New Triterpenoid Saponins from Green Vegetable Soya Beans and Their Anti-Inflammatory Activities

Abstract

Ten compounds were isolated and identified from green vegetable soya beans, of which five are new triterpenoid saponins (1-5) and five are known compounds (6-10). The chemical structures of the five triterpenoid saponins (1-5) were elucidated to be 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 1; 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-(3″-O-formyl)-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 2; 22-keto-3β,24-dihydroxy oleanane-12-ene 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-(3″-O-formyl)-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 3; 3β,22β,24-trihydroxy oxyolean-18(19)-ene-29-acid 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 4; and punicanolic acid 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 5 from the spectroscopic data (IR, GTC/FID, HR-ESI-MS, and 1D and 2D NMR). The nitric oxide release inhibitions of compounds 1-10 in LPS-stimulated RAW264.7 cells were evaluated, and the data suggested that compounds 1, 2, and 5 might possess moderate anti-inflammatory activities, with IC values of 18.8, 16.1, and 13.2 μM, respectively.

Soyasaponins reduce inflammation by downregulating MyD88 expression and suppressing the recruitments of TLR4 and MyD88 into lipid rafts

“…First, results from this study further support the in vivo anti-inflammatory bioactivities of soyasaponins. In recent years, many studies have demonstrated that soyasaponins exhibit anti-inflammatory bioactivities by reducing the pro-inflammatory cytokines and/or mediators (TNFа, IL- [7][8][9][10][11][12][13][14][16][17][18][19]. However, only a few of investigations provided in vivo evidences.…”

“…Kinjo et al (2000) reported that soyasaponin III had antiinflammatory properties by exhibiting in vitro anticomplementary activity [15]. More recently, Lan et al isolated and identified five new triterpenoid saponins from green vegetable soya beans and found that three of them exhibited moderate anti-inflammatory activities by inhibiting the release of NO in LPS-stimulated RAW264.7 cells [16]. We recently found that soyasaponins (A 1 , A 2 or I) inhibited inflammation (reduced PGE 2 production and COX-2 expression) by suppressing the reactive oxygen species (ROS)-mediated activation of the phosphoinositide 3-kinase (PI3K)/protein kinase B (Akt)/ NF-κB signaling pathway [17].…”

Enhanced β-Amyrin Synthesis in Saccharomyces cerevisiae by Coupling An Optimal Acetyl-CoA Supply Pathway

“…Triterpenoids are highly diverse natural products widely distributed in plants with various biological activities. , For instance, glycyrrhizin, a triterpenoid extracted from licorice, is applied as medicine and a natural sweetener due to its various pharmacological effects and strong sweetness . β-Amyrin is also a kind of triterpenoid with similar pharmacological activities as glycyrrhizin and serves as a key precursor to a wide range of triterpenoid products .…”

Atypical Nitrogen-Containing Flavonoid in the Fruits of Cumin (Cuminum cyminum L.) with Anti-inflammatory Activity

“…Their anti-inflammatory activities were investigated by the Griess reagent. Generally, nitric oxide (NO) modulates important cellular signaling pathways involved in immunity and inflammation, and nitric oxide synthases (NOSs) play a substantial role in producing NO. , The Griess reagent was employed for the determination of nitrite, the reaction product of NO with O 2 , to quantitate NO production. , On the basis of the successful inflammatory model, all isolated compounds from cumin seeds were employed to detect their inhibitory effect on the nitrite level using LPS-stimulated RAW264.7 macrophage cells. As shown in Figure A, the majority of the compounds displayed significant inhibitory influence on the nitrite level.…”