3,4-seco-Dammarane Triterpenoid Saponins with Anti-Inflammatory Activity Isolated from the Leaves of Cyclocarya paliurus

Abstract

Cyclocarya paliurus is commonly used for the prevention and treatment of hypertension, diabetes, and inflammation in South China. Although research on the anti-inflammatory effects of C. paliurus leaves has been reported, no active anti-inflammatory compounds have been identified. In the present study, RAW 264.7 cells were used to establish a bioactivity-guided identification model to verify the inhibitory effects of C. paliurus leaves on inflammation and identify the anti-inflammatory constituents. The active fraction was isolated to yield 18 dammarane triterpenoid saponins, including 11 new 3,4-seco-dammarane triterpenoid saponins (1–11), the structures of which were identified on the basis of analyses of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) and comparison with literature data. Compounds 7, 8, 10, and 11 showed strong inhibition on nitric oxide (NO) productions, with IC50 values ranging from 8.23 to 11.23 μM. These four compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2), and interleukin 6 (IL-6) in lipopolysaccharide-activated RAW 264.7 cells. Furthermore, compound 7 decreased the expression of the proteins cyclooxygenase-2 (COX-2), inducible nitric-oxide synthase (iNOS), and nuclear factor kappa-B (NF-κB/p65). In addition, the structure–activity relationships of the isolates were investigated. The results suggest that 3,4-seco-dammarane triterpenoid saponins may be used as potential anti-inflammatory drugs and warrant further investigation.

Genome-Wide Identification MIKC-Type MADS-Box Gene Family and Their Roles during Development of Floral Buds in Wheel Wingnut (Cyclocarya paliurus)

“…Modern pharmacological studies have found that many potential bioactive compounds (triterpenoids, polysaccharides, flavonoids, etc.) in the leaves of C. paliurus have beneficial effects on antihypertensive activity, hypoglycemic activity, hypolipidemic activity, and antioxidant activity [ 10 ]. Due to the lack of breakthroughs in its asexual reproduction technology, sexual reproduction is still the main means of reproduction.…”

Acute Toxicity, Phytochemical Screening, Analgesic, and Anti-Inflammatory Activities of Aqueous and Methanol Root Extracts of Maerua triphylla A. Rich. (Capparaceae)

“…is suggests that the saponins in the methanol root extract of M. triphylla could be responsible for the better potency of the methanol extract in inhibiting inflammation in comparison to the aqueous extract [45].…”

Anti-Hyperglycemic Effects of Refined Fractions from Cyclocarya paliurus Leaves on Streptozotocin-Induced Diabetic Mice

“…A total of 29 compounds were identified, including 3 phenolic acids, 10 flavonoids, and 16 triterpenoids (Table 1). These compounds were 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, catechin, isoquercetin, quercetin-3-Oglucuronide, kaempferol-3-O-galactoside, kaempferol-3-O-glucuronide, kaempferol-3-Oglucoside, quercetin-3-O-rhamnoside, myricetin, kaempferol-3-O-rhamnoside, quercetin, kaempferol, 3β,19α,23-trihydroxy-1-oxo-olean-12-en-28-oic acid, arjunolic acid, cyclocaric acid B, asiatic acid, pterocaryoside B, cyclocarioside I, cyclocarioside K, pterocaryoside A, cyclocariol C, (20S,24R)-20,24-epoxy-25-hydroxy-12β-(α-L-arabinopyranosyloxy)-3,4-secodammara-4-( 28)-en-3-oic acid, cyclocarioside B, hederagenin, cyclocarioside H, cyclocarioside X, cypaliuruside E, and ursolic acid [17,[30][31][32][33][34][35][36][37][38][39][40].…”

“…A total of 29 compounds were identified, including 3 phenolic acids, 10 flavonoids, and 16 triterpenoids (Table 1). These compounds seco-dammara-4-( 28)-en-3-oic acid, cyclocarioside B, hederagenin, cyclocarioside H, cyclocarioside X, cypaliuruside E, and ursolic acid [17,[30][31][32][33][34][35][36][37][38][39][40].…”