• Natural Product Sciences
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• 제18권4호
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• pp.233-238
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• 2012

Nine compounds (1 - 9), ${\alpha}$-linolenic acid (1), cis-5,8,11,14,17-elcosapentaenoic acid (2), phytol (3), loliolide (4), uridine (5), thymidine (6), deoxyadenosine (7), adenine (8), and adenosine (9), were isolated from the n-hexane, methylene chloride, ethyl acetate and n-butanol fractions of Capsosiphon fulvescens. The structures of these compounds were elucidated on the basis of spectroscopic evidence. Compounds 1 - 9 exhibited acetylcholinesterase (AChE) inhibitory activities with $IC_{50}$ values ranging from 114.91 to $252.40{\mu}M$, whereas 2 - 4 showed butyrylcholinesterase (BChE) inhibitory activities with $IC_{50}$ values ranging from 251.18 to $499.16{\mu}M$.

• Archives of Pharmacal Research
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• 제27권10호
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• pp.1029-1033
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• 2004

From the methanol extract of the whole plants of Carpesium macrocephalum $F_R$. et $S_{AV}$., five sesquiterpene lactones (1: carabron, 2: tomentosin, 3: ivalin, 4: 4H-tomentosin, 5: carabrol) and three terpenoids (6: loliolide, 7: vomifoliol, 8: citrusin C) were isolated. The structures and stereochemistry of compounds 1-8 were established on the basis of chemical analysis as well as 1D- and 2D-NMR spectroscopy. Among them, compounds 2, 4, and 6-8 were isolated for the first time from Carpesium species.

• 생명과학회지
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• 제22권9호
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• pp.1166-1172
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• 2012

비파 잎의 항산화 활성을 탐색하고 활성물질을 분리하여 규명하기 위하여, 동결 건조한 비파 잎을 마쇄하여 n-hexane, ethyl acetate (EtOAc)와 methanol (MeOH)로 용매 분획하였다. 각 추출물에 대하여 정량적으로 DPPH 소거활성, SOD 유사활성을 측정하고, 페놀 화합물과 플라보노이드 함량을 측정하였으며, 각 용매에 따른 추출물 중 비교적 활성이 강한 EtOAc 추출물과 MeOH 추출물에 대하여 column chromatography를 이용하여 얻은 분획물들 중 강한 활성을 보인 각 1개의 분획물에서 3개의 화합물을 분리하였으며, GC/MS 분석에서 phytol, ${\beta}$-sitosterol 및 (-)-Loliolide으로 동정하였다.

• Natural Product Sciences
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• 제26권2호
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• pp.151-157
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• 2020

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B₅ (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B₂ (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.

• Journal of Applied Biological Chemistry
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• 제59권3호
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• pp.207-213
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• 2016

Little information about the biological activities of Citrus limon (lemon) leaves has been reported, whereas the fruit of Citrus limon (lemon) has been well-documented to contain various pro-health bio-functional compounds. In the present study, the antiproliferative activities of the lemon leaves were evaluated using several cancer cell lines. From the n-hexane, chloroform, ethyl acetate, n-butanol, and water fractions of methanolic extract of the leaves, the chloroform fraction of lemon leaves (CFLL) showed the most potent antiproliferative activity in the AGS human gastric cancer cells. The current study demonstrates that CFLL induces apoptosis in AGS cells, as evidenced by an increase in apoptotic bodies, cell population in the sub-G1 phase, Bax/Bcl-2 ratio, and cleavage of poly (ADP-ribose) polymerase (PARP), caspase-3 and caspase-9. Compositional analysis of the CFLL using gas chromatography mass spectrometry (GC-MS) resulted in the identification of 27 compounds including trans, trans-farnesol (3.19 %), farnesol (3.26 %), vanillic acid (1.45 %), (-)-loliolide (5.24 %) and palmitic acid (6.96 %). Understanding the modes of action of these compounds individually and/or synergistically would provide useful information about their applications in cancer prevention and therapy.

• Natural Product Sciences
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• 제24권2호
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• pp.132-138
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• 2018

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 - 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-${\beta}$-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), ${\beta}$-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-${\beta}$-D-glucopyranoside (10), pinoresinol-4'-O-${\beta}$-D-glucopyranoside (11), luteolin (12), quercetin-3-O-${\beta}$-D-glucopyranoside (13), and luteolin 6-C-${\beta}$-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 - 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 - 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with $IC_{50}$ values of $9.70{\mu}M$.

• Archives of Pharmacal Research
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• 제26권8호
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• pp.585-590
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• 2003

Activity-guided fractionation of the EtOAc-soluble extract of the whole plants of Sida acuta using a bioassay based on the induction of quinone reductase (OR) in cultured Hepa 1c1c7 mouse hepatoma cells, led to the isolation of ten active compounds of previously known structure, quindolinone (1), cryptolepinone (2), 11-methoxyquindoline (3), N-trans-feruloyltyramine (4), vomifoliol (5), loliolide (6), 4-ketopinoresinol (7), scopoletin (8), evofolin-A (9), and evofolin-B (10), along with five inactive compounds of known structure, ferulic acid, sinapic acid, syringic acid, ($\pm$)-syringaresinol, and vanillic acid. These isolates were identified by physical and spectral data measurement. A new derivative of quindolinone, 5,10-dimethylquindolin-11-one (1a) was synthesized and characterized spectroscopically. Of the active substances, compounds 1-3 and 1a exhibited the most potent QR activity, with observed CD (concentration required to double induction) values ranging from 0.01 to 0.12 $\mu$ g/mL. Six compounds were then evaluated in a mouse mammary organ culture assay, with cryptolepinone (2), N-trans-feruloyltyramine (4), and 5,10-dimethylquindolin-11-one (1a) found to exhibit 83.3, 75.0, and 66.7% inhibition of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions, respectively, at a dose of 10 $\mu\textrm{g}$/mL.