Asarone - I wonder what it smells like

  • volatile aromatic ether (structure) continuously brought into this cruel, cruel world by plants of the genus Acorus, particularly Acorus calamus and Acorus gramineus, and Guatteria gaumeri, a member of the Annonaceae family
    • oil of calamus, the essential oil of Acorus calamus, contains a significant amount of asarone, and has been used as a flavouring agent in the food and pharmaceutical industries and a scent in perfumes (these days the asarone is removed first)
  • comes in alpha and beta varieties (cis-trans isomers)
  • allegedly a precursor in the synthesis of 2,4,5-trimethoxyamphetamine (TMA-2), a psychedelic analog of mescaline that is used recreationally and has been sold semi-legally for “research purposes” (hehe)
  • the alpha form has been shown to inhibit a liver enzyme called HMG-CoA reductase, lowering blood cholesterol levels and increasing bile flow
    • HMG-CoA reductase is the rate-limiting enzyme in the mevalonate pathway (by which cholesterol is ultimately produced), such that when it is inhibited, the liver reacts by increasing the amount of low density lipoprotein (along with the "bad" cholesterol it carries) that is excreted via the bile (which you poop out), thus lowering LDL-cholesterol levels
    • statins (y'know, like Lipitor) also lower LDL-cholesterol levels by inhibiting HMG-CoA reductase
  • the beta form is active against a number of annoying bacterial and fungal plant pathogens as well as certain insects
  • both forms cause liver toxicity and cancer in rodents, likely as a result of their bioactivation to a reactive metabolite, putting a wee bit of a damper on drug development
- Hasheminejad G, Caldwell J. Genotoxicity of the alkenylbenzenes alpha- and beta-asarone, myristicin and elimicin as determined by the UDS assay in cultured rat hepatocytes. Food Chem Toxicol. 1994 Mar;32(3):223-31.
- Lee JY, Lee JY, Yun BS, Hwang BK. Antifungal activity of beta-asarone from rhizomes of Acorus gramineus. J Agric Food Chem. 2004 Feb 25;52(4):776-80.
- Rodriguez-Paez L et al. Alpha-asarone inhibits HMG-CoA reductase, lowers serum
LDL-cholesterol levels and reduces biliary CSI in hypercholesterolemic rats.
Phytomedicine. 2003;10(5):397-404
- http://www.inchem.org/documents/jecfa/jecmono/v16je04.htm
- http://en.wikipedia.org/wiki/Asarone

1 chemically inspired comments:

Anonymous said...

TMA-2 is some awesome shit.

asarone smells and tastes horrible