Solution - 27.6 Steroids

In addition to fats, phospholipids, eicosanoids, and terpenoids, the lipid extracts of plants and animals also contain steroids, molecules that are derived from the triterpenoid lanosterol (FIGURE 27.7) and whose structures are based on a tetracyclic ring system. The four rings are designated $A, B, C$, and $D$, beginning at the lower left. The three 6 -membered rings ( $\mathrm{A}, \mathrm{B}$, and C ) adopt chair conformations but are prevented by their rigid geometry from undergoing the usual cyclohexane ring-flips (Section 4.6).
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Solution - 27.6 Steroids

A steroid ( $\mathrm{R}=$ various side chains)


Solution - 27.6 Steroids

Two cyclohexane rings can be joined in either a cis or a trans manner. With cis fusion to give cis-decalin, both groups at the ring-junction positions (the angular groups) are on the same side of the two rings. With trans fusion to give trans-decalin, the groups at the ring junctions are on opposite sides.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0995.jpg?height=592&width=1028&top_left_y=1382&top_left_x=538)


Solution - 27.6 Steroids

As shown in FIGURE 27.12, steroids can have either a cis or a trans fusion of the $A$ and $B$ rings, but the other ring fusions (B-C and C-D) are usually trans.


Solution - 27.6 Steroids


Solution - 27.6 Steroids

FIGURE 27.12 Steroid conformations. The three 6-membered rings have chair conformations but are unable to undergo ring-flips. The $A$ and $B$ rings can be either cis-fused or trans-fused.


Solution - 27.6 Steroids

Substituent groups on the steroid ring system can be either axial or equatorial. As with simple cyclohexanes, equatorial substitution is generally more favorable than axial substitution for steric reasons. The hydroxyl group of cholesterol, for example, has the more stable equatorial orientation.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0996.jpg?height=256&width=788&top_left_y=1246&top_left_x=278)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0996.jpg?height=277&width=730&top_left_y=1241&top_left_x=1104)


Steroid Hormones -

In humans, most steroids function as hormones, chemical messengers that are secreted by endocrine glands
and carried through the bloodstream to target tissues. There are two main classes of steroid hormones: the sex hormones, which control maturation, tissue growth, and reproduction, and the adrenocortical hormones, which regulate a variety of metabolic processes.