Chemical constituents from barks of Betula platyphylla / 中草药

Objective: To study the chemical constituents from the barks of Betula platyphylla. Methods: The chemical constituents were isolated by silica gel column chromatography and HPLC, and its structure were identified by their spectral data and physicochemical properties analysis. Results: A total of 20 compounds were isolated from B. platyphylla, which were identified as 3-oxo-24-methylenecycloartan (1), sitosterone (2), 3β-acetyl oleanolic acid (3), lupeol (4), citrostadienol (5), betulinaldehyde (6), 3β-acetoxyl-11α,12α-epoxy-oleanan-13β,28-olide (7), oleanolic acid (8), erythrodiol (9), 3-hydroxy-1,7-bis(4',4″- dihydroxyphenyl)- heptane (10), β-sitosterol (11), 3β,20-dihydroxylupane (12), 3β-O-caffeoyl-betulin (13), platanic acid (14), 3β,12α-dihydroxyoleanan- 13β,28-olide (15), 30-norlupane-3β,28-diol-20-one (16), betulinic acid (17), betulin (18), 1,7-bis (4',4″-dihydroxyphenyl)-hept- 4-ene-3-one (19), and 5-hydroxy-1,7-bis (4',4″-dihydroxyphenyl)-hept-3-one (20). Conclusion: Compounds 1, 5, 7, 12, 14-16 are isolated from B. platyphylla for the first time, and compounds 1, 5, 7, 14-16 are isolated from betula genus for the first time.

Study on diarylheptanoids from flowers of Juglans regia / 中草药

Objective: To investigate the diarylheptanoids from the flower of Juglans regia. Methods: The compounds were isolated and purified by various column chromatographies, and their structures were identified by physiochemical properties and spectroscopic data. And MTT assays were performed to detect the in vitro cytotoxicity of compounds. Results: A total of 11 diarylheptanoids were isolated from the EtOH extract of the flower of J. regia, which were identified as tsaokoarylone (1), rhoiptelol C (2), (3S,7S)-3,7-dihydroxy-1-(4-hydroxyphenyl)-7-(3-methoxy-4-hydroxyphenyl)-heptane (3), 3-hydroxy-1-(3-methoxy-4-hydroxyphenyl)-7- (4-hydroxyphenyl) heptane (4), 1-(4-hydroxyphenyl)-7-(3-methoxy-4-hydroxyphenyl)-4-heptene-3-one (5), juglanin A (6), 2-oxatrycyclo[13.2.2.13,7]eicosa-3,5,7-(20),15,17,18-hexane-10,16-diol (7), 2-oxatrycyclo[13.2.2.13,7]eicosa-3,5,7-(20),15,17,18-hexane- 10-one (8), pterocarine (9), (8R)-32-methoxy-2-oxa-1(1,3),3(1,4)-dibenzenacyclodecaphane-16,8-diol (10), and juglanin B (11). Conclusion: Compounds 1-2, 4-5, and 7-8 are isolated from this genus for the first time. Compounds 1-11 are isolated from this plant for the first time, and compound 8 inhibited the proliferation of HCT-116, HepG2, BGC-823, NCI-H1650, and A2780 cancer cell lines in vitro, with IC50 values of 3.56, 2.26, 1.39, 2.62, and 1.18 μmol/L, respectively.

Identification and characterization of major constituents in Juglans mandshurica using ultra performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-ESI-Q-TOF/MS) / 中国天然药物

The present study was designed to identify and characterize the major constituents in Juglans mandshurica Maxim. A simple, efficient and sensitive ultra performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-ESI-Q-TOF/MS) method was established and validated under positive and negative ion modes. The separation was performed on a Waters ACQUITY UPLC BEH C column (2.1 mm × 100 mm, 1.7 μm) by gradient elution with a mobile phase (Phase A: 0.1% aqueous formic acid solution, Phase B: 0.1% formic acid acetonitrile solution). A total of 165 compounds were rapidly selected by Targeted and Non-Targeted Peak Finding approaches, and then tentatively identifled by comparing with reference substances or inferred through mass spectrometry fragment ion analysis and literature data. These compounds included 68 naphthalenequinones, 20 diarylheptanoids, 29 flavonoids, 20 triterpenes, and 28 phenolic acids. In conclusion, the present study provided an effective approach to identifying components in complex matrices of herbal medicines such as Juglans mandshurica Maxim.

Chemical constituents from Dioscorea opposite / 中草药

Objective To study the chemical constituents of Dioscorea opposita. Methods The constituents were isolated and purified by silica gel, Sephadex LH-20, and ODS column chromatography. Their structures were elucidated by NMR spectra comparison with reference data. Results Fourteen compounds were isolated from 95% ethanol extract of D. opposite. All of them included eight diarylheptanoids (1-8) and six nitrogen compounds (9-14). They were elucidated by spectroscopic data as 5-ethoxy-1,7-diphenylheptan-3-one (1), 5-hydroxy-1,7-bis(4-hydroxyphenyl)-heptan-3-one (2), 1,7-diphenyl-4-hepten-3-one (3), 1,7-bis (4-hydroxyphenyl)-4-hepten-3-one (4), hannokinol (5), 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-3,5-heptanediol (6), 1,7-bis (4-hydroxy-3-methoxyphenyl)-3,5-heptanediol (7), 1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane (8), trans-N- coumaroyltyramine (9), trans-N-feruloyltyramine (10), cis-N-coumaroyltyramine (11), trans-N-cinnamoyltyramine (12), pyrrolezanthine-6-ethyl ether (13), divaricataester A (14). Conclusion Compounds 1 is a new natural product, named as dioscoheptone A. Compounds 3, 4, 10, 12, 13, and 14 are isolated from the family of dioscoreaceae for the first time. Compounds 2, 6, and 8 are isolated from D. opposita for the first time.

Identification and characterization of major constituents in Juglans mandshurica using ultra performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-ESI-Q-TOF/MS) / 中国天然药物

The present study was designed to identify and characterize the major constituents in Juglans mandshurica Maxim. A simple, efficient and sensitive ultra performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-ESI-Q-TOF/MS) method was established and validated under positive and negative ion modes. The separation was performed on a Waters ACQUITY UPLC BEH C column (2.1 mm × 100 mm, 1.7 μm) by gradient elution with a mobile phase (Phase A: 0.1% aqueous formic acid solution, Phase B: 0.1% formic acid acetonitrile solution). A total of 165 compounds were rapidly selected by Targeted and Non-Targeted Peak Finding approaches, and then tentatively identifled by comparing with reference substances or inferred through mass spectrometry fragment ion analysis and literature data. These compounds included 68 naphthalenequinones, 20 diarylheptanoids, 29 flavonoids, 20 triterpenes, and 28 phenolic acids. In conclusion, the present study provided an effective approach to identifying components in complex matrices of herbal medicines such as Juglans mandshurica Maxim.

The Cytotoxic Constituents of Betula platyphylla and their Effects on Human Lung A549 Cancer Cells

During the screening for cytotoxic compounds from plants grown in Korea, Betula platyphylla (BP) showed potent activity against the adenocarcinomic human alveolar basal epithelial A549 cell line. To identify the cytotoxic components from BP, the CH₂Cl₂ fraction with the most significant cytotoxic effect was applied to the column chromatographies. Seven compounds were isolated: lupeol (1), betulinic acid (2), (−)-rhododendrol (3), platyphyllenone (4), platyphyllone (5), (−)-centrolobol (6), and oleanolic acid (7). Among them, three diarylheptanoids (4 – 6) exhibited cytotoxicity toward A549 cells. Especially, 50 µM of 4 reduced A549 cell viability to 18.93 ± 0.82% compared to control (100.00 ± 21.48%). Lactate dehydrogenase (LDH) leakage and intracellular reactive oxygen species (ROS) production were also induced by 50 µM 4. This is the first report on the cytotoxic effect of BP-derived diarylheptanoids 4–6 against A549 cells. The compound 4 may be useful for the development of early hit compounds for non-small cell lung carcinoma, but the consideration about selectivity of 4 is required since 4 also showed the cytotoxicity in the human normal lung epithelial BEAS-2B cell line.

Distribution of phytoestrogenic diarylheptanoids and sesquiterpenoids components in Curcuma comosa rhizomes and its related species

Abstract Curcuma comosa Roxb., Zingiberaceae, a phytoestrogen-producing herb with vernacularly named "Wan Chak Mod Loog" in Thailand, has been traditionally used for treatment of gynecologic diseases and sold as food supplement in the market. However, similar rhizomes of its related species may lead to the confusion in the uses of this plant. This study was aimed to investigate the phytochemical constituents of different Curcuma spp. that used as "Wan Chak Mod Loog". Characteristic major compounds were isolated and identified. Phytochemical analysis of 45 Curcuma samples representing Curcuma sp., C. latifolia, and C. comosa were analyzed and compared with their phylogenetic relationship inferred by Amplified Fragment Length Polymorphism analysis. Phytoestrogen diarylheptanoids were found in all samples of C. comosa while sesquiterpenoids including hepatoxic zederone were found in C. latifolia and Curcuma sp. samples.

Identification and characterization of chemical constituents in Cortex Juglandis Mandshuricae based on UPLC-Q-TOF/MS / 中草药

Objective: To identify the major chemical constituents in Cortex Juglandis Mandshuricae by ultra performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-Q-TOF/MS). Methods: The separation was performed on Waters Acquity UPLC BEH C18 column (100 mm×2.1 mm, 1.7 μm), with a mobile phase using water with 0.1% formic acid (A) and acetonitrile with 0.1% formic acid (B) for gradient elution; Q-TOF/MS and electrospray ion (ESI) source was applied for the analysis under the positive and negative ion modes; Target search and non-target search were performed by Peakview 2.0/masterview1.0 or Markerview 1.2.1 software. Then the formulas of compounds were determined by accurate mass and isotopic abundance ratio from target screening function of software. Their structures were determined by analysis of MS/MS fragment or comparison with standard substances and references. Results: Forty-four major chemical compounds including 13 naphthalene quinones, 3 diarylheptanoids, 15 flavonoids, and 13 other compounds were identified or inferred in Cortex Juglandis Mandshuricae. Conclusion: UPLC-Q-TOF/MS method which develops a new strategy can identify the main chemical constituents from Cortex Juglandis Mandshuricae rapidly and accurately, main chemical constituents can be used for quality evaluation and pharmacological research.

Study on diarylheptanoids from green peel of Juglans sigillata / 中国中药杂志

The chemical constituents from green peel of Juglans sigillata were isolated by column chomatographies over silica gel, Sephadex LH-20, and MCI. Four diarylheptanoids were isolated and their structures were characterized as dihydropterocarine(1), 3',4″-epoxy-1-(4'-hydroxy-phenyl)-7-(3″-methoxyl-phenyl)-heptan-3α-ol(2), pterocarine(3), and 1-(4'-hydroxy-phenyl)-7-(3″-methoxy-4″-hydroxyphenyl)-heptan-3α-ol(4). Compound 1 is a new compound, named as dihydropterocarine. Compounds 2-4 were isolated from the plant of J. sigillata for the first time.

Analysis on major chemical compounds in exocarp of Juglans mandshurica based on UPLC-Q-TOF/MS / 中草药

Objective: To identify the major chemical compounds in 78 batches of the exocarp of Juglans mandshurica from different origins by ultra performance liquid chromatography coupled with time-of-fight mass spectrometry (UFLC-Q-TOF/MS) and determine the major active chemical components. Methods: The separation was performed on Waters Acquity UPLC BEH C18 column (100 mm × 2.1 mm, 1.7 μm), with a mobile phase using water with 0.1% formic acid (A) and acetonitrile with 0.1% formic acid (B) for gradient elution; Q-TOF/MS and electrospray ion (ESI) source were applied for the analysis under the positive ion mode; One thousand ions were extracted through Markerview 1.2.1 software from 78 batches. And common ions (compounds) were selected according to the following principles: One ion can be detected in all samples, and the relative strength is greater than the e4. Then the formula of common ions were determined by accurate mass and isotopic abundance ratio from target screening function of Peakview 2.0/masterview1.0 software. Their structures were determined by analysis of MS/MS fragment or comparison with standard substances and references. Results: Thirty-one major chemical compounds including eleven naphthalene quinones, three diarylheptanoids, three flavonoids, eight triterpenes, and six other compounds were identified or inferred in the exocarp of J. mandshurica. Conclusion: UPLC-Q-TOF/MS method which develops a new strategy can identify the main chemical constituents from the exocarp of J. mandshurica rapidly and accurately, main chemical constituents can be used for the quality evaluation and efficacy material research.