Phenolic Components of the Aerial Parts of Achillea alpina

Zhang, Qing; Zhou, Qiqi; Huo, Changhong; Wu, Yibing; Zhang, Manli; Li, Ligeng; Jin, Shu‐Guang; Shi, Qing; Gu, Yu‐Cheng

doi:10.1007/s10600-019-02683-x

Cited by 8 publications

(13 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…13 C-NMR (100 MHz, DMSO- d 6 ) δ : 177.4 (C-4), 164.2 (C-7), 161.2 (C-5), 156.3 (C-2), 156.2 (C-9), 148.5 (C-4′), 144.8 (C-3′), 133.2 (C-3), 121.6 (C-6′), 121.2 (C-1′), 116.2 (C-5′), 115.2 (C-2′), 104.0 (C-10), 100.9 (C-1″), 98.7 (C-6), 93.5 (C-8), 77.6 (C-5″), 76.5 (C-3″), 74.1 (C-2″), 69.9 (C-4″), 61.0 (C-6″). Thus, the structure of 2 was defined as isoquercitrin by comparison of its MS, 1 H-and 13 C-NMR data with literature data [22].…”

Section: Resultsmentioning

confidence: 99%

“…13 C-NMR (DMSO- d 6 , 100 MHz) δ : 182.0 (C-4), 164.4 (C-2), 163.0 (C-7), 161.8 (C-5), 161.1 (C-4′), 157.0 (C-9), 128.6 (C-2′, 6′), 120.7 (C-1′), 116.1 (C-3′, 5′), 105.3 (C-10), 103.0 (C-3), 99.9 (C-6), 99.5 (C-1′′), 94.8 (C-8), 77.2 (C-3′′), 76.5(C-5′′), 73.1 (C-2′′), 69.6 (C-4′′), 60.6 (C-6′′). Thus, the structure of 5 was defined as apigenin-7- O -β- d -glucopyranoside by comparison of its MS, 1 H- and 13 C-NMR data with literature data [22].…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Separation of Five Flavonoids from Aerial Parts of Salvia Miltiorrhiza Bunge Using HSCCC and Their Antioxidant Activities

et al. 2019

View full text Add to dashboard Cite

The aerial parts of Salvia miltiorrhiza Bunge, as the non-medicinal parts, are always discarded during harvesting, resulting in a huge waste of resources and environmental pressure. Due to the high flavonoid content and their antioxidant activities characteristics, the aerial parts of S. miltiorrhiza can be developed into natural antioxidants and used in foods. A high-speed counter-current chromatography (HSCCC) method, using a two-phase solvent system composed of tert-butyl methyl ether/n-butanol/acetonitrile/water (3:1:1:20, v/v), was the first to successfully isolate five flavonoids from the aerial parts of S. miltiorrhiza in one attempt, and separately categorized as rutin (1), isoquercitrin (2), kaempferol-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (3), kaempferol-3-O-β-d-glucopyranoside (4) and apigenin-7-O-β-d-glucopyranoside (5) after identification. The purities of these plant isolates were 97.3%, 99.5%, 92.8%, 98.1% and 98.7%, respectively. All the flavonoids were identified by HR-ESI-MS, 1D and 2D NMR. Compounds 3 and 5 were firstly isolated from the plant of S. miltiorrhiza. Results from antioxidant assays showed that rutin (1) and isoquercitrin (2) had higher antioxidant capacities compared to L-ascorbic acid as the positive control.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Separation of Five Flavonoids from Aerial Parts of Salvia Miltiorrhiza Bunge Using HSCCC and Their Antioxidant Activities

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Isochlorogenic acid B (1): light yellow powder; 1 H-NMR (500 MHz, CD 3 OD) δ 7.58 (1H, d, J = 15.9 Hz, H-7 ), 7.50 (1H, d, J = 15.9 Hz, H-7"), 7.06 (1H, d, J = 2.0 Hz, H-2 ), 7.01 (1H, d, J = 2.0 HZ, H-2"), 6.93 (1H, dd, J = 8.2, 2.0 Hz, H-6 ), 6.88 (1H, dd, J = 8.2, 2.0 Hz, H-6"), 6.77 (1H, d, J = 8.2 HZ, H-5 ), 6.74 (1H, d, J = 8.2 Hz, H-5"), 6.30 (1H, d, J = 15.9 Hz, H-8 ), 6.24 (1H, d, J = 15.9 Hz, H-8"), 5.63 (1H, m, H-3), 5.19 (1H, m, H-4), 4.13 (1H, m, H-5), 2.18 (1H, dd, J = 13.5, 4.0 Hz, H-6a), 2.08 (1H, m, H-6b), 2.06 (2H, m, H-2); 13 The above data were in agreement with the previous literature [35], so the structure was identified as isochlorogenic acid A.…”

Section: Isolation and Identificationmentioning

confidence: 99%

“…As a traditional Chinese medicine, the aerial parts of A. alpina were recorded in Pharmacopoeia of the People's Republic of China with effects of detoxification, clearing dampness, blood circulation promotion, and relieving pain. In terms of phytochemistry, studies of the extracts of the aerial parts of A. alpina led to the isolation of organic acids, flavonoids, terpenoids, alkaloids, steroids, lignanoids, quinones, and several other compounds, some of which exhibited antioxidant, antimelanogenic, anti-inflammatory, antipyretic, analgesic, sedative, and cardiovascular protective activities [9][10][11][12][13][14]. In our continuing search for TRPV3 channel antagonists from medicinal plants [7,8], the ethanol extract of whole herbs of A. alpina showed an inhibitory activity on TRPV3 channel by using a calcium fluorescent assay.…”

Section: Introductionmentioning

confidence: 99%

“…C-NMR (125 MHz, CD 3 OD) δ 182.0 (C-7), 168.4 (C-9 , 9"), 149.8 (C-4 ), 149.6 (C-4"), 147.4 (C-7 ), 147.2 (C-7"), 146.9 (C-3 ), 146.8 (C-3"), 127.8 (C-1 ), 127.7 (C-1"), 123.2 (C-6 ), 123.1 (C-6"), 116.5 (C-5 , 5"), 115.2 (C-2 , 2"), 115.1 (C-8 ), 115.0 (C-8"), 75.6 (C-1), 74.5 (C-4), 69.9 (C-3), 67.8 (C-5), 39.5 (C-2), 38.2 (C-6); ESI-MS m/z 517 [M + H] + . The above data were in agreement with those reported in the literature[35], so the structure was identified as isochlorogenic acid B.Isochlorogenic acid A (2): light yellow powder; 1 H-NMR (500 MHz, CD 3 OD) δ 7.61 (1H, d, J = 15.9 Hz, H-7 ), 7.57 (1H, d, J = 16.0 Hz, H-7"), 7.07 (1H, d, J = 1.1 Hz, H-2 ), 7.06 (1H, d, J = 1.1 Hz, H-2"), 6.97 (2H, dd, J = 8.2, 1.1 Hz, H-6 , 6"), 6.78 (2H, d, J = 8.2 Hz, H-5 , 5"), 6.37 (1H, d, J = 15.9 Hz, H-8 ), 6.27 (1H, d, J = 16.0 Hz, H-8"), 5.45 (1H, m, H-5), 5.42 (1H, m, H-3), 3.94 (1H, dd, J = 8.4, 2.9Hz, H-4), 2.30 (1H, m, H-6a), 2.18 (2H, m, H-2), 2.15 (1H, m, H-6b);13 C-NMR (125 MHz, CD 3 OD) δ 180.0 (C-7), 169.1 (C-9 ), 168.6 (C-9"), 149.6 (C-4 ), 149.5 (C-4"), 147.1 (C-3 ), 147.0 (C-3"), 146.8 (C-7 ), 146.8 (C-7"), 128.0 (C-1 ), 127.9 (C-1"), 123.0 (C-6 , 6"), 116.6 (C-5 , 5"), 115.8 (C-2 ), 115.4 (C-2"), 115.2 (C-8 , C-8"), 76.0 (C-1), 73.4 (C-3), 72.3 (C-5), 71.7 (C-4), 39.0 (C-6), 37.0 (C-2); ESI-MS m/z 517 [M + H] + .…”

mentioning

confidence: 99%

See 1 more Smart Citation

Identification of Transient Receptor Potential Vanilloid 3 Antagonists from Achillea alpina L. and Separation by Liquid-Liquid-Refining Extraction and High-Speed Counter-Current Chromatography

et al. 2020

View full text Add to dashboard Cite

Bioassay-guided fractionation of the ethanol extract of whole herbs of Achillea alpina led to the isolation of isochlorogenic acids A and B as transient receptor potential vanilloid 3 (TRPV3) channel antagonists by using a calcium fluorescent assay. The structures were identified by spectroscopic analysis and the inhibitory activities of isochlorogenic acids A and B were confirmed by whole-cell patch clamp recordings of human embryonic kidney 293 (HEK293) cells expressing human TRPV3. Molecular docking results revealed that these two compounds reside in the same active pocket of human TRPV3 channel protein with lower binding energy than the agonist 2-aminoethoxydiphenyl borate (2-APB). High-speed counter-current chromatography (HSCCC) coupled with a liquid-liquid extraction approach was successfully established for the separation of isochlorogenic acids A and B from the whole herbs of A. alpina. Ethyl acetate and n-hexane-ethyl acetate-water (3:3:4 and 1:5:4, v/v/v) were selected as liquid-liquid extraction solvent systems to remove high- and low-polarity impurities in the mixture. Sixty g of ethanol extract was refined by solvent partition to yield 1.7 g of the enriched fraction, of which 480 mg in turn obtained 52.5 mg of isochlorogenic acid B (purity 98.3%) and 37.6 mg isochlorogenic acid A (purity 96.2%) after HSCCC with n-hexane-ethyl acetate-water containing 1% acetic acid (1:4:8, v/v/v).

show abstract

Chemical constituents from the aerial parts of Achillea alpina and their chemotaxonomic significance

Guo

et al. 2022

Biochemical Systematics and Ecology

View full text Add to dashboard Cite

Phenolic Components of the Aerial Parts of Achillea alpina

Cited by 8 publications

References 10 publications

Separation of Five Flavonoids from Aerial Parts of Salvia Miltiorrhiza Bunge Using HSCCC and Their Antioxidant Activities

Separation of Five Flavonoids from Aerial Parts of Salvia Miltiorrhiza Bunge Using HSCCC and Their Antioxidant Activities

Identification of Transient Receptor Potential Vanilloid 3 Antagonists from Achillea alpina L. and Separation by Liquid-Liquid-Refining Extraction and High-Speed Counter-Current Chromatography

Chemical constituents from the aerial parts of Achillea alpina and their chemotaxonomic significance

Contact Info

Product

Resources

About