• Title/Summary/Keyword: dihydrophaseic acid

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Chemical Constituents of Nelumbo nucifera Seeds

  • Rho, Taewoong;Yoon, Kee Dong
    • Natural Product Sciences
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    • v.23 no.4
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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.

Isolation of Dihydrophaseic Acid from Seed Extract of Nelumbo nucifera (연자육으로부터 식물호르몬 Dihydrophaseic Acid의 분리 및 동정)

  • Seo, Jee-Hee;Choi, Yeon-Hee;Yoo, Mi-Young;Hong, Kyung-Sik;Lee, Byung-Hoi;Yon, Gyu-Hwan;Kim, Young-Sup;Kim, Young-Kyoon;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.37 no.4 s.147
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    • pp.290-293
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    • 2006
  • Phytochemical investigation of the seed extract of Nelumba nucifera Gaerth (Nymphaeaceae) resulted in the isolation of a plant hormon, dihydrophaseic acid (1), a abscisic acid derivative. The chemical structure of 1 was elucidated by 2D-NMR spectroscopic analysis, COSY, DEPT, HMQC and HMBC.

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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    • v.24 no.4
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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.

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

  • Joo, Sun-Woo;Kim, Hyoung-Geun;Oh, Eun-Ji;Ko, Jung-Hwan;Lee, Yeong-Geun;Kang, Se-Chan;Lee, Dae Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.62 no.1
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    • pp.7-10
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    • 2019
  • The whole plants of Loranthus tanakae were repeatedly extracted with 80% aqueous MeOH and the concentrate was partitioned into ethyl acetate (EtOAc), n-butyl alcohol (n-BuOH) and $H_2O$ fractions. The repeated silica gel ($SiO_2$), octadecyl $SiO_2$ (ODS), and Sephadex LH-20 column chromatographies for the n-BuOH fraction led to isolation of a cyclofarnesane sesquiterpene glucoside. The chemical structure including stereo structure was determined to be a (1'R,3'S,5'R,8'S,2E,4E)-dihydrophaseic acid $3^{\prime}-O-{\beta}-{\text\tiny{D}}$-glucopyranoside on the basis of spectroscopic analyses. This compound was isolated for the first time from L. tanakae in this study. Compound 1 showed a moderate dose-dependent cytotoxicity against human Caucasian gastric adenocarcinoma cells and human hepatocyte cari-noma cells cell lines at higher than $50{\mu}g/mL$.

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

  • Woo, Kyeong Wan;Sim, Mi Ok;Park, Eel Jong;Kim, Min Suk;Suh, Won Se;Cho, Hyun Woo;Kwon, Hak Cheol;Park, Jong Cheol;Lee, Kang Ro
    • Korean Journal of Pharmacognosy
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    • v.47 no.3
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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.

Changes in Abscisic Acid, Carbohydrate, and Glucosinolate Metabolites in Kimchi Cabbage Treated with Glutamic Acid Foliar Application under Extremely Low Temperature Conditions (이상저온 시 글루탐산 엽면 처리에 의한 배추의 ABA, 탄수화물 및 Glucosinolate 대사체 변화)

  • Sim, Ha Seon;Jo, Jung Su;Woo, Ui Jeong;Moon, Yu Hyun;Lee, Tae Yeon;Lee, Hee Ju;Wi, Seung Hwan;Kim, Sung Kyeom
    • Journal of Bio-Environment Control
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    • v.31 no.3
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    • pp.170-179
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    • 2022
  • Glutamic acid is a precursor of essential amino acids that play an important role in plant growth and development. It is one of the biostimulants that reduce cold stress damage by stimulating biosynthetic pathways leading to cryoprotectants. This study evaluated the effects of glutamic acid foliar application on Kimchi cabbage under low-temperature stress. There were six treatments, combining three photo-/dark periods temperature levels (11/-1℃ extremely low, E; 16/4℃ moderately low, M; and 21/9℃ optimal, O) with and without glutamic acid foliar application (0 and 10 mg·L-1; Glu 0 and Glu 10). Glutamic acid foliar application was sprayed once 10 days after transplanting, and then temperature treatment immediately after glutamic acid foliar application was conducted for up to four days. After four days of treatment, abscisic acid (ABA), phaseic acid (PA), dihydrophaseic acid (DPA), and abscisic acid-glucose ester (ABA-GE) contents were higher with Glu 10 treatment than Glu 0 treatment in M treatment. Glucose content was highest in E with Glu 10 treatment (52.1 mg·100 g-1 dry weight), while fructose content was highest in O with Glu 0 treatment (134.6 mg·100 g-1 dry weight). The contents of glucolepiddin (GLP), glucobrassicin (GBS), 4-methoxyglucobrassicin (4MGBS), neoglucobrassicin (GNBS), and gluconasturtiin (GNS) were highest among all treatments in E with Glu 10 treatments (0.72, 2.05, 1.67, 9.40 and 0.85 µmol·g-1 dry weight). After two days of treatment, rapid changes in PA and DPA contents of E with Glu 10 treatments were confirmed, and several individual glucosinolate contents (GLP, GBS, 4MGBS, GNBS, and GNS) were significantly different depending on low temperature and glutamic acid treatment. In addition, the content of fructose was significantly lower than that of O treatment in E and M treatments after four days of treatment. Therefore, although the changes in PA, DPA, glucose, fructose, and individual glucosinolates according to low temperature and glutamic acid foliar treatment were shown. A clear correlation between low temperature and glutamic acid effects could not be evaluated. Results indicated that Brassica crops are cryophilic vegetables, do not react sensitively to low temperatures, and mostly have cold resistance.