• Title/Summary/Keyword: Iridoid glycoside

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Inhibitory Effect on TNF-${\alpha}$-Induced IL-8 Production in the HT29 Cell of Constituents from the Leaf and Stem of Weigela subsessilis

  • Thuong Phuong Thien;Jin WenYi;Lee JongPill;Seong RackSeon;Lee Young-Mi;Seong YeonHee;Song KyungSik;Bae KiHwan
    • Archives of Pharmacal Research
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    • v.28 no.10
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    • pp.1135-1141
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    • 2005
  • Twelve compounds were isolated from the MeOH extract of the leaf and stem of the Korean endemic plant Weigela subsessilis L. H. Bailey. Their chemical structures were elucidated on the basis of physicochemical and spectroscopic data and by comparison with those of published literatures. These compounds were identified as three sterols, ${\beta}$-sitosterol acetate (2), ${\beta}$-sitosterol (3), daucosterol (11), eight triterpenoids, squalene (1), ursolic acid (4), ilekudinol A (5), corosolic acid (6), ilekudinol B (7), esculentic acid (8), pomolic acid (9), asiatic acid (10), and one iridoid glycoside, alboside I (12). This is the first report pertaining to the isolation of these compounds from Weigela subsessilis L. H. Bailey. In addition, three compounds 7, 9, and 12 were found to display a strong inhibitory effect on the production of IL-8 in the HT29 cells stimulated by TNF-${\alpha}$.

Antioxidative Constituents from the Twigs of Vitex rotundifolia

  • Kim, Dae-Keun
    • Biomolecules & Therapeutics
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    • v.17 no.4
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    • pp.412-417
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    • 2009
  • In the course of screening for antioxidant compounds by measuring the radical scavenging effect on DPPH (1,1-diphenyl- 2-picrylhydrazyl), a total extract of the twigs of Vitex rotundifolia (Verbenaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of three iridoid compounds, 10-O-vanilloylaucubin (1), 10-O-p-hydroxybenzoylaucubin (2) and aucubin (3), two C-glycoside flavones, vitexin (4) and orientin (5), and a quinic acid derivative, 3,4-di-O-caffeoylquinic acid (6). Their structures were elucidated by spectroscopic studies. Among them, compounds 5 and 6 showed the significant antioxidative effects on DPPH free radical scavenging test. In riboflavin-NBT-light and xanthine-NBT-xanthine oxidase systems, compounds 5 and 6 exhibited the formation of the blue formazan in a dose-dependent manner. Compounds 5 and 6 showed better superoxide quenching activities than vitamin C.

Iridoid Glycoside (V) -Shanzhiside methyl ester from the Root of Phlomis umbrosa Turcz- (Iridoid 배당체(配糖體) (V) -속단(續斷)에서 Shanzhiside methyl ester의 단리(單離)-)

  • Chung, Bo-Sup;Kim, Jin-Woong;Kim, Jin-Cheon;Kim, Young-Ho
    • Korean Journal of Pharmacognosy
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    • v.14 no.1
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    • pp.5-8
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    • 1983
  • Phlomis umbrosa Turcz. ('Sok-dan') is a perennial herb in Labiatae plants. Shanzhiside methyl ester was isolated from butanol extract of this plant. It was obtained as amorphous powder and its molecular formula is $C_{17}H_{26}O_{11}$. Its structure was determined by chemical reactions, spectral analysis and compared with authentic sample of its pentaacetate.

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Loganin Inhibits α-MSH and IBMX-induced Melanogenesis by Suppressing the Expression of Tyrosinase in B16F10 Melanoma Cells (마우스 흑색종 B16F10세포에서 loganin의 티로시나아제 발현 억제를 통한 멜라닌 생성 억제에 대한 기전연구)

  • Jung, Hee Jin;Bang, EunJin;Kim, Byeong Moo;Jeong, Seong Ho;Lee, Gil Han;Chung, Hae Young
    • Journal of Life Science
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    • v.29 no.11
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    • pp.1200-1207
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    • 2019
  • Ultraviolet radiation exposure is a major cause of extrinsic skin aging, which leads to skin hyperpigmentation. Loganin, a major iridoid glycoside obtained from Corni fructus, has anti-inflammatory, anti-diabetic, and neuroprotective effects. In this study, we investigated the mechanisms underlying the anti-melanogenic effects of loganin in B16F10 melanocytes treated with ${\alpha}$-melanocyte stimulating hormone (${\alpha}-MSH$) and 3-isobutyl-1-methylxanthine (IBMX). Anti-melanogenic activity was measured by treating cells with loganin at concentrations between 1 and $20{\mu}m$. Cell viability assays confirmed that doses of loganin up to $20{\mu}m$ were not cytotoxic. Loganin significantly and dose-dependently decreased intracellular melanin production. We also investigated potential molecular signaling pathways for the anti-melanogenesis effects of loganin. Western blotting showed that treatment with ${\alpha}-MSH$ and IBMX increased the phosphorylation of cAMP response element-binding protein (CREB) and the gene expressions of microphthalmia-associated transcription factor (MITF) and tyrosinase. Addition of loganin suppressed these increases, while promoting the phosphorylation of extracellular signal regulated kinase (ERK) and the anti-melanogenesis response. Our data therefore indicated that loganin could attenuate the increased melanin synthesis induced by ${\alpha}-MSH$ and IBMX treatment of B16F10 melanocytes. This attenuation appears to occur by downregulation of CREB phosphorylation and MITF and tyrosinase gene expression and upregulation of ERK phosphorylation. These finding suggests that loganin could be a valuable candidate for treatment of skin diseases related to hyperpigmentation.

Simultaneous Determination of Asperosaponins and Iridoid Glycosides from Dipsaci Radix by Using LC-ESI-MS Spectrometry (속단(Dipsaci Radix) 중 Asperosaponins 및 Iridoid glycosides의 LC-ESI-MS에 의한 동시분석)

  • Cho, Hwang-Eui;Son, In-Seop;Kim, Sun-Cheun;Son, Kun-Ho;Woo, Mi-Hee;Moon, Dong-Cheul
    • Korean Journal of Pharmacognosy
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    • v.43 no.2
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    • pp.137-146
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    • 2012
  • Dipsaci Radix (Dipsacaceae) has been used as a tonic, an analgesic, anti-inflammatory and anti-complement agents in traditional herbal medicine for the therapy of low back pain, knee pain, rheumatic arthritis, traumatic hematoma, and bone fractures. A high-performance liquid chromatography-electrospray ionization-mass spectrometric method (HPLC-ESI-MS) was developed for the simultaneous quantitation method of the five compounds from the herbal drug: asperosaponin VI and asperosaponin XII (terpene glycosides), sweroside, loganin and dipsacus A(iridoid glycosides). HPLC separation of the analytes was achieved on a C18 column ($150{\times}2.0$ mm i.d., 5 ${\mu}m$) using the aqueous methanol containing 5 mM ammonium acetate with gradient flow of the mobile phase. Detection of the analytes was performed by positive ion electrospray ionization, and selected ion monitoring was used for data acquisition using m/z corresponding molecular adduct ion, $[M+NH_4]^+$ and $[M+H]^+$. Calibration graphs showed good linearity ($r^2$=0.9997) over the wide range of the analytes; intra- and inter-day precisions (RSD, %) were within 9.1% and the accuracy between 94.0-111.0%. Recoveries of the analytes through the assay procedure were in the range of 93.7-110.8%. Analytical results of the herbal drugs of Dipsaci Radix (17 samples) show wide distribution of the five marker compounds and clear difference of the species from Phlomidis Radix (4 samples). The developed method would provide a practical guide for the quality control of the herbal drug.

Analysis of Iridoid Glycoside and GABA Content in the Roots of the Rehmannia glutinosa Cultivars (지황 품종별 뿌리에서 Iridoid 배당체와 GABA 분석)

  • Lee, Sang Hoon;Yoon, Jeong Su;Kim, Jae Kwang;Park, Chun Geun;Chang, Jae Ki;Kim, Yeon Bok
    • Korean Journal of Medicinal Crop Science
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    • v.25 no.3
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    • pp.146-151
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    • 2017
  • Background: Rehmannia glutinosa is a perennial herb belonging to the family Scrophulariaceae. Its roots have been utilized as a traditional medicine. The aim of this study was to elucidate the basic information of the roots of the R. glutinosa cultivars and their utilization. Methods and Results: The roots of R. glutinosa cultivars were harvested in the end of March. The two iridoid glycosides, aucubin and catalpol, were analyzed by liquid chromatography/mass spectrometry (LC/MS), whereas ${\gamma}-aminobutyric$ acid (GABA) was analyzed by gas chromatography/mass spectrometry (GC/MS). The aucubin content was the highest in the Dakang cultivar, whereas no aucubin was detected in the five cultivars. All cultivars had more than 12 mg/g catalpol content, and the maximum catalpol content was found in Jihwang 1. The GABA content was the highest in Suwon 1, and it was 40 times more than that in the Yeongang cultivar. Conclusions: The highest aucubin, catapol and GABA contents were detected in the Dakang, Jihwang 1, and Suwon 1, cultivars respectively. This study provides the crucial information regarding the versatile utilization and pedigree selection of R. glutinosa cultivars.

Phytochemical Constituents from the Whole Plants of Diodia teres

  • Kim, Dae-Keun;Park, Hee-Wook;Eun, Jae-Soon;Baek, Nam-In
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.200.4-201
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    • 2003
  • Ten compounds were isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as three iridoid glycosides, a coumarin glycoside, and six flavonoids by spectroscopic analysis. These compounds were isolated for the first time from D. teres.

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Isolation and quantitative analysis of metabolites from Scrophularia buergeriana and their hepatoprotective effects against HepG2 Cells (현삼 (Scrophularia buergeriana)에서 분리한 화합물의 함량분석 및 간세포 보호 효과)

  • Na, Hyeon Seon;Oh, Seon Min;Shin, Woo Cheol;Bo, Jeon Hwang;Kim, Hyoung-Geun;Yoon, Dahye;Yang, Seung Hwan;Lee, Young-Seob;Kim, Geum-Soog;Baek, Nam-In;Lee, Moon-Soon;Lee, Dae Young
    • Journal of Applied Biological Chemistry
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    • v.62 no.4
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    • pp.399-406
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    • 2019
  • The roots of Scrophularia buergeriana were extracted with 80% aqueous Methanol and the concentrates were partitioned into EtOAc, n-BuOH, and H2O fractions. The repeated silica gel or octadecyl SiO2column, and medium pressure liquid chromatographies for the n-BuOH fraction led to isolation of phenylethanoid glycosides and iridoid glycosides. The chemical structures of these compounds were determined as harpagoside (1), angoroside C (2), aucubin (3) and acetoside (4) based on spectroscopic analyses including nuclear magnetic resonance and MS. A simple and efficient HPLC with UV detection method for the simultaneous determination of the four compounds (1-4) has been developed and applied to their content determination in the S. buergeriana. The roots were extracted by 80% methanol, and the contents of 1, 2, 3, and 4 were determined to 11.5, 7.6, 41.2, and 4.8 mg/g, respectively. Additionally, angoroside C (2) and acetoside (4) exhibited hepatoprotective effect against ethanol-induced hepatotoxicity in HepG2 cell line.

Plants with Liver Protective Activities (IV) -Chemistry and Pharmacology of Plantaginis Semen et Folium- (강간제(强肝劑)로 사용(使用)된 생약(生藥)의 조사연구(調査硏究) (IV) -보간성(補肝性) 생약(生藥) 차전자(車前子)의 성분분리(成分分離) 및 약리연구(藥理硏究)-)

  • YunChoi, Hye-Sook;Chang, Il-Moo;Chi, Hyung-Joon;Lee, Soe-Yun
    • Korean Journal of Pharmacognosy
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    • v.11 no.2
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    • pp.57-60
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    • 1980
  • Water fractions prepared from Plantaginis Semen and Plantaginis Folium exhibited both significant liver-protective activities against $CCl_4$ intoxication. Aucubin, an iridoid glycoside. isolated from both leaves and seeds of Plantago asiatica(Plantaginaceae) also showed potent liver protective activities against the animal model of hepatitis induced by $CCl_4$ intoxication.

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