A new anti-inflammatory triterpene saponin isolated from Anabasis setifera

Abstract

A bio-guided fractionation of Anabasis setifera Moq. (Chenopodiaceae) for anti-inflammatory activity was carried out using carrageenin rat paw edema model in rats. On the basis of percent edema inhibition after 3 h of carrageenin injection, n-butanol fraction showed promising activity through a significant (p < 0.05) decrease in paw volume by 85.6 % from control using indomethacin as reference standard. Moreover, the n-butanol fraction significantly (p < 0.05) decreased PGE2 and TNF-α in the exudates of rat paw edema. Chemical investigation of n-butanol fraction afforded α-amyrin 3-O-glucopyranoside (1), patuletin 7-O-glucopyranoside (2), myricitrin (3) and a new oleanane triterpene saponin derivative (4), sophradiol 3-O-α-L-(1)C4-rhamnopyranosyl-(1'''→4'')-O-β-D-(4)C1-galactopyranosyl (1''→6')-O-β-D-(4)C1-glucopyranoside. The structure of the new compound was determined by comprehensive analyses of their 1D and 2D NMR, mass spectral data and comparison with previously known analogs. Only compound 4 revealed a significant (p < 0.05) inhibition of cyclooxygenase 1 and 2 (COX) activities.

Optimizing methods to characterize caffeic, ferulic, and chlorogenic acids in Salicornia sinus-persica and Salicornia bigelovii extracts by tandem mass spectrometry (LC-MS/MS)

“…Some of the reported effects include the prevention of cardiovascular diseases, as well as anti-inflammatory, anti-carcinogenic, antioxidant, antimicrobial, anti-viral, anti-fungal, and anti-diabetic properties (Arakawa et al 1982;Taha and Alsayed 2000;Bandaranayake 2002;Radwan and Shams 2007;Akbar and Al-Yahya 2011;Hamed et al 2011;Al-Azzawi et al 2012;Custódio et al 2012;Oueslati et al 2012;Yin et al 2012;Abdou et al 2013). Furthermore, valuable components that are used in the cosmetic and food industries have been identified, e.g., lauric acid and aromatic compounds from the bark of grey mangrove tree (Avicennia marina) (Zhu et al 2009) and different terpenoids from essential oils of Sesuvium portulacastrum and Salsola annua, which are known as effective antiseptic compounds (Filipowicz et al 2003;Magwa et al 2006;Abdou et al 2013). Several of the halophytes are edible and contain important free radical scavenging anti-inflammatory compounds, such as Suaeda vermiculata, which indicate their possible use in nutraceuticals (Oueslati et al 2012).…”

Anti-Inflammatory Activity of Selected Plants from Saudi Arabia

“…Of a total of thirteen investigated plant species, the methanolic extracts of V. shimperi, A. articulata, and T. trichodesmoides possessed signifi cant anti-infl ammatory activity, presumably due to their phenolic and/or saponin contents. This activity is likely to be mediated, at least in part, through reduction of PGE 2 and TNF-α levels and COX-2 activity (Abdou et al, 2013). All three plant extracts inhibited both COX enzymes, but with more selectivity towards the COX-2 isozyme, contrary to indomethacin.…”

“…Flavonoids have been reported to inhibit the expression of isoforms of inducible nitric oxide synthase, cyclooxygenase, and lipoxygenase, with subsequent elevation of nitric oxide, prostanoids, and leukotrienes, as well as other mediators of the infl ammatory process such as cytokines, chemokines or adhesion molecules (Tuñón et al, 2009). The saponins in Anabasis and Vernonia species are another factor that may be responsible for the anti-infl ammatory effect of the studied plants (Safayhi and Sailer, 1997;Abdou et al, 2013).…”

“…Phytochemical screening of A. articulata revealed the presence of saponins as major constituents of the n-butanol fraction. The anti-infl ammatory activity of A. articulata may be attributed to its saponin content as proven for A. setifera, a related species containing cyclooxygenase inhibitory saponins (Abdou et al, 2013) Finally, the least effective plant of the three, T. trichodesmoides, belongs to the family Boraginaceae. Trichodesma species have been examined for pyrrolizidine alkaloids (Wassel et al, 1987) and triterpenes (Singh et al, 2006).…”

Phytochemical composition of some common coastal halophytes of the United Arab Emirates

“…Identified triterpenoids included: alpha-amyrin glucopyranoside, patuletin glucopyranoside, myricitrin and a newly discovered oleanane triterpene saponin derivative -sophradiol glucopyranoside (Abdou et al, 2013). All of these compounds were found to inhibit acute and chronic inflammatory agents in rats, and thus were concluded to exhibit anti-inflammatory properties (Abdou et al, 2013).…”