Dembitsky VM et al. (2021), Antitumor Profile of Carbon-Bridged Steroids (C...

ECB-ART-49095

Mar Drugs 2021 Jun 03;196:. doi: 10.3390/md19060324.

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Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids.

Dembitsky VM , Gloriozova TA , Poroikov VV .

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This review focuses on the rare group of carbon-bridged steroids (CBS) and triterpenoids found in various natural sources such as green, yellow-green, and red algae, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in amoebas, fungi, fungal endophytes, and plants. For convenience, the presented CBS and triterpenoids are divided into four groups, which include: (a) CBS and triterpenoids containing a cyclopropane group; (b) CBS and triterpenoids with cyclopropane ring in the side chain; (c) CBS and triterpenoids containing a cyclobutane group; (d) CBS and triterpenoids containing cyclopentane, cyclohexane or cycloheptane moieties. For the comparative characterization of the antitumor profile, we have added several semi- and synthetic CBS and triterpenoids, with various additional rings, to identify possible promising sources for pharmacologists and the pharmaceutical industry. About 300 CBS and triterpenoids are presented in this review, which demonstrate a wide range of biological activities, but the most pronounced antitumor profile. The review summarizes biological activities both determined experimentally and estimated using the well-known PASS software. According to the data obtained, two-thirds of CBS and triterpenoids show moderate activity levels with a confidence level of 70 to 90%; however, one third of these lipids demonstrate strong antitumor activity with a confidence level exceeding 90%. Several CBS and triterpenoids, from different lipid groups, demonstrate selective action on different types of tumor cells such as renal cancer, sarcoma, pancreatic cancer, prostate cancer, lymphocytic leukemia, myeloid leukemia, liver cancer, and genitourinary cancer with varying degrees of confidence. In addition, the review presents graphical images of the antitumor profile of both individual CBS and triterpenoids groups and individual compounds.

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	Figure 1. Bioactive steroids containing an additional 3-membered ring in molecule.
	Figure 2. Bioactive steroids containing an additional 3-membered ring in the steroid molecule.
	Figure 3. Bioactive steroids containing an additional 3-membered ring in the steroid molecule.
	Figure 4. Bioactive steroids containing an additional 3-membered ring in the steroid molecule.
	Figure 5. Bioactive steroids containing an additional 3-membered ring in the steroid molecule.
	Figure 6. Bioactive cyclopropane-containing steroids and meroterpenoids.
	Figure 7. Bioactive cyclopropane-containing steroids.
	Figure 8. Bioactive sterols and triterpenoids with cyclopropane ring in the side chain.
	Figure 9. Bioactive sterols and triterpenoids with cyclopropane ring in the side chain.
	Figure 10. Bioactive cyclopropane-containing steroids and triterpenoids.
	Figure 11. Bioactive steroids containing an additional 3-membered ring in the steroid molecule.
	Figure 12. Bioactive synthetic cyclopropane-containing steroids.
	Figure 13. Bioactive cyclobutane-containing steroids and triterpenoids.
	Figure 14. Bioactive cyclobutane-containing steroids and triterpenoids.
	Figure 15. Bioactive natural and synthetic cyclobutane-containing steroids and triterpenoids.
	Figure 16. Bioactive synthetic steroids containing an additional 4-membered ring in the steroid molecule.
	Figure 17. Bioactive steroids containing an additional 5- or 6-membered ring in molecule.
	Figure 18. Bioactive cyclopentane- and cyclohexane-containing steroids.
	Figure 19. Bioactive synthethic steroids containing an additional 5- or 6-membered ring in molecule.
	Figure 20. Bioactive steroids containing additional 6-membered ring in molecule.
	Figure 21. Bioactive steroids containing additional 6- or 7-membered ring in molecule.
	Figure 22. The 3D graph (X and Y views) shows the predicted and calculated antitumor activity of carbon- bridged steroids (CBS) with a cyclopropane ring in the side chain (compound numbers: 103, 105, 112, 118, 119 and 120) showing the highest degree of confidence, more than 91%. These steroids derived from marine sponges Petrosia weinbergi, Xestospongia sp., Poecillastra compressa, and Tethya sp., and can be used in clinical medicine as potential agents with strong antitumor activity.
	Figure 23. The 3D graph shows the predicted and calculated antitumor and related activities of cyclopropane-containing triterpenoid saponins (compound numbers: 146, 147, and 148) showing the highest degree of confidence, more than 96%, which were isolated from the leaves and flowers extracts of Verbesina virginica, and can be used in clinical medicine as potential agents with strong antitumor activity.
	Figure 24. The 3D graph shows the predicted and calculated antitumor and related activities of cyclobutane-containing steroids (compound numbers: 197, 206, and 214) showing the highest degree of confidence, more than 90%.
	Figure 25. The 3D graph shows the predicted and calculated pharmacological activities of taccalonolide Q (271). Taccalonolide Q, similar to other taccalonolides, is a class of highly acetoxylated pentacyclic steroids containing 28 carbons, known microtubule stabilizing cytotoxic agents isolated from the genus Tacca that have selective anti- cancer properties. Taccalonolide Q has a C2–C3 epoxide group and an enol-γ-lactone fused with the unique E ring. In addition to total antineoplastic activity with a high confidence level of 93%, taccalonolide Q demonstrates selective activity against renal cancer, sarcoma, pancreatic cancer, lymphocytic leukemia, myeloid leukemia, and genitourinary cancer.