Paeonidanin

Monoterpene glycosides with anti-inflammatory activity from Paeoniae Radix.[Pubmed:31398448]

Fitoterapia. 2019 Oct;138:104290.

Six new monoterpene glycosides, named 6'-O-nicotinoylalbiflorin (1), 4'-O-vanillylalbiflorin (2), Paeonidanin L (3), paeoniflorigenin-1-O-beta-d-xyloside (4), 6'-(2-hydroxypropanoyl)-paeoniflorin (5), oxylactiflorin (6), together with 16known ones (7-22) were isolated from the 70% ethanol extract of Paeoniae Radix. Their structures were elucidated based on spectroscopic analysis (1D and 2D NMR, HRESIMS, IR and UV), chemical evidences and comparison with literatures. The inhibitory effects of all the isolates were evaluated against lipopolysaccharide (LPS) stimulated PGE(2) production in RAW 264.7 macrophages.

Anti-Inflammatory Effects, SAR, and Action Mechanism of Monoterpenoids from Radix Paeoniae Alba on LPS-Stimulated RAW 264.7 Cells.[Pubmed:28468284]

Molecules. 2017 Apr 29;22(5):715.

Nine monoterpenoids from Radix Paeoniae Alba, including paeoniflorin derivatives, paeoniflorin (PF), 4-O-methylpaeoniflorin (MPF), 4-O-methylbenzoylpaeoniflorin (MBPF); Paeonidanin derivatives, Paeonidanin (PD), Paeonidanin A (PDA), albiflorin derivatives, albiflorin (AF), benzoylalbiflorin (BAF), galloylalbiflorin (GAF), and debenzoylalbiflorin (DAF), were obtained in our previous phytochemistry investigations. Their anti-inflammatory effects were determined in the present study. The expression and production of pro-inflammatory cytokines in lipopolysaccharides (LPS)-stimulated RAW 264.7 cells were measured using an Elisa assay and nitric oxide (NO) release was determined using the Griess method. The results demonstrated that the most of the monoterpenoids suppressed the LPS-induced production of NO, interleukin-6 (IL-6), and tumor necrosis factor alpha (TNF-alpha). The anti-inflammatory activities of these monoterpenoids were closely related to their structural characteristics. Paeoniflorins and Paeonidanins presented stronger anti-inflammatory activities than those of albiflorin derivatives. Furthermore, the action mechanisms of MBPF, having a strong anti-inflammatory effect, were investigated using quantitative reverse transcription polymerase chain reaction (RT-PCR) and Western blot methods. The results indicated that MBPF could down-regulate the mRNA and protein expression level of inducible nitric oxide synthase (iNOS) in LPS-stimulated RAW 264.7 cells. The mitogen-activated protein kinase (MAPK), phosphatidylinositol 3-kinase (PI3K)/AKT and nuclear factor kappaB (NF-kappaB) signaling pathways are involved in mediating the role of MBPF in suppressing the expression and production of pro-inflammatory cytokines in RAW 264.7 cells.

Monoterpene glycosides from Paeonia veitchii.[Pubmed:27268664]

J Asian Nat Prod Res. 2017 Jan;19(1):22-27.

The EtOH extract of the roots of Paeonia veitchii afforded two new monoterpene glycosides Paeonidanin I (1) and Paeonidanin J (2), and a new dimeric monoterpene glycoside Paeonidanin K (3). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products.

Monoterpenes from Paeonia albiflora and their inhibitory activity on nitric oxide production by lipopolysaccharide-activated microglia.[Pubmed:19691309]

J Nat Prod. 2009 Sep;72(9):1579-84.

Eleven new monoterpenes, paeonidangenin (1), Paeonidanin A (2), Paeonidanin B (3), Paeonidanin C (4), Paeonidanin D (5), Paeonidanin E (6), paeoniflorone (7), 4-O-methylbenzoylpaeoniflorin (8), 4-O-methylgalloylpaeoniflorin (9), 4-O-methyldebenzoylpaeoniflorin (10), and 4-O-methylalbiflorin (11), were isolated from the 60% ethanol extract of the roots of Paeonia albiflora. Their structures were determined primarily on the basis of 1D and 2D NMR techniques and MS studies. Paeonidanins D (5) and E (6) are unprecedented examples of "cage-like" monoterpene dimers. The inhibitory effects of the isolated compounds on nitric oxide production by lipopolysaccharide (LPS)-activated N9 microglia were evaluated.

[Study on chemical constituents of bark of Paeonia suffruticosa].[Pubmed:17260795]

Zhongguo Zhong Yao Za Zhi. 2006 Nov;31(21):1793-5.

OBJECTIVE: To study the chemical constituents of the bark of Paeonia suffruticosa. METHOD: The 95% ethanol extract was re-extracted with EtOAc, and then separated and purified by column chromatography using silica gel, Sephadex LH -20 and RP-18 as packing materials. The structures were identified on the basis of spectral analysis and physico-chemical characters. RESULT: Six compounds were isolated and identified as (+)-catechin (1), Paeonidanin (2), paeoniflorigenone (3), 2, 5-dihydroxy-4-methoxyacetophenone (4), paeonol (5), gallic acid (6). CONCLUSION: The compound 1 was isolsted from the genus Paeonia for the first time. The compounds 2, 3 were isolated from this plant for the first time.

Vasorelaxant effect of the rootbark extract of Paeonia moutan on isolated rat thoracic aorta.[Pubmed:17051461]

Planta Med. 2006 Nov;72(14):1338-41.

The vascular relaxant effect of the rootbark extract of Paeonia moutan was evaluated in isolated rat thoracic aorta. The methanolic extract of the rootbark showed a vasorelaxant activity in rat aortic preparations precontracted with 0.3 microM phenylephrine (IC50 value: 16.8 microg/mL). The activity-guided fractionation of the extract led to the isolation of five active principles such as paeoniflorin (1), Paeonidanin (2), methylpaeoniflorin (4), tetragalloylglucose (5) and pentagalloylglucose (6), and these active ingredients potently relaxed phenylephrine-induced contraction of rat aortic preparations in a concentration-dependent manner (IC50 values: 19.4, 7.9, 10.1, 5.1 and 3.6 microM, respectively). These results suggest that pinane glycosides and galloylglucoses might be the components responsible for the vasorelaxant properties of the rootbark extract of P. moutan, and their vasorelaxant effects may be mediated through increases in the release of nitric oxide from endothelial cells.