Chemical Constituents and an Antineuroinflammatory Lignan, Savinin from the Roots of Acanthopanax henryi

Abstract

The phytochemical investigation on the roots of Acanthopanax henryi (Araliaceae) resulted in the discovery of twenty compounds whose chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass spectrometry data, other physicochemical properties, and a comparison of the spectral data with the literature. They were identified as (-)-sesamin (1), helioxanthin (2), savinin (3), taiwanin C (4), 6-methoxy-7-hydroxycoumarin (5), behenic acid (6), 3-O-caffeoyl-quinic acid (7), 5-O-caffeoyl-quinic acid (8), 1,3-di-O-caffeoyl-quinic acid (9), 1,4-di-O-caffeoyl-quinic acid (10), 1,5-di-O-caffeoyl-quinic acid (11), (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (12), (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (13), ferulic acid (14), caffeic acid (15), stigmasterol (16), β-sitosterol (17), adenosine (18), syringin (19), and trans-coniferin (20). Among these isolates, compound 3 showed inhibitory activity against lipopolysaccharide- (LPS-) induced nitric oxide (NO) and prostaglandin E2 (PGE2) production with IC50 values of 2.22 ± 0.11 and 2.28 ± 0.23 μM, respectively. The effects of compound 3 were associated with the suppression of LPS-induced expression of the inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein. Furthermore, compound 3 negatively regulated the production of interleukin- (IL-) 1β and tumor-necrosis factor- (TNF-) α at the transcriptional level in LPS-stimulated BV2 microglial cells. These antineuroinflammatory effects of compound 3 were mediated by p38 mitogen-activated protein kinase (MAPK).

Coniferyl Aldehyde Inhibits the Inflammatory Effects of Leptomeningeal Cells by Suppressing the JAK2 Signaling

“…CA is a nontoxic compound extracted from natural plants. It is proved that CA can protect cells from radiation and neuroinflammation [ 58 , 59 ]. Akram et al [ 26 ] found the inhibitory effect of CA on paw edema of rat models induced by carrageenan (CRG).…”

Enhancing and Complementary Mechanisms of Synergistic Action of Acori Tatarinowii Rhizoma and Codonopsis Radix for Alzheimer’s Disease Based on Systems Pharmacology

“…The top 6 ingredients were kaempferol (SCP93), apigenin (DS77), 7-methoxy-2-methyl isoflavone (DS45), stigmasterol (DS37), syringin (DS38), and HMF (DS75) with a CS sum of 45.20%; these were active ingredients from both ATR and CR, especially apigenin and HMF, the shared ingredients. For instance, syringin exhibits anti-inflammatory activity and enhances the synthesis of acetylcholine in the hippocampus [ 69 , 108 ]. HMF can mitigate the impairment of cognition and memory function induced by A β , inhibit beta-secretase activity, and increase antioxidative enzyme activities [ 109 ].…”

Acanthopanax henryi: Review of Botany, Phytochemistry and Pharmacology

“…Rosin (34) and eugenol glucoside (43) were isolated from fruits and flowers of AH, respectively [12,21]. Ferulic acid (35), syringin (37), and trans-coniferin (38) have been obtained from the roots of AH [19]. Meanwhile, trans-p-hydroxycinnamic acid (39), (E)-caffeic acid methyl ester (40), trans-coniferyl aldehyde (41), and trans-sinapaldehyde (42) were retrieved from the stem part of this plant [20].…”

“…Meanwhile, trans-p-hydroxycinnamic acid (39), (E)-caffeic acid methyl ester (40), trans-coniferyl aldehyde (41), and trans-sinapaldehyde (42) were retrieved from the stem part of this plant [20]. Additionally, caffeic acid (36) was purified from both roots and stems of AH [19,20] (Figure 6).…”

“…It has been shown that four of them are caffeoyl monosubstituted compounds (50-53), and the other nine are caffeoyl disubstitutes and their methyl esters (44-49, 54-56) (Figure 7). This type of compound exists throughout the plant, including fruit [13], root [19], stem [20], flower [21], and leaf [22]. The information on the caffeoyl quinic acids is shown in Table 1.…”