Three new cardenolides from the fruits of Cascabela thevetia (L.) Lippold and their cytotoxic activities

References

• Abe F, Yamauchi T, Nohara T. 1992a. C-Nor-D-homo-cardenolide glycosides from Thevetia neriifolia. Phytochemistry. 31(1):251–254.
   Web of Science ®Google Scholar
• Abe F, Yamauchi T, Wan ASC. 1992b. Cardiac glycosides from the leaves of Thevetia neriifolia. Phytochemistry. 31(9):3189–3193.
   Web of Science ®Google Scholar
• Abe F, Yamauchi T, Yahara S, Nohara T. 1994. Glycosides of 19-formylthevetiogenin and 5α-thevetiogenin from Thevetia neriifolia. Phytochemistry. 37(5):1429–1432.
   PubMed Web of Science ®Google Scholar
• Alonso-Castro AJ, Villarreal ML, Salazar-Olivo LA, Gomez-Sanchez M, Dominguez F, Garcia-Carranca A. 2011. Mexican medicinal plants used for cancer treatment: pharmacological, phytochemical and ethnobotanical studies. J Ethnopharmacol. 133(3):945–972.
   PubMed Web of Science ®Google Scholar
• Bedir E, Karakoyun Ç, Doğan G, Kuru G, Küçüksolak M, Yusufoğlu H. 2021. New cardenolides from biotransformation of gitoxigenin by the endophytic fungus Alternaria eureka 1E1BL1: characterization and cytotoxic activities. Molecules. 26(10):3030.
   PubMed Web of Science ®Google Scholar
• Begum S, Adil QS, Siddiqui B, Siddiqui S. 1993. Constituents of the leaves of Thevetia neriifolia. J Nat Prod. 56(4):613–617.
   Web of Science ®Google Scholar
• Cheng HY, Tian DM, Tang JS, Shen WZ, Yao XS. 2016. Cardiac glycosides from the seeds of Thevetia peruviana and their pro-apoptotic activity toward cancer cells. J Asian Nat Prod Res. 18(9):837–847.
   PubMed Web of Science ®Google Scholar
• Decosterd L, Gustafson KR, Cardellina II JH, Cragg GM, Boyd MR. 1994. The differential cytotoxicity of cardenolides from Thevetia ahouia. Phytother Res. 8(2):74–77.
   Web of Science ®Google Scholar
• Drakenberg T, Brodelius P, Mcintyre D, Vogel HJ. 1990. Structural studies of digitoxin and related cardenolides by two-dimensional NMR. Can J Chem. 68(2):272–277.
   Web of Science ®Google Scholar
• Du Z, Li G, Ge H, Zhou X, Zhang J. 2021. Design, Synthesis and biological evaluation of steroidal glycoconjugates as potential antiproliferative agents. Chem Med Chem. 16(9):1488–1498.
   Google Scholar
• Goschke R, Weiss EK, Reichstein R. 1961. CCXXIII. Partial synthesis of carpogenin and carpogenol, as well as the identification of substance HPU 28 from Pachycarpus schinzianus as cannogenin. Helv Chim Acta. 44(4):1031–1040.
   Google Scholar
• Inoue H, Nakayama H, Tsuhako M. 2000. A one-step phosphorylation of D-aldohexoses and D-aldopentoses with inorganic cyclo-triphosphate. Carbohyd Res. 324(1):10–16.
   PubMed Web of Science ®Google Scholar
• Kolkhof P, Geerts A, Schafer S, Torzewski J. 2010. Cardiac glycosides potently inhibit C-reactive protein synthesis in human hepatocytes. Biochem Biophys Res Commun. 394(1):233–239.
   PubMed Web of Science ®Google Scholar
• Li X-S, Chen T-J, Xu Z-P, Long J, He M-Y, Zhan H-H, Zhuang H-C, Wang Q-L, Liu L, Yang X-M, et al. 2022. Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents. Bioorg Med Chem. 54:116581.
   PubMed Web of Science ®Google Scholar
• Li XS, Hu MJ, Liu J, Liu Q, Huang ZX, Li SL, Hao XJ, Zhang XK, Yao XS, Tang JS. 2014. Cardiac glycosides from the bark of Antiaris toxicaria. Fitoterapia. 97:71–77.
   PubMed Web of Science ®Google Scholar
• Li XS, Ren YC, Bao YZ, Liu J, Zhang XK, Zhang YW, Sun XL, Yao XS, Tang JS. 2018. Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities. Eur J Med Chem. 145:252–262.
   PubMed Web of Science ®Google Scholar
• Miyagawa T, Ohtsuki T, Koyano T, Kowithayakorn T, Masami I. 2009. Cardenolide glycosides of Thevetia peruviana and triterpenoid saponins of Sapindus emarginatus as TRAIL resistance-overcoming compounds. J Nat Prod. 72(8):1507–1511.
   PubMed Web of Science ®Google Scholar
• Nasu K, Nishida M, Ueda T, Takai N, Bing S, Narahara H, Miyakawa I. 2005. Bufalin induces apoptosis and the G0/G1 cell cycle arrest of endometriotic stromal cells: a promising agent for the treatment of endometriosis. Mol Hum Reprod. 11(11):817–823.
   PubMed Web of Science ®Google Scholar
• Pádua RM, Oliveira AB, Souza Filho JD, Vieira GJ, Takahashi JA, Braga FC. 2005. Biotransformation of digitoxigenin by Fusarium ciliatum. J Braz Chem Soc. 16(3B):614–619.
   Web of Science ®Google Scholar
• Pei YH, Hua HM, Li ZL, Chen G. 2011. Application of nuclear magnetic resonance to the determination of the configuration of glycoside bond. Acta Pharm Sin. 46(2):127–131.
   Google Scholar
• Ren Y, Chen WL, Lantvit DD, Sass EJ, Shriwas P, Ninh TN, Chai HB, Zhang X, Soejarto DD, Chen X, et al. 2017. Cardiac glycoside constituents of Streblus asper with potential antineoplastic activity. J Nat Prod. 80(3):648–658.
   PubMed Web of Science ®Google Scholar
• Rimpelová S, Zimmermann T, Drašar PB, Dolenský B, Bejček J, Kmoníčková E, Cihlářová P, Gurská S, Kuklíková L, Hajdůch M, et al. 2021. Steroid glycosides hyrcanoside and deglucohyrcanoside: on isolation, structural identification, and anticancer activity. Foods. 10:36.
   Web of Science ®Google Scholar
• Schoner W, Scheiner-Bobis G. 2007. Endogenous and exogenous cardiac glycosides: their roles in hypertension, salt metabolism, and cell growth. Am J Physiol Cell Physiol. 293:509–536.
   PubMed Web of Science ®Google Scholar
• Siddiqui S, Siddiqui BS, Adil Q, Begum S. 1992. Cardenolides and triterpenoids of the leaves of Thevetia neriifolia. Phytochemistry. 31(10):3541–3546.
   Web of Science ®Google Scholar
• Tian DM, Cheng HY, Jiang MM, Shen WZ, Tang JS, Yao XS. 2016. Cardiac glycosides from the seeds of Thevetia peruviana. J Nat Prod. 79(1):38–50.
   PubMed Web of Science ®Google Scholar
• Tian D, Dmitrieva RI, Doris PA, Crary JF, Sondhi R, Sacktor TC, Bergold PJ. 2008. Protein kinase M zeta regulation of Na/K ATPase: a persistent neuroprotective mechanism of ischemic preconditioning in hippocampal slice cultures. Brain Res. 1213:127–139.
   PubMed Web of Science ®Google Scholar
• Xue R, Han N, Sakurai H, Saiki I, Ye C, Yin J. 2013. Cytotoxic cardiac glycosides from the roots of Streptocaulon juventas. Planta Med. 79(2):157–162.
   PubMed Web of Science ®Google Scholar
• Xue R, Han N, Ye C, Wang L, Yang J, Wang Y, Yin J. 2014. The cytotoxic activities of cardiac glycosides from Streptocaulon juventas and the structure-activity relationships. Fitoterapia. 98(1):228–233.
   PubMedGoogle Scholar
• Zhu XL, Wen C, Ye QM, Xu W, Zou DL, Liang GP, Zhang F, Chen WN, Jiang RW. 2018. Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids. RSC Adv. 8(10):5071–5078.
   PubMed Web of Science ®Google Scholar