Glochidionionosides A-D: Megastigmane Glucosides from Leaves of Glochidion zeylanicum (GAERTN.) A. JUSS.

Otsuka, Hideaki; Kijima, Hidehiko; Hirata, Eiji; Shinzato, Takakazu; Takushi, Anki; Bando, Mai; Takeda, Yoshio

doi:10.1248/cpb.51.286

Cited by 32 publications

(15 citation statements)

References 16 publications

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“…The second sub-fraction (13.6 mg) with a blue fl uorescence (UV 366 nm) showed two major compounds (fi gure 4) when analyzed by gas chromatography-FID and gas G1 G2 G3 G4 G5 G6 G7 G8 G9 G10 G11 G12 Nist. (Otsuka et al 2003). The third sub-fraction (4.2 mg) with a green fl uorescence (UV 366 nm) had fi ve major compounds: 9-hydroxy-4-megastigmen-3-one (RT = 11.6 min, m/z 210), isololiolide (RT = 12.0 min, m/z 196), (-) loliolide (RT = 12.3 min, m/z 196), palmitic acid (RT = 14.1 min, m/z 256) and lupeol (RT = 28.4 min, m/z 189).…”

Section: Resultsmentioning

confidence: 99%

Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)

Cardoso-Lopes¹,

Paula²,

Barbo³

et al. 2009

Rev. bras. Bot.

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− (Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)). Pera glabrata (Schott) Baill. was selected for this study after showing a preliminary positive result in a screening of Atlantic Forest plant species in the search for acetylcholinesterase inhibitors and antifungal compounds. The bioassays were conducted with crude ethanol extract of the leaves using direct bioautography method for acetylcholinesterase and antifungal activities. This extract was partitioned with hexane, chloroform and ethyl acetate solvents. The active chloroform fraction was submitted to silica gel chromatography column affording 12 groups. Caffeine, an alkaloid, which showed detection limits of 0.1 and 1.0 μg for anticholinesterasic and antifungal activities, respectively, was isolated from group nine. After microplate analyses, only groups four, nine, 10, 11 and 12 showed acetylcholinesterase inhibitory activity of 40% or higher. The group 12 was purifi ed by preparative layer chromatography affording four sub-fractions. Two sub-fractions from this group were analyzed by gas chromatography-mass spectrometry and gas chromatography-fl ame ionization detector. The fi rst sub-fraction showed anticholinesterasic activity and contained two major compounds: 9-hydroxy-4-megastigmen-3-one (84%) and caffeine (6%). The second sub-fraction presented fi ve major compounds identifi ed as 9-hydroxy-4-megastigmen-3-one, isololiolide, (-) loliolide, palmitic acid and lupeol and did not show activity. Key words -9-hydroxy-4-megastigmen-3-one, biological activities, caffeine, EuphorbiaceaeResumo -(Composição química, atividades inibidora da acetilcolinesterase e antifúngica de Pera glabrata (Schott) Baill. (Euphorbiaceae)). Pera glabrata (Schott) Baill. foi selecionada para este estudo a partir de uma triagem de espécies vegetais da Mata Atlântica na busca de substâncias com atividades anticolinesterásica e antifúngica. A técnica da bioautografi a direta foi utilizada para a detecção das atividades anticolinesterásica e antifúngica. O extrato etanólico bruto obtido das folhas foi particionado com hexano, clorofórmio e acetato de etila. A fração clorofórmica ativa foi fracionada por cromatografi a em coluna de sílica gel fornecendo 12 grupos. Do grupo nove foi isolado o alcalóide cafeína com limites de detecção de 0,1 e 1,0 μg para as atividades anticolinesterásica e antifúngica, respectivamente. Após bioensaio em microplaca, somente os grupos quatro, nove, 10, 11 e 12 apresentaram inibição da acetilcolinesterase maior ou igual a 40%. O grupo 12 foi purifi cado por cromatografi a em camada delgada preparativa de sílica gel fornecendo quatro sub-frações. Duas sub-frações deste grupo foram analisadas por cromatografi a a gás-espectrometria de massas e cromatografi a a gás com detector de ionização de chama. A primeira sub-fração contém dois compostos majoritários: 9-hidroxi-4-megastigmen-3-ona (78%) e cafeína (6%), e apresentou atividade anticolinesterásica. A segunda

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Section: Resultsmentioning

confidence: 99%

Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)

Cardoso-Lopes¹,

Paula²,

Barbo³

et al. 2009

Rev. bras. Bot.

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“…UV spectra were obtained on a 210A doublebeam spectrophotometer (Shimadzu, Kyoto, Japan). 1D-and 2D-NMR spectra were run on Bruker DRX-500 and AV-600 instruments operating at 500 and 600 MHz for 1 H, and 125 and 150 MHz for 13 C, respectively. The MS data were recorded on a VG Auto Spec-3000 spectrometer (VG, Manchester, U.K.).…”

Section: Methodsmentioning

confidence: 99%

“…(1), was isolated from the whole plants of G. eriocarpum, together with eight ionon (2-9), six phenolic (10)(11)(12)(13)(14)(15), and two lignan (16,17) glucosides (Figure 1). Their structures were elucidated by extensive spectroscopic analyses.…”

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confidence: 99%

“…Compound 1, obtained as a white powder, has the molecular formula C 18 H 26 O 9 established by HREIMS m/z 386.1572 [M] + (calcd for C 18 H 26 O 9 , 386.1577) and 13 C NMR (DEPT) data, requiring for six degrees of unsaturation. The H COSY, and HMBC spectra revealed that 1 contained a phloroglucinol moiety linked with the isovaleryl unit at C-1, which caused the upfield shifting of C-3 and C-5.…”

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confidence: 99%

“…Therefore, the relative configurations of 2 and 3 were established as shown in Figure 1. methyl-2-cyclohexen-l-one (4), 9 (6R,9S)-3-oxo--ionol -Dglucopyranoside (5), 10 (6S,9S) roseoside (6), 11 blumenol C glucoside (7), 12 glochidionionoside C (8), 13 glcochidionionoside A (9), 13 1,2-dimethoxyphenyl-4-O--D-glucoside (10), 14 koaburaside monomethyl ether (11), 15 koaburaside (12), 15 1--D-glucopyranosyloxy-3-methoxy-5-hydroxybenzene (13), 16 syringin (14), 17 bergenin (15), 18 7R,8S-(16) 19 and 7S,8R- (17) 19 dihydrodehydrodiconiferyl alcohol 4-O--D-glucopyranoside by comparing their spectroscopic data with those reported in literatures. Compounds 16 and 17 were isolated as a mixture of chiral isomers in a ratio of 1:1 as estimated by CD spectra and optical rotation.…”

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confidence: 99%

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A New Phloroglucinol Glucoside from the Whole Plants of Glochidion eriocarpum

Wang¹,

Zhu²,

Wang³

et al. 2014

Bulletin of the Korean Chemical Society

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