• 제목/요약/키워드: Dihydrophaseic acid 3'-O-${\beta}$-D-glucopyranoside

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Efficient Isolation of Dihydrophaseic acid 3'-O-β-D-Glucopyranoside from Nelumbo nucifera Seeds Using High-performance Countercurrent Chromatography and Reverse-phased High-performance Liquid Chromatography

  • Rho, Taewoong;Yoon, Kee Dong
    • Natural Product Sciences
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    • 제24권4호
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    • pp.288-292
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    • 2018
  • High-performance countercurrent chromatography (HPCCC) coupled with reversed-phase highperformance liquid chromatography (RP-HPLC) method was developed to isolate dihydrophaseic acid 3'-O-${\beta}$-D-glucopyranoside (DHPAG) from the extract of Nelumbo nucifera seeds. Enriched DHPAG sample (2.3 g) was separated by HPCCC using ethyl acetate/n-butanol/water system (6:4:10, v/v/v, normal-phase mode, flow rate: 4.0 mL/min) to give 23.1 mg of DHPAG with purity of 88.7%. Further preparative RP-HPLC experiment gave pure DHPAG (16.3 mg, purity > 98%). The current study demonstrates that utilization of CCC method maximizes the isolation efficiency compared with that of solid-based conventional column chromatography.

Chemical Constituents of Nelumbo nucifera Seeds

  • Rho, Taewoong;Yoon, Kee Dong
    • Natural Product Sciences
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    • 제23권4호
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    • pp.253-257
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    • 2017
  • The phytochemical study for the extract of Nelumbo nucifera (Nymphaceae) seeds has led to the isolation of ten compounds including five simple phenolic compounds, two indole derivatives, a flavonoid glycoside, two abscisic acid derivatives. The interpretation of 1D and 2D NMR and ESI-Q-TOF-MS spectroscopic data revealed the chemical structures of isolates to be p-hydroxybenzoic acid (1), protocatechuic acid (2), (E)-p-coumaric acid (3), (E)-ferulic acid (4), (E)-sinapate-4-O-${\beta}$-$\text\tiny{D}$-glucopyranoside (5), tryptophan (6), 3-indoleacetic acid (7), isoschaftoside (8), dihydrophaseic acid (9), dihydrophaseic acid 3'-O-${\beta}$-$\text\tiny{D}$-glucopyranoside (10). To the best of our knowledge, 1 - 5 and 7 were identified for the first time from N. nucifera seeds, and the presence of dihydrophaseic acid (9) and its glucoside (10) were demonstrated secondly in this plant.

배롱나무의 항산화 활성 성분 (Chemical Constituents from the Stems of Lagerstroemia indica and Their Anti-oxidant Effect)

  • 우경완;심미옥;박종일;김민석;서원세;조현우;권학철;박종철;이강노
    • 생약학회지
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    • 제47권3호
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    • pp.204-210
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    • 2016
  • Phytochemical investigation of the 80% MeOH extract from the stems of Lagerstroemia indica resulted in the isolation of eighteen compounds; four norsesquiterpenes, fourteen phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be tachioside (1), isotachioside (2), 2,4,6-trimethoxyphenyl ${\beta}$-D-glucopyranoside (3), gallic acid 4-methyl ether (4), protocatechuic acid (5), gallic acid (6), vanillic acid (7), vanillin (8), 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6"-galloyl)-${\beta}$-D-glucopyranoside (9), 2,4,6-trimethoxyphenol-1-O-${\beta}$-D-(6'-O-galloyl)-glucopyranoside (10), 4-hydroxy-3-methoxyphenyl-1-O-(6'-O-galloyl)-${\beta}$-D-glucopyranoside (11), vomifoliol (12), vomifoliol 9-O-${\beta}$-D-glucopyranoside (13), 6R,9R-3-oxo-${\alpha}$-ionol-9-O-${\beta}$-D-glucopyranoside (14), dihydrophaseic acid 4'-O-${\beta}$-D-glucopyranoside (15), ${\beta}$-hydroxypropiovanillone 3-O-${\beta}$-D-glucopyranoside (16), myrciaphenone A (17), and coumaric acid (18). Compounds 1-5 and 7-18 were isolated for the first time from this plant. Compounds 1-18 were investigated for their antioxidant properties using DPPH and ABTS radical scavenging capacity assay, $Fe^{2+}$ chelating, and FRAP assay. It was found that 4, 6, and 11 possessed the highest antioxidant capacities.

'꼬리겨우살이'(Loranthus tanakae) 전초로부터 cyclofarnesane sesquiterpene glucoside의 분리 동정 및 세포독성 (Cyclofarnesane sesquiterpene glucoside from the whole plant of Loranthus tanakae and its cytotoxicity)

  • 주선우;김형근;오은지;고정환;이영근;강세찬;이대영;백남인
    • Journal of Applied Biological Chemistry
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    • 제62권1호
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    • pp.7-10
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    • 2019
  • 꼬리겨우살이(Loranthus tanakae) 전초를 80% MeOH 수용액으로 4회 반복 추출한 뒤, 감압 농축한 추출물을 ethyl acetate(EtOAc), n-butyl alcohol (n-BuOH)과 $H_2O$층으로 계통 분획을 실시하였다. n-BuOH 분획에 대하여 silica gel ($SiO_2$), octadecyl silica gel (ODS), Sephadex LH-20 column chromatographies를 반복실시하여 1종의 cyclofarnesane sesquiterpene glucoside 화합물을 분리 및 정제하였다. 스펙트럼 데이터를 분석하여 입체 구조를 포함한 화합물의 구조를 (1'R,3'S,5'R,8'S,2E,4E)-dihydrophaseic acid $3^{\prime}-O-{\beta}-{\text\tiny{D}}$-glucopyranoside로 구조동정 하였다. 이 화합물은 이번 실험을 통하여 꼬리겨우살이로 부터는 최초로 분리되었다. 분리한 단일 물질은 AGS (Caucasian gastric adenocarcinoma cells)와 Hepatocyte carcinoma cells에 대하여 $50{\mu}g/mL$ 이상에서 농도 의존적으로 유의한 정도의 세포독성을 보이는 것이 확인되었다.