Chiaki Tanaka

Kyushu University, Hukuoka, Fukuoka, Japan

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Publications (35)74.15 Total impact

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    ABSTRACT: Two new sappanin-type homoisoflavonoids, (3R)-7-hydroxy-8-methoxy-3′,4′-methylenedioxyhomoisoflavanone (trifasciatine A) 1 and (3R)-3,7-dihydroxy-8-methoxy-3′,4′-methylenedioxyhomoisoflavanone (trifasciatine B) 2 were isolated as minor components from the EtOAc soluble fraction of the methanol extract of Sansevieria trifasciata collected in Cameroon together with the known 1-(stearoyl)-glycerol 3 and spirosta-5,25(27)-dien-1β,3β-diol-1-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside 4. Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D NMR) and HRESIMS. Compounds 1 and 2 were screened for their antiproliferative activity on HeLa cells and no significant effect was observed when compare to 5-FU (fluorouracil) used as positive control.
    Phytochemistry Letters 06/2015; 12:262-266. DOI:10.1016/j.phytol.2015.04.017 · 1.54 Impact Factor
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    ABSTRACT: Six new polyacetylenic alcohols, termed strongylotriols A and B; pellynols J, K, and L; and isopellynol A, together with three known polyacetylenic alcohols, pellynols A, B, and C were isolated from the marine sponges Petrosia sp., and Halichondria sp. collected in Okinawa, Japan. Their planer structures were determined based on 2D-NMR and mass spectrometric analysis of the degraded products by RuCl3 oxidation. The absolute stereochemistry of isolates was examined by their Mosher's esters. The strongylotriols were found to be optically pure compounds, whereas the pellynols are diastereomeric mixtures at the C-6 position. Proliferation experiments using the HeLa and K562 cell lines suggested that the essential structural units for activity are the "hexa-2,4-diyn-1,6-diol" and "pent-1-en-4-yn-3-ol" on the termini.
    Chemical & pharmaceutical bulletin 04/2015; 63(6). DOI:10.1248/cpb.c15-00203 · 1.38 Impact Factor
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    ABSTRACT: Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. "Yellow Coast", and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.
    Natural product communications 01/2015; 10(1):37-8. · 0.92 Impact Factor
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    ABSTRACT: Three new steroidal saponins, named diospreussinosides A-C (1-3), along with two known ones (4, 5) were isolated from rhizomes of Dioscorea preussii. Their structures were elucidated mainly by 1D and 2D NMR spectrocopic analysis and mass spectrometry as (25S)-17α,25-dihydroxyspirost-5-en-3β-yl-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)- β-D-glucopyranoside (1), (25S)-17α,25-dihydroxyspirost-5-en-3β-yl-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (2), and (24S,25R)-17α,24,25-trihydroxyspirost-5-en-3β-yl-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3). The spirostane-type skeleton of compound 3 possessing an unusual dihydroxylation pattern on the F-ring is reported for the first time. Cytotoxicity of compounds 2-5 was evaluated against two human colon carcinoma cell lines (HT-29 and HCT 116).
    Fitoterapia 06/2014; 97. DOI:10.1016/j.fitote.2014.06.006 · 2.22 Impact Factor
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    ABSTRACT: Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylquillaic acid 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-fucopyranosyl ester (1), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-fucopyranosyl ester (2), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranosyl ester (3), gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-{6-O-[3-hydroxy-3-methylglutaryl]-β-d-glucopyranosyl-(1→6)}-β-d-galactopyranosyl ester (4). Three compounds were evaluated against one human colon cancer cell line SW480 and one rat cardiomyoblast cell line H9c2.
    Phytochemistry 04/2014; 102. DOI:10.1016/j.phytochem.2014.02.018 · 3.35 Impact Factor
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    ABSTRACT: Four and one know triterpenoid saponins (1–5) were isolated from Polycarpaea corymbosa Lamk. var. eriantha Hochst. 16α,22α-diacetyl-camilliagenin A was not previously described. Two aglycones were reported for the first time in saponins of the Caryophyllaceae family. Their cytotoxicity was also evaluated and the 13,28-epoxyoleanane-type saponin exhibited a significant activity.
    Phytochemistry 04/2014; DOI:10.1016/j.phytochem.2013.12.005 · 3.35 Impact Factor
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    ABSTRACT: Steroidal saponins from Dioscorea preussii Turibio Kuiate Tabopda, Anne-Claire Mitaine-Offer, Chiaki Tanaka, Tomofumi Miyamoto, Jean-François Mirjolet, Olivier Duchamp, Bonaventure Tchaleu Ngadjui, and Marie-Aleth Lacaille-Dubois Three new steroidal saponins, named diospreussinosides A–C (1–3), along with two known ones (4, 5) were isolated from rhizomes of Dioscorea preussii. The spirostane-type skeleton of compound 3 with an unusual dihydroxylation pattern on the F-ring is reported for the first time. Cytotoxicity of 2–5 was evaluated against two human colon carcinoma cell lines (HT-29 and HCT 116). The most active compound was a derivative of pennogenin (5).
    Fitoterapia 01/2014; · 2.22 Impact Factor
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    ABSTRACT: Graphical abstract Four triterpene saponins and two known compounds were isolated from two species of the genus Gypsophila. Their structures were established by spectroscopic methods. The cytotoxic activity of three saponins was evaluated against SW480 and H9c2 cell lines.
    Phytochemistry 01/2014; · 3.35 Impact Factor
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    ABSTRACT: The phytochemical investigation of the root barks of Pittosporum verticillatum Bojer subsp. verticillatum led to the isolation of three new triterpene saponins, 3-O-[β-D-glucopyranosyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranosyl-21-O-(2-acetoxy-2-methylbutanoyl)-R1-barrigenol (1), 3-O-[β-D-glucopyranosyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranosyl-21-O-(2-acetoxy-2-methylbutanoyl)-28-O-acetyl-R1-barrigenol (2), 3-O-[β-D-glucopyranosyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[α-L-arabinofuranosyl-(1→4)]-β-D-glucuronopyranosyl-21-O-β,β-dimethylacryloyl-22-O-angeloyl-R1-barrigenol (3), and one known saponin senaciapittoside B (4). Their structures were elucidated mainly by 1D- and 2D-NMR spectroscopy and HRESIMS. Compounds 1-4 were evaluated for their cytotoxicity against one human cancer cell line (SW480) and one rat cardiomyoblast cell line (H9c2).
    Fitoterapia 09/2013; 91. DOI:10.1016/j.fitote.2013.09.002 · 2.22 Impact Factor
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    ABSTRACT: An optically inactive C-20 bisacetylenic alcohol, (4E,16E)-icosa-4,16-diene-1,19-diyne-3,18-diol, was isolated from a marine sponge Callyspongia sp. as a result of screening of antilymphangiogenic agents from marine invertebrates. An optical resolution using chiral-phase HPLC gave each enantiomer, (-)-1 and (+)-2. Because the natural and synthetic enantiomers 1 and 2 showed different biological properties, we investigated the structure-activity relationships of bisacetylenic alcohols using 11 synthetic derivatives, and it is clarified that the essential structural unit for antiproliferative activity is the "1-yn-3-ol" on both termini and that there is a minimum chain length that connects the "1-yn-3-ol" moieties.
    Journal of Natural Products 07/2013; 76(7). DOI:10.1021/np400297p · 3.95 Impact Factor
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    ABSTRACT: Three new steroidal saponins and ten known ones were isolated from the bark of Dracaena marginata, along with two known steroidal saponins from the roots. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments and mass spectrometry as (25R)-26-(beta-D-glucopyranosyloxy)3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (1), (25R)-26-(beta-D-glucopyranosyloxy)-3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-sulfo-alpha-L-arabinopyranoside (2), and (25S)-3beta-hydroxyspirost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-sulfo-alpha-L-arabinopyranoside (3).
    Natural product communications 02/2013; 8(2):157-60. · 0.92 Impact Factor
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    ABSTRACT: A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of four spirostane-type glycosides (1-4), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25S)-spirost-5-en-3β,12β,21-triol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (1), (20S,25S)-spirost-5-en-3β,11α,21-triol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (2), laxogenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (3), and (25R)-5α-spirostan-3β,11α-diol 3-O-β-d-glucopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→4)]-β-d-galactopyranoside (4). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines.
    Phytochemistry 01/2013; DOI:10.1016/j.phytochem.2012.12.001 · 3.35 Impact Factor
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    ABSTRACT: Metastasis occurs when cancer cells detach from a tumor, travel to distant sites in the body and develop into tumors in these new locations. Most cancer patients die from metastases. Among the various forms of cancer metastasis, lymphatic metastasis is an important determinant in cancer treatment and staging. In this study, we investigated lymphangiogenesis inhibitors from crude drugs used in Japan and Korea. The three crude drugs Saussureae Radix, Psoraleae Semen and Aurantti Fructus Immaturus significantly inhibited the proliferation of temperature-sensitive rat lymphatic endothelial (TR-LE) cells in vitro. By a chromatographic method using bioassay-guided fractionation methods, costunolide (1) and dehydrocostus lactone (2) from S. Radix, p-hydroxybenzaldehyde (3), psoralen (4), angelicin (5), psoracorylifol D (6), isobavachalone (7), bavachinin (8) Δ(3),2-hydroxybakuchiol (9) and bakuchiol (10) from P. Semen and cis-octadecyl ferulate (11), (2R)-3β,7,4'-trihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (12), (2S)-7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (13) and umbelliferone (14) from A. F. Immaturus were obtained. Three compounds (compounds 11-13) from A. F. Immaturus were isolated for the first time from this medicinal plant. Among isolated compounds, ten compounds (compounds 1, 2, 6-12, 13) showed an inhibitory effect on the proliferation and the capillary-like tube formation of TR-LE cells. In addition, all compounds except compound 12 showed selective inhibition of the proliferation of TR-LE cells compared to Hela and Lewis lung carcinoma (LLC) cells. These compounds might offer clinical benefits as lymphangiogenesis inhibitors and may be good candidates for novel anti-cancer and anti-metastatic agents.
    Biological & Pharmaceutical Bulletin 01/2013; 36(1):152-7. DOI:10.1248/bpb.b12-00871 · 1.78 Impact Factor
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    Natural product communications 01/2013; 8(5):573-574. · 0.92 Impact Factor
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    ABSTRACT: Seven steroidal glycosides have been isolated from the fruits of Solanum torvum Swartz. Their structures were established by 2D NMR spectroscopic techniques ((1)H,(1)H-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as (25S)-26-(β-d-glucopyranosyloxy)-3-oxo-5α-furost-20(22)-en-6α-yl-O-β-d-xylopyranoside (1), (25S)-26-(β-d-glucopyranosyloxy)-3-oxo-22α-methoxy-5α-furostan-6α-yl-O-β-d-xylopyranoside (2), (25S)-26-(β-d-glucopyranosyloxy)-3β-hydroxy-22α-methoxy-5α-furostan-6α-yl-O-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranoside (3), (25S)-3β-hydroxy-5α-spirostan-6α-yl-O-β-d-xylopyranoside (4), (25S)-3-oxo-5α-spirostan-6α-yl-O-β-d-xylopyranoside (5), (25S)-3β-hydroxy-5α-spirostan-6α-yl-O-β-d-glucopyranoside (6), (25S)-3β,27-dihydroxy-5α-spirostan-6α-yl-O-β-d-glucopyranoside (7).
    Phytochemistry 12/2012; 86. DOI:10.1016/j.phytochem.2012.10.010 · 3.35 Impact Factor
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    ABSTRACT: Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β-galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4)-8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-2A, and 1-O-[β-galacto furanosyl-(1→3)-α-galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.
    Marine Drugs 12/2012; 10(11):2467-80. DOI:10.3390/md10112467 · 3.51 Impact Factor
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    ABSTRACT: Two new oleanane-type triterpene saponins, afrocyclamins A and B (1 and 2, resp.), were isolated from a MeOH extract of the roots of Cyclamen africanum Boiss. & Reuter, together with three known triterpenoid saponins, lysikokianoside, deglucocyclamin I, and its dicrotalic acid derivative. The structures were elucidated, on the basis of 1D-and 2D-NMR experiments and mass spectrometry as (3b,20b)-13,28-epoxy-16-oxo-3-{O-b-d-xylopyranosyl-(1 ! 2)-O-b-d-glucopyranosyl-(1 ! 4)-O-[b-d-glucopyranosyl-(1 ! 2)]-a-l-arabinopyranosyl}oxy}oleanan-29-al (1) and (3b,16a,20b)-16,28,29-trihy-droxy-olean-12-en-3-yl O-4-O-(4-carboxy-3-hydroxy-3-methyl-1-oxobutyl)-b-d-xylopyranosyl-(1 ! 2)-O-b-d-glucopyranosyl-(1 ! 4)-O-[b-d-glucopyranosyl-(1 ! 2)]-a-l-arabinopyranoside (2). Introduction. – Cyclamen is a genus of 23 species of flowering plants belonging to the Primulaceae family [1], many of them being reported to contain pentacyclic triterpenoids [2], with a wide range of bioactivities, such as somatic embryogenesis [3], fungicidal, antitumor, and uterocontractile activities [4], and in the treatment against infertility [5]. As part of our continuing studies on saponins from the genus Cyclamen [6] [7], we chose Cyclamen africanum, an endemic plant of northern Algeria (Bejaia), which was used in folk medicine against warts. A previous report revealed the presence of the sapogenin cyclamiretin A [8], but no systematic study on the saponins of this plant has been reported so far. We describe in this work the isolation and structure elucidation of two new triterpene saponins named afrocyclamins A and B (1 and 2, resp.) and of three known saponins from the rhizome MeOH extract of C. africanum.
    Helvetica Chimica Acta 09/2012; 95(9):1573-1580.. DOI:10.1002/hlca.201200041 · 1.39 Impact Factor
  • 8th Joint Meeting of AFERP, ASP, GA, PSE and SIF; 07/2012
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    ABSTRACT: A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of seven new spirostane-type glycosides (1-7) while 1-6 were obtained as three pairs of inseparable (R)/(S)-isomers derivatives 1/2, 3/4, 5/6, and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-spirost-5-en-3β,12β,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (1) and its (25S)-isomer (2), (20S,25R)-spirost-5-en-3β,11α,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3) and its (25S)-isomer (4), laxogenin 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (5) and its (25S)-isomer (6), and (25R)-5α-spirostan-3β,11α-diol 3-O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside (7). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines.
    2012 International Congress on Natural Products Research; 07/2012