• Title/Summary/Keyword: C-glycosides

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Metabolisrrt of Dammarane Triterpene Glycosides of Korean Ginseng(I) (인삼 사포닌의 체내 대사에 관한 연구(I) 동위원소 표지 사포닌의 흡수, 체내 분포 및 배설에 관하여)

  • 한병훈;장일무
    • Journal of Ginseng Research
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    • v.2 no.1
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    • pp.17-33
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    • 1977
  • Panax Saponin A(PSA) , one of dammarane glycosides of Korean ginseng, was labeled with $^{3}H$ or $^{14}C$ by our Previously reported Procedures of organic synthesis. Tracer studies with $^{3}H$-PSA in wino yielded the following results: 1). Oral and intraperitoneal administration of $^{3}H$-PSA resulted in the rapid appearance and prolonged retention of $^{3}H$-PSA in all organs such as liver, brain, bone marrow and spleen of mice. 2). The amount pi cellular intake of $^{3}H$-PSA was shown to have a certain level of saturation ranging from 0.4mg to 0. 7mg Per 20gm body weight of mice. Administration of $^{3}H$-PSA within the dosage of the saturation point did net give urinary excretion of 3H-PSA. On the contrary, excessive administration of $^{3}H$-PSA resulted in rapid excretion of the substance in the urine of mice.

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Antioxidative Activity of Flavonoids Isolated from Jindalrae Flowers (Rhododendron mucronulatum Turcz.) (진달래꽃으로부터 분리된 플라보노이드 화합물의 항산화성에 관한 연구)

  • Kim, Mi-Ae;Jones, A. Daniel;Chung, Tae-Yung
    • Applied Biological Chemistry
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    • v.39 no.4
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    • pp.320-326
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    • 1996
  • Seven antioxidative flavonoids were isolated from Jindalrae flowers (Rhododendron mnonulatum Turcz.), an edible plant in Korea. These compounds were identified as afzelin, ampelopsin, catechin, myricetin, myricitrin, quercetin and quercitrin on the basis of IR, UV, FAB-MS, $^1H\;NMR,\;and\;^{13}C\;NMR$ data. These compounds were consisted of two flavonols, three flavonol glycosides, a flavane, and a dihydroflavonol. The flavonol glycosides (14.4 g) present in th ethyl ether and ethyl acetate fractions comprised up to 82% of their total flavonoid amount (17.6 g) finally recovered by means of polyamide C-200 column chromatography, preparative TLC, recrystallization, and Sephadex LH-20 column chromatography. The antioxidant activities were measured in an ethanol solution of linoleic acid in the presence of ferric thiocyanate. The antioxidant efficiency increased in the order of afzrlin<$\alpha-tocopherol$

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Phenolic glycosides from Pyrola japonica-(II)

  • Kim, Ju-Sun;Kang, Sam-Sik;Son, Kun-Ho;Chang, Hyeun-Wook;Kim, Hyun-Pyo;Bae, Ki-Hwan
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.202.3-202.3
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    • 2003
  • Two Known compounds, syringaresinol monoglucoside(8), chimaphilin(14), together with three new compounds, (9)[mp. $106{\sim} 111^{\circ}C$, C_{29}H_{44}O_{13}$], (10)[mp. $180{\sim}182^{\circ}C$, $C_{15}H_{20}O_{9}$] and (11)[mp. $100{\sim}105^{\circ}C$, $C_{18}H_{28}O_{8}$] were isolated from the BuOH fractionof Pyrola japonics(Pyrolaceae). The structures of the known compounds were determined by chemical and spectorscopic methods. The assignments of the $^{1}H-$ and $^{13}C-NMP$ spectra of these compounds were carried out by two-dimensional $^1H-^1H-COSY$, NOESY and $^1H-^{13}C$ multiple-bond, multiplequantum spectroscopic correlation techniques. The characterization of the three new compounds is now in progress.

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Anticancer and Antiviral Effect of Some Triterpenes Isolated from the Natural Sources

  • Kim, Young-Sup;Choi, Sang-Un;Lee, Chong-Ock;Lee, Chong-Kyo;Ryu, Shi-Yong
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.138-139
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    • 2002
  • The diverse, widespread, and exceedingly numerous family of natural products constructed from five carbon building-units and so comprising compounds with $C_{5}$, $C_{10}$, $C_{15}$, $C_{20}$, ${\cdots}$, $C_{40}$ skeletons (together with a few higher members) are synoymously termed terpenes or terpenoids. Among the terpene classes, the triterpenes ($C_{30}$ skeletones) form the largest group and are widely distributed in the plant kingdom, either in the free state or as esters or glycosides, although a few important members found in the animal kingdom such as squalene and a number of tetracyclic component including lanosterol. (omitted)

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Phytochemical Constituents of Salsola komarovii and Their Effects on NGF Induction

  • Cho, Hyeon Kyung;Suh, Won Se;Kim, Ki Hyun;Kim, Sun Yeou;Lee, Kang Ro
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.95-101
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    • 2014
  • Five lignan glycosides, seven megastigmane glycosides, and seven phenolic compounds were isolated by repeated column chromatography from the MeOH extract of Salsola komarovii. Their structures were determined to be lariciresinol-9-O-${\beta}$-$\small{D}$-glucopyranoside (1), alangilignoside C (2), conicaoside (3), (+)-lyoniresinol 9'-O-${\beta}$-$\small{D}$-glucopyranoside (4), (8S,8'R,7'R)-9'-[(${\beta}$-glucopyranosyl)oxy]lyoniresinol (5), blumenyl B ${\beta}$-$\small{D}$-glucopyranoside (6), blumenyl A ${\beta}$-$\small{D}$-glucopyranoside (7), staphylionoside D (8), icariside $B_2$ (9), (6R,9S)-3-oxo-${\alpha}$-ionol ${\beta}$-$\small{D}$-glucopyranoside (10), 3-oxo-${\alpha}$-ionol 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (11), blumenol B 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (12), benzyl 6-O-${\beta}$-$\small{D}$-apiofuranosyl-${\beta}$-$\small{D}$-glucopyranoside (13), canthoside C (14), tachioside (15), isotachioside (16), biophenol 2 (17), 2-(3,4-dihydroxy)-phenyl-ethyl-${\beta}$-$\small{D}$-glucopyranoside (18), and cuneataside C (19) by spectroscopic methods. All the isolated compounds 1 - 19 were reported from this source for the first time. Compounds 2, 3 and 6 upregulated NGF secretion to $118.8{\pm}3.6%$, $128.2{\pm}9.3%$ and $111.1{\pm}7.1%$ without significant cell toxicity.

SYNTHESIS OF THE GINSENG GLYCOSIDES AND THEIR ANALOGS

  • Elyakov G. B.;Atopkina L. N.;Uvarova N. I.
    • Proceedings of the Ginseng society Conference
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    • 1993.09a
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    • pp.74-83
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    • 1993
  • In an attempt toward the synthesis of the difficulty accessible ginseng saponins the four dammarane glycosides identical to the natural $ginsenosides-Rh_2,$ - F2, compound K and chikusetsusaponin - LT8 have been prepared from betulafolienetriol(=dammar-24-ene-$3{\alpha},12{\beta}\;20(S)-triol).\;3-O-{\beta}-D-Glucopyranoside$ of 20(S) - protopanaxadiol $(=ginsenoside-Rh_2)$ have been obtained by the regio - and stereoselective glycosylation of the $12-O-acetyldammar-24-ene-3{\beta},\;12{\beta},$ 20(S)-triol. The 12-ketoderivative of 20(S)-protopanaxadiol has been used as aglycon in synthesis of chikusetsusaponin - LT8. Attempted regio - and stereoselective glycosylation of the less reactive tertiary C - 20 - hydroxyl group in order to synthesize the $20-O-{\beta}-D-glucopyranoside$ of 20(S)-protopanaxadiol(=compound K) using 3, 12 - di - O - acetyldammar - 24 - ene - $3{\beta},12{\beta},20(S)$-trial as aglycon was unsuccessful. Glycosylation of 3, 12 - diketone of betulafolienetriol followed by $NaBH_4$ reduction yielded the $20-O-{\beta}-D-glucopyranoside\;of\;dammar-24-ene-3{\beta},12{\alpha},$ 20(S)-triol, the $12{\alpha}-epimer$ of 20(S) - protopanaxadiol. Moreover, a number of semisynthetic ocotillol - type glucosides, analogs of natural pseudoginsenosides, have been prepared.

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Flavonol Glycosides with Antioxidant Activity from the Aerial Parts of Epimedium koreanum Nakai

  • Kim, Eun-Sil;Kim, Mi-Kyung;Kang, Hyun-Kyu;Park, Young-In;Dong, Mi-Sook;Kim, Dong-Hyun;Chung, Ha-Sook
    • Natural Product Sciences
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    • v.14 no.4
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    • pp.233-238
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    • 2008
  • The aerial parts of Epimedium koreanum Nakai have been used to stimulate hormone secretion in treating impotence. Ten flavonol glycosides, 3,4,5-trihydroxy-8-prenylflavone 7-O-[${\beta}$-D-glucopyranosyl($1{\rightarrow}2$)-${\beta}$-D-glucopyranoside] (1), hyperoside (2), icarisid II (3), 2"-O-Rhamnosylicarisid II (4), epimedin A (5), epimedin B (6), epimedin C (7), icariin (8), hexandraside E (9), and epimedoside A (10) were isolated from the an ethylacetate soluble extracts of the aerial parts of Epimedium koreanum Nakai through activity-monitord fractionation and isolation method. The structures of compounds 1 - 10 were elucidated by high resolution fast atom bombardment mass spectrometry and two dimentional nuclear magnetic resonance spectroscopy analysis. Compounds 1 and 4 showed potent antioxidant activity, with $IC_{50}$ values of 19.7 and 11.5 ${\mu}g$/mL and 88.2 and 90.5 ${\mu}M$, respectively.

Subacute Toxicity of Nerium oleander Ethanolic Extract in Mice

  • Abdou, Rania H.;Basha, Walaa A.;Khalil, Waleed F.
    • Toxicological Research
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    • v.35 no.3
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    • pp.233-239
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    • 2019
  • Nerium oleander (N. oleander) is a well-known poisonous shrub that is frequently grown in gardens and public areas and contains numerous toxic compounds. The major toxic components are the cardiac glycosides oleandrin and neriin. The aim of our study was to evaluate the toxic effects of an ethanolic N. oleander leaf extract on haematological, cardiac, inflammatory, and serum biochemical parameters, as well as histopathological changes in the heart. N. oleander extract was orally administered for 14 and 30 consecutive days at doses of 100 and 200 mg of dried extract/kg of body weight in 0.5 mL of saline. The results showed significant increases in mean corpuscular volume, white blood cell counts, platelet counts, interleukins (IL-1 and IL-6), tumour necrosis factor alpha, C reactive protein, alanine aminotransferase, lactate dehydrogenase, creatine kinase and creatine kinase MB, especially at high doses. Marked pathological changes were perceived in the heart tissue. Thus, it can be concluded that exposure to N. oleander leaf extract adversely affects the heart and liver.

Quantitative Analsysis of Flavanone Glycosides and Peroxynitrite Scavenging Effect of the Five Oriental Medicinal Drugs (Aurantii nobilis Pericarpium, Citrii unshiu Pericarpium, Citrii unshiu Semen, Aurantii Fructus, Poncirii Fructus) (5종 생약(진피, 청피, 귤핵, 지실, 지각)의 Flavanone Glycoside 함량분석과 Peroxynitrite 소거효과)

  • Nugroho, Agung;Park, Myung-Gon;Jin, Seong-Eun;Choi, Jae-Sue;Park, Hee-Juhn
    • Korean Journal of Pharmacognosy
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    • v.40 no.4
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    • pp.370-375
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    • 2009
  • Overproduction of peroxynitrite ($ONOO^-$) causes a variety of disease such as atherosclerosis, hypercholesterolemia, diabetes mellitus or obesity. Peroxynitrite scavenging activities and HPLC analysis on the five Oriental medicinal drugs belonging to the genus Citrus, Aurantium or Poncirus (Rutaceae family) and HPLC analysis were taken to evaluate flavanone glycosides with peroxynitrite scavenging activity. The $IC_{50}s$ of the five crude drugs were shown as follows: Aurantii nobilis Pericarpium (Jinpi, 18.3 ${\mu}g$/ml), Citrii unshiu Pericarpium (Chungpi, 7.50${\mu}g$/ml), Citrii unshiu Semen (Gyulhaek, >50.0${\mu}g$/ml), Aurantii Fructus (Jigak, 18.3${\mu}g$/ml), and Poncirii Fructus (Jisil, >50.0${\mu}g$/ml) where Korean crude drug's names are noted in the parenthesis. Peroxynitrite scavenging effect of flavanones or their glycosides usually contained in Citrus species were observed as follows: hesperetin (1.89 ${\mu}g$/ml), naringenin (7.77 ${\mu}g$/ml), hesperidin (8.44 ${\mu}g$/ml), poncirin (>50.0 ${\mu}g$/ml)and ponciretin(>50.0 ${\mu}g$/ml). The activities of naringin and poncirin with ${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}2$)-${\beta}$-D-glucopyranosyl moiety were weak. HPLC analytical data revealed that Jinpi (the peels of mature fruits of Citrus unshiu) and Chungpi (the peels of immature fruits of C. unshiu) had high quantities of hesperidin as the value of 142.1${\pm}$0.21 and 104.51${\pm}$1.10 mg/g dried weight, respectively. Poncirin was clearly detected in only Jisil and naringenin and naringin were not observed on the HPLC chromatogram of the five crude drugs.