Bioactive 3,4-seco-Triterpenoids from the Fruits of Acanthopanax sessiliflorus

Abstract

Eight new 3,4-seco-lupane triterpenes and glycosides, acanthosessiligenins I and II (1, 3) and acanthosessiliosides A-F (2, 4-8), as well as six known 3,4-seco-lupane triterpenes (9-14) were isolated from an ethanolic extract of Acanthopanax sessiliflorus fruits. The chemical structures of 1-8 were determined by spectroscopic data interpretation. All isolated compounds were tested for their cytotoxicity against six human cancer cell lines and their ability to inhibit LPS-induced nitric oxide production in RAW 264.7 macrophages.

Anti-Inflammatory Cycloartane-Type Saponins of Astragalus membranaceus

“…This conclusion was also supported by the HMBC spectrum, which showed 2 J , 3 J , and long range correlation between the proton signal of H-17 (δ H 1.51) and the carbon signals of C-13 (δ C 45.8), C-16 (δ C 28.7), C-20 (δ C 28.6), C-18 (δ C 18.6) and C-21 (δ C 18.3) ( Figure 2 ). The d -configurations of xylose and glucose units were established after hydrolysis of 1 followed by GC analysis [ 15 ]. Finally, the structure of 1 was determined to be 3- O - β -(2'- O -acetyl)- d -xylopyranosyl-6- O - β - d -glucopyranosyl-(24 S )-3 β ,6 α ,24 α ,25-tetrahydroxy-9,19-cyclolanostane, and named agroastragaloside V. Comparisons of NMR and MS data for the known compounds 2 – 5 with reported values led to their identification as agroastragaloside I ( 2 ) [ 16 ], agroastragaloside II ( 3 ) [ 14 ], isoastragaloside II ( 4 ) [ 13 ] and astragaloside IV ( 5 ) [ 16 ], respectively ( Figure 1 ).…”

New Lignans from the Flower of Forsythia koreana and Their Suppression Effect on VCAM‐1 Expression in MOVAS Cells

“…[41] Compounds 1 and 2 (2.5 mg) were hydrolyzed with 2 N HCl (1 mL) in H 2 O at 80°C for 6 h, followed by neutralization with Ag 2 CO 3 and filtered. [41] Compounds 1 and 2 (2.5 mg) were hydrolyzed with 2 N HCl (1 mL) in H 2 O at 80°C for 6 h, followed by neutralization with Ag 2 CO 3 and filtered.…”

“…[41] [42] Western Blot Analysis Western blot analysis was performed as previously described method. [41] [42] Western Blot Analysis Western blot analysis was performed as previously described method.…”

“…Determination of the kind and absolute configuration of the sugar assay was performed as previously described method. [41] Compounds 1 and 2 (2.5 mg) were hydrolyzed with 2 N HCl (1 mL) in H 2 O at 80°C for 6 h, followed by neutralization with Ag 2 CO 3 and filtered. The filtrate was dried in vacuo and dissolved in 0.1 M L-cysteine methyl ester hydrochloride (75 lL) and pyridine (50 lL).…”

Chiisanoside, a triterpenoid saponin, exhibits anti-tumor activity by promoting apoptosis and inhibiting angiogenesis

“…[7][8][9][10][11][12] Most plants of the Acanthopanax species are safe and nontoxic, especially the leaves of A. sessiliorus and A. senticosus, which can be eaten as traditional vegetables and tea in China. The leaves of Acanthopanax species, such as A. sessiliorus, A. senticosus, A. divaricatus, A. subinermis, A. koreanus and so on, have traditionally been used as a tonic and sedative, as well as in the treatment of rheumatism and diabetes, and one of their main active ingredients is a lupane triterpenoid chiisanoside, [13][14][15] which exhibits a series of signicant pharmacological effects, such as anti-osteoporosis, 16 anti-inammation, [17][18][19][20] antibacterial, 21 anti-platelet aggregating, 22 treatment of glycationassociated diseases, 23 anti-rotaviral, 24 and the inhibition of lipase. 25,26 However, the reports related to the effects of chiisanoside on hepatic carcinoma, and the pharmacokinetics properties and tissue distribution characteristics have not been found.…”