Three new tirucallane triterpenoids from the fruits of Chukrasia tabularis and their biological activities

Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity

“…The 1 H-NMR (Table 1) and 13 C-NMR (Table 2) along with the HSQC data of 4 revealed the presence of one methoxy group, five carbonyl carbons, seven methyls, six methylenes and eight methines with four oxygenated and nine quarternary carbons. These data were similar to those of phragmalin 3-isobutyrate 30-propionate (8), suggesting that compound 4 was also an 1,8,9-phragmalin ortho ester. The main differences between them were the presence of a lactone carbonyl (δ C 169.1) signal and an acetal methine (δ H 6.18; δ C 97.5) signal and the absence of two olefinic methine signals in 4 compared to phragmalin 3-isobutyrate 30-propionate (8).…”

“…These data were similar to those of phragmalin 3-isobutyrate 30-propionate (8), suggesting that compound 4 was also an 1,8,9-phragmalin ortho ester. The main differences between them were the presence of a lactone carbonyl (δ C 169.1) signal and an acetal methine (δ H 6.18; δ C 97.5) signal and the absence of two olefinic methine signals in 4 compared to phragmalin 3-isobutyrate 30-propionate (8). HMBC correlations between H-22/C-20, C-21, C-23, H-17/C-20, H-17/C-21 and H-17/C-22 indicated that a β-furyl ring moiety located at C-17 in phragmalin 3-isobutyrate 30-propionate was replaced by a 21-hydroxy-20(22)-en-21,23-γ-lactone moiety in 4.…”

“…The further investigation of limonoids from this plant, provided five new phragmalintype limonoids, chuktabamalins A-E (1-5) (Figure 1) and four known compounds (6)(7)(8)(9), which were isolated from the EtOH extracts of the fruits of Chukrasia tabularis. Herein, the isolation and structure elucidation of the new compounds as well as their anti-inflammatory evaluation are reported.…”

Targeted triterpenoids from Dysoxylum alliaceum stem barks as cytotoxic agents in human cancer and normal cells

“…The cells were cultured in RPMI-1640, supplemented with 10% fetal bovine serum and antibiotics in 5% CO 2 at 37 C. Additionally, both were seeded into 96-well plates at an initial cell density of approximately 3 x 10 4 cells cm − 3 and incubated for 24 h. The compounds were dissolved in 2% aqueous DMSO with the required concentrations of 500, 250, 125, 62. According to the above data, the existence of seven tertiary methyls, one secondary methyl, four nonoxygenated quaternary carbons, and one pair of ole nic groups showed that compound 1 possessed nearly identical tirucallane-type triterpenoid [13]. The tirucallane-type triterpenoid with a double bond at position C-7 δ C 118.4 (δ H 5.35 (1H, td, J = 3.5, 5.5 Hz)) and C-8 at δ C 145.7 also ketone carbonyl at C-3 δ C 216.9 were a distinctive feature of tirucallane-7-ene with ketone carbonyl at C-3 [14].…”

“…Meanwhile, the FTIR spectrum revealed the presence of hydroxy (3444 cm − 1 ) and carbonyl (1707 cm − 1 ) groups. Its 125 MHz 13 C NMR spectrum in CDCl 3 with the assistance of DEPT experiments indicated 30 carbon resonances that came from eight methyls which are typical for triterpenoid, seven methylenes, seven methines (three ole nic and one oxygenated methine), and seven quaternary carbons (one oxygenated quaternary carbon, one ole nic, and one carbonyl). Examination of 500 MHz 1 H NMR spectrum in CDCl 3 exhibited eight methyl groups including seven tertiary mehthyls and one secondary methyl at δ 0.84, 1.00, 1.20, 1.15, 1.05, 1.12, 1.02, 0.98 (J = 6.0 Hz), one oxygenated methine as a doublet at δ 3.84 (J = 7.0 Hz), and the remaining three at δ 5.30, 5.61, 5.44 were ole nic methine groups.…”