Conceptual Paper
Volume 9 Issue 4 - 2020
An Introduction to Spiral Steroids
Fred Chasalow1,2*
1Managing Partner, IOMA LLC, CA, USA
2Visiting Professor, Department of Laboratory Medicine, VAMC, San Francisco, CA, USA
*Corresponding Author: Fred Chasalow, Managing Partner, IOMA LLC, CA, USA.
Received: March 06, 2020; Published: March 20, 2020




Keywords: DLM; Ionotropin; Spiral Steroids; Orphan Ligands; Phosphocholine Steroid Conjugates

Abbreviations

DLM: Digoxin-Like Materials; RIA: Radioimmunoassay; K+: Potassium; Na+: Sodium; MBG: Marinobufagenin; NMR: Nuclear Magnetic Resonance; MS: Mass Spectrometry; PC: Phosphocholine; DHT: 5α-Dihydrotestosterone

An introduction to spiral steroids 

What are spiral steroids: Spiral steroids have several unusual structural features: two of the four valences of carbon 17 form part of Ring D while the other two valences form Ring E (See figure 1). Thus, carbon 17 is part of both rings. None of the common endogenous steroids have a spiral structure. The four rings (A, B, C and D) of most steroids form a plane (more or less) with axial methyl groups sticking up. In contrast, although Ring E is also planar, the plane is perpendicular to ABCD plane. Finally, when the Δ5-6 alkene is reduced, the stereochemistry must be 5β. In contrast, when testosterone is reduced, the product is 5α-dihydrotestosterone (DHT). The enzyme that catalyzes the reduction requires the substrate to be a Δ4-3-ketone. The spiral steroids are all 3-phosphoesters and would not be substrates for the 5α-reductase. A separate reductase enzyme is used for synthesis of bile acids such as cholic acid. This enzyme doesn’t require Δ4-3-ketone substrates but forms 5β-products. This difference is significant because, despite the huge concentrations of the PC-steroids, the difference would be expected to prevent binding to the nuclear receptors for the classical steroids.

References

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  17. Chasalow F. “A new concept for the regulation of electrolytes in pregnancy: the role of Ionotropin: The endogenous potassium sparing hormone”. EC Paediatrics 7.6 (2018): 527-532. 
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Citation: Fred Chasalow. “An Introduction to Spiral Steroids”. EC Paediatrics 9.4 (2020): 83-87.

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