Natural anti-HIV agents—part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata

Hoàng, Vũ Đình; Tan, Ghee Teng; Zhang, Hongjie; Tamez, Pamela A.; Hùng, Nguyễn Văn; Cường, Nguyễn Mạnh; Soejarto, Djaja D.; Fong, Harry H. S.; Pezzuto, John M.

doi:10.1016/s0031-9422(01)00454-x

Cited by 69 publications

(49 citation statements)

References 13 publications

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“…It is found mainly in India and South China to Malaysia, Australia and the Western pacific islands. Previous phytochemical studies revealed the presence of alkaloids (Hart et al 1969;Bhakuni and Gupta, 1983;Holloway and Scheinmann, 1973), butanolides (Cheng et al 2001;Chen et al 1998), and sesquiterpenoids (Hoang et al 2002;Zhang et al 2001;Zhang et al 2003a;Zhang et al 2003b) in the genus Litsea. Few records are found in the literature with respect to the isolation of flavonoids from Litsea species (Wang et al 2009).…”

Section: Introductionmentioning

confidence: 97%

In vitro antioxidant and antinociceptive potentialities of methanolic extract of Litsea glutinosa

Rumzhum

Rahman

Sharukh

et al. 2013

Bangladesh J. Sci. Ind. Res.

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The methanolic extract of Litsea glutinosa (Lauraceae) was evaluated for in vitro antioxidant activity by determination of hydrogen peroxide scavenging activity, total antioxidant capacity, assay of nitric oxide scavenging activity and reducing power test and in vivo antinociceptive effect in acetic acid induced writhing model in swiss albino mice. The results revealed the presence of pronounced antioxidant property as compared with ascorbic acid used as standard and a dose-dependent (250 and 500 mg/kg) analgesic effect. The antioxidant and antinociceptive properties observed seem to be in good accordance with the traditional uses of Litsea glutinosa.

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Section: Introductionmentioning

confidence: 97%

In vitro antioxidant and antinociceptive potentialities of methanolic extract of Litsea glutinosa

Rumzhum

Rahman

Sharukh

et al. 2013

Bangladesh J. Sci. Ind. Res.

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“…Previous phytochemical studies revealed the presence of alkaloids, [1][2][3] butanolides, 4,5) and sesquiterpenoid in the genus Litsea. [6][7][8][9] Few records are found in the literature with respect to the isolation of flavonoids from Litsea species.…”

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confidence: 99%

A New 2′-Oxygenated Flavone Glycoside fromLitsea glutinosa(Lour.) C. B. Rob.

Wang

Huang

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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A new 2 0 -oxygenated flavone glycoside, named glutin, was isolated from Litsea glutinosa (Lour.) C. B. Rob. along with four known compounds. The structure was identified as 2 0 ,5,7-trihydroxy-6-methoxyflavone 2 0 -O--D-glucopyranoside (1) on the basis of extensive spectroscopic analysis.Key words: flavonoids; Litsea glutinosa (Lour.) C. B. Rob.; glutinThe genus Litsea (Lauraceae) comprises nearly 200 species, which are distributed widely throughout tropical and subtropical Asia, North America and subtropical South America. Previous phytochemical studies revealed the presence of alkaloids, 1-3) butanolides, 4,5) and sesquiterpenoid in the genus Litsea.6-9) Few records are found in the literature with respect to the isolation of flavonoids from Litsea species. 10)Litsea glutinosa (Lour.) C. B. Rob., locally known as ''Chan Gao Shu'' in China, is an evergreen mediumsized tree. Its bark and leaves are used as a demulcent and mild astringent for diarrhea and dysentery, and the roots are used to poultice sprains and bruises.11) To date, there have been few phytochemical studies on the species Litsea glutinosa (Lour.) C. B. Rob. 12) Our previous investigation resulted in the isolation of two new aporphine alkaloids from this species.13) As part of continuous research on plants of the Litsea genus, the chemical constituents of the leaves and twigs of L. glutinosa (Lour.) C. B. Rob. were reinvestigated.Powdered leaves and twigs of Litsea glutinosa (Lour.) C. B. Rob. (12.0 kg) were repeatedly extracted with EtOH at room temperature. The extract was then concentrated under reduced pressure to give a brown syrup, which was partitioned in H 2 O and extracted with solvents into a petroleum ether-fraction (80 g), an EtOAc-fraction (54 g), and an n-BuOH-fraction (108 g) fraction. The petroleum-ether fraction was subjected to silica gel column chromatography eluted with petroleum ether-EtOAc (10:1-1:1), by which five fractions (I-V) were obtained. Fraction II was resubmitted to silica gel column chromatography to yield compounds 2 (20 mg) and 3 (55 mg). The EtOAc-fraction was subjected to silica gel column chromatography eluted with CHCl 3 -MeOH (99:1-1:1) to afford eight fractions (I-VIII). Fraction III was resubmitted to silica gel column chromatography by gradient elution using petroleum ether-EtOAc, and crystals from Fraction III were purified by recrystallization (CHCl 3 -MeOH 1:1) to give compounds 5 (38 mg). Fraction IV was resubmitted to Sephadex LH-20 (using MeOH as eluent) and RP C-18 (MeOH-H 2 O 7:3, 0.7 liter; 6:4, 0.5 liter) to yield compounds 1 (8 mg). Fraction V was rechromatographed on a silica gel column, and eluted with CHCl 3 containing increasing amounts of MeOH, and then to Sephadex LH-20 column chromatography (using acetone as eluent) to give compounds 4 (12 mg).Compound 1 was isolated as a yellow amorphous powder. A positive Shinoda and Fiegel's test indicated that compound 1 was a flavonoid glycoside.14) Its formula, C 22 H 22 O 11 , was derived from positive HR-ESI-MS measurements of the molecular-rela...

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“…1) The terpenoids (1 and 2) exhibited considerably high anti-HIV activity (IC 50 , 5.0 and 2-3 mg/ml, respectively) by inhibiting the replication of HIV-1, but they also showed cytotoxicity against HOG.R5 cells (a reporter cell line) 2) with CC 50 values of 13.2 and 5.7 mg/ml, respectively. Quite interestingly, these natural products were obtained as racemic mixtures (i.e., their specific rotation values were both zero).…”

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confidence: 99%

Enantioselective Synthesis of the (1S,5R)-Enantiomer of Litseaverticillols A and B

Morita

Kiyota

Kuwahara

2006

Bioscience, Biotechnology, and Biochemistry

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An enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B was accomplished in line with our previously reported synthetic pathway for their (1R,5S)-enantiomer. The use of ''EtSCeCl 2 '' prepared from EtSLi and CeCl 3 , instead of previously employed EtSLi itself, for the formation of thiol ester intermediates prevented any undesirable epimerization occurring in the process.

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Natural anti-HIV agents—part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata

Cited by 69 publications

References 13 publications

In vitro antioxidant and antinociceptive potentialities of methanolic extract of Litsea glutinosa

In vitro antioxidant and antinociceptive potentialities of methanolic extract of Litsea glutinosa

A New 2′-Oxygenated Flavone Glycoside fromLitsea glutinosa(Lour.) C. B. Rob.

Enantioselective Synthesis of the (1S,5R)-Enantiomer of Litseaverticillols A and B

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