Arylnaphthalene neolignans from Virola calophylla

Martínez, Claudia; Yoshida, Massayoshi; Gottlieb, Otto R.

doi:10.1016/0031-9422(90)85206-u

Cited by 15 publications

(11 citation statements)

References 9 publications

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“…The structures of the isolated compounds were identified as meso-dihydroguaiaretic acid (1) and otobaphenol (2) by analysis of NMR and MS data (Fig. 1), together with comparison of their spectral data with those in the literature (Braz Fo et al, 1984;Song et al, 2004;Martinez et al, 1990). As shown in Table 1, compounds 1 and 2 inhibited the activity of PTP1B in a dose-dependent manner with IC 50 values of 19.6 ± 0.3 and 48.9 ± 0.5 µM, respectively.…”

Section: Resultsmentioning

confidence: 98%

Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans

Yang

Jang

et al. 2006

Phytotherapy Research

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Inhibition of protein tyrosine phosphatase 1B (PTP1B) has been proposed as one of the drug targets for treating type 2 diabetes and obesity. Bioassay-guided fractionation of a MeOH extract of the semen of Myristica fragrans Houtt. (Myristicaceae) afforded PTP1B inhibitory compounds, meso-dihydroguaiaretic acid (1) and otobaphenol (2). Compounds 1 and 2 inhibited PTP1B with IC(50) values of 19.6 +/- 0.3 and 48.9 +/- 0.5 microM, respectively, in the manner of non-competitive inhibitors. Treatment with compound 1 on 32D cells overexpressing the insulin receptor (IR) resulted in a dose-dependent increase in the tyrosine phosphorylation of IR. These results indicate that compound 1 can act as an enhancing agent in intracellular insulin signaling, possibly through the inhibition of PTP1B activity.

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Section: Resultsmentioning

confidence: 98%

Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans

Yang

Jang

et al. 2006

Phytotherapy Research

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“…The petroleum ether-and EtOAc-soluble fractions were subjected to silica gel, Sephadex LH-20, and MCI column chromatography followed by repeated RP C 18 HPLC to afford compounds 1−14 (Figure 1). Compound 1 was obtained as a colorless oil with a negative specific rotation, [α] D 20 −39 (c 0.9, CHCl 3 ), and its molecular formula was assigned as C 21 H 22 O 7 based on the 13 C NMR spectroscopic data and an HRESIMS ion at m/z 409.1258 [M + Na] + (calcd 409.1263). The IR spectrum exhibited absorption bands from phenyl (1598 cm −1 ) and carbonyl (1713 cm −1 ) moieties.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Lignans from the Fruit ofSchisandra glaucescenswith Antioxidant and Neuroprotective Properties

Chen

Sun

et al. 2014

J. Nat. Prod.

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Two rare 7,8-seco-lignans (1, 2), three new lignan glycosides (3, 4a, 4b), and 10 known lignans (5-14) were isolated from the fruit of Schisandra glaucescens Diels. The absolute configurations of 1 and 2 were determined by comparing their experimental and calculated electronic circular dichroism spectra. The molecular structures of the new compounds (3, 4a, and 4b), including their absolute configurations, were determined using various spectroscopic methods and hydrolysis reactions. The antioxidant activities of the isolated compounds were tested using 2,2-diphenyl-1-picrylhydrazyl and ferric reducing antioxidant power assays. Compounds 4, 7, 8, 10, 11, and 12 exhibited antioxidant activities of varying potential in both assays. Of these compounds, 7 showed the strongest 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity, with IC50 values of 15.7 (150 μM DPPH) and 34.6 μM (300 μM DPPH), respectively, and 4, 12, and 7 displayed higher total antioxidant activities than Trolox in the ferric reducing antioxidant power assay. The neuroprotective effects of these compounds against Aβ25-35-induced cell death in SH-SY5Y cells were also investigated. Compounds 1, 2, 6, 7, 8, 11, and 12 exhibited statistically significant neuroprotective effects against Aβ25-35-induced SH-SY5Y cell death compared with the group treated only with Aβ25-35.

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“…In addition, the 13 C NMR spectra of 1-3 confirmed the occurrence of dibenzylbutane neolignans derivatives due to the presence of signals at δ 107-148, attributed to aromatic carbons C-1 to C-6 and C-1´to C-6', and peaks of C 3 unit at δ 41.1 (C-7/C-7'), 37.5-39.2 (C-8/C-8'), and δ 13.9 (C-9/C-9'). Finally, based on chemical shifts of C-7/C-7', C-8/C-8' and C-9/C-9' and comparison with data described in the literature, 22,23 the isolated neolignans 1-3 displayed a threo configuration between methyl groups. LREIMS of 1-3 displayed peaks in the spectra that corresponded to molecular ions at m/z 326, 328 and 330 consistent, respectively, with molecular masses C 20 [23][24][25] threo-austrobailignan-6 (2) 26 and threo-dihydroguaiaretic acid (3).…”

Section: Resultsmentioning

confidence: 99%

ISOLATION OF CYTOTOXIC NEOLIGNANS FROM Saururus cernuus L. (SAURURACEAE) USING IONIC LIQUID IN THE MICROWAVE ASSISTED EXTRACTION (MAE)

Brito¹,

Camilo²,

Figueiredo³

et al. 2018

Quim. Nova

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In the present work, dried leaves of Saururus cernuus (Saururaceae) were subjected to extraction using an ionic liquid (1-butyl-3-methylimidazolium bromide -BMImBr) in the microwave assisted extraction (MAE). The obtained extract was partitioned using n-hexane and cytotoxicity activity of this organic phase against murine melanoma cell line (B16F10-Nex2) was evaluated in vitro. Since this extract displayed activity (100% of cell death at 200 µg mL -1 ) it was subjected to a bioactivity-guided fractionation to afford four related neolignans: threo-austrobailignan-5 (1), threo-austrobailignan-6 (2), threo-dihydroguaiaretic acid (3) and saucernetin (4). Their chemical structures were established based on NMR and MS spectral analysis. Among the isolated neolignans, compound 2 exhibited the highest cytotoxic activity against HeLa (human cervical melanoma) cells with IC 50 of 28.3 ± 3.9 µg mL ). The obtained results provide important data for the selection of bioactive neolignans with promising cytotoxic potential using a simple and fast method employing a green solvent as 1-butyl-3-methylimidazolium bromide (BMImBr).

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Arylnaphthalene neolignans from Virola calophylla

Cited by 15 publications

References 9 publications

Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans

Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans

Lignans from the Fruit ofSchisandra glaucescenswith Antioxidant and Neuroprotective Properties

ISOLATION OF CYTOTOXIC NEOLIGNANS FROM Saururus cernuus L. (SAURURACEAE) USING IONIC LIQUID IN THE MICROWAVE ASSISTED EXTRACTION (MAE)

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