• Title/Summary/Keyword: Hederagenin saponins

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Saponins from the Roots of Pulsatilla koreana

  • Kang, Sam-Sik
    • Archives of Pharmacal Research
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    • v.12 no.1
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    • pp.42-47
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    • 1989
  • From the roots of Puisatiila koreana, three monodesmosides(pulsatilla saponins A, B and D) and two bisdesmosides(pulsatilla saponins F and H) were isolated. The structure of these saponins have been determined as hederagenin 3-O-${\beta}$-L-rhamnopyranosyl($1{\to}2$)- ${\alpha}$-L-arabinopyranoside(A), hederagenin 3-O-${\beta}$-D-glucopyrano syl($1{\to}4$) - ${\alpha}$-L-arabinopyranoside(B), hederagenin 3-O- ${\alpha}$-L-rhamnopyranosyl ($1{\to}2$)-[${\beta}$-D-glucopyranosyl($1{\to}4$]-${\alpha}$-L-arabinopyranoside(D), 3-O-${\alpha}$-L-rhamnopyranosyl($1{\to}2$)-{${\alpha}$-L-arabinopyranosyl hederagenin 28-O-${\alpha}$-L-rhamnopyrano syl($1{\to}4$)-${\beta}$-D-glucopyrano syl($1{\to}6$)-${\beta}$-D-glucopyranosyI ester (F) and 3-O-${\alpha}$-L-rhamnopyranosyl($1{\to}2$)-[${\beta}$-D-glucopyranosyl($1{\to}4$)]- ${\alpha}$-L-arabinopyranosyl hederagenin 28-O-${\alpha}$-L-lharnnopyranosyl($1{\to}4$)-${\beta}$-D-glucopyranosyl($1{\to}6$)-${\beta}$-D-glucop yranosyl ester(H) on the basis of chemical and spectral studies. Pulsatilla saponin B is the first report of its presence in plants but saponins A, D, F, and H have recently been isolated from the same genus p. cernua.

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In Vitro Anticomplementary Activity of Hederagenin Saponins Isolated from Roots of Dipsacus asper

  • Oh, Sei-Ryang;Jung, Keun-Young;Son, Kun-Ho;Park, Si-Hyung;Lee, Im-Seon;Ahn, Yung-Seop;Lee, Hyeong-Kyu
    • Archives of Pharmacal Research
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    • v.22 no.3
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    • pp.317-319
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    • 1999
  • Anticomplementary activity of hederagenin and related saponins isolated from Dipsacus asper was investigated in vitro. HN saponin F (3) was most potent with $IC_{50}$ value of$ 3.7{\times}10^{-5} M$ followed by 3-O-${\beta}-D-glucopyranosyl-(1{\rightarrow} 3)-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)-{\beta}-L-arabinopyranosyl$ hederagenin $28-O-{\beta}-D-glucopyranosyl-(1{\rightarrow}6)-beta$-D-glucopyrano side (8), $3-O-{\beta}-L-arabinopyranosyl$ hederagenin $28-O-{\beta}-D-glucopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (5), dipsacus saponin A (4), and hederagenin (1) on the classical pathway (CP) of complement system, while the saponins 3-5 did not show the inhibition of hemolysis and rather increase the hemolysis on the alternative pathway (AP). However, all of C-3 monodesmosides [prosapogenin CP (2), dipsacus saponin B (6), and dipsacus saponin C (7)] evoked hemolysis directly on the erythrocytes.

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Saponins from the Stem Bark of Kalopanax pictum var. magnificum (I)

  • Park, Myung-Ja;Hahn, Dug-Ryong
    • Archives of Pharmacal Research
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    • v.14 no.1
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    • pp.7-11
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    • 1991
  • Three triterpenoid saponins were isolated from the methanol extract of the stem bark of Kalopanax pictum Nakai var. magnificum (Araliaceae). The structures of these saponins were identified as hederagenin 3-O-${\alpha}$-L-arabinopyranoside, hederagenin-3-O-${\alpha}$-L-rhamnopyranosyl$(1{\rightarrow}2)$-${\alpha}$-L-arabinopyranoside and 3-O-${\alpha}$-L-rhamnopyranosyl(1{\rightarrow}2)-${\alpha}$-L-arabinopyranosyl hederagenin 28-O-${\alpha}$-L-rhamnopyranosyl$(1{\rightarrow}4)$-${\beta}$-D-glucopyranosyl$(1{\rightarrow}6)$-${\beta}$-D-glucopyranosyl ester.

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Cytotoxic Saponins from the Root of Dipsacus asper Wall

  • Hung Tran Manh;Jin WenYi;Thuong Phuong Thien;Song Kyung Sik;Seong Yeon Hee;Bae KiHwan
    • Archives of Pharmacal Research
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    • v.28 no.9
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    • pp.1053-1056
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    • 2005
  • Cytotoxic activitiy of seven hederagenin saponins isolated from the root of Dipsacus asper were investigated in vitro against L1210, HL-60 and SK-OV-3 tumor cell lines by the MTT method. $3-O-\alpha-L-rhamnopyranosyl-(1{\rightarrow}2)-\alpha-L -arabinopyranosyl$ hederagenin (2),\;$3-O-\beta-D­xylopyranosyl-( 1{\rightarrow}3)-\alpha-L-Rhamnopyranosyl-(1{\rightarrow}2)-\alpha-L -arabinopyranosyl$ hederagenin (6) and $3-O-\beta-D-glucopyranosyl-(1{\rightarrow}3)-\alpha-L-rhamnopyranosyl-( 1{\rightarrow}2)-\alpha-L-arabinopyranosyl$ hederagenin (7) exhibited the potent cytotoxicity against the three tumor cell lines with $IC_{50}$ values ranging from 4.7 to 8.7 ${\mu}g/mL$, with the exception of compound 7, which exhibited weak cytotoxic activity against SK-OV-3 $(IC_{50}\;22.5\;{\mu}g/mL)$. Other compounds did not exhibit any cytotoxic activity $(IC_{50}>30{\mu}g/mL)$.

Saponins from the Aerial Parts of Aralia continentalis

  • Kim, Ju-Sun;Kang, Sam-Sik
    • Natural Product Sciences
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    • v.4 no.1
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    • pp.45-50
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    • 1998
  • Seven triterpenoid saponins such as oleanolic acid 28-O-{\beta}-D-glucopyranosyl$ ester, hederagenin $28-O-{\beta}-D-glucopyranosyl$ ester, chikusetsusaponin IVa, udosaponin A, salsoloside C, udosaponins F and C were isolated from the aerial parts of Aralia continentalis, among which two $28-O-{\beta}-D-glucopyranosyl$ esters of oleanolic acid and hederagenin are isolated for the first tome from this plant. These results suggested that the chemical components of Korean Dokwhal are practically identical to those of japanese Udo supporting the chemotaxonomical point of view.

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Studies on the Constituents of Caltha minor(I) - Saponin from the Leaves - (동이나물의 성분 (I) - 잎의 Saponin-)

  • 윤광로;한덕룡
    • YAKHAK HOEJI
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    • v.35 no.3
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    • pp.236-239
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    • 1991
  • Two triterpenoid saponins were isolated from the methanol extract of Caltha minor leave(Ranunculaceae). The structure of these saponin were elucidated as hederagenin-3-O-$\alpha$-rhamnopyranosyl(1$\rightarrow$2)-$\alpha$-L-arabinopyrano side and 3-O-$\alpha$-L-rhamnopyranosyl(1$\rightarrow$2)-$\alpha$-L-arabinopyranosyl hederagenin 28-O-$\alpha$-L-rhamnopyranosyl(1$\rightarrow$4)-$\beta$-D-glucopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranosyl ester.

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Inhibition of Mouse Ear Edema by Steroidal and Triterpenoid Saponins

  • Kim, Sung-Yong;Son, Kun-Ho;Chang, Hyeun-Wook;Kang, Sam-Sik;Kim, Hyun-Pyo
    • Archives of Pharmacal Research
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    • v.22 no.3
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    • pp.313-316
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    • 1999
  • Certain steroids and triterpenoids isolated from diverse plant families were known to posses anti-inflammatory activity. In the course of finding new anti-inflammatory natural products, some steroidal and triterpenoid saponins were isolated and evaluated for their anti-inflammatory activity using in vivo mouse ear edema test. At the oral dose of 100 mg/kg, several steroidal saponins and triterpenoid saponins such as hederagenin glycosides showed significant inhibition of ear edema (20∼37% inhibition), though less potent than indomethacin and hydrocortisone.

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Triterpenoidal Saponins from the Leaves of Kalopanax pictum var. chinense

  • Lee, Min-Won;Hahn, Dug-Ryong
    • Archives of Pharmacal Research
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    • v.14 no.2
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    • pp.124-129
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    • 1991
  • One new triterpenoidal bisdesmoside, saponin C (3) were isolated from the leaves of Kalopanax pictum var. chinense along with two known saponins, saponin B (2, sapindoside C) and saponin A (1, sapoindoside B). On the basis of chemical and spectral evidences, the structure of a new triterpenoidal saponin has been elucidated to be 3-O-$\beta$-D-glucopyranosyl (1$\rightarrow$4)$\beta$-D-xylopyranosyl (1$\rightarrow$3)-$\alpha$-L-rhamnopyranosyl (1$\rightarrow$2)-$\alpha$-L-arabino-pyranosyl-23-hydroxyolean-12-en-28-O-$\alpha$-L-rhamnopyrano syl (1$\rightarrow$4)-$\beta$-D-glucopyranosyl (1$\rightarrow$6)-$\beta$-D-glucopyranosyl ester.

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Cytotoxic and Apoptotic Effects of Saponins from Akebia quinata on HepG2 Hepatocarcinoma Cells (으름유래 사포닌의 HepG2 간암세포에 대한 세포독성 및 세포자살유도 효과)

  • Kang, Hye-Sook;Kang, Jae-Seon;Jeong, Woo-Sik
    • Food Science and Preservation
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    • v.17 no.3
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    • pp.311-319
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    • 2010
  • Four saponins (1~4) were isolated from Akebia quinata pericarp through bioassay-guided fractionation. Pericarps of A. quinata were extracted with ethanol and sequentially fractionated with dichloromethane, ethyl acetate, butanol and water. Compounds 1~4 from the butanol fraction were identified as 3-O-${\alpha}$-L-arabinopyranosyl hederagenin (${\delta}$-hederin), 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$2) ${\alpha}$-L-arabinopyranoly oleanolic acid (${\beta}$-hederin), 3-O-${\beta}$-D-xylopyranosyl (1${\rightarrow}$3) ${\alpha}$-L-arabinopyranosyl hederagenin (saponin C), and 3-O ${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$2) ${\alpha}$-L-arabinopyranosyl hederagenin (${\alpha}$-hederin) based on the spectroscopic evidences, respectively. Oleanolic acid and hederagenin were identified as the corresponding sapogenins by acid-hydrolysis. These compounds exhibited strong cytotoxic activity in MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxy-methoxyphenyl)-2-(4-sulfophenyl)-2H- tetrazolium, inner salt] assay on HepG2 cells. ${\beta}$-Hederin obviously attenuated the expression of bcl-2, an anti-apoptotic protein. All of the compounds also induced the activity of caspase-3, an apoptotic enzyme, while ${\alpha}$-hederin was the most potent activator of the enzyme. Our data demonstrate for the first time the apoptosis-inducing activity of A. quinata. These results suggest that A. quinata could be used as a potential source of natural cancer chemopreventive agents.

Studies on the Saponins in the Shoot of Aralia Elata (II) -Identification of the Saponins- (두릅나무 순의 Saponin에 관한 연구 (II) - Saponin 의 동정 -)

  • Kim, Young-Hee;Lee, Mee-Kyoung;Lee, Mahn-Jung
    • Journal of the Korean Society of Food Culture
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    • v.5 no.2
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    • pp.243-251
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    • 1990
  • We determined the structure of main saponin which extracted from the shoot of Aralia Elata. The results were as follows. 1. The main aglycons and suger of the total saponins of Nr2 sample were identified as oleanolic acid and hederagenin, and glucose, arabinose and rhamnose. A probable new aglycon was isolated and inferred as 1, 3-methylenedioxy-3-dehydroxyoleanolic acid. 2. One compound of Fh saponin (named as Elatoside $Fh_2$) which was obtained first in this species was elucidated as 3-O-$({\alpha}-L-arabinopyranosyl(1{\rightarrow}2)-{\beta}-D-gluco-pyranosyl)$-28-O-${\beta}-D-glucophyranosyl$ oleanolic acid on the basis of chemical and spectral evidence of IR, $^1H$, $^{13}C-NMR$ and MS.

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