Isoflavonoids and norneolignan from Caragana changduensis

Guo, Liang; Yang, Xuedong; Sun, Xiwen; Wu, Xun

doi:10.1016/j.phytol.2017.03.009

Cited by 7 publications

(5 citation statements)

References 15 publications

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“…Three compounds were extracted from CC‐4, and separated and purified by normal phase and reversed phase HPLC. Compounds 8 and 6 were identified as 7,2′‐dihydroxy‐4′‐methoxyisoflavanone 14 and 6,7,2′‐trihydroxy‐4′‐methoxyisoflavone 10 by comparison of the spectroscopic data (HR‐ESI‐MS, 1 H‐ and 13 C‐NMR) with those reported in the literature. Although compound 4 was generated as a predicted metabolite by BioTransformer, there is no report on its real existence 15,16 .…”

Section: Resultsmentioning

confidence: 96%

“…Among them, flavonoids, such as isoflavones, pterocarpans and isoflavanones account for more than 80% of the total number of compounds in LIC. These compounds have been reported to be related to the therapeutic effects of LIC 8–10 . At present, only the analyses of a single component, formononetin in LIC by thin‐layer chromatography (TLC) and high‐performance liquid chromatography (HPLC) 11 and total flavonoids by ultraviolet (UV) have been reported 12,13 .…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive quality evaluation of Lignum Caraganae and rapid discrimination of Caragana jubata and Caragana changduensis based on characteristic compound fingerprints by HPLC‐UV and HPLC‐MS/MS coupled with chemometrics analysis

Wang

Yang

et al. 2020

Phytochemical Analysis

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Introduction: Caragana jubata Poir (CJ) and Caragana changduensis Liou f. (CC) are the two main original plants of Lignum Caraganae (LIC, a clinically effective Tibetan materia medica) and the red heartwoods of CJ and CC have been used for the treatment of polycythemia, hypertension and menstrual disorders. Objective: To establish a comprehensive method for rapid quality assessment of LIC based on revealing the characteristic components of LIC and to discriminate the plant sources and LIC from its adulterations. Methodology: A multi-index and synthetically balanced orthogonal design L 9 (3 4) experiment was performed to obtain an efficient ultrasonic extraction condition of LIC sample. High-performance liquid chromatography coupled with an ultraviolet detector (HPLC-UV) techniques were developed for fingerprinting and quantitative analysis of 14 major compounds in LIC, and the main components were identified by HPLC tandem mass spectrometry (HPLC-MS/MS). HPLC fingerprint and chemometrics analysis were employed to visualise the distinction and relationship of LIC obtained from CJ and CC and to determine their potential characteristic markers. Results: Fourteen compounds including a new compound were identified and quantified in LIC. The potential characteristic markers in LIC were identified based on qualitative and fingerprint analysis. The hierarchical cluster analysis (HCA) and principle component analysis (PCA) showed obvious discrimination between LIC obtained from CJ and CC. Five batches of LIC samples were authenticated, and its adulterations were successfully found. Conclusion: A facile HPLC combined with fingerprint and chemometrics methods could rapidly evaluate the quality of LIC and discriminate LIC obtained from CJ and CC.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Comprehensive quality evaluation of Lignum Caraganae and rapid discrimination of Caragana jubata and Caragana changduensis based on characteristic compound fingerprints by HPLC‐UV and HPLC‐MS/MS coupled with chemometrics analysis

Wang

Yang

et al. 2020

Phytochemical Analysis

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“…The structures of known compounds ( 5 – 36 ) were confirmed to be formononetin ( 5 ), 8-methylretusin ( 6 ), 5,7,4′-trihydroxy-6,8-dimethoxyisoflavone ( 7 ), afromosin ( 8 ), 4,6,7-trimethoxyisoflavone ( 9 ), 2′-hydroxy-5′-methoxybiochanin A ( 10 ), 5,7,3′-trihydroxy-6,4′-dimethoxyisoflavone ( 11 ), pratensein ( 12 ), abrusprecatin A ( 13 ), (6a R ,11a R )-vesticarpan ( 14 ), abrusprecatin B ( 15 ), abrusprecatin C ( 16 ), medicarpin ( 17 ), (6a R , 11a R )-3-hydroxy-9,10-dimethoxy pterocarpan ( 18 ), (6a R ,11a R )-(−)-2-methoxymaackiain ( 19 ), 2( S )-7,4′-dihydroxy-3′-methoxyflavanone ( 20 ), 2( R )-liquirtigenin ( 21 ), 2( R )-7-hydroxy-4′- methoxy dihydroflavones ( 22 ), isoliquiritigenin ( 23 ), 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-propan-1-one ( 24 ), 4′- O -methyldavidigenin ( 25 ), (3 R )-2′,3′-dihydroxy-6,7,4′-trimethoxyisoflavane ( 26 ), pterosonins F ( 27 ), 2-(2′-methoxy,4′-hydroxy)-aryl-3-methyl-6-hydroxy benzofuran ( 28 ), (8 R ,8’ R )-(−)-trans-3,4-divanillyltetrahydrofuran ( 29 ), (8 R ,7’ S ,8’ R )-(+)-isoshonanin ( 30 ), (8 S )-2,4-dihydroxy-8-hydroxymethyl-4′-methoxydeoxybenzoin ( 31 ), 1 H -indole-3-carboxylic acid, methyl ester ( 32 ), 3,3a-dihydro-1 H -benzo[ d ]pyrrolo[2,1- b ][1,3] oxazine-1,5(2 H )-dione ( 33 ), 2,3,3a,5-tetrahydro-1 H -benzo[ d ]pyrrolo[2,1- b ][1,3]oxazin-1-one ( 34 ), N -[4′-hydroxy-( Z )-cinnamoyl]- l -tyrosine methyl ester ( 35 ), and N -[4′-hydroxy-( E )- cinnamoyl]- l -tyrosine methyl ester ( 36 ).…”

Section: Results and Discussionmentioning

confidence: 99%

“…Furthermore, the characteristic coupling constants of J H-2 12.4, 2.7 Hz and J H-2 ″12.8, 3.0 Hz as well as the positive Cotton effect at 311 nm for 4 in the CD spectrum (Figure 3) further confirmed that its configuration was 2S, 2″S. 36,37 Then, its structure was finally elucidated and named mollisone D. The structures of known compounds (5−36) were confirmed to be formononetin (5), 38 8-methylretusin (6), 39 5,7,4′-trihydroxy-6,8-dimethoxyisoflavone (7), 40 afromosin (8), 41 4,6,7-trimethoxyisoflavone ( 9), 42 2′-hydroxy-5′-methoxybiochanin A (10), 43 5,7,3′-trihydroxy-6,4′-dimethoxyisoflavone (11), 44 pratensein (12), 45 abrusprecatin A (13), 35 (6aR,11aR)-vesticarpan ( 14), 34 abrusprecatin B (15), 35 abrusprecatin C ( 16), 35 medicarpin (17), 46 (6aR, 11aR)-3hydroxy-9,10-dimethoxy pterocarpan (18), 47 (6aR,11aR)-(−)-2-methoxymaackiain ( 19), 48 2(S)-7,4′-dihydroxy-3′-me- thoxyflavanone (20), 49 2(R)-liquirtigenin (21), 50 2(R)-7hydroxy-4′-methoxy dihydroflavones ( 22), 51 isoliquiritigenin (23), 52 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-propan-1-one (24), 53 4′-O-methyldavidigenin (25), 54 (3R)-2′,3′dihydroxy-6,7,4′-trimethoxyisoflavane (26), 55 pterosonins F (27), 56 2-(2′-methoxy,4′-hydroxy)-aryl-3-methyl-6-hydroxy benzofuran (28), 57 (8R,8'R)-(−)-trans-3,4-divanillyltetrahydrofuran (29), 58 (8R,7'S,8'R)-(+)-isoshonanin (30), 59 (8S)-2,4-dihydroxy-8-hydroxymethyl-4′-methoxydeoxybenzoin (31), 60 1H-indole-3-carboxylic acid, methyl ester (32), 61 63 N-[4′-hydroxy-(Z)-cinnamoyl]-Ltyrosine methyl ester (35), 64 and N-[4′-hydroxy-(E)cinnamoyl]-L-tyrosine methyl ester (36)…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

From Tea to Health: Exploring Abrus mollis for Liver Protection and Unraveling Its Potential Mechanisms

Zhang,

Wang,

Kuang

et al. 2023

J. Agric. Food Chem.

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Abrus mollis Hance is a characteristic medicinal herb which is used in Guangdong and Guangxi provinces of China for making soup, medicinal meals, and herbal tea to treat dampheat jaundice and rib discomfort. Current phytochemical study on A. mollis led to the isolation of four new flavones, mollisone A-D (1–4), and thirty two known compounds (5–36). Their structures were characterized by an extensive analysis of spectroscopic data including IR, UV, HR-ESI-MS, and 1D and 2D NMR, as well as electronic circular dichroism calculation. In addition, in order to initially understand their biological activities for traditional applications, in vitro antioxidant and hepatoprotective tests were carried out, whose results illustrated that 25 compounds had significant free radical scavenging ability, and compounds 13 and 16 exhibited protective activities on D-GalN-induced LO2 cell damage than the positive control. Moreover, network pharmacological analysis revealed that the hepatoprotective activity of A. mollis involved multitargets and multipathways such as PI3K/Akt, MAPK, and JAK-STAT pathways and various biological processes such as positive regulation of phosphorylation and regulation of kinase activity. These results suggested that this species could serve as a potential hepatoprotective agent for functional food or medicinal use.

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“…The instruments used to isolate compounds, measure optical rotations, and record UV, ECD, IR, and NMR spectra are the same as reported previously . Bruker MicroTOFQ II or Thermo Fisher Q Exactive HF Orbitrap spectrometers were used to measure the HRESIMS.…”

Section: Methodsmentioning

confidence: 99%

Anti-inflammatory Chalcone–Isoflavone Dimers and Chalcone Dimers from Caragana jubata

et al. 2019

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Two new chalcone–isoflavone dimers, caraganins A (1) and B (2), two new chalcone dimers, caraganins C (3) and D (4), and eight known compounds (5–12) were obtained from the red heartwood of the rhizomes of Caragana jubata. The structures of caraganins A–D were established by 1D and 2D NMR spectroscopy, HRMS and ECD analysis, and comparison with previously known compounds. The anti-inflammatory activities of the new compounds were evaluated by measuring the production of NO, IL-6, and TNF-α in mouse RAW 264.7 macrophages induced by lipopolysaccharide. Among these, compounds 2 and 4 showed the most potent inhibitory activities (IC50: 4.1 and 5.2 μM, respectively) on nitric oxide formation, and compounds 1 and 4 displayed the most potent inhibitory activities on the secretion of inflammatory factor TNF-α, with IC50 values of 11.4 and 14.7 μM. The possible biosynthetic pathways of the chalcone–isoflavone dimers and the chalcone dimers are proposed.

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Isoflavonoids and norneolignan from Caragana changduensis

Cited by 7 publications

References 15 publications

Comprehensive quality evaluation of Lignum Caraganae and rapid discrimination of Caragana jubata and Caragana changduensis based on characteristic compound fingerprints by HPLC‐UV and HPLC‐MS/MS coupled with chemometrics analysis

Comprehensive quality evaluation of Lignum Caraganae and rapid discrimination of Caragana jubata and Caragana changduensis based on characteristic compound fingerprints by HPLC‐UV and HPLC‐MS/MS coupled with chemometrics analysis

From Tea to Health: Exploring Abrus mollis for Liver Protection and Unraveling Its Potential Mechanisms

Anti-inflammatory Chalcone–Isoflavone Dimers and Chalcone Dimers from Caragana jubata

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