Neolignans from Anaxagorea clavata

Díaz, Aura M. P. de

doi:10.1016/s0031-9422(96)00541-9

Cited by 14 publications

(4 citation statements)

References 6 publications

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“…Norneolignans 3 and 4 contain a C 3 unit joined to C-5 of the 2-(3,4-methylenedioxyphenyl)benzofuran skeleton. They were first isolated from the wood of Anaxagorea clavata [5]. Our 1 H NMR spectra are essentially the same as those reported for these compounds; however, the chemical shifts of the 13 C NMR spectrum of 4 have not been previously reported.…”

supporting

confidence: 76%

2-Arylbenzofuran Neolignans from the Bark of Nectandra purpurascens (Lauraceae)

Ríos-Motta

Avella

2010

Natural Product Communications

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The toluene extract of the stem bark of N. purpurascens (R&P) Mez. contained a large amount of these 2-arylbenzofurans including methyl 7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran-5-carboxylate (2), a new benzofuran, along with three known compounds identified as kumatakenin (1), 5-(2-propenyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran (3), and egonoic acid (4). The structure of the new compound was established on the basis of spectroscopic analysis.

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supporting

confidence: 76%

2-Arylbenzofuran Neolignans from the Bark of Nectandra purpurascens (Lauraceae)

Ríos-Motta

Avella

2010

Natural Product Communications

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“…The genus Anaxagorea (Annonaceae) comprises 30 species distributed in the neotropics and tropical Asia . Previous phytochemical studies with plants of this genus revealed the presence of xanthones, flavonoids, − neolignans, terpenoids, and alkaloids, − with some of them exhibiting remarkable biological activities. The analysis of the essential oil from the leaves of Anaxagorea brevipes has revealed the presence of mono- and sesquiterpenes such as α-, β-, and γ-eudesmol, guaiol, and caryophyllene oxide.…”

Section: Introductionmentioning

confidence: 99%

Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

et al. 2020

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Six sesquiterpenoids with unprecedented macrocyclic humulene-type structures, namely, dolichocarpols A-E (1− 5) with ether-bridged bicyclic rings between C-10 and C-2, C-10 and C-7, C-10 and C-6 (×2), and C-6 and C-3 and dolichocarpol F (6) cyclized between C-7 and C-2 and with an ether bridge between C-10 and C-3, were isolated from Anaxagorea dolichocarpa roots. The structures of the compounds were elucidated by NMR, MS, and IR data. Absolute configurations of compounds 1−3 and 6 were established on the basis of data from electronic circular dichroism, whereas relative configurations of compounds 4 and 5 were suggested by the NOESY spectrum. In addition, a putative biosynthetic pathway of the compounds is proposed. Furthermore, the cytotoxicity of 3, 4, and 6 against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) was evaluated.

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“…The main differences in the 1 H and 13 C NMR spectra of 17 and 16 were the absence of signals at δ H 9.74 (H-3″ in 16 ) and δ C 202.9 (C-3″ in 16 ) and the presence of a signal at δ C 177.0, which confirmed the carboxylic function. Therefore, 17 was established as the known 3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propionic acid (egonoic acid) …”

Section: Resultsmentioning

confidence: 99%

“…Subsequently, the reaction mixture was poured into water and extracted with ether, the organic phase was dried over anhydrous Na 2 SO 4 and filtered, and the solvent was evaporated in vacuo. The residue was purified by CCC (petroleum ether–EtOAc; linear gradient from 1:0 to 2:3) to give 17 (35.0 mg, 84%) …”

Section: Methodsmentioning

confidence: 99%

Benzofurans from Styrax agrestis As Acetylcholinesterase Inhibitors: Structure–Activity Relationships and Molecular Modeling Studies

et al. 2011

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An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxyegonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure-activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced Aβ aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 μM) and, for 1, Aβ aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.

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Neolignans from Anaxagorea clavata

Cited by 14 publications

References 6 publications

2-Arylbenzofuran Neolignans from the Bark of Nectandra purpurascens (Lauraceae)

2-Arylbenzofuran Neolignans from the Bark of Nectandra purpurascens (Lauraceae)

Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

Benzofurans from Styrax agrestis As Acetylcholinesterase Inhibitors: Structure–Activity Relationships and Molecular Modeling Studies

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