Norsteroid

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Class of steroids

title: "Norsteroid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["steroids"] description: "Class of steroids" topic_path: "general/steroids" source: "https://en.wikipedia.org/wiki/Norsteroid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Class of steroids ::

Norsteroids (nor-, L. norma, from "normal" in chemistry, indicating carbon removal) are a structural class of steroids that have had an atom or atoms (typically carbon) removed, biosynthetically or synthetically, from positions of branching off of rings or side chains (e.g., removal of methyl groups), or from within rings of the steroid ring system. Norsteroids are systematically classified into four categories, A-, B-, C-, and D-norsteroids depending on ring if modified. Natural sources of norsteroids include but are not limited to sponges, corals, terrestrial plants, fungi, and bacteria. For instance, 19-norsteroids (e.g., 19-norprogesterone) constitute an important class of natural and synthetic steroids derived by removal of the methyl group of the natural product progesterone; the equivalent change between testosterone and 19-nortestosterone (nandrolone) is illustrated below.

Examples

Norsteroid examples include: 19-norpregnane (from pregnane), desogestrel, ethylestrenol, etynodiol diacetate, ethinylestradiol, gestrinone, levonorgestrel, norethisterone (norethindrone), norgestrel, norpregnatriene (from pregnatriene), quinestrol, 19-norprogesterone (from a progesterone), nomegestrol acetate, 19-nortestosterone (from a testosterone), and norethisterone acetate.

:{| |- align="center" | [[File:Progesterone.svg|140px]] || || [[File:19-Norprogesterone.svg|140px]] |- | progesterone || || 19-norprogesterone |- | [[File:Testosteron.svg|140px]] || || [[File:Nandrolone.svg|140px]] |- | testosterone || || nandrolone (nortestosterone) |}

Ganonorsterone A

In 2023 under the guidance of the Zhao research group from the Henan University of Chinese Medicine, in Zhengzhou, China, they discovered the compound ganonorsterone A. Obtained as a colorless oil, this compound was proved to be a dicyclic norsteroid. Using analysis of nuclear magnetic resonance (NMR) data along with high-performance liquid chromatography (HPLC), and electronic circular dichroism (ECD) it was concluded the formula of the compound to be . This compound exhibited moderate inhibition on nitric oxide production in macrophages demonstrating potential anti-inflammatory activity; however, no cytotoxicity, or the ability to damage or kill cells, was discovered against five human cancer cell lines including but not limited to HL-60 (acute promyelocytic leukemia), SMMC-7721 (hepatocellular carcinoma), A549 (lung adenocarcinoma), MCF-7 (breast adenocarcinoma), and SW-480 (colorectal adenocarcinoma).

References

References

  1. (2006). norsteroid. In Cammack, R., Atwood, T., Campbell, P., Parish, H., Smith, A., Vella, F., & Stirling, J. (Eds.), Oxford Dictionary of Biochemistry and Molecular Biology. : Oxford University Press. Retrieved 10 Dec. 2025, from [https://www.oxfordreference.com/view/10.1093/acref/9780198529170.001.0001/acref-9780198529170-e-13842. https://www.oxfordreference.com/view/10.1093/acref/9780198529170.001.0001/acref-9780198529170-e-13842.]
  2. International Union of Pure and Applied Chemistry (IUPAC), 1999, "RF-4.1 Removal of Skeletal Atoms," in "RF-4. Skeletal Modifications" in Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999), see [http://www.chem.qmul.ac.uk/iupac/sectionF/RF41.html#41] {{Webarchive. link. (2016-03-04, accessed 20 May 2014. See also IUPAC, 1976, "Nomenclature of Organic Chemistry: Section F - Natural Products and Related Compounds, Recommendations 1976", IUPAC Information Bulletin Appendices on Tentative Nomenclature, Symbols, Units, and Standards, No. 53, December, 1976, also in ''Eur. J. Biochem.'' 1978, '''86''', 1-8.)
  3. {{MeshName. Norsteroids
  4. Dembitsky, Valery. (2024-05-06). "Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application". Biomedicines.
  5. (December 1996). "The antigonadotropic activity of progestins (19-nortestosterone and 19-norprogesterone derivatives) is not mediated through the androgen receptor". J. Clin. Endocrinol. Metab..
  6. (2024-08-02). "Ganonorsterone A, a norsteroid from the medicinal fungus Ganoderma lingzhi". Journal of Asian Natural Products Research.

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