I have just discovered imino sugars. I can't believe I have not run across them before. I still have to learn more about them, but this is what I know so far. These molecules look very much like sugar rings. That is, they are covered with hydroxyl groups and are ring shaped. Yet, where you would expect to see the ring oxygen, there is a nitrogen in its place.
These are common in plants, one article says in tomatoes and potatoes (partlicularly nightshade plants or just plants in general, I wonder?) and "crips" (OK this is the cute British term for potato chips, which are not preciselya plant. I think it is amusing that the British author lists "potatoes, tomoatoes and crips" as if they were all different plant sources of imino sugars.)
I first was clued into the topic of imino sugars by a podcast from biotech nation. It was watered down as far as technical detail, so I had to look up more info. I was a bit annoyed by the podcast, as it went on about how wonderful it is that some of these imino sugars nonspecifically provoke the immune system. This could (they hope) be helpful in fighting tumors in cancer patients. I certainly hope they are right, but of course, inflammation (ie, an overly provoked immune system) can make metastasis more likely, and can exacerbate cancer, so it bothered me a bit. Wouldn't you want to target the immune response and make it more specific? But I do not know, I should read more.
One imino sugar has been N-alkylated to create something called meglitol, which is used in diabetes treatment. I thought at first that, based on the name, it would be like the meglitinides, which stimulate insulin secretion. But no, meglitol has a quite different structure from the meglitinides. Meglitol is an alpha-glucosidase inhibitor, that is, it prevents the digestion of starch and certain other saccharides, so I suppose you do not absorb the simple sugars. So it lowers blood sugar after eating.
A lot of these imino sugars apparently resemble the transition states of alpha-glucosidase doing its thing, so they mess with sugar metabolism in various ways. When I described this action to Tim he said with his usual flair for delicacy, "So it could be an anti-fat ass medication?" I have not heard it described as such, but again, if people can make that logical leap, we have to watch out for the usual parade of hype associated with a new natural diet aid crapola.
Now, what dose of imino sugars are we getting when we eat the plants that contain them? And what is their potency at these doses? Insignificant? Or what?
I understand many occur as glycosides, so you perhaps need active gut bateria to cut off their attached sugars to make them active?
Finally, what do they taste like? Are they bitter because of the basic nitrogen? Looking at meglitol, there is no adjacent place for nitrogen's basic electron pair to be withdrawn onto via resonance. So it looks basic to me.