• Title/Summary/Keyword: triterpenoid glycoside

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Chemical Constituents from tile Fruit Peels of Fortunella japonica

  • Cho, Jeong-Yong;Kawazoe, Kazuyoshi;Moon, Jae-Hak;Park, Keun-Hyung;Murakami, Kotaro;Takaishi, Yoshihisa
    • Food Science and Biotechnology
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    • v.14 no.5
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    • pp.599-603
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    • 2005
  • Chemical constituents of fruit peels of Fortunella japonica Swingle were investigated, and ten compounds were purified and isolated through various chromatographic procedures. Through NMR analysis, isolated compounds were identified as ${\alpha}$-tocopherol (1), lupenone (2), ${\beta}$-amyrin (3), ${\alpha}$-amyrin (4), ${\beta}$-sitosterol (5), ${\beta}$-sitosteryl 3-O-glucopyranoside (6), kaempferide 3-O-rhanmopyranoside (7), 3',5'-di-C-${\beta}$-glucopyranosylphloretin (8), acacetin 7-O-neohesperidoside (9), and acacetin 8-C-neohesperidoside (10). Compounds 1-7 were identified for the first time by our group from fruit peels of F. japonica.

Triterpenoid Saponins from the Root Barks of Aralia elata

  • Kang, Sam-Sik;Kim, Ju-Sun;Kim, Ok-Kyung;Lee, Eun-Bang
    • Archives of Pharmacal Research
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    • v.16 no.2
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    • pp.104-108
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    • 1993
  • From the root barks of Araila elata Seem.(Araliaceae) three known saponins together with oleanolic acid and $\beta$-sitosterol $3-O-\beta$-D-glucoside were isolated. The saponins were identified as oleanolic acid $28-O-\beta$-D-glucoside were isolated. The saponins were identified as oleanolic acid $28-O-\beta$-D-glucopyranosyl ester, oleanolic acid $3-O-\beta$-D-glucuronopyranoside and oleanolic acid $3-O-\alpha$-L-arabinofuranoysyl-(1$\rightarrow$4)-$\beta$-D-glucuronopyranoside(narcissiflo on the basis of chemical and spectra data. The latter two saponins were isolated as their dimethylesters as well as monomethylesters.

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Analysis of the Characterizing Compounds of Korean Mistletoes (Viscum album var. coloratum) (한국산 겨우살이의 지표성분 분석 연구(제 1 보) (기주식물과 생장지역에 따른 지표성분 변화 분석))

  • Choi, Kyung;Park, Kwang Woo;Hwang, Keum Hee
    • Korean Journal of Pharmacognosy
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    • v.44 no.2
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    • pp.138-148
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    • 2013
  • The three biochemical constituents pointed out as the bioactive principles of anticancer activity of Korean mistletoes, Viscum album var. colorantum, epiphyting to different host trees, different region, and different growth environments were compared. The characterizing compounds were lectin, which was glycoprotein reported has anticancer activity, homoflavoyadorinin-B, which was flavonoid glycoside reported as an antioxidant and oleanolic acid, as an anticancerous triterpenoid. We established the analysis methods for three characterizing compounds and determined by HPLC spectrophotometer, respectively. The average content of the lectin in V. album was 1.75 mg/g of dried plants and those of homoflavoyadorinin-B and oleanolic acid were 3.51 and 5.37 mg/g, respectively. The variations of contents of the three characterizing compounds according to epiphytic trees and growth region were observed but not found statistical significance clearly. We came to the conclusion that the contents of bioactive constituents of V. album except homoflavoyadorinin-B are not affected by epiphyting trees or growth environments.

Immunomodulatory Effects of ZYM-201 on LPS-stimulated B Cells

  • Lee, Ye Eun;Kim, Soochan;Jung, Woong-Jae;Lee, Hyung Soo;Kim, Mi-Yeon
    • IMMUNE NETWORK
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    • v.14 no.5
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    • pp.260-264
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    • 2014
  • ZYM-201 is a methyl ester of triterpenoid glycoside from Sanguisorba officinalis which has been used for treatment of inflammatory and metabolic diseases. In this study, immunomodulatory effects of ZYM-201 on B cells were examined in vitro and in vivo. When splenocytes were activated with lipopolysaccharide (LPS), the major population which had shown an increase in cell numbers was B cells. However, when the B cells were treated with ZYM-201 after LPS activation, their cell numbers and the expression of major costimulatory molecules, CD80 and CD86, were decreased. Furthermore, the effect of LPS, which induces activation of NF-${\kappa}B$, was abolished by ZYM-201: LPS-stimulated B cells showed decrease of phosphorylation after treatment of ZYM-201. The same results were shown in vivo experiments. These results suggest that ZYM-201 may play a role in the modulation of inflammatory responses through inhibiting NF-${\kappa}B$ activation and downregulating the expression of costimulatory molecules on B cells.

Structure-Activity Relationship of Triterpenoids Isolated from Mitragyna stipulosa on Cytotoxicity

  • Tapondjou, Leon Azefack;Lontsi, David;Sondengam, Beiham Luc;Choudhary, Muhammad Iqbal;Park, Hee-Juhn;Choi, Jong-Won;Lee, Kyung-Tae
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.270-274
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    • 2002
  • Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.

Structure-Activity Relationships of Polyhydroxyursane-type Triterpenoids on the Cytoprotective and Anti-inflammatory Effects

  • Jung, Hyun-Ju;Nam, Jung-Hwan;Lee, Kyung-Tae;Lee, Yong-Sup;Choi, Jong-Won;Kim, Won-Bae;Chung, Won-Yoon;Park, Kwang-Kyun;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.13 no.1
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    • pp.33-39
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    • 2007
  • Eleven polyhydroxyursane triterpenoids (PHUTs) were tested to determine their cytoprotective, immunosuppressive and anti-inflammatory effects. To compare the bioactivities of $19{\alpha}$-hydroxyursane-type triterpenoids {23-hydroxytormentic acid (6), its methyl ester (7), tormentic acid (8), niga-ichigoside $F_1$ (9),euscaphic acid (10) and kaji-ichigoside $F_1$ (11)} of the Rosaceae crude drugs (Rubi Fructus and Rosa rugosae Radix) with PHUTs possessing no $19{\alpha}-hydroxyl$ of Centella asiatica (Umbelliferae), the four PHUTs, asiaticoside (1), madecassoside (2), asiatic acid (3), and madecassic acid (4) were isolated from C. asiatica and 23-hydroxyursolic acid (5) from Cussonia bancoensis. Cytoprotective effects were assessed by measuring cell viabilities against cisplatin-induced cytotoxocity in $LLC-PK_1$, cells (proximal tubule, pig kidney) to determine whether these agents have protective effects against nephrotoxicity caused by cisplatin. The inhibitory effect of 11 PHUTS on nitric oxide (NO) and prostaglandin $E_2\;(PGE_2)$ were evaluated by measuring nitrite accumulation in lipopolysaccharide (LPS)-induced macrophage RAW 264.7 cells, and their anti-inflammatory effects were tested in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema model. Six MHUTs (compounds 1, 2, 4, 6, 10, and 11) exhibited higher cell viabilities during cisplatin-induced cytotoxicity testing even at a concentration of $200\;{\mu}g/ml$ than cisplatin only-treated group, suggesting that ese compounds have the potentcytoprotective efffcts. Compounds 1 and 3 of the C. asiatica and niga-ichigoside $F_1$ exhibited no inhibitory effect on NO and/or $PGE_2$ production whereas other PHUTs produced mild to significant NO and/or $PGE_2$ production.The four compounds (2, 5, 9, and 10) potently inhibited mouse ear edema induced by TPA whereas two compounds (1 and 3) had no activity in this test. These results suggest that many PHUTs are potentchemopreventives. Structure-activity relationship (SAR) was also discussed in each assay with regard to the significant role of OHs at the position of 2, 3, 6, 19, and 23 and to the glycoside linkage at the 28-carboxyl.