• Title/Summary/Keyword: Lupane

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Studies on the Constituents of the Leaves of Acanthopanax divaricatus forma flavi-flos

  • Nam, Sang-Gil;Yook, Chang-Soo;Kim, In-Seon;Choi, Hyun-Sik;Park, Sang-Yong
    • Natural Product Sciences
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    • v.12 no.3
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    • pp.119-121
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    • 2006
  • Four 3,4-seco-lupane trierpenoids were isolated from the MeOH extract of the leaves of Acanthopanax divaricatus forma flavi-flos Yook by using various column chromatography. The chemical structures of isolates were identified as chiisanogenin, chiisanoside, isochiisanoside and 11-deoxyisochiisanoside on the basis of physico-chemical and spectroscopic date($^1H-NMR,\;^{13}C-NMR$M$, 2D-NMR and FAB-MS). These compounds were isolated for the first time from A. divaricatus forma flavi-flos.

Structure Determination of a New Lupane-type Triterpene, Tiarellic Acid, Isolated from Tiarella polyphylla

  • Lee, Hyeong-Kyu;Park, Si-Hyung;Oh, Sei-Ryang;Ahn, Kyung-Seop;Kim, Jae-Gil
    • Archives of Pharmacal Research
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    • v.25 no.1
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    • pp.57-60
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    • 2002
  • A new 27-carboxylic lupane-type triterpene, tiarellic acid (1), was isolated from Tiarella polyphylla together with corosolic acid (2) and tormentic acid (3). Tiarellic acid was characterized as 3,23-dihydroxy-20(29)-lupen-27-oic acid and its NMR data were unambiguously assigned using 2-D NMR techniques.

Anti-inflammatory Activities of Lupane-triterpenoids In Vitro and Their Phytochemical Fingerprinting from Leaves of Acanthopanax gracilistylus

  • Li, Xiao Jun;Dai, Ling;Li, Zhi;Zhang, Xiao Dan;Liu, Xiang Qian;Zou, Qin Peng;Xie, Xia
    • Natural Product Sciences
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    • v.21 no.2
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    • pp.104-110
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    • 2015
  • The activities on the inhibition of NO on LPS-induced RAW 264.7 macrophages were investigated in this work. A simple and sensitive method has been developed and validated for fingerprinting analysis of leaves of Acanthopanax gracilistylus W.W. Smith (AGS). The cytotoxicity and inhibition of NO on LPS-induced RAW 264.7 cells of the extract and triterpenoids were determined. Optimal conditions of HPLC analysis were established as follows. The separation was performed with an ODS-C18 column at $30^{\circ}C$, the detected wavelength was 210 nm, the flow rate was 1 mL/min, and the mobile phase consisted of acetonitrile (0.05% phosphoric acid)-0.05% phosphoric acid solution with gradient elution. Our results showed that impressic acid and acankoreaogenin was more effective on the inhibition of NO than the methanol extract and other compounds. There were seventeen peaks coexisted with similarities above 0.95 and nine lupane-triterpenoids including acankoreaogenin and impressic acid detected and identified. The result of anti-inflammatory activities provides a potential explanation for the use of AGS leaves as a herbal medicine in the treatment of inflammatory diseases. Our results also show that acankoreanogenin and impressic acid may be potentially useful in developing new anti-inflammatory agents. In addition, the fingerprint chromatography clearly illustrated and confirmed the material basis for the anti-inflammatory activities of this plant.

Random Amplified Polymorphic DNA Analysis of Genetic Relationships Among Acanthopanax Species

  • Park, Sang-Yong;Yook, Chang-Soo;Nohara, Toshihiro;Mizutani, Takayuki;Tanaka , Takayuki
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1270-1274
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    • 2004
  • Random amplified polymorphic DNA (RAPD) analysis was used to determine the genetic relationships among seventeen species of the Acanthopanax species. The DNA isolated from the leaves of the samples was used as template in polymerase chain reaction (PCR) with twenty random decamer primers in order to distinguish plant subspecies at the level of their genomes. The RAPD patterns were compared by calculating pairwise distances using Dice similarity index, and produced to the genetic similarity dendrogram by unweighted pair-group method arithmetic averaged (UPGMA) analysis, showing three groups; a major cluster(twelve species), minor cluster (4 species) and single-clustering species. The results of RAPD were compatible with the morphological classification, as well as the chemotaxonomic classification of the Acanthopanax species. The Acanthopanax species containing 3,4-seco-lupane type triterpene compounds in their leaves corresponded to the major cluster, another species having oleanane or normal lupane type constituents to minor clusters, and one species not containing triterpenoidal compound to single-cluster.

Chiisanoside, A Lupane Triterpenoid from Acanthopanax Leaves, Stimulates Proliferation and Differentiation of Osteoblastic MC3T3-E1 Cells

  • Choi, Eun-Mi;Ding, Yan;Nguyen, Huu Tung;Park, Sang-Hyuk;Nguyen, Xuan Nhiem;Liang, Chun;Lee, Jung-Joon;Kim, Young-Ho
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.21-26
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    • 2008
  • The leaves of Acanthopanax species have traditionally been used as a tonic and a sedative as well as in the treatment of rheumatism and diabetes. Chiisanoside is the major active lupane triterpenoid of Acanthopanax leaves. To investigate the bioactivities of chiisanoside, which act on bone metabolism, the effects of chiisanoside on the function of osteoblastic MC3T3-E1 cells were studied. Chiisanoside $(0.02{\sim}20\;{\mu}M)$ significantly increased the growth of MC3T3-E1 cells and caused a significant elevation of alkaline phosphatase (ALP) activity, collagen content, and nodules mineralization in the cells (P < 0.05). The effect of chiisanoside (2 ${\mu}M$) in increasing ALP activity was completely prevented by the presence of tamoxifen, suggesting that the effect of chiisanoside might be partly estrogen receptor mediated. Moreover, cotreatment of p38 inhibitor SB203580 or JNK inhibitor SP600125 inhibited chiisanoside-mediated ALP upregulation, suggesting that the induction of differentiation by chiisanoside is associated with increased activation of p38 and JNK mitogen-activated protein kinases. Our data indicate that the enhancement of osteoblast function by chiisanoside may result in the prevention for osteoporosis.