Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Chiaki Tanaka Last modified date:2018.06.28

Assistant Professor / Natural Product Chemistry / Department of Chemo-Pharmaceutical Sciences / Faculty of Pharmaceutical Sciences


Papers
1. Nampoina Andriamisain, Anne-Claire Mitaine-Offer, Benoist Pruvot, Johanna Chlub, Tomofumi Miyamoto, Chiaki Tanaka and Marie-Aleth Lacaille-Dubois, Phytochemistry of Weigela x “kosteriana variegata” (Caprifoliaceae), Nat. Prod. Commun., 2018, 13 (4), 387-512., 13, 4, 387-512, 2018.06.
2. Rengifo Carrillo M, Mitaine-Offer AC, Tomofumi Miyamoto, Chiaki Tanaka, Pouységu L, Quideau S, Rojas LB, Rosquete Porcar C, Marie-Aleth Lacaille-Dubois, Oleanane-type glycosides from Pittosporum tenuifolium "variegatum" and P. tenuifolium "gold star"., Phytochemistry, 10.1016/j.phytochem, 140, 166-173, 2017.08, The phytochemical study of two cultivars of Pittosporum tenuifolium Banks & Sol. ex Gaertn, "variegatum" and "gold star", led to the isolation of eight oleanane-type glycosides: seven previously undescribed and a known one. Their aglycons are oxygenated oleanane derivatives as barringtogenol C, camelliagenin A, hederagenin, and 22α-hydroxyoleanolic acid. Their structures were established by 2D NMR spectroscopic techniques and mass spectrometry as 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21-O-angeloyl-22-O-acetylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21,22-di-O-angeloylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-22-O-angeloylcamelliagenin A, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-22-O-[(6-O-acetyl)-β-D-glucopyranosyl]camelliagenin A, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 4)]-β-D-glucuronopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-arabinofuranosyl-(1 → 4)-β-D-glucuronopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 4)]-β-D-glucuronopyranosyl-22α-hydroxyoleanolic acid 28-O-β-D-glucopyranosyl ester, and the known ilexoside XLIX. These results represent a significative contribution to the chemotaxonomy of the genus Pittosporum, highlighting hederagenin-type saponins as chemotaxonomic markers of P. tenuifolium cultivars..
3. Karima Ounaissia, David Pertuit, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Dalila Smati, Marie-Aleth Lacaille-Dubois, New pregnane and phenolic glycosides from Solenostemma argel., Fitoterapia, 10.1016/j.fitote.2016.08.002., 114, 98-104, 2016.09, From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D - and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9-59.0μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3μM and 27.6μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481-9617μmoleq. Trolox/100g..
4. Remy Bertrand Teponno, Chiaki Tanaka, Bai Jie, Leon Azefack Tapondjou, Tomofumi Miyamoto, Trifasciatosides A-J, Steroidal Saponins from Sansevieria trifasciata., Chem. Pharm. Bull., 10.1248/cpb.c16-00337 , 64, 9, 1347-1355, 2016.07, Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including (1)H-NMR, (13)C-NMR, (1)H-(1)H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells..
5. David Sibel Avunduka, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Marie-Aleth Lacaille-Dubois, Cycloartane-Type Saponins from Astragalus tmoleus var. tmoleus, Natural Product Communications, 11, 1, 37-38, 2016.01, Five known cycloartane-type glycosides were isolated from the roots of A. tmoleus Boiss. var. tmoleus. The identification of these compounds was mainly achieved by 1D and 2D NMR spectroscopic techniques and FABMS. The results of our studies confirm that t.
6. Abdelmalek Rezgui, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Marie-Aleth Lacaille-Dubois, Oleanolic acid and hederagenin glycosides from Weigela stelzneri., Phytochemistry, 10.1016/j.phytochem.2015.12.016., 123, 40-47, 2016.01, Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-xylopyranosyl-(1 → 6)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid and 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively..
7. Remy Bertrand Teponno, Chiaki Tanaka, Bai Jie, Leon Azefack Tapondjou, Tomofumi Miyamoto, Trifasciatosides A-N, steroidal saponins from Sansevieria trifasciata Prain, , Phytochemistry, 12, 262-266, 2015.11, Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including (1)H-NMR, (13)C-NMR, (1)H-(1)H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells..
8. David Pertuita, Anne-Claire Mitaine-Offera, Tayebe Baghery Lotfabadb, Tomofumi Miyamoto, Chiaki Tanaka, Marie-Aleth Lacaille-Dubois, Two New Triterpene Saponins from Acanthophyllum laxiusculum, Helvetica Chimica Acta, 10.1248/cpb.c15-00203, 98, 0, 611-617, 2015.07, Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika..
9. Billy T. Tchegnitegni, Rémy B. Teponno, Chiaki Tanaka, Adeyemi F. Gabriel, Léon A. Tapondjou, Tomofumi Miyamoto, Sappanin-type homoisoflavonoids from Sansevieria trifasciata Prain, Phytochemistry Letters, 12, 262-266, 2015.04, [URL], Two new sappanin-type homoisoflavonoids, (3R)-7-hydroxy-8-methoxy-30,40-methylenedioxyhomoisoflavanone (trifasciatine A) 1 and (3R)-3,7-dihydroxy-8-methoxy-30,40-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-1b,3b-diol-1-O-a-L-rhamnopyranosyl-(1
→2)-a-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..
10. Adeyemi F. Gabriel, Zhen Li, Ryouhei Kusuda, Chiaki Tanaka, Tomofumi Miyamoto, Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp., Chem. Pharm. Bull., 10.1248/cpb.c15-00203, 63, 6, 469-475, 2015.04, 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..
11. David Pertuita, Anne-Claire Mitaine-Offera, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasurec, Patrick Dutartrec, Marie-Aleth Lacaille-Dubois, A New Aromatic Compound from the Stem Bark of Terminalia catappa, Natural Product Communications, 10, 6, 1005-1015, 2015.03, A new aromatic compound 3,4,5-trimethoxyphenyl-1-O-(4-sulfo)-β-D-glucopyranoside (1), in addition to two triterpenoid saponins (chebuloside II,
arjunoglucoside II), two triterpenes (arjunolic acid and 3-betulinic acid) and sitosterol-3-O-β-D-glucopyranosi.
12. David Pertuit, Tayebe Baghery Lotfabad, A.-C. Mitaine-Offer, Chiaki Tanaka, Tomofumi Miyamoto, Marie-Aleth Lacaille-Dubois, Two New Triterpene Saponins from Acanthophyllum laxiusculum, Helvetica Chimica Acta, 98, 611-617, 2015.01, Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika. The structures of the new compounds were established by extensive 1D- and 2D-NMR spectroscopic experiments and MS analyses as 23-O-b-d-galactopyranosylgypsogenic acid 28-O-{b-d-glucopyranosyl-(1!2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]- b-d-glucopyranosyl-(1!6)}-[b-d-glucopyranosyl-(1!3)]-b-d-galactopyranosyl ester (1) and gypsogenic acid 28-O-{b-d-glucopyranosyl-(1!2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-bd-glucopyranosyl-(1!6)}-[b-d-glucopyranosyl-(1!3)]-b-d-galactopyranosyl ester (2)..
13. Rezgui A, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Marie-Aleth Lacaille-Dubois, Spirostane-type saponins from Dracaena fragrans "Yellow Coast"., Nat Prod Commun, 10, 1, 37-38, 2015.01, 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..
14. David Pertuit, Sibel Avunduk, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Thomas Paululat, Stéphanie Delemasure, Patrick Dutartre, Marie-Aleth Lacaille-Dubois, Triterpenoid saponins from the roots of two Gypsophila species, Phytochemistry, 102, 182-188, 2014.06.
15. T. K. Tabopda, Anne-Claire Mitaine-Offer, Chiaki Tanaka, Tomofumi Miyamoto, J-F. Mijolet, B. T. Ngadjui, Marie-Aleth Lacaille-Dubois, Steroidal saponins from Dioscorea preussii, Fitoterapia, 10.1016/j, 97, 198-203, 2014.06, 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 spectroscopic 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)..
16. Mahenina Jaovita Manase, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Marie-Aleth Lacaille-Dubois, Triterpenoid saponins from Polycarpaea corymbosa Lamk. var. eriantha Hochst, Phytochemistry, 100, 150-155, 2014.04, [URL], Four triterpenoid saponins (1–4) were isolated from Polycarpaea corymbosa Lamk. var. eriantha Hochst
along with the known apoanagallosaponin IV (5). Their structures were elucidated by spectroscopic data
analysis. Among the compounds 1, 3–5 which were evaluated for their cytotoxicity against three tumor
cell lines (SW480, DU145 and EMT6), compound 1 exhibited cytotoxicity with IC50 values ranging from
4.61 to 22.61 lM, which was greater than that of etoposide. Compound 2 was tested only against SW480
and a cardiomyoblast cell line (H9c2), and was inactive..
17. Mahenina Jaovita Manase, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Marie-Aleth Lacaille-Dubois, Triterpenoid saponins from Polycarpaea corymbosa Lamk. var. eriantha Hochst., Phytochemistry, 10.1016/j.phytochem.2013.12.005. , 100, 150-155, 2014.04, Four triterpenoid saponins (1-4) were isolated from Polycarpaea corymbosa Lamk. var. eriantha Hochst along with the known apoanagallosaponin IV (5). Their structures were elucidated by spectroscopic data analysis. Among the compounds 1, 3-5 which were evaluated for their cytotoxicity against three tumor cell lines (SW480, DU145 and EMT6), compound 1 exhibited cytotoxicity with IC50 values ranging from 4.61 to 22.61 μM, which was greater than that of etoposide. Compound 2 was tested only against SW480 and a cardiomyoblast cell line (H9c2), and was inactive.
.
18. Mahenina Jaovita Manase, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Marie-Aleth Lacaille-Dubois, Newtriterpenoid estersaponins fromthe root barks of Pittosporum verticillatum subsp. verticillatum and evaluation of cytotoxicities, Fitoterapia, 91, 231-235, 2013.09, [URL], 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)..
19. Takayuki Shirouzu, Kousuke Watari, MAYUMI ONO, Keiichi Koizumi, Ikuo Saiki, Chiaki Tanaka, Rob W. M. van Soest, Tomofumi Miyamoto, Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp., Journal of Natural Products, 10.1021/np400297p, 76, 7, 1337-1342, 2013.07, [URL].
20. Gaoussou Timité, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Jean-François Mirjolet, Olivier Duchamp, Marie-Aleth Lacaille-Dubois, Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum Original Research Article
, Volume 88, April 2013, Pages , Phytochemistry, 88, 61-66, 2013.04.
21. Alida Pérez Colmenares, Luis B. Rojas, Anne-Claire Mitaine-Offer, Laurent Pouységu, Stéphane Quideau, Tomofumi Miyamoto, Chiaki Tanaka, Thomas Paululat, Alfredo Usubillaga, Marie-Aleth Lacaille-Dubois, Steroidal saponins from the fruits of Solanum torvum Original Research Article
, Phytochemistry, 86, 137-143, 2013.02.
22. G. Timite, A.-C. Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, J.-C. Mirjolet, O. Duchamp, M.-A. Lacaille-Dubois, Structure and Cytotoxicity of Steroidal Glycosides from Allium schoenoprasum, Nat. Prod. Commun, 8, 2, 157-160, 2013.02.
23. Dami Jeong, Kousuke Watari, Mayumi Ono, K.Koizumi, I. Saiki, Y.-C. Kim, Chiaki Tanaka, Ryuichi Higuchi, Tomofumi Miyamoto, Studies on Lymphangiogenesis Inhibitors from Korean and Japanese Crude Drugs, Biol. Pharm. Bull.,36,2,152-157,2013.01., Biol. Pharm. Bull., 36, 2, 152-157, 2013.01.
24. Ke Pan, Chiaki Tanaka, masanori inagaki, Ryuichi Higuchi, Tomofumi Miyamoto, Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus, 10.3390/md10112467, 2467-2480, 2012.11.
25. Mahenina Jaovita Manase, Anne-Claire Mitaine-Offer, David Pertuit, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Jean-François Mirjolet, Olivier Duchamp, Marie-Aleth Lacaille-Dubois, Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: Confirmation of their synonymy., Fitoterapia, 10.1016, 2012.05, A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3β,23-diol 3-O-{β-d-xylopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→4)-[O-α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five human cancer cell lines and for antioxidant and cytoprotective activity..
26. T.K. Tabopda, A. C. Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, B.D. Ngadjui, M. A. Lacaille-Dubois, Secondary Metabolites from Polar Fractions of Piper umbellatum, 7, 595-596, 2012.03.
27. Turibio Kuiate Tabopda, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Jean-François Mirjolet, Olivier Duchamp, Bonaventure Tchaleu Ngadjui, Marie-Aleth Lacaille-Dubois, Triterpenoid saponins from Hydrocotyle bonariensis Lam, Phytochemistry, 10.1016/j, 73, 142, 2012.01, Phytochemical investigation of the under-ground parts of Hydrocotyle bonariensis led to the isolation of five oleanane-type triterpenoid saponins, 3-O-{β-D-glucopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl}-21-O-(2-methylbutyroyl)-22-O-acetyl-R(1)-barrigenol, 3-O-{β-D-glucopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl}-21-O-(2-methylbutyroyl)-28-O-acetyl-R(1)-barrigenol, 3-O-{β-D-glucopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl}-21-O-acetyl-R(1)-barrigenol, 3-O-{β-D-glucopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl}-R(1)-barrigenol, and 3-O-{β-D-glucopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl}-22-O-(2-methylbutyroyl)-A(1)-barrigenol, together with the known saniculoside-R1. Their structures were established by 2D NMR techniques and mass spectrometry. Six compounds were evaluated against two human colon cancer cell lines, HCT 116 and HT-29. Two compounds showed weak cytotoxicity with IC(50) 24.1 and 24.0, 83.0 and 83.6 μM against HT-29 and HCT 116, respectively..
28. Soumeya Bencharif-Betina, Tomofumi Miyamoto, Chiaki Tanaka, Zahia Kabouche, Anne-Claire Mitaine-Offer, Marie Aleth Lacaille-Dubois, Two New Triterpene Saponins from Cyclamen africanum Boiss. & Reuter, 95, 2012.01, 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-dglucopyranosyl-(
1!2)]-a-l-arabinopyranosyl}oxy}oleanan-29-al (1) and (3b,16a,20b)-16,28,29-trihydroxy-
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)..
29. Elier Galarraga, Anne-Claire Mitaine-Offer, Juan Manuel Amaro-Luis, Tomofumi Miyamoto, Chiaki Tanaka, Laurent Pouységu, Stéphane Quideau, Luis B Rojas, Marie-Aleth Lacaille-Dubois , Steroidal saponins from the fruits of Cestrum ruizteranianum, Natural product communications, 6, 1825, 2011.12, Seven spirostane and furostane-type glycosides were isolated from the aqueous methanolic extract of the fruits of Cestrum ruizteranianum and characterized mainly by 2D NMR spectroscopy and mass spectrometry. These known saponins belong to the delta5-spirostene and delta5-furostene series and are reported in this species for the first time..
30. T. Kuiate Tabopda, A-C. Mitaine-Offera, T. Miyamoto, C. Tanaka, B. T. Ngadjui, J-F. Mirjolet, O. Duchamp, and M-A. Lacaille-Dubois, Three New Medicagenic Acid Saponins from Polygala micrantha Guill. & Perr., Helvetica Chimica Acta, 94, 914-922, 2011.05.
31. Turibio Kuiate Tabopdaa, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Jean-FranÅois Mirjolet, Olivier Duchamp, Bonaventure Tchaleu Ngadjui,and Marie-Aleth Lacaille-Dubois, Acylated Triterpene Saponins from Atroxima liberica Stapf, Helvetica Chimica Acta, 94, 2066, 2011.04, The four new acylated triterpene saponins 1 – 4, isolated as two pairs of isomers and named
libericosides A1/A2 and B1/B2 , one pair of isomers 5/6, the (Z)-isomer libericoside C2 (5) being new, one
new sucrose ester, atroximoside (7), and eight known compounds were isolated from the roots of
Atroxima liberica by repeated MPLC and VLC on normal and reversed-phase silica gel. Their structures
were elucidated on the basis of extensive 1D- and 2D-NMR studies (1H- and 13C-NMR, DEPT, COSY,
TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3-O-b-d-glucopyranosylpresenegenin
28-{O-a-l-arabinopyranosyl-(1!3)-O-b-d-xylopyranosyl-(1!4)-O-a-l-rhamnopyranosyl-(1!2)-4-
O-[(E)-3,4-dimethoxycinnamoyl]-b-d-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-b-d-glucopyranosylpresenegenin
28-{O-a-l-arabinopyranosyl-(1!4)-O-b-d-xylopyranosyl-(1!4)-O-a-l-rhamnopyranosyl-(
1!2)-O-[O-b-d-xylopyranosyl-(1!3)-b-d-glucopyranosyl-(1!3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]-
b-d-fucopyranosyl} ester (3) and its (Z)-isomer 4, 3-O-b-d-glucopyranosylpresenegenin 28-
{O-b-d-xylopyranosyl-(1!4)-O-a-l-rhamnopyranosyl-(1!2)-O-[6-O-acetyl-b-d-glucopyranosyl-(1! 3)]-4-O-[(Z)-3,4-dimethoxycinnamoyl]-b-d-fucopyranosyl} ester (5), and 3-O-[(Z)-feruloyl]-b-d-fructofuranosyl
a-d-glucopyranoside (7). Compounds 1 – 6 and the known saponins 8/9 were evaluated
against the human colon cancer cells HCT 116 and HT-29 and showed moderate to weak cytotoxicity..
32. G. Timite, A-C. Mitaine-Offer, T. Miyamoto, C. Tanaka, J-F. Mirjolet, O. Duchamp, M. A. Lacaiile-Dubois, Unusual oleanane-type saponins from Arenaria montana, Phytochemistry, 72, 503-507, 2011.02.
33. Aymen Jabrane, Hichem Ben Jannet, Tomofumi Miyamoto, Chiaki Tanaka, Jean-François Mirjolet, Olivier Duchamp, Féthia Harzallah-Skhiri, Marie-Aleth Lacaille-Dubois, Glaucasides A-C, three saikosaponins from Atriplex glauca L. var. ifiniensis (Caball) Maire., Magnetic Resonance in Chemistry, 10.1002/mrc.2696, 49, 83-89, 2011.02, From the roots of Atriplex glauca L. var. ifiniensis (Caball) Maire (syn. of Atriplex parvifolia Lowe var. genuina Maire), three new saikosaponins designated as glaucasides A-C (1-3) were isolated together with the known 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galactopyranosyl-saikogenin F (4). The structures of the new compounds were elucidated by extensive analysis of one-dimensional and two-dimensional NMR spectroscopy, FABMS, HR-ESIMS and chemical evidence as 13β,28-epoxy-16β,21β-dihydroxyolean-11-en-3β-yl O-β-D-[2-O-sulfate]-glucopyranosyl-(1 → 2)-α-L-arabinopyranoside (1), 13β,28-epoxy-16β,21β-dihydroxyolean-11-en-3β-yl O-β-D-[2-O-sulfate]-glucopyranosyl-(1 → 2)-α-L-arabinopyranosyl 21-O-{4-(secbutylamido)-butanoyl ester} (2) and 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galactopyranosyl saikogenin G (3). The cytotoxic activities of these compounds were evaluated against the HT-29 and HCT 116 human colon cancer cell lines..
34. Sibel Avunduk, Özgen Alankuş-Çalişkan, Tomofumi Miyamoto, Chiaki Tanaka and Marie-Aleth Lacaille-Dubois, Secondary Metabolites from the Roots of Paronychia chionaea, Natural Product Communications, 6, 2, 205-208, 2011.01, Two novel secondary metabolites, compounds (1–2) were isolated from the roots of Paronychia chionaea. On the basis of spectroscopic data
including 1D and 2D NMR experiments (COSY, TOCSY, HSQC, and HMBC), and mass spectroscopy, their structures were established as
6-C-[α-L-arabinopyranosyl-(1→2)-β-D-glucopyranosyl]-7-O-[β-D-glucopyranosyl]-luteolin 3´-methyl ether (1), and 2-(methoxy)-2-(3,5-
dimethoxy 4-hydroxyphenyl)-ethane-1,2-diol 1-O-β-D-glucopyranoside (2)..
35. Sibel Avunduk, Özgen Caliskan, Tomofumi Miyamoto, Chiaki Tanaka, Marie-Aleth Lacaille-Dubois, Secondary Metabolites from the Roots of Paronychia chionaea, Natural Product Communications, Natural Product Communications, 6, 205-208, 2011.01.
36. J. Linnek, A-C. Mitaine-Offer, T. Miyamoto, C. Tanaka, T. Paululat, S. Acunduk, O. Alankus-Caliskan, M. A. Lacaiile-Dubois, Cycloartane Glycosides from Three Species of Astragalus (Fabaceae), Helvetica Chimica Acta, 94, 230-237, 2011.01.
37. G. Timite, A-C. Mitaine-Offer, T. Miyamoto, C. Tanaka, T. Paululat, C. Delaude, M. A. Lacaiile-Dubois, Presenegin Glycosides from Securidaca welwotschii, Helvetica Chimica Acta, 93, 2237-2244, 2010.10.
38. M. Wanzola, T. Furuta, Y. Kohno, S. Fukumitsu, S. Yasukochi, K. Watari, C. Tanaka, R. Higuchi, and T. Miyamoto, Four New Cembrane Diterpenes Isolated from an Okinawan Soft Coral Lobophytum crassum with Inhibitory Effects on Nitric Oxide Production, Chem. Pharm. Bull. , 58, 9, 1203—1209, 2010.09.
39. Guy Beddos Kougan, Tomofumi Miyamoto, Chiaki Tanaka, Thomas Paululat, Jean-François Mirjolet, Olivier Duchamp, Beibam Lucas Sondengam, Marie-Aleth Lacaille-Dubois, Steroidal Saponins from Two Species of Dracaena, Journal of Natural Products , 10.1021/np100153m, 73, 1266–1270, 2010.07, Four new steroidal saponins (1-4) were isolated from the stem and bark of two species of Dracaena: deistelianosides A and B (1 and 2) from D. deisteliana and arboreasaponins A and B (3 and 4) from D. arborea. Six known saponins and one known sapogenin were also isolated. The structures of 1-4 were established as diosgenin 3-O-[3-O-sulfate-alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranoside (1), 1-O-beta-d-xylopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-fucopyranosyl(23S,24S)-spirosta-5,25(27)-diene-1beta,3beta,23alpha,24alpha-tetrol 24-O-alpha-l-arabinopyranoside (2), pennogenin-3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-[6-O-acetyl]-beta-d-glucopyranoside (3), and 24alpha-hydroxypennogenin 3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-glucopyranoside (4) using extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry. Cytotoxic activity of several of these compounds was evaluated against the HT-29 and HCT 116 human colon cancer cell lines..
40. Ke Pan, Masanori Inagaki, Nagisa Ohno, Chiaki Tanaka, Ryuichi Higuchi, Tomofumi Miyamoto, Identification of Sixteen New Galactocerebrosides from the Starfish Protoreaster nodosus, Chem. Pharm. Bull., 58, 2010.01.
41. Ke PAN, Masanori INAGAKI, Nagisa OHNO, Chiaki TANAKA, Ryuichi HIGUCHI, and Tomofumi MIYAMOTO*, Identification of Sixteen New Galactocerebrosides from the Starfish
Protoreaster nodosus, Chem. Pharm. Bull., 58, 4, 470—474, 2010.01.
42. M. Agena, C. Tanaka, N. Hanif, M. Hirose, and J. Tanaka, New cytotoxic spongian diterpens from the sponge Dysidea cf. arenaria, Tetrahedron , 2009, 65, 1495-1499., 2009.03.
43. N. Hanif, J. Tanaka, A. Setiawan, A. Trianto, N. J. de Voogd, A. Murni, C. Tanaka, and T. Higa, Polybrominated Diphenyl Ethers from the Indonesian Sponge Lamellodysidea herbacea, Journal of Natural Products , 70, 432-435, 2007.06.
44. C. Tanaka, J. Tanaka, R.F. Bolland, G. Marriott, and T. Higa, Seragamides A-F, New Actin-targeting Depsipeptides from the Sponge Suberites japonicus Thiele, Tetrahedron, 10.1016/j.tet., 62, 3536-3542, 2006.02, Six new depsipeptides, seragamides A–F (1–6), and a known geodiamolide I (7) have been isolated as cytotoxic metabolites from the Okinawan sponge Suberites japonicus. Their structures were elucidated by means of spectroscopic analysis and chemical transformations. Seragamide A (1) promotes the polymerization of G-actin and stabilizes F-actin filaments..
45. J. Tanaka, M. Kuniyoshi, C. Tanaka, H. H. Issa, W. Balansa, M. Otsuka, W. P. Githige, and T. Higa, Diverse Metabolites of Coral Reef Organisms, Pure & Appl. Chem. , 77, 83-89., 2005.04.
46. C. Tanaka, Y. Yamamoto, M. Otsuka, J. Tanaka, T. Ichiba, G. Marriott, R. Rachmat, and T. Higa, Briarane Diterpenes from Two Species of Octocorals, Ellisella sp. and Pteroeides sp. , Journal of Natural Products, 10.1021/np049923o, 67, 1368-1373, 2004.12, Eight new briarane diterpenes (1-4, 7-10) have been isolated from two species of octocorals and the structures elucidated by spectroscopic analysis. Two diterpenes (2, 3) from the gorgonian Ellisella sp. inhibited cytokinesis, causing multinuclei formation on NBT-II cells, while a known briarane (12) from the sea pen Pteroeides sp. showed reversal of multidrug resistance..
47. M. Hirakawa, S. Sonoda, C. Tanaka, H. Murakami, and H. Yamakawa, Electron Emission Properties of Carbon Nanotubes, Applied Surface Science , 169, 662-665., 2001.10.
48. H. Murakami, M. Hirakawa, C. Tanaka, and H. Yamakawa, Field Emission from Well-aligned, Patterned, Carbon Nanotube Emitters, Applied Physics Letters , 76, 1776-1778., 2000.10.