• Journal of Ginseng Research
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• 제46권6호
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• pp.738-749
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• 2022

Background: Ginseng possesses antitumor effects, and ginsenosides are considered to be one of its main active chemical components. Ginsenosides can further be hydrolyzed to generate secondary saponins, and 20(R)-panaxotriol is an important sapogenin of ginsenosides. We aimed to synthesize a new ginsengenin derivative from 20(R)-panaxotriol and investigate its antitumor activity in vivo and in vitro. Methods: Here, 20(R)-panaxotriol was selected as a precursor and was modified into its derivatives. The new products were characterized by ¹H-NMR, ¹³C-NMR and HR-MS and evaluated by molecular docking, MTT, luciferase reporter assay, western blotting, immunofluorescent staining, colony formation assay, EdU labeling and immunofluorescence, apoptosis assay, cells migration assay, transwell assay and in vivo antitumor activity assay. Results: The derivative with the best antitumor activity was identified as 6,12-dihydroxy-4,4,8,10,14-pentamethyl-17-(2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl(tert-butoxycarbonyl)glycinate (A11). The focus of this research was on the antitumor activity of the derivatives. The efficacy of the derivative A11 (IC₅₀ < 0.3 µM) was more than 100 times higher than that of 20(R)- panaxotriol (IC₅₀ > 30 µM). In addition, A11 inhibited the protein expression and nuclear accumulation of the hypoxia-inducible factor HIF-1α in HeLa cells under hypoxic conditions in a dose-dependent manner. Moreover, A11 dose-dependently inhibited the proliferation, migration, and invasion of HeLa cells, while promoting their apoptosis. Notably, the inhibition by A11 was more significant than that by 20(R)-panaxotriol (p < 0.01) in vivo. Conclusion: To our knowledge, this is the first study to report the production of derivative A11 from 20(R)-panaxotriol and its superior antitumor activity compared to its precursor. Moreover, derivative A11 can be used to further study and develop novel antitumor drugs.

• 분석과학
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• 제7권2호
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• pp.213-224
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• 1994

선택적으로 중수소를 치환시킨 싸이클로옥타논의 여러 동위원소 이성질체들을 합성하였다. 고유동위원소 효과에 의해 영향을 받는 $^{13}C$ NMR 화학적 이동값들을 각 이성질체에 대해 저온에서 계통적으로 관찰하였다. 특히 싸이클로옥타논이 선호하는 안정한 형태 이성질체인 클 boat-chair 형과 연관시켜 이 효과들을 논의하였다.

• 대한화학회지
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• 제37권11호
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• pp.951-960
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• 1993

수용액상에서 $Hg^{2+}$에 의한 trans-[Co(3,2,3-tet)$X_2]^+$ (3,2,3-tet = 4,7-diazadecane-1,10-diamine, $X_2\;=\;Cl_2,\;(NO_2)Cl,\;Br_2,\;(NO_2)Br,\;(NO_3)_2)$ 착물의 아쿠아 반응이 연구되었다. 생성물을 확인하고 반응메카니즘을 추정하기 위하여 크로마토그래피를 사용하였고 전자흡수 스펙트럼을 측정하였다. 그 결과 네자리 리간드인 3,2,3-tet가 배위된 여러가지 $trans-[Co(3,2,3-tet)X_2]^+$ 착물은 각각 아쿠아된 trans-[Co(3,2,3-tet)$(OH_2)_2]^{3+}$ 착물을 거쳐 cis-${\beta}$-[Co(3,2,3-tet)$(OH_2)_2]^{3+}$ 착물이 생성되었다. $Hg^{2+}$에 의한 trans-$[Co(3,2,3-tet)Cl_2]^+$ 착물과 trans-[Co(3,2,3-tet)$(NO_2)Cl]^+$ 착물의 아쿠아 반응에 대한 메카니즘을 추정하기 위하여 속도론적 조사를 하였따. 그 결과 $trans-[Co(3,2,3-tet)Cl_2]^+$ 착물은 D(dissociative)-메카니즘으로 진행되었고, trans-[Co(3,2,3-tet)$(NO2_)Cl]^+ $착물은 $I_d$(interchange dissociative)-메카니즘으로 진행되었다. 그리고 입체화학적인 거동을 조사하기 위하여 라세미(R,R:S,S)3,2,3-tet 대신에 키랄성이 R,R인 3,2,3,-tet를 배위시킨 trans-$[Co(R,R-3,2,3-tet)Cl_2]^+$ 착물에 $Hg^{2+}$를 용리시켰을 때 아쿠아 반응에 대한 원편광이색성(circular dichroism) 스펙트럼을 측정하여 그 절대구조를 확인한 결과 ${\Delta}-cis-{\beta}$-[Co(R,R-3,2,3-tet)$(OH_2)_2]^{3+}$ 착물이 생성되었다.