Iridoids from the Roots of <i>Patrinia scabra</i> and Their Inhibitory Potential on LPS-Induced Nitric Oxide Production

Lee, Da Hye; Shin, Ji Sun; Kang, Shin Young; Lee, Seung Bin; Lee, Jin Su; Ryu, Seung Mok; Lee, Kyung Tae; Lee, Dong‐Ho; Jang, Dae Sik

doi:10.1021/acs.jnatprod.8b00229

Cited by 23 publications

(14 citation statements)

References 28 publications

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“…3-to-1, revealing the presence of a chlorine atom and a molecular formula of C 24 H 29 ClO 11 . Direct comparison of the NMR (Tables and ) of 5 and 3 showed that their only difference was a chlorine atom in 5 instead of the C-10 OH group in 3 , which resulted in a C-10 upfield shift from δ C 66.2 in 3 to δ C 47.3 in 5 . − The planar structure of 5 could be confirmed by detailed 2D NMR spectroscopic data analysis (Figure S4, Supporting Information). The relative configuration of 5 was identified as being the same as that of 3 on the basis of similar NMR data and ROESY correlations of H-5/H-9, H-5/H-10a, and H-9/H-10b (Figure S4, Supporting Information).…”

Section: Results and Discussionmentioning

confidence: 85%

Iridoid Constituents of Viburnum brachybotryum

Rao

et al. 2021

J. Nat. Prod.

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Eleven new iridoids, brachybones A–K (1–11), were isolated from the twigs of Viburnum brachybotryum. Their structures including absolute configurations were determined by spectroscopic data analysis and from the electronic circular dichroism (ECD) spectra. All of the compounds 1–11 possess one or two acetoxysenecioate substituents. Furthermore, compounds 5–7 and 11 feature a Cl atom in the molecule, while compounds 9–11 exhibit a cagelike rigid skeleton through an unusual oxo bridge from C-3 to C-8 or C-10. The isolates were evaluated for cytotoxic activity against the HCT-116, A549, and Hela cell lines, and the results showed compounds 10 and 11 to be active against HCT-116 cells.

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Section: Results and Discussionmentioning

confidence: 85%

Iridoid Constituents of Viburnum brachybotryum

Rao

et al. 2021

J. Nat. Prod.

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“…Iridoids are an important type of chemical constituents of the genus Patrinia . Previous investigations showed that some iridoids from P. heterophylla and P. scabra possessed significant anti-inflammatory activity [ 35 , 36 , 37 ]. However, studies on the iridoids in P. scabiosifolia were mainly focused on their cytotoxic and AChE inhibitory activities, and studies on the anti-inflammatory activity of the iridoids from this plant are still insufficient [ 22 , 25 ].…”

Section: Resultsmentioning

confidence: 99%

Two New Iridoid Glucosides from the Whole Plant of Patrinia scabiosifolia Link

Sun

Liu

et al. 2021

Molecules

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As a traditional Chinese medicine, Patrinia scabiosifolia Link has been used to treat various inflammatory-related diseases, and recent studies have shown that it possesses potent anti-inflammatory activity. Therefore, phytochemical investigation on whole plants of P. scabiosifolia were carried out, which led to the isolation of two new iridoid glucosides, patriniscabiosides A (1) and B (2), together with six known compounds (3–8). The structural elucidation of all compounds was performed by HRESIMS and extensive spectroscopic analyses including IR, 1D, 2D NMR, and electronic circular dichroism (ECD). All the isolated compounds were tested for their anti-inflammatory activity using the NF-κB-Dependent Reporter Gene Expression Assay, and compound 3 displayed anti-inflammatory activity through the inhibition of the NF-κB pathway, with an inhibitory rate of 73.44% at a concentration of 10 μM.

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“…There was reported that 70% ethanol extraction of the roots from P. scabra exhibited anti-inflammatory activity towards lipopolysaccharide (LPS)-induced nitric oxide (NO). Two novel iridoids and one reported patrineolignan B have been found to significantly decrease the LPS-induced NO production in a concentration-dependent manner [ 11 ]. Considering the chemical structure of iridoid, it was speculated that the ethyl group in the iridoids may play a role in the anti-inflammatory effects [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Optimization for ultrasonic-microwave synergetic extraction of total iridoid glycosides and screening of analgesic and anti-inflammatory active fractions from patrinia scabra Bunge (Valerianaceae)

Deng

et al. 2022

BMC Complement Med Ther

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Background Patrinia scabra Bunge is a well-known herbal medicine for its favorable treatment on inflammatory diseases owing to its effective ingredients, in which iridoid glycoside plays an extremely significant role. This article aimed to improve the content of total iridoid glycosides in crude extract through a series optimization of extraction procedure. Moreover, considering that both pain and inflammation are two correlated responses triggered in response to injury, irritants or pathogen, the article investigated the anti-inflammatory and analgesic activities of P. scabra to screen out the active fraction. Method P. scabra was extracted by ultrasonic-microwave synergistic extraction (UMSE) to obtain total iridoid glycosides (PSI), during which a series of conditions were investigated based on single-factor experiments. The extraction process was further optimized by a reliable statistical method of response surface methodology (RSM). The elution fractions of P. scabra extract were prepared by macroporous resin column chromatography. Through the various animal experiment including acetic acid-induced writhing test, formalin induced licking and flinching, carrageenan-induced mice paw oedema test and xylene-induced ear edema in mice, the active fractions with favorable analgesic and anti-inflammatory effect were reasonably screen out. Results The content of PSI could reach up to 81.42 ± 0.31 mg/g under the optimum conditions as follows: ethanol concentration of 52%, material-to-liquid ratio of 1:18 g/mL, microwave power at 610 W and extraction time of 45 min. After gradient elution by the macroporous resin, the content of PSI increased significantly. Compared with other concentrations of elution liquid, the content of PSI in 30 and 50% ethanol eluate was increased to reach 497.65 and 506.90 mg/g, respectively. Owing to the pharmacology experiment, it was reasonably revealed that 30 and 50% ethanol elution fractions of P. scabra could relieve pain centrally and peripherally, exhibiting good analgesic and anti-inflammatory activities. Conclusion Patrinia scabra possessed rich iridoids and exhibited significant analgesic and anti-inflammatory activities.

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Iridoids from the Roots of Patrinia scabra and Their Inhibitory Potential on LPS-Induced Nitric Oxide Production

Cited by 23 publications

References 28 publications

Iridoid Constituents of Viburnum brachybotryum

Iridoid Constituents of Viburnum brachybotryum

Two New Iridoid Glucosides from the Whole Plant of Patrinia scabiosifolia Link

Optimization for ultrasonic-microwave synergetic extraction of total iridoid glycosides and screening of analgesic and anti-inflammatory active fractions from patrinia scabra Bunge (Valerianaceae)

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