Antiallergic Activity of Aqueous Extracts and Constituents of Taxus yunnanensis

Koyama, Junko; Morita, Izumi; Kobayashi, N.; Hirai, Kei-Ichi; Simamura, Eriko; Nobukawa, Takahiro; Kadota, Shigetoshi

doi:10.1248/bpb.29.2310

Cited by 21 publications

(22 citation statements)

References 7 publications

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“…The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy and confirmed by comparison of its NMR data with those reported in the literature for 2-[2-hydroxy-5-(3-hydroxypropyl)-3-methoxyphenyl]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (1) (Koyama et al, 2006). Compounds 2-5b were identified by comparison of their NMR data with those reported in the literature for pinoresinol (2) (Ragasa et al, 2000), fatty alcohols (3) (Ragasa et al, 2014a), triglycerides (4) (Ragasa et al, 2015), β-sitosterol (5a) (Ragasa et al, 2014b), and stigmasterol (5b) (Jamal et al, 2008).…”

Section: Resultsmentioning

confidence: 66%

“…Cycasin, a carcinogenic toxin was isolated from the most studied Cycas species, C. revoluta Thunb. and C. circinalis L. (Nishida et al, 1955;Laqueur et al, 1963). Biflavonoids, lignans, flavan-3-ols, flavone-C-glucosides, norisoprenoids, and a flavanone were obtained from the methanolic extract of the leaflets of C. circinalis L. and the chloroform extract of C. revoluta Thunb.…”

Section: * Corresponding Authormentioning

confidence: 99%

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Chemical Constituents of Cycas aenigma

Ng¹,

Agoo²,

Shen³

et al. 2015

J App Pharm Sci

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Chemical investigation of Cycas aenigma, a plant endemic to the Philippines, led to the isolation of a rare neolignan, 2-[2-hydroxy-5-(3-hydroxypropyl)-3-methoxyphenyl]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (1), pinoresinol (2), and fatty alcohols (3) from the leaflets; and triglycerols (4), and a mixture of β-sitosterol (5a) and stigmasterol (5b) from the petiole and rachis. The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy, while those of 2-5b were identified by comparison of their 1 H and/or 13 C NMR data with literature data.

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Section: Resultsmentioning

confidence: 66%

Section: * Corresponding Authormentioning

confidence: 99%

Chemical Constituents of Cycas aenigma

Ng¹,

Agoo²,

Shen³

et al. 2015

J App Pharm Sci

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“…1). The molecular formula of 1 was established as C 30 )] were recognized. Heteronuclear multiple bond connectivity (HMBC) correlations of H-2/C-1(A), C-2(A) and C-6(A); H-3/C-1(B), C-2(B) and C-6(B); H-6/C-4(B); H-7/C-9; H-11/C-2(A), C-3(A) and C-4(A) indicated the presence of a dibenzenacycloundecaphane ring system (Fig.…”

Section: Resultsmentioning

confidence: 99%

DNA Topoisomerase Inhibitory Activity of Constituents from the Fruits of <i>Illicium verum</i>

Kim

Shin

Kim

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Three new compounds, a sesquilignan (1) and two glucosylated phenylpropanoids (2, 3), and seven known compounds (4-10), were isolated from the fruits of Illicium verum HOOK. FIL. (Illiciaceae). The structures of 1-3 were determined based on one and two dimensional (1D-and 2D-) NMR data and electronic circular dichroism (ECD) spectra analyses. Compounds 3, 5, 6, and 8-10 exhibited potent inhibitory activities against topoisomerase II with IC 50 values of 54.6, 25.5, 17.9, 12.1, 0.3 and 1.0 µM, respectively, compared to etoposide, the positive control, with an IC 50 of 43.8 µM.Key words Illicium verum; topoisomerase I; topoisomerase II; cytotoxicity Star anise (the fruits of Illicium verum HOOK. FIL., Illiciaceae) has been used as a traditional medicine to treat diverse disease such as stomach aches, insomnia, and skin inflammation in Asia.1,2) Several sesquiterpenoids, flavonoids, phenylpropanoids and lignans have been previously isolated from this plant [3][4][5][6] and been reported to possess anti-human immunodeficiency virus (HIV), cancer chemopreventive and antifungal activities.7-9) The authors previously reported medicinal plant derived compounds that inhibit topoisomerases I and II. [10][11][12][13][14][15] Topoisomerases are enzymes that control DNA topology in cells and are targets of anticancer drugs.16,17) Topoisomerase I cleaves and reseals one DNA strand at a time without requiring ATP to pass the complementary strand through the enzyme-linked strand break, and thus affect DNA relaxation. On the other hand, topoisomerase II cleaves both strands of DNA during catalysis. In a reaction coupled to ATP binding and hydrolysis, these proteins were found to cleave one DNA duplex, transport a second duplex through the break, and then ligate the cleaved duplex. [18][19][20] Camptothecin (CPT) and etoposide (VP-16) are well-known inhibitors of topoisomerases I and II, respectively. 16,17) Here, the authors report the isolation of ten compounds, including a new sesquilignan and two new glycosylated phenylpropanoids, from the fruits of I. verum, and describe cytotoxicity and their DNA topoisomerases I and II inhibitory activities. Results and DiscussionThree new (1-3) and seven known compounds (4-10) were isolated by various chromatographic separations from the EtOAc extract of the fruits of I. verum (Fig. 1). The molecular formula of 1 was established as C 30

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“…The Kadota research group (Toyama Univ., Toyama, Japan) has characterized and identified many novel active compounds isolated from the water-extract of Taxus yunnanensis. [10][11][12][13][14][15][16] Recently, they reported a novel isoflavans [compound 1 (A)], a novel degraded compound 2 (B) from compound 4 (isotaxiresinol)] and a novel lignan compound 3 (C), which significantly inhibit the activity of cytochrome P450-3A4 in vitro. 17) Compound 6 (E) is identified as a known lignin of tanegool.…”

Section: )mentioning

confidence: 99%

“…[10][11][12][13][14][15][16] Recently, they reported a novel isoflavans [compound 1 (A)], a novel degraded compound 2 (B) from compound 4 (isotaxiresinol)] and a novel lignan compound 3 (C), which significantly inhibit the activity of cytochrome P450-3A4 in vitro. 17) Compound 6 (E) is identified as a known lignin of tanegool.18) Since several Taxus compounds have been characterized to exhibit antioxdant, anti-inflammatory and neuroprotective effects, [10][11][12][13][14][15][16] we preliminarily tested the effects of at least 15 Taxus compounds, including five novel Taxus lignans (compounds A-E) on the GSK-3β-mediated phosphorylation of three brain proteins [bMBP, rhTP and rat collapsin response mediator protein-2 (rCRMP-2, pI=6.0)] in vitro. By our preliminary screening, five Taxus compounds (A-E) exhibiting significant stimulatory effects on the GSK-3β-mediated phosphorylation of two basic proteins (bMBP and rhTP) were selected and furRegular Article…”

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confidence: 99%

Biochemical Characterization of Novel Lignans Isolated from the Wood of Taxus yunnanensis as Effective Stimulators for Glycogen Synthase Kinase-3β and the Phosphorylation of Basic Brain Proteins by the Kinase in Vitro

Ohtsuki

Miyai

Yamaguchi

et al. 2012

Biological & Pharmaceutical Bulletin

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The stimulatory and inhibitory effects of several compounds and lignans isolated from the water extract of Taxus yunnanensis on the phosphorylation of three functional brain proteins (bovine myelin basic protein (bMBP), recombinant human tau protein (rhTP) and rat collapsin response mediator protein-2 (rCRMP-2)) by glycogen synthase kinase-3β (GSK-3β) were quantitatively compared in vitro, using ( )-epigallocatechin-3-gallate [( )EGCG] as a positive control. We found that (i) three selected Taxus lignans [(3S,4R)-4′-hydroxy-6,3′-dimethoxyisoflavan-4-ol,(7R)-7-hydroxytaxiresinol and tanegool] highly stimulated the autophosphorylation of GSK-3β and the GSK-3β-mediated phosphorylation of two basic brain proteins [bMBP (pI 11.3) and rhTP (pI 8.2)], but inhibited dose-dependently the phosphorylation of an acidic protein (rCRMP-2, pI 6.0) by the kinase; (ii) these three Taxus lignans showed binding-affinities with bMBP as well as rhTP, but had low affinities with rCRMP-2; (iii) the binding of tanegool and (7R)-7-hydroxytaxiresinol to these two basic proteins induced their novel potent phosphorylation sites for GSK-3β; and (iv) these three Taxus lignans, but not EGCG, induced Tyr-phosphorylation of GSK-3β in vitro. These results provided here suggest that (i) these three Taxus lignans act as novel effective activators for GSK-3β and the GSK-3β-mediated phosphorylation of their binding basic proteins (rhTP and bMBP); and (ii) tanegool (IC 50 1 μM) is an effective inhibitor for the phosphorylation of rCRMP-2 by the kinase in vitro.Key words Taxus lignan; glycogen synthase kinase-3β; stimulatory effect; protein phosphorylation Recently, we reported that (i) plant polyphenol epigallocatechin-3-gallate (EGCG), not quercetin and luteolin, highly stimulates the phosphorylation of human recombinant tau protein (hrTP, pI=8.2) and bovine myelin basic protein (bMBP, pI=11.3) by glycogen synthase kinase-3β (GSK-3β); (ii) EGCG has a binding-affinity with rhTP as well as bMBP; and (iii) the direct binding of EGCG to these two basic brain proteins (bMBP and rhTP) induces their novel potent phosphorylation sites for GSK-3β, and leads to highly stimulate their phosphorylation by the kinase in vitro.1) Also, we previously reported that phosphatidylinositol (PI) and two sulfated lipids [sulfatide and heparin (SH)] function as effective stimulators for the autophosphorylation of GSK-3β and the GSK-3β-mediated phosphorylation of SH-binding proteins in vitro.2) From these previous reports, 1,2) we conclude that both EGCG and SH may function as effective stimulators for the GSK-3β-mediated phosphorylation of these two basic brain proteins (bMBP and rhTP), containing multiple potent phosphorylation sites for the kinase in vitro. 1,2)Glycogen synthase kinase 3 (GSK-3) is a constitutively active, proline-directed serine (Ser)/threonine (Thr) protein kinase encoded by two isoforms [GSK-3α (approx. 51 kDa) and GSK-3β (approx. 47 kDa, pI=8.98)], which possess similar biochemical characteristics and substrate specificities.3-5) GSK-3 is originally ...

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Antiallergic Activity of Aqueous Extracts and Constituents of Taxus yunnanensis

Cited by 21 publications

References 7 publications

Chemical Constituents of Cycas aenigma

Chemical Constituents of Cycas aenigma

DNA Topoisomerase Inhibitory Activity of Constituents from the Fruits of <i>Illicium verum</i>

Biochemical Characterization of Novel Lignans Isolated from the Wood of Taxus yunnanensis as Effective Stimulators for Glycogen Synthase Kinase-3β and the Phosphorylation of Basic Brain Proteins by the Kinase in Vitro

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