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Aldose Reductase Inhibitory Alkaloids from Corydalis ternata.

Wonse SEO ; Sang Hoon JUNG ; Sang Hee SHIM

Natural Product Sciences.2016;22(2):102-106. doi:10.20307/nps.2016.22.2.102

A methanolic extract of Corydalis ternata having aldose reductase inhibitory activity was examined as a possible aldose reductase (ALR2) inhibitor, a key enzyme involved in diabetic complications. Seven alkaloids, tetrahydrocoptisine (1), corydaline (2), tetrahydropalmatine (3), isocorybulbine (4), corybulbine (5), dehydrocorydaline (6), and N-methyltetrahydroberbinium (7) were isolated from CHCl₃ fraction of C. ternata methanol extract. Among them, compounds 1, 5, and 7 exhibited 5.04 ± 1.97%, 5.00 ± 1.26%, and 1.80 ± 2.33% inhibitions, respectively at 40 µM. The activities of the single compounds were not comparable to that of the whole extract, suggesting that the whole combination of each single compound was responsible for the activity of the extract as shown in many cases of natural medicines. Even though this is the second report on aldose reductase inhibition activity of C. ternata, recombinant human aldose reductase was employed in this study unlike in the previous report. Furthermore, the aldose reductase inhibitory activities of isocorybulbine, corybulbine, and N-methyltetrahydroberbinium, to the best of our knowledge, were evaluated for the first time in this study. These results suggest a use of the extract of C. ternata for ameliorating diabetic complications.
Aldehyde Reductase* ; Alkaloids* ; Corydalis* ; Diabetes Complications ; Humans ; Methanol

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Qualitative and Quantitative Analysis of Thirteen Marker Components in Traditional Korean Formula, Samryeongbaekchul-san using an Ultra-Performance Liquid Chromatography Equipped with Electrospray Ionization Tandem Mass Spectrometry.

Chang Seob SEO ; Hyeun Kyoo SHIN

Natural Product Sciences.2016;22(2):93-101. doi:10.20307/nps.2016.22.2.93

For efficient quality control of the Samryeongbaekchul-san decoction, a powerful and accurate an ultra-performance liquid chromatography (UPLC) coupled with electrospray ionization (ESI) tandem mass spectrometry (MS) method was developed for quantitative analysis of the thirteen constituents: allantoin (1), spinosin (2), liquiritin (3), ginsenoside Rg1 (4), liquiritigenin (5), platycodin D2 (6), platycodin D (7), ginsenoside Rb1 (8), glycyrrhizin (9), 6-gingerol (10), atractylenolide III (11), atractylenolide II (12), and atractylenolide I (13). Separation of the compounds 1 - 13 was performed on a UPLC BEH C₁₈ column (2.1 × 100 mm, 1.7 µm) at a column temperature of 40 ℃ with a gradient solvent system of 0.1% (v/v) formic acid aqueous-acetonitrile. The flow rate and injection volume were 0.3 mL/min and 2.0 µL. Calibration curves of all compounds were showed good linearity with values of the correlation coefficient ≥ 0.9920 within the test ranges. The values of limits of detection and quantification for all analytes were 0.04 - 4.53 ng/mL and 0.13 - 13.60 ng/mL. The result of an experiment, compounds 2, 6, 12, and 13 were not detected while compounds 1, 3 - 5, and 7 - 11 were detected with 1,570.42, 5,239.85, 299.35, 318.88, 562.27, 340.87, 12,253.69, 73.80, and 115.01 µg/g, respectively.
Allantoin ; Calibration ; Chromatography, Liquid* ; Glycyrrhizic Acid ; Limit of Detection ; Methods ; Quality Control ; Tandem Mass Spectrometry*

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Tea Flavonoids Induced Differentiation of Peripheral Blood-derived Mononuclear Cells into Peripheral Blood-derived Endothelial Progenitor Cells and Suppressed Intracellular Reactive Oxygen Species Level of Peripheral Blood-derived Endothelial Progenitor C.

Wahyu WIDOWATI ; Laura WIJAYA ; Dian Ratih LAKSMITAWATI ; Rahma Micho WIDYANTO ; Pande Putu ERAWIJANTARI ; Nurul FAUZIAH ; Indra BACHTIAR ; Ferry SANDRA

Natural Product Sciences.2016;22(2):87-92. doi:10.20307/nps.2016.22.2.87

Endothelial dysfunction in atherosclerosis is associated with increasing oxidative stress that could be reversed by antioxidant. Therefore epigallocatechin gallate (EGCG), epicatechin gallate (ECG), epigallocatechin (EGC) and catechin (C) of tea flavonoids were investigated for their roles in regenerating endothelial cell. Peripheral blood mononuclear cells (PB-MNCs) were isolated, plated and cultured in medium with/without treatment of EGCG, ECG, EGC and C. Results showed that among all EGCG, ECG, EGC and C concentrations tested, 12.5 µmol/L was not cytotoxic for peripheral blood-derived endothelial progenitor cells (PB-EPCs). Treatment of EGCG, ECG, EGC or C increased the percentages of CD34, CD133, VEGFR-2 expressions and suppressed hydrogen peroxide-induced percentages of reactive oxygen species (ROS) level in PB-EPCs. Taken together, our current results showed that EGCG, ECG, EGC or C of tea flavonoids could induce differentiation of PB-MNCs into PB-EPCs as well as protect PB-EPCs from oxidative damage by suppresing the intracellular ROS levels.
Apoptosis ; Atherosclerosis ; Catechin ; Electrocardiography ; Endothelial Cells ; Endothelial Progenitor Cells* ; Flavonoids* ; Hydrogen ; Oxidative Stress ; Reactive Oxygen Species* ; Tea* ; Vascular Endothelial Growth Factor Receptor-2

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Compounds from a jellyfish-derived fungus Aspergillus fumigates.

Guan Yu TAO ; Juan LIU ; Jee H JUNG ; Wei GUO ; Xiao Qiong WEN ; Yonghong LIU

Natural Product Sciences.2016;22(2):82-86. doi:10.20307/nps.2016.22.2.82

Six compounds were isolated from the secondary metabolites of the jellyfish-derived fungus Aspergillus fumigates, whose structures were identified by chemical methods and spectroscopic analysis as pseurotin F1 (1), azaspirofurans B (2), (22E, 24R)-24-methyl-5α-cholesta-7,22-diene-3β,5,6β-triol (3), 5α,8α-epidioxyergosta-6,22-dien-3β-o1 (4), cyclo-(L-Pro-L-Tyr) (5), fumitremorgin C (6). The compounds 1 - 5 were isolated from the fungus Aspergillus fumigates for the first time. The isolated compounds (1 - 6) were evaluated for antibiotic activity and cytotoxicity against six bacterial strains and ten human tumor cell lines, respectively.
Aspergillus* ; Cell Line, Tumor ; Fungi* ; Humans

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Simultaneous HPLC Analysis of Three Flavonoids in the Extracts of Artocarpus heterophyllus Heartwoods.

Abdi Wira SEPTAMA ; Pharkphoom PANICHAYUPAKARANANT

Natural Product Sciences.2016;22(2):77-81. doi:10.20307/nps.2016.22.2.77

A reversed-phase high-performance liquid chromatographic method is described for the simultaneous determination of three antibacterial flavonoids, artocarpanone, artocarpin, and cycloartocarpin in ethyl acetate extracts from Artocarpus heterophyllus heartwoods. Separation was achieved using a TSK-gel ODS-80Tm column (5 µm, 4.6 × 150 mm) at 25℃ with a gradient elution system of methanol and water as follows: 0-8 min, 60:40; 8-27 min, 80:20; 27-35 min, 60:40, v/v, at a flow rate of 1 mL/min, and a quantitative UV detection at 285 nm. The method was validated by measuring the key parameters, including specificity, linearity, sensitivity, accuracy, repeatability and reproducibility. A high degree of specificity and sensitivity was achieved. The calibration curves for all three flavonoids showed good linearity with a coefficient of determinations (R²) of ≥ 0.9995. The recoveries of the method were from 98-104%, with good reproducibility and repeatability (RSD values of less than 2%) were also achieved. Ethyl acetate was the best solvent for extraction of these three flavonoids using the heat reflux conditions for 1 h. This optimized sample preparation and HPLC method can be practically used for a routine standardization process of the extracts from the A. heterophyllus heartwoods.
Artocarpus* ; Calibration ; Chromatography, High Pressure Liquid* ; Flavonoids* ; Hot Temperature ; Methanol ; Methods ; Sensitivity and Specificity ; Water

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Quercetin Relaxed the Smooth Muscle of Rabbit Penile Corpus Cavernosum by Activating the NO-cGMP Signaling Pathway.

Bo Ram CHOI ; Hye Kyung KIM ; Jong Kwan PARK

Natural Product Sciences.2017;23(3):169-174. doi:10.20307/nps.2017.23.3.169

The aim of this study was to investigate the effect and action mechanism of quercetin on penile corpus cavernosum smooth muscle (PCCSM). PCCSM precontracted with phenylephrine (Phe) was treated with four different concentrations of quercetin (10−7, 10−6, 10−5 and 10−4 M). PCCSM were preincubated with N-Nitro-L-arginine methyl ester hydrochloride (L-NAME) and 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ) to block nitric oxide synthase and guanylate cyclase, respectively. The changes in PCCSM tension were recorded, and cyclic nucleotides in the perfusate were measured by radioimmunoassay. The interactions of quercetin with phosphodiesterase type 5 inhibitors (PDE5-Is) such as sildenafil, udenafil and mirodenafil, were also evaluated. PCCSM relaxation induced by quercetin occurred in a concentrationdependent manner. The application of quercetin to PCCSM pre-treated with L-NAME and ODQ significantly inhibited the relaxation. Quercetin significantly increased cGMP in the perfusate. Furthermore, quercetin enhanced PDE5-Is-induced relaxation of PCCSM. Quercetin relaxed the PCCSM by activating the NO-cGMP signaling pathway, and it may be a therapeutic candidate or an alternative treatment for patients with erectile dysfunction who do not completely respond to PDE5-Is.
Erectile Dysfunction ; Guanylate Cyclase ; Humans ; Male ; Muscle, Smooth* ; NG-Nitroarginine Methyl Ester ; Nitric Oxide Synthase ; Nucleotides, Cyclic ; Phenylephrine ; Phosphodiesterase 5 Inhibitors ; Quercetin* ; Radioimmunoassay ; Relaxation ; Sildenafil Citrate

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Inhibitory Activity of Cordyceps bassiana Extract on LPS-induced Inflammation in RAW 264.7 Cells by Suppressing NF-κB Activation.

Deok Hyo YOON ; Changwoo HAN ; Yuanying FANG ; Shankariah GUNDETI ; In Sook HAN LEE ; Won O SONG ; Ki Chul HWANG ; Tae Woong KIM ; Gi Ho SUNG ; Haeil PARK

Natural Product Sciences.2017;23(3):162-168. doi:10.20307/nps.2017.23.3.162

Cordyceps bassiana has long been used as an oriental medicine and reported to possess diverse biological activities. The fruiting bodies of Cordyceps bassiana was extracted with ethanol and then further fractionated with n-hexane, ethyl acetate, n-butanol and water. The butanol fraction from Cordyceps bassiana (CBBF) exhibited the most effective in anti-inflammatory activity in RAW 264.7 macrophages and the roles of CBBF on the anti-inflammation cascade in LPS-stimulated RAW 264.7 cells were studied. To investigate the mechanism by which CBBF inhibits NO, iNOS and COX-2, the activation of IκB and MAPKs in LPS-activated macrophage were examined. Our present results demonstrated that CBBF inhibits NO production and iNOS expression in LPS-stimulated RAW 264.7 macrophage cells, and these effects were mediated through the inhibition of IκB-α, JNK and p38 phosphorylation. Also, CBBF suppressed activation of MAPKs including p38 and SAPK/JNK. Furthermore, CBBF significantly suppressed LPS-induced intracellular ROS generation. Its inhibition on iNOS expression, together with its antioxidant activity, may support its anti-inflammatory activity. Thus Cordyceps bassiana can be used as a useful medicinal food or drug for further studies.
1-Butanol ; Cordyceps* ; Ethanol ; Fruit ; Inflammation* ; Macrophages ; Medicine, East Asian Traditional ; Phosphorylation ; RAW 264.7 Cells* ; Water

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Reserpine treatment activates AMP activated protein kinase (AMPK).

Rackhyun PARK ; Kang Il LEE ; Hyunju KIM ; Minsu JANG ; Thi Kim Quy HA ; Won Keun OH ; Junsoo PARK

Natural Product Sciences.2017;23(3):157-161. doi:10.20307/nps.2017.23.3.157

Reserpine is a well-known medicine for the treatment of hypertension, however the role of reserpine in cell signaling is not fully understood. Here, we report that reserpine treatment induces the phosphorylation of AMP activated protein kinase (AMPK) at threonine 172 (T172) in PC12 cells. Phosphorylation of AMPK T172 is regulated by upstream signaling molecules, and the increase of phospho-T172 indicates that AMPK is activated. When we examined the FOXO3a dependent transcription by using the FHRE-Luc reporter assay, reserpine treatment repressed the FHRE-Luc reporter activity in a dose dependent manner. Finally, we showed that reserpine treatment induced the phosphorylation of AMPK as well as cell death in MCF-7 cells. These results suggest that AMPK is a potential cellular target of reserpine.
AMP-Activated Protein Kinases* ; Animals ; Cell Death ; Hypertension ; MCF-7 Cells ; PC12 Cells ; Phosphorylation ; Reserpine* ; Threonine

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New Azafluorenone Derivative and Antibacterial Activities of Alphonsea cylindrica Barks.

Munirah Abdul TALIP ; Saripah Salbiah Syed Abdul AZZIZ ; Chee Fah WONG ; Khalijah AWANG ; Humera NAZ ; Yuhanis Mhd BAKRI ; Mohamad Syahrizal AHMAD ; Marc LITAUDON

Natural Product Sciences.2017;23(3):151-156. doi:10.20307/nps.2017.23.3.151

A phytochemical study of Alphonsea cylindrica King (unreported) has led to the isolation of six alkaloids. The compounds were identified as kinabaline (1; azafluorenone alkaloid), muniranine (2), O-methylmoschatoline (3; oxoaporphine alkaloid), lysicamine (4), atherospermidine (5) and N-methylouregidione (6; 4, 5-dioxoaporphine alkaloid). The structures of the isolated compounds were determined based on the spectroscopic techniques and by comparison with data reported in the literature. Alkaloid 2 was isolated as a new derivative of azafluorenone while alkaloids 1, 3 - 6 were isolated for the first time from Alphonsea species. In addition, alkaloid 3 and 4 showed inhibition zone against Staphylococcus aureus, Pseudomonas aeruginosa and Bacillus cereus in disc diffusion test. The minimum inhibition concentration (MIC) values of lysicamine (4) against S. aureus, B. cereus and P. aeruginosa were found to be smaller than O-methylmoschatoline (3). Therefore, the reported antibacterial activity showed the potential of this plant as natural antibacterial agent and supported the documented traditional use of Alphonsea sp. in the treatment of diarrhea and fever.
Alkaloids ; Bacillus cereus ; Diarrhea ; Diffusion ; Fever ; Plants ; Pseudomonas aeruginosa ; Staphylococcus aureus

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Quantitative Analysis of the Flavonoid Content in the Leaves of Boehmeria nivea and Related Commercial Products.

Dong Gu LEE ; Sunghun CHO ; Jaemin LEE ; Sanghoon YANG ; Yong Su JUNG ; Ho Bang KIM ; Eun Ju CHO ; Sanghyun LEE

Natural Product Sciences.2015;21(1):66-70.

Content analysis of flavonoids (epicatechin, epicatechin gallate, and rutin) present in the leaves of Boehmeria nivea (originating from Geumsan-myeon, Biin-myeon, Hansan-myeon, and Baeksu-eup) and their commercial products (ramie tteok, ramie songpyeon, ramie bory-tteok, and ramie tea) was conducted by HPLC. The content of epicatechin, epicatechin gallate, and rutin was highest in the leaves of B. nivea from Geumsanmyeon (0.138 mg/g), Baeksu-eup (1.654 mg/g) and Geumsan-myeon (12.205 mg/g), respectively. With respect to commercial products, the content of epicatechin and epicatechin gallate was highest in ramie tea, with concentrations of 1.879 and 1.090 mg/g, respectively. Given these flavonoid concentrations, B. nivea leaf extracts have the potential to be used as additives in natural medicinal products, health supplements, and beverages.
Beverages ; Boehmeria* ; Catechin ; Chromatography, High Pressure Liquid ; Flavonoids ; Rutin ; Tea

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