• Title/Summary/Keyword: Lupane

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Lupane Derivatives-I: Synthesis and Cytotoxic Activity (루판 유도체의 합성 및 세포독성-I)

  • You, Young-Jae;Kim, Yong;Ahn, Byung-Zun
    • YAKHAK HOEJI
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    • v.46 no.5
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    • pp.295-300
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    • 2002
  • To observe the structure-activity relationship of lupane derivatives both on cytotoxic and antiangiogenic activity, twelve lupane derivatives were prepared; their antiangiogenic and cytotoxic activities were evaluated. Among them, four compounds were more cytotoxic than betulinic acid. Carboxylic acid at C28 seemed to be essential for cytotoxic activity. But, a selective cytotoxicity toward SK-MEL-2 was not observed. As for antiangiogenic activity, none of the compounds except lupeol showed antiangiogenic activity at 30 $\mu\textrm{g}$/mL.

Lupane Triterpenoids from Pyrus pyrifolia

  • Yoo, Ji-Hye;Yang, Ki-Sook
    • Natural Product Sciences
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    • v.18 no.1
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    • pp.13-15
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    • 2012
  • Three lupane type triterpenoids were isolated from the methanol extract of Pyrus pyrifolia fruit peel through repeated silica gel column chromatography. Based on the spectroscopic methods, their structures were determined to be lupeol (1), betulin (2), and betulinic acid (3).

A New Lupane-Triterpene Glycoside from the Leaves of Acanthopanax gracilistylus

  • Liu, Xiang-Qian;Chang, Seung-Yeup;Park, Sang-Yong;Nohara, Toshihiro;Yook, Chang-Soo
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.831-836
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    • 2002
  • A new and two known lupane-triterpene glycosides were isolated from the hot MeOH fraction of the leaves of Acanthopanax gracilistylus W. W. Smith. Based on the physical properties and spectroscopic data, their chemical structures were determined as acankoreoside A (1), acankoreoside D (2), and $3{\alpha}-hydroxy-lup-23-al-20(29)-en-28-oic$ acid $28-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}4)-{$beta}-D-glucopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranosyl$ ester (3), respectively. To our best knowledge, compand 3 appears to be novel, which was named as wujiapioside A.

Effects of Lupane-Triterpenoids on Mitogen-induced Proliferation of Lymphocytes (Lupane계 Triterpenoid류가 임파구 분열에 미치는 효과)

  • 김영옥;조대현;정혜주;김진호;장승엽;육창수;양기숙;오오진
    • YAKHAK HOEJI
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    • v.43 no.2
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    • pp.208-213
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    • 1999
  • The effects of five lupane-triterpenoids from leaves of two Acanthopanax spp., chiisanogenin, chisanoside and $22{\alpha}-hydroxychiisanogenin$, acakoreoside A and acantrifoside A on the mitogen-induced proliferation were investigated in vitro. T cell proliferation (TCP) to concanavalin A (Con A) and the B cell proliferation (BCP) to lipopolysaccharide (LPS) were increased by chiisanogenin. TCP to Con A was significantly increased by chiisanoside and acankoreoside A, but not affected by chiisanogenin, $22{\alpha}-hydroxychiisanogenin$ and acantrifoside A, BCP to LPS was significantly increased by acankoreoside A and acantrifoside A, and slightly increased by chiisanoside, chiisanogenin and $22{\alpha}-hydroxychiisanogenin$.

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Lupane-Triterpenes from the Leaves of Brassaiopsis glomerulata

  • Kiem, Phan-Van;Dat, Nguyen-Tien;Minh, Chau-Van;Lee, Jung-Joon;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • v.26 no.8
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    • pp.594-596
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    • 2003
  • Three known lupane-triterpenes, 3a-hydroxy-lup-20(29)-en-23,28-dioic acid (1), 3$\alpha$-hydroxylup-20(29)-en-23,28-dioic acid 28-Ο-$\alpha$-L-rhamnopyranosyl-(1$\rightarrow4)-\beta-D-glucopyranosyl-(1\rightarow6)-\beta$-D-glucopyranosyl ester (acankoreoside A, 2) and $3\alpha$, $11\alpha$-dihydroxy-23-oxo-lup-20(29)-en-28-oic acid (3) were isolated from the leaves of Brassaiopsis glomerulata (Blume) Regel, a species of Araliaceae family growing in Vietnam. Their structures were determined on the basis of spectroscopic data.

Synthesis and Cytotoxic Activity-II, Aminoacetyl Derivatives (루판 유도체의 합성 및 세포독성-II: 아미노아세칠 유도체)

  • You, Young-Jae;Kim, Yong;Nam, Nguyen-Hai;Ahm, Byung-Zun
    • YAKHAK HOEJI
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    • v.46 no.5
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    • pp.301-306
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    • 2002
  • To increase the water solubility, sixteen lupane derivatives bearing aminoacetyl moiety at C3 were synthesized. Their cytotoxic activities against three cancer cell lines, SK-MEL-2, A549, and B16, were tested. Among them, six derivatives showed significant cytotoxic activity.

Constituents of Acanthopanax koreanum Leaves (섬오갈피나무잎의 성분 (I))

  • 정지연;한덕룡
    • YAKHAK HOEJI
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    • v.35 no.3
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    • pp.240-244
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    • 1991
  • A new lupane triterpenoid saponin, 3, 11-dihydroxy-lupan-20-en-28-oic acid 28-o-$\alpha$-L-rhamnopyranosyl-(1$\rightarrow$4)-$\beta$-D-glucopyranosyl-(1$\rightarrow$6)-B-D-glucopyranosyl ester, have been isolated from the leaves of Acanthopanax koreanum Nakai (Araliaceae) together with one known flavonol glycoside, rutin. The structure were elucidated on the basis of spectral and chemical evidence.

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A New 24-Nor-Lupane-Glycoside of Acanthopanax trifoliatus

  • Kiem, Phan-Van;Minh, Chau-Van;Cai, Xing-Fu;Lee, Jung-Joon;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • v.26 no.9
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    • pp.706-708
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    • 2003
  • A new 24-nor-lupaneglycoside was isolated from the leaves of Acanthopanax trifoliatus. Based on spectroscopic data its chemical structure was determined as 24-nor-11$\alpha$-hydroxy-3-oxo-lup-20(29)-en-28-oic acid 28-Ο-$\alpha$-L-rhamnopyranosyl-(1$\rightarrow4)-\beta-D-glucopyranosyl-(1\rightarrow6)-\beta$-D-glucopyranosyl ester.