Norsteroid

Last updated

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), [1] or from within rings of the steroid ring system. [2] [3] 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. [4] 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.

Contents

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, [5] [ non-primary source needed ] 19-nortestosterone (from a testosterone), and norethisterone acetate. [5] [ non-primary source needed ]

Progesterone.svg    19-Norprogesterone.svg
progesterone 19-norprogesterone
Testosteron.svg    Nandrolone.svg
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 C19H28O2. 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). [6]

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.
  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 Archived 2016-03-04 at the Wayback Machine , 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. ↑ Norsteroids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  4. ↑ Dembitsky, Valery (2024-05-06). "Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application". Biomedicines. 12 (5): 1021. doi: 10.3390/biomedicines12051021 . ISSN   2227-9059. PMC   11117879 . PMID   38790983.
  5. 1 2 Couzinet B, Young J, Brailly S, Chanson P, Thomas JL, Schaison G (December 1996). "The antigonadotropic activity of progestins (19-nortestosterone and 19-norprogesterone derivatives) is not mediated through the androgen receptor". J. Clin. Endocrinol. Metab. 81 (12): 4218–23. doi: 10.1210/jcem.81.12.8954018 . PMID   8954018.
  6. ↑ Du, Jia-Hui; Zhao, Xuan; Zhang, Fei; Wang, Yan; Du, Kun; Ding, Si-Yi; Feng, Wei-Sheng; Zhao, Zhen-Zhu (2024-08-02). "Ganonorsterone A, a norsteroid from the medicinal fungus Ganoderma lingzhi". Journal of Asian Natural Products Research. 26 (8): 1001–1008. Bibcode:2024JANPR..26.1001D. doi:10.1080/10286020.2024.2340691. ISSN   1028-6020. PMID   38607260.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.