New Cytotoxic Tetrahydrofuran- and Dihydrofuran-Type Lignans from the Stem of<i>Beilschmiedia tsangii</i>

Chen, Jih Jung; Chou, En Tzu; Duh, Chang‐Yih; Yang, Sheng Zehn; Chen, Ih Sheng

doi:10.1055/s-2005-916220

Cited by 51 publications

(64 citation statements)

References 12 publications

(15 reference statements)

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“…17 These isolated compounds were found for the first time in this plant. There are several reports on lignans neolignans isolated from the Beilschmiedia species, such as B. tsangii, 9 B. volckii, 21 and B. kunstleri.…”

Section: β-Sitosterol (8)mentioning

confidence: 96%

Anticholinesterase and Anti-inflammatory Constituents fromBeilschmiedia pulverulentaKosterm

et al. 2016

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− Phytochemical investigation from the stem bark of Beilschmiedia pulverulenta resulted in the isolation of five lignans, (+)-yangambin (1), (+)-sesartemin (2), (+)-excelsin (3), (+)-sesamin (4), and (+)-syringaresinol (5), together with lupeol (6), lupenone (7), β-sitosterol (8), and β-sitostenone (9). Their structures were established by the analysis of their spectroscopic (1D and 2D NMR) and spectrometric (MS) data, as well as by comparison with those reported in the literature. The isolated lignans were tested for their anticholinesterase (AChE: acetylcholine esterase and BChE: butyryl cholineesterase) and anti-inflammatory (COX-2: cyclooxygenase-2 and LOX: lipoxygenase) activities. All the isolated lignans (1 -5) exhibited significant inhibition activities in AChE/BChE and COX-2/LOX assays with IC 50 values ranging from 168.8 -504.2 µM and 21.0 -59.4 µM, respectively.

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Section: β-Sitosterol (8)mentioning

confidence: 96%

Anticholinesterase and Anti-inflammatory Constituents fromBeilschmiedia pulverulentaKosterm

et al. 2016

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“…[47]. Chen et al [50] studied the in vitro cytotoxicity of several compounds isolated from B. tsangii. They found that tsangin A-B, α-tocospiro B and beilschmin A displayed from medium to strong activity against the P-388 (murine leukemia cell) line.…”

Section: Cytotoxicity Activitymentioning

confidence: 99%

A Review on Chemical Constituents and Biological Activities of the Genus <i>Beilschmiedia</i> (Lauraceae)

et al. 2015

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“…The known isolates were readily identified by a comparison of physical and spectroscopic data (UV, IR, 1 H NMR, [D] D , and MS) with corresponding authentic samples or literature values, and this included two amides, N-trans-feruloyltyramine (2) [13] and N-trans-feruloyloctopamine (3) [14], a benzenoid, vanillin (4) [15], a benzoquinone, D-tocopheryl quinone (5) [16], and three steroids, E-sitostenone (6) [17], E-sitosterol (7) [18], and 6D-hydroxystigmast-4-en-3-one (8) [8].…”

mentioning

confidence: 99%

Beilschamide, a New Amide, and Cytotoxic Constituents of Beilschmiedia erythrophloia

Chen

Kuo²,

Sung

et al. 2015

Chem Nat Compd

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A new amide, beilschamide (1), has been isolated from the stem of Beilschmiedia erythrophloia, together with seven known compounds, N-trans-feruloyltyramine (2), N-trans-feruloyloctopamine (3), vanillin (4), D-tocopheryl quinone (5), E-sitostenone (6), E-sitosterol (7), and 6D-hydroxystigmast-4-en-3-one (8). The structure of the new compound 1 was determined through spectroscopic and MS analyses. N-trans-Feruloyloctopamine (3) and beilschamide (1) exhibited cytotoxic effects with IC 50 values of 10.3 and 21.2 Pg/mL, respectively, against CCRF-CEM cell line. Beilschmiedia erythrophloia Hay. (Lauraceae) is an evergreen tree, distributed throughout South Mainland China, Hainan Island, the Ryukyus, and Taiwan [1]. Alkaloids [2, 3], flavonoids [4], endiandric acids [5-7], lignans [8, 9], benzenoids [7, 8], steroids [6-9], triterpenoids [7,9], fatty acid esters [7,9], and their derivatives are widely distributed in plants of the genus Beilschmiedia. Many of these compounds exhibit diverse biological activities, including cytotoxic [8] and antitubercular [7,9] activities. In a preliminary screening, the methanolic extract of the root of this species showed cytotoxic activities in vitro. The current phytochemical investigation of the stem of this plant has led to the isolation of a new amide, beilschamide (1), along with seven known compounds. The structural elucidation of 1 and its cytotoxic property are described herein.Extensive fractionation of the EtOAc-soluble portion of a MeOH extract of leaves of Beilschmiedia erythrophloia using silica gel column chromatography (CC), MPLC, and preparative TLC afforded compounds 1-8.Compound 1 was isolated as a yellowish amorphous powder. The HR-ESI-MS gave an [M + Na] + ion at m/z 380.1470 (calcd for C 20 H 23 NO 5 Na, 380.1474), consistent with a molecular formula of C 20 H 23 NO 5 . IR absorptions for NH, OH (3355, 3265 cm -1 ), and carbonyl (1652 cm -1 ) functions were observed. The signals of the 1 H and 13 C NMR spectra of 1 were assigned to a 3,4-dimethoxyphenyl, a 4-hydroxyphenyl, a conjugated double bond, a methoxy, an oxymethine, and a methylene. Comparison of the 1 H and 13 C NMR data of 1 with those of 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide [10] suggested that their structures were closely related, except for the 3,4-dimethoxyphenyl group [G H 3.87 (6H, s, 3, 4-OMe), 6.96 (1H, d, J = 8.5 Hz, H-5), 7.13 (1H, dd, J = 8.5, 2.0 Hz, H-6), 7.16 (1H, d, J = 2.0 Hz, H-2); at C-7 of 1 replacing the 4-hydroxy-3-methoxyphenyl group of 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide [10].

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New Cytotoxic Tetrahydrofuran- and Dihydrofuran-Type Lignans from the Stem ofBeilschmiedia tsangii

Cited by 51 publications

References 12 publications

Anticholinesterase and Anti-inflammatory Constituents fromBeilschmiedia pulverulentaKosterm

Anticholinesterase and Anti-inflammatory Constituents fromBeilschmiedia pulverulentaKosterm

A Review on Chemical Constituents and Biological Activities of the Genus <i>Beilschmiedia</i> (Lauraceae)

Beilschamide, a New Amide, and Cytotoxic Constituents of Beilschmiedia erythrophloia

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