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Review
. 2025 Feb 19;10(8):7493-7509.
doi: 10.1021/acsomega.4c08577. eCollection 2025 Mar 4.

Anticancer Activities of Natural and Synthetic Steroids: A Review

Daniel F Mendoza Lara  1 , M Elena Hernández-Caballero  2 , Joel L Terán  3 , Jesús Sandoval Ramírez  4 , Alan Carrasco-Carballo  1   5
Affiliations
Review

Anticancer Activities of Natural and Synthetic Steroids: A Review

Daniel F Mendoza Lara et al. ACS Omega. .

Abstract

Steroids have demonstrated a wide field of research on the subject of anticancer compounds, particularly antiproliferative with cell lines, with special emphasis on the historical link between steroids and cancer and the use of in silico technologies to understand the impact of natural and synthetic steroids on cancer cells focused on finding common denominators of the type of structural changes that give antiproliferative and/or cytotoxic properties, both in control and cancer cell lines. Through this review and classification by origin and/or synthesis, it is found that steroidal saponins are highly cytotoxic, although with low selectivity against control cells, while on the part of the aglycone the presence of heteroatoms such as nitrogen and oxygen increases the antiproliferative activity, mainly via cell cycle arrest and the induction of apoptosis, mechanisms that have been partially proven, using semisynthetic derivatives, as well as bioconjugates between saponins and nitrogenous steroids with now a high cytotoxicity and selectivity against control cell lines. This gives rise to the idea that steroids as a study model for the design of anticancer agents are an excellent template with a wide field of study.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Cholesterol (steroid) (1) and lanosterol (triterpene) (2).
Figure 2
Figure 2
Molecular mechanism of steroids’ effect on cells. Built from refs (−.)
Figure 3
Figure 3
Structure of diosgenin (3).
Figure 4
Figure 4
(a) General structure of brassinosteroids. (b) Structure of epibrassinolide.
Figure 5
Figure 5
Last step of the biosynthesis of brassinolide (5) from catasterone (6).
Figure 6
Figure 6
Progenin III structure (7).
Figure 7
Figure 7
Structure of PP9 (8).
Figure 8
Figure 8
Structure of dioscin (9).
Figure 9
Figure 9
Structure of T-17 (10).
Figure 10
Figure 10
Isolated structure from Aspidistra triradiate (11).
Figure 11
Figure 11
Compound A-24 (12).
Figure 12
Figure 12
Structure of phytosterols (13).
Figure 13
Figure 13
Structure of phytosterol RinoxiaB (14).
Figure 14
Figure 14
Structure of β-sitosterol (15).
Figure 15
Figure 15
Structures of stigmasterol (16) and brassicasterol (17).
Figure 16
Figure 16
Structure of a stigmastadiene phytosterol (18).
Figure 17
Figure 17
Structure of campesterol (19).
Figure 18
Figure 18
Structure of dendrosterone (20).
Figure 19
Figure 19
Structure of compounds 21 and 22.
Figure 20
Figure 20
Structure of peimine (23).
Figure 21
Figure 21
Structure of solasodine (24).
Figure 22
Figure 22
Structure of solasonine (25).
Figure 23
Figure 23
Structure of tomatidine (26).
Figure 24
Figure 24
Structures of erianoside A (27) and erianoside B (28).
Figure 25
Figure 25
Structure of zhebeirine (29).
Figure 26
Figure 26
Structure of cyclovirobuxine D (30).
Figure 27
Figure 27
Structures of chenodeoxycholic acid (31) and ursodeoxycholic acid (32).
Figure 28
Figure 28
Structures of deoxycholic acid (33) and lithocholic acid (34).
Figure 29
Figure 29
Structures of estradiol (35) and dihydrotestosterone (36).
Figure 30
Figure 30
Examples of natural and synthetic progestins.
Figure 31
Figure 31
Structures of polyoxygenated steroids isolated from Haliclona gracilis.
Figure 32
Figure 32
Structural difference between winter and summer extracts content.
Figure 33
Figure 33
Structure of abeo-steroid 57 and ergostane derivative 58.
Figure 34
Figure 34
Structures of steroids 59, 60, and 61 isolated from Phyllospongia sp.
Figure 35
Figure 35
Novel steroidal 62 and 63 structures isolated from Acanthaster planci.
Figure 36
Figure 36
Anticancer steroids isolated from Asterias microdiscus.
Figure 37
Figure 37
Structure of asterosaponin P1 (66).
Figure 38
Figure 38
Structure of fucosterol (67).
Figure 39
Figure 39
Structures of compounds isolated from Cystophora xiphocarpa.
Figure 40
Figure 40
Steroids isolated from sea star Protoreaster lincki.
Scheme 1
Scheme 1. (i) Steroidal Oxime Obtained; (ii) TsOH, py; KOAc, aq.; and (iii) NBS; NH2OH·HCl
Scheme 2
Scheme 2. (i) Jones Reagent; (ii) NH2OH·HCl, NaOAc; and (iii) SOCl2
Scheme 3
Scheme 3. (i) Ac2O, Et2O·BF3; (ii) NaNO2, Et2O·BF3, Ac2O/AcOH; and (iii) Na2CO3
Scheme 4
Scheme 4. Testosterone Oxime Derivates: (i) NH2OH·HCl, CH3COONa·3H2O, Methanol, 40 °C
Scheme 5
Scheme 5. (i) NH2OH HCl, NaOH; (ii) HNO3, AcOH; (iii) I2; (iv) DDQ; and (v) N-Bromosuccinimide
Scheme 6
Scheme 6. Synthesis of Chalcone-Deoxycholic Acid Conjugates 114 and 116
Figure 41
Figure 41
Organotin derivatives of cholic acid.
Figure 42
Figure 42
Structure of LLC-202 (121).
Figure 43
Figure 43
Structures of ursodeoxycholic acid (32) and its conjugate with dihydroartemisin (122).
Scheme 7
Scheme 7. (i) Ac2O, Et2O·BF3/Et3N; HCl aq.; (ii) pTsCl/Py/DMAP; (iii) NaI; and (iv) Amine/CH3CN
Figure 44
Figure 44
Structure of compound 128.
Figure 45
Figure 45
Structures of compounds 129 and 130.
See this image and copyright information in PMC

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