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Secosteroid Biosynthesis: History
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Contributor: Yu Peng

Secosteroid biosynthesis denotes the formation of secosteroids—steroidal compounds in which one of the parent rings of the tetracyclic nucleus, most commonly the B-ring, has undergone scission—through photochemical or enzymatic mechanisms [1]. The prototypical pathway is the UV-B–driven photolysis of a 5,7-diene sterol precursor: in vertebrates, 7-dehydrocholesterol in the skin absorbs UV-B radiation (290–315 nm), causing cleavage of the B-ring between C9 and C10 to yield previtamin D3, which then undergoes a temperature-dependent rearrangement to cholecalciferol (vitamin D3); an analogous photoconversion of ergosterol yields vitamin D2 in fungi [2]. Secosteroid biosynthesis also encompasses enzyme-catalyzed routes, notably cytochrome P450 CYP11A1–mediated hydroxylation of 7-dehydrocholesterol or vitamin D3, which generates hydroxylated secosteroid metabolites with modified A-ring or side-chain structures that can be further transformed by UV-B [3]. The term additionally covers the formation of diverse 9,11-, 5,6-, and other secosteroid classes in marine invertebrates and microorganisms, where oxidative cleavage of sterol rings produces structurally distinct secosteroid scaffolds [1][4]. Secosteroid biosynthesis thus spans non-enzymatic photochemical ring opening and enzyme-dependent oxidative routes that together generate the secosteroid class from sterol precursors [1][2][3].

  • secosteroids
  • vitamin D
  • sterol photochemistry
  • hydroxylation

References

  1. Donato Sica; Domenica Musumeci; Secosteroids of marine origin. Steroids 2004, 69, 743-756, 10.1016/j.steroids.2004.09.001.
  2. Ariam Abraham; Dorota Bartusik-Aebisher; Barbara Smolak; Klaudia Dynarowicz; Edward Kowalczyk; Wiesław Guz; David Aebisher; Gabriela Henrykowska; Vitamin D in Photosynthetic Organisms and Fungi: Sterol Photochemistry, UV-B Availability, and Biofortification Potential. Curr. Issues Mol. Biol. 2026, 48, 760, 10.3390/cimb48080760.
  3. Andrzej T. Slominski; Wei Li; Tae-Kang Kim; Igor Semak; Jin Wang; Jordan K. Zjawiony; Robert C. Tuckey; Novel activities of CYP11A1 and their potential physiological significance. J. Steroid Biochem. Mol. Biol. 2015, 151, 25-37, 10.1016/j.jsbmb.2014.11.010.
  4. Valery M. Dembitsky; Alexander O. Terent’ev; Microbial Steroids: Novel Frameworks and Bioactivity Profiles. Microbiol. Res. 2026, 17, 15, 10.3390/microbiolres17010015.
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