Spiral Steroids: Proposed Structures for compounds isolated to >90% homogeneity
Phosphoesters with these molecular masses were isolated from bovine adrenal extracts. The mass spectrum of each one was characterized by ions at 184 Da which is characteristic of phosphocholine esters. P31 NMR confirmed the presence of a phosphate.
Trial and error analysis identified only one molecular composition consistent with the mass spectrum for both C341 and C363. We attributed C337, 339, and 361 to the addition of 2, 1 and 1 double bonds, respectively. It is possible that the molecules may be isomers of the proposed structures,
Chasalow F. A New Concept: Ionotropin May be a Factor in Mobilization for [a] Flight or Fight Response and [b] Child Birth. EC Paediatrics (2018) 7.9: 909-918.
There are three colors of highlighting. Yellow indicates that the mass spectrum is the sodium cation. The green highlights the lactone ring or the atoms that could comprise the ring. The blue highlights the 7-dehydrosterol bond. The enzyme that catalyses its reduction is defective in patients with Smith-Lemli-Opitz syndrome, suggesting that compounds with this bond reduced will not be present in normal levels.
What is the stereochemistry at carbon 5? 5a vs 5b. 5a-testosterone is synthesized by reduction of delta-4, 3- ketone to 5a, 3b-steroids. In contrast, bile acids are synthesized by reduction of delta-5-steroids to 5b-bile acids. Thus, the proposed structures have a 5b- configuration.
These compounds are the first steroid phosphocholine steroids discovered. Occam's razor suggests that the compounds are likely to be related as metabolites and products. How the phosphocholine is generated is shown Phosphorylation.
Chasalow F, Pierce-Cohen L. "Ionotropin is the mammalian digoxin-like material (DLM). It is a phosphocholine ester of a steroid with 23 carbon atoms.. Steroids. (2018) 136: 63-75.