather it is flattening the tires of the tanker trucks that fill it up. Without fuel, our bodies shut down and die.
And poisoning due to toxic tempeh bongrek can be serious. In Indonesia between 1951 and 1975, there was an average of 288 poisonings and 34 deaths *a year*. Because of this, Indonesia banned the manufacturing and sale of tempeh bongkrek.
But we all know how well prohibition works out. Tempeh bongkrek is popular and cheap, so it is still made in clandestine kitchens. You can imagine the results - poisonings still occur.
Now, you're probably wondering why we don't see this infection in regular tempeh. It happens that B. cocovenenans (and thus bongkrekic acid formation) thrives in the high-fat environment of coconuts, and doesn't care for the relatively lower fat soybeans.
So that's the story of toxic tempeh and BONGKREKIC ACID, the bacterial toxin that shuts down our gas stations and forces us to use up all of our secondary energy stores, resulting in fatigue, coma, and death.
BONUS: For an awesome tempeh recipe, one we all enjoy - including the three girls - check out this recipe from 101 Cookbooks: 101cookbooks.com/tlt-sandwich/

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More from @NaturesPoisons

Mar 15
Yesterday I mentioned PRACTICAL MAGIC and one of my favorite poisoning tales, and it's been a few years and 5K followers since I last posted it, so I thought I'd re-up it. So settle in for a murder gone wrong and "Justin's Three Rules of Murder." A long 🧵. Image
I ❤️ Sandra Bullock. And I ❤️PRACTICAL MAGIC. It's a classic tale of "Girl meets boy, boy is an abusive serial killer who kidnaps the girl and her sister, sister poisons bad boy’s tequila with belladonna, bad boy dies. Throw in some magic for good measure." We’ve all been there. Image
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Mar 4
For some #PenAndInkPoison today I want to talk about thebaine, mentioned briefly yesterday when discussing laudanosine and papaverine. Morphine gets all the glory as an opium poppy alkaloid, but I'd argue that thebaine is much, much more important.
Thebaine is not used therapeutically but is used commercially in the synthesis of some of the most important opioids we have on the market today. In anywhere from 2 to 8 steps you can produce all of the opioids shown below - there are more, but these are the important ones.
On the right, we have the opioid agonists oxycodone, oxymorphone, hydrocodone, and hydromorphone. Hydrocodone is the most frequently prescribed opioid analgesic (pain reliever) in the U.S. We all know about oxycodone (Oxycontin). And hydromorphone is used a ton in hospitals.
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Mar 3
It's Thursday! I hate Thursdays, it's a cruel reminder that it's not yet Friday. To help us feel better, let's look at how the world of nature's poisons can intersect with postmortem forensic toxicology. I present to you LAUDANSOSINE and PAPAVERINE.
Laudanosine and papaverine are minor alkaloids found in the opium poppy (Papaver somniferum), but they don't get near the attention of the heavy-hitter opiate morphine, which is made (rather simply) into heroin. Other alkaloids found in opium poppy are codeine and thebaine.
Laudanosine sounds very similar to laudanum, the opium tincture that was common in the 1800s. It was ~10% opium alkaloids, and when drunk, had the same effects of opiates/opioids today, like euphoria, but also the same side effects, namely respiratory depression and dependence.
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Mar 2
Do you need a break? Are y'all up for a quick Pen & Ink Poison? This magnificent beast is Brevetoxin-1. I love all the polycyclic ethers and the fact that it has 5, 6, 7, 8, and 9-membered rings. But as lovely as she is, she's quite harmful, both physically and economically. Image
There are about a dozen structurally similar brevetoxins that are produced by the dinoflagellate (a.k.a. algae) Karenia brevis. This algae is responsible for the "red tides" along the Gulf Coast in states like Florida.
"Red tides" are harmful algal blooms (HABs), and the name is a bit of a misnomer because not all infected water is "red" and not associated with tides. But I digress. HABs due to Karenia brevis will shut down beaches and cause people to flee. Image
Read 12 tweets
Mar 1
It's ToxTuesday. I know we could use a little breather from *all this*, so let's take a look at a scary toxin, ORELLANINE, and admire another pretty @twsbi pen. (If you want to sponsor me, TWSBI, hit me up! 😅)
Orellanine is a mycotoxin, a toxin produced by fungi. Specifically, it is found in Cortinarius orellanus and Cortinarius rubellus, commonly known as "fools webcap" and "deadly webcap" mushrooms.
Pro tip: Don't eat things with "deadly" in their name.
Ingestion of these mushrooms is a horrible idea because orellanine is nephrotoxic - it destroys your kidneys. Absolutely ravages them. The exact mechanism of toxicity is unclear, but it could be due to interfering with redox reactions in the cell and increasing oxidative stress.
Read 12 tweets
Feb 22
It's ToxTuesday and we're going to talk about nicotine. I know what you're thinking, "nicotine poisoning isn't sexy," but I'm here to change your mind. So I present to you Green Tobacco Sickness. Image
North Carolina, and Durham, was founded on tobacco. There was huge money in tobacco, but even though the industry is in decline, it's still important to NC with revenue of ~$1B/yr. As an aside, the Durham Bulls were originally named the Tobacconists in 1902 (cc @stephaniekays). Image
Downtown Durham is full of abandoned tobacco warehouses, in the process of being turned into trendy overpriced "urban lofts." But drive five miles north, and you'll still see small tobacco farms. Image
Read 12 tweets

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