Organic Synthesis of New Secosteroids from Fucosterol, Its Intestinal Absorption by Caco-2 Cells, and Simulation of the Biological Activities of Vitamin D
Shiro Komba | Megumi Hase | Eiichi Kotake-Nara
We previously examined the cellular uptake of six types of vitamin D in human intestinal Caco-2 cells. Since vitamins D<sub>5</sub>–D<sub>7</sub> were commercially unavailable, we synthesized these compounds organically before studying them. This process led us to understand that new secosteroids could be generated as vitamin D candidates, depending on the sterol used as the starting material. We obtained two new secosteroids—compounds <b>3</b> and <b>4</b>—from fucosterol in the current study. We investigated the intestinal absorption of these compounds using Caco-2 cells cultured in Transwells and compared the results with vitamin D<sub>3</sub>, a representative secosteroid. The intestinal absorption of compound <b>4</b> was comparable to that of vitamin D<sub>3</sub>. Compound <b>3</b> showed similar uptake levels but transported about half as much as vitamin D<sub>3</sub>. These compounds demonstrated intestinal absorption at the cellular level. Vitamin D is known for its diverse biological activities manifest after intestinal absorption. Using PASS online simulation, we estimated the biological activity of compound <b>3</b>’s activated form. In several items indicated by PASS, compound <b>3</b> exhibited stronger biological activity than vitamins D<sub>2</sub>–D<sub>7</sub> and was also predicted to have unique biological activities.
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