Bioassay-guided Isolation of Antiproliferative Triterpenoids from Euonymus alatus Twigs

Abstract

Euonymus alatus (Celastraceae) has been used as an anticancer agent in Korean traditional medicine. However, the potential bioactive contributors to the anticancer effects have not been thoroughly studied. Our screening test revealed that the MeOH extract of E. alatus twigs exhibited significant cytotoxicity against A549, SK-OV-3, and SK-MEL-2 cell lines. A bioassay-guided separation of the MeOH extract of E. alatus twigs resulted in the isolation and identification of 14 triterpenes as main phytochemicals. The structures of the compounds were elucidated on the basis of spectroscopic evidence as lupeol (1), betulin (2), 3β,28,30-lup-20(29)-ene triol (3), lupenone (4), betulone (5), 28,30-dihydroxy-3-oxolup-20(29)-ene (6), messagenin (7), glut-5-en-3β-ol (8), maslinic acid (9), hederagenin (10), 3-oxo-11α-methoxyolean-12-ene (11), 3β-hydroxy-1-oxo-olean-12-en-28-oic acid (12), ursolic acid (13), and 2α-hydroxy-ursolic acid (14). Of these compounds, 3, 6–8, and 10–14 were isolated for the first time from this plant. All isolated triterpenoids had consistent antiproliferative activities against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines. Compounds 2, 5, and 7 showed significant cytotoxicity against all four cell lines tested, with IC50 values of 3.26–8.61 μM.

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

“…The cytotoxicity was evaluated on the basis of the growth inhibitory effects of the isolated compounds Table 2). Betulinic acid (10) is a well-known anticancer agent inhibiting eukaryotic topoisomerase I [36] and its derivatives have been reported to display cytotoxic activity [13,[37][38][39][40]. The acquired cytotoxicity data of compounds 9-11 are consistent with the previous studies.…”

Euonymus alatus: A Review on Its Phytochemistry and Antidiabetic Activity

“…Other triterpenes include oleanic acid (45), wilforlide A (46) [ 24 ], hop-(22)-29-en-3 β -ol (47) [ 25 ], 3 β -hydroxy-21 α H-hop-22(29)-en-30-ol (48), 2 α ,3 β -dihydroxyurs-12,19-dien-23,28-oic acid (49) [ 21 ], arborinone (50), taraxerol (51) and germanicol (52) [ 22 ], 11-keto- β -boswellic acid (53), acetyl 11-keto- β -boswellic acid (54), camaldulenic acid (55) [ 23 ], 3 β ,28,30-lup-20(29)-ene triol (56), 28,30-dihydroxy-3-oxolup-20(29)-ene (57), glut-5-en-3 β -ol (58), maslinic acid (59), hederagenin (60), 3-oxo-11alpha-methoxyolean-12-ene (61), 3 β -hydroxy-1-oxo-olean-12-en-28-oic acid (62), ursolic acid (63), and 2 α -hydroxy-ursolic acid (64) [ 26 ]. The structures of compounds 45–64 are shown in Figure 1 .…”

Synthesis and Antitumor Evaluation in Vitro of NO‐Donating Ursolic Acid‐Benzylidene Derivatives

“…eu-azarolus MAIRE, Ixora coccinea L. (Rubiaceae), Ligustrum lucidum and Eriobotrya japonica. [1][2][3][4][5] Previous study showed that UA is responsible for many biological activities, such as antioxidant, anti-inflammatory, antibacterial, antitumor and hepatoprotection. [6] Recently, UA is of great concern because of its outstanding antitumor activity.…”

“…[10 -12] Apoptosis plays an important role in antitumor activity of UA. It has been well-known that several signal transduction pathway may be involved in UA-induced cell apoptosis, such as 1 These authors made equal contribution to this work.…”