• Title/Summary/Keyword: 12$\beta$-diol

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Preparation and Structure Determination of a New Glycoside, (20E)-Ginsenoside $Rh_3$, and its isomer from Diol-type Ginseng Saponins (인삼의 diol계 사포닌으로부터 새로운 배당체 (20E)-Ginsenoside $Rh_3$ 및 그의 입체이성체의 제조와 구조결정)

  • 김동선;백남인;박종대;이유희;정소영;이천배;김신일
    • YAKHAK HOEJI
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    • v.39 no.1
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    • pp.85-93
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    • 1995
  • Acidic and alkaline hydrolysis of diol-type ginseng saponins produced a new glycoside, (20E)-ginsenoside Rh$_{3}$, and its stereoisomer (20Z)-, which were further subjected to alkaline by drolysis to give their aglycones, (20E)- and (20Z)-3$\beta$, 12$\beta$-dihydroxy-dammar-20(22),24-diene. The ratio of stereoisomeric mixtures was estimated to be ca. 5:1 from intensities of the peaks in $^{1}$H- and $^{13}$C-NMR spectra. The $^{1}$H- and $^{13}$C-NMR signals of ginsenoside Rh$_{3}$, which have remained unclarified, were completely assigned by the extensive application of modern NMR techniques.

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Diterpenoids from Eragrostis ferruginea (Eragrostis ferruginea에서 추출된 Diterpenoids)

  • 이상래
    • Korean Journal of Plant Resources
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    • v.4 no.2
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    • pp.35-38
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    • 1991
  • Two new diterpene compounds have been isolate from the roots of Eragrostis ferruginea (Thunb.) Beauv. and their structures were elucidated as isopimara-9(11), 15-0ien-l9-ol-3-one and cassa-13(14), 15-diene-3, 12-dione by various spectroscopic me-thods. We have also isolated a known diterpene diol isopimara-9(11). 15-diene-3$\beta$, 19-dio1.

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Four New Darnmarane-Glycosidesl Ginsenosides $Rg_5, Rh_4, Rs_3, AND Ff_2$, from Korean Red Ginsengs the Root off]unarm ginseng C. A. Meyer

  • Jong Dae Park;Nam
    • Proceedings of the Ginseng society Conference
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    • 1998.06a
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    • pp.115-126
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    • 1998
  • Four new dammarnae-glycosides named ginsenosides Rgs, Rh4, RsB and Rf2 have been isolated 1'rom Korean red ginseng, the root of Panax ginseng C. A. Meyer (Araliaceae) and their chemical structures have been elucidated by chemical and spectroscopic methods, including'H-'H COSY, HMQC, HMBC, NOESY, as 3-0- [$\beta$-D-glucopyranosyl(1 ~2)-$\beta$-D-glucopyranosyl] dammar-20(22) , B4-diene-3P,12P-diol (ginsenoside Rgs),6-0-$\beta$-D-glucopyranosyl-dammar-20(22),24-diene-3P,6P, 12P-triol (ginsenoside Rh4),3-0- [6" -0-acetyl-D-glucopyranosyl(1 ~2)--D-glucopyranosyl] 20(5)- protopanaxadiol (ginsenoside Rs3) and 6-0- [u-L-rhamno-pyranosyl(1 ~2)-$\beta$-D-glucopyranosyl] dammarane -3$\beta$, 6a, 12 $\beta$, 20(R),25-pentol(ginsenoslde Rfa). The absolute stereo structure of a double bond at C-20(22) was determined as entgegen type by applying NOESY.OESY.

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Phytochemical Constituents of Cirsium nipponicum (MAX.) Makino (울릉엉겅퀴의 식물화학적 성분연구)

  • Lee, Jong-Hwa;Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.36 no.2 s.141
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    • pp.145-150
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    • 2005
  • Nine compounds were isolated from the methanol extract of the aerial parts of Cirsium nipponicum. Their structures were identified to be phytene-1,2-diol (1), ${\beta}-sitosterol$ (2), pectolinarigenin (3), epilupeol acetate (4), 9,12-octadecadienoic acid (5), pinoresinol (6), apigenin (7), linaroside (8) and siparunoside (9) by spectroscopic means.

Phytochemical Constituents of Allium victorialis var. platyphyllum

  • Woo, Kyeong Wan;Lee, Kang Ro
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.221-226
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    • 2013
  • Phytochemical investigation of the 80% MeOH extract from the leaves of Allium victorialis var. platyphyllum resulted in the isolation of seventeen compounds; two terpenes, three norsesquiterpenes, one furofuran lignan, and eleven phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be trans-phytol (1), phytene-1,2-diol (2), icariside B2 (3), (6S,9S)-roseoside (4), sedumoside G (5), pinoresinol-4-O-glucoside (6), 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7), 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), Benzyl ${\beta}$-D-glucopyranoside (9), methyl ferulate (10), trans-ferulic acid (11), methyl-p-hydroxycinnamate (12), glucosyl methyl ferulate (13), linocaffein (14), siringin (15), 2-(4-hydroxy-3-methoxyphenyl)-ethyl-O-${\beta}$-Dglucopyranoside (16), and pseudolaroside C (17). All compounds were isolated for the first time from this plant.

Ginsenoside $Rg_5$, A Genuine Dammarane Glycoside from Korean Red Ginseng

  • Kim, Shin-Il;Park, Jeong-Hill;Ryu, Jae-Ha;Park, Jong-Dae;Lee, You-Hui;Park, Jae-Hyun;Kim, Tae-Hee;Kim, Jong-Moon;Baek, Nam-In
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.551-553
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    • 1996
  • A genuine dammarane glycoside, named ginsenoside $Rg_{5}$, has been isolated by repeated column chromatography and preparative HPLC from the MeOH extract of Korean red ginseng (Panax ginseng C.A. Meyer). The chemical structure of ginsenoside$ Rg_{5}$ was determined as $3-O-[{\beta}-D-glucopyranosyl (1{\rightarrow}2)-{\beta}-D-glucopyranosyl]$ dammar-20(22), $24-diene-3{\beta},12{\beta}-diol$ by spectral and chemical methods. The stereostructure of a double bond at C-20(22) of ginsenoside $Rg_{5}$ was characterized as (E) from the chemical shift of C-21 in the $^{13}C-NMR $and a NOESY experiment in the $^{1}H-NMR$.

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Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity

  • Cha, Joon Min;Kim, Dong Hyun;Lee, Tae Hyun;Subedi, Lalita;Kim, Sun Yeou;Lee, Kang Ro
    • Natural Product Sciences
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    • v.24 no.2
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    • pp.132-138
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    • 2018
  • Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 - 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-${\beta}$-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), ${\beta}$-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-${\beta}$-D-glucopyranoside (10), pinoresinol-4'-O-${\beta}$-D-glucopyranoside (11), luteolin (12), quercetin-3-O-${\beta}$-D-glucopyranoside (13), and luteolin 6-C-${\beta}$-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 - 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 - 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with $IC_{50}$ values of $9.70{\mu}M$.

Two Acylglycerylgalactosides and a New Sesquiterpene Galactoside from the Flowers of Hemisteptia lyrata Bunge

  • Ha, Tae-Joung;Lee, Jin-Hwan;Hwang, Seon-Woo;Lee, Jun;Kang, Nam-Suk;Park, Keum-Yong;Suh, Duck-Yong;Park, Ki-Hun;Yang, Min-Suk
    • Journal of Applied Biological Chemistry
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    • v.49 no.1
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    • pp.16-20
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    • 2006
  • The flowers of Hemisteptia lyrata B. afforded two known acylglycerylgalactosides, 2',3'-di-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (1) and 2'-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (2), and a new sesquiterpene galactopyranoside, 7-eudesmene-1${\beta}$,4${\beta}$-diol-1-O-${\beta}$-D-galactopyranoside (3). This is the first time that galactopyranosides (1-3) have been isolated from the genus Hemisteptia. Their structures and stereochemistry were elucidated by 1D and 2D NMR data, including COSY, NOESY and HMBC experiments.

Phytochemical Studies on Lonicera Caulis (1) - Sterols and Triterpenoids (인동의 성분연구 (1) - Sterol 및 Triterpenoid 화합물)

  • Kim, Ju-Sun;Yean, Min-Hye;Lee, So-Young;Lee, Je-Hyun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.40 no.4
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    • pp.319-325
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    • 2009
  • Twelve compounds were isolated from the 70% ethanol extract of Lonicera Caulis (Caprifoliaceae) and their structures were identified as six triterpenoids [(24S)-cycloart-25-en-$3{\beta}$,24-diol (1), pomolic acid (7), ursolic acid (8), euscaphic acid (9), hederagenin (10), and 23-hydroxytormentic acid (12)] and six sterols [obtusifoliol (2), gramisterol (3), citrostadienol (4), ${\beta}$-sitosterol (5), ergosterol peroxide (6) and ${\beta}$-sitosterol glucoside (11)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. All the compounds were isolated from this plant parts for the first time.