Motoo Tori

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Organization: Tokushima Bunri University

Department: Faculty of Pharmaceutical Sciences

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Chemicals
References

What is the absolute configuration of (+)-crispatanolide isolated from Makinoa crispata (liverwort)?

Co-reporter:Katsuyuki Nakashima, Hiroyuki Kawano, Minako Kumano, Hikari Kodama, Masayo Kameoka, Akiyo Yamamoto, Reiko Mizutani, Masakazu Sono, Motoo Tori

Tetrahedron Letters 2015 Volume 56(Issue 34) pp:4912-4915

Publication Date(Web):19 August 2015

DOI:10.1016/j.tetlet.2015.06.083

•Absolute configuration of (+)-crispatanolide (liverwort sesquiterpenoid) was established.•(+)-Crispatanolide possessed ent-cycloeudesmane skeleton.•Chirality introduction was done by CBS reduction of 3-substituted-2-bromocyclohex-2-en-1-one.Crispatanolide, which was isolated from Makinoa crispata (liverwort) in 1980, was synthesized in its chiral form starting from 3-substituted-2-bromocyclohex-2-en-1-one using CBS reduction. The absolute configuration was established using the modified Mosher method on the CBS reduction product. This synthesis established the absolute configuration of the natural product, which is presumably derived from a 10β-methyl-7-βH-eudesmane type precursor.

Terpenoids from Ligularia virgaurea collected in China: the first example of two bakkane derivatives with an anhydride-type ring C and nineteen new chemical constituents

Co-reporter:Yoshinori Saito, Saori Iga, Katsuyuki Nakashima, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori

Tetrahedron 2015 Volume 71(Issue 44) pp:8428-8435

Publication Date(Web):4 November 2015

DOI:10.1016/j.tet.2015.09.011

Further chemical investigation of two Ligularia virgaurea samples collected in China resulted in the isolation of 21 new compounds, two of which were bakkane-type sesquiterpenoids bearing an anhydride-type ring C, which was a previously unknown partial structure. These samples belonged to the V-type (the major component was virgaurenone) among the five chemotypes found in this species.

Structure and cytotoxic evaluation of five 12-oxygenated eremophilanes from Ligularia lingiana

Co-reporter:Yoshinori Saito, Yoko Sasaki, Teppei Komiyama, Ayumi Ohsaki, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori

Tetrahedron 2014 70(35) pp: 5878-5883

Publication Date(Web):

DOI:10.1016/j.tet.2014.06.030

Chemical and genetic similarity and diversity of Ligularia anoleuca and L. fischeri collected in the Hengduan Mountains of China

Co-reporter:Anna Shimizu, Yurika Suzuki, Ryo Hanai, Yasuko Okamoto, Motoo Tori, Xun Gong, Chiaki Kuroda

Phytochemistry 2014 Volume 102() pp:137-144

Publication Date(Web):June 2014

DOI:10.1016/j.phytochem.2014.03.019

•Seventeen furanoeremophilanes were isolated from L. anoleuca and L. fischeri.•The presence of three chemotypes was detected by LCMS analysis.•Differences in chemical composition of L. anoleuca and L. fischeri are small.•L. anoleuca and L. fischeri are indistinguishable in the neutral DNA sequences.The sesquiterpenoid composition in the root and the DNA sequences of evolutionarily neutral regions were studied in Ligularia anoleuca and Ligularia fischeri (Asteraceae) collected in the Sichuan Province of China. LC–MS analysis showed that L. anoleuca populations from different localities had different chemical compositions. However, the isolated compounds were similar to each other, indicating that the differences in chemical composition were not large. The DNA analysis suggested that the two species were indistinguishable. Seventeen furanoeremophilanes and an eremophilane acetal were isolated.Graphical abstractThe two title species were indistinguishable both in the root chemicals and in neutral DNA sequences examined.

Twelve new compounds from Ligularia melanothyrsa; isolation of melanothyrsins A–E, normelanothyrsin A, and other eremophilane sesquiterpenoids

Co-reporter:Yoshinori Saito, Mayu Ichihara, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori

Tetrahedron 2014 70(16) pp: 2621-2628

Publication Date(Web):

DOI:10.1016/j.tet.2014.02.080

Structures of six new compounds from Ligularia brassicoides

Co-reporter:Yoshinori Saito, Yoko Sasaki, Ayumi Ohsaki, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori

Tetrahedron 2014 70(51) pp: 9726-9730

Publication Date(Web):

DOI:10.1016/j.tet.2014.10.003

Samarium (II) iodide-induced intermolecular coupling of α,β-unsaturated esters with ketones: reactions of methyl propiolate and ethyl buta-2,3-dienoate with cyclohexanone and its application to synthesis of a terpene carboxylic acid

Co-reporter:Masakazu Sono, Natsuki Doi, Eri Yoshino, Sachiko Onishi, Daiki Fujii, Motoo Tori

Tetrahedron Letters 2013 Volume 54(Issue 15) pp:1947-1950

Publication Date(Web):10 April 2013

DOI:10.1016/j.tetlet.2013.01.120

The reactions of methyl propiolate and ethyl buta-2,3-dienoate with cyclohexanone induced by SmI2 occurred either at α- or β-position to yield different products depending on with or without a proton source. The synthesis of terpenic acid was demonstrated using this reaction.

Chemical and genetic diversity of Cremanthodium lineare

Co-reporter:Yoshinori Saito, Mayu Ichihara, Koji Takiguchi, Yui Tanio, Yasuko Okamoto, Ryo Hanai, Chiaki Kuroda, Takayuki Kawahara, Xun Gong, Motoo Tori

Phytochemistry 2013 Volume 96() pp:184-190

Publication Date(Web):December 2013

DOI:10.1016/j.phytochem.2013.08.009

•Sixteen compounds were isolated from six samples of Cermanthodium lineare.•Three samples produced furanoeremophilanes, and the other three contained eremophilan-8-ones.•The DNA sequences supported the existence of two chemotypes in C. lineare.•Eremophilane sesquiterpenoids from Cremanthodium species were previously unknown.Chemical constituents and evolutionally neutral DNA sequences of six samples of Cremanthodium lineare Maxim., collected in the Sichuan Province of China, were studied. Three samples produced furanoeremophilanes and the other three, eremophilan-8-ones. The chemotypes were found to be correlated with DNA sequence types, suggesting that the chemical diversity observed has a genetic origin. Production of furanoeremophilanes by a Cremanthodium species suggests an evolutionary relationship between Cremanthodium and Ligularia species, and possibly to related genera.Three of six samples of Cremanthodium lineare produced furanoeremophilanes, and the other three contained eremophilan-8-ones; two chemotypes were thus found. These are correlated with DNA sequence types.

Four new compounds from Ligularia virgaurea: isolation of eremophilane and noreremophilane sesquiterpenoids and the absolute configuration of 2α-hydroxyeremophil-11-en-9-one by CD spectrum and DFT calculation

Co-reporter:Yoshinori Saito, Mizuho Taniguchi, Teppei Komiyama, Ayumi Ohsaki, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori

Tetrahedron 2013 69(39) pp: 8505-8510

Publication Date(Web):

DOI:10.1016/j.tet.2013.06.104

Chemical and genetic diversity of Ligularia virgaurea collected in northern Sichuan and adjacent areas of China. Isolation of 13 new compounds

Co-reporter:Yoshinori Saito, Yuriko Takashima, Aya Kamada, Yurika Suzuki, Midori Suenaga, Yasuko Okamoto, Yoichi Matsunaga, Ryo Hanai, Takayuki Kawahara, Xun Gong, Motoo Tori, Chiaki Kuroda

Tetrahedron 2012 68(48) pp: 10011-10029

Publication Date(Web):

DOI:10.1016/j.tet.2012.09.042

First Direct Evidence of Radical Intermediates in Samarium Diiodide Induced Cyclization by ESR Spectra

Co-reporter:Masakazu Sono, Shin-ichi Hanamura, Midori Furumaki, Hisao Murai, and Motoo Tori

Organic Letters 2011 Volume 13(Issue 21) pp:5720-5723

Publication Date(Web):October 6, 2011

DOI:10.1021/ol202403q

The mechanism of samarium diiodide (SmI2)-induced cyclization of α,β-unsaturated esters and ketones to bicyclic compounds was examined using ESR spectroscopy. This is the first report of direct evidence of the radical intermediates in the SmI2 reaction. The preferential reduction of the α,β-unsaturated carbonyl part in some substrates should be recognized as a main route.

Five new subspicatins and noreremophilane from Parasenecio petasitoides collected in China

Co-reporter:Yoshinori Saito, Mayu Ichihara, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori

Tetrahedron Letters 2011 Volume 52(Issue 48) pp:6388-6391

Publication Date(Web):30 November 2011

DOI:10.1016/j.tetlet.2011.09.063

Five new 1β-angeloyloxyeremophilanolides (subspicatins H–L) and 1β-angeloyloxytetranoreremophilanone (norsubspicatin A), were isolated from the EtOAc extracts of Parasenecio petasitoides and their structures established on the basis of spectroscopic analyses. They are biogenetically mutually related to each other and represent a new category in the Parasenecio group. These findings suggest that there is diversity in this species, too.

Nine New Norlabdane Diterpenoids from the Leaves of Austroeupatorium inulifolium

Co-reporter:Yoshinori Saito;Sachie Matsuo;Suyatno Sutoyo

Helvetica Chimica Acta 2011 Volume 94( Issue 2) pp:313-326

Publication Date(Web):

DOI:10.1002/hlca.201000207

Abstract

Nine new norlabdane diterpenoids were isolated from the leaves of Austroeupatorium inulifolium collected in Indonesia. All of them have an acyl-furan unit connected to C(11), and oxygenated functions at C(2) and C(3). The structure elucidations and the assignment of the absolute configurations of the isolated natural products were carried out by extensive spectroscopic analysis and the extended Mosher method, as well as chemical correlations. Antimicrobial activities and cytotoxicity against HL-60 cells were determined using bioassays.

Overlapping chemical and genetic diversity in Ligularia lamarum and Ligularia subspicata. Isolation of ten new eremophilanes and a new seco-bakkane compound

Co-reporter:Yoshinori Saito, Masato Hattori, Yuko Iwamoto, Yuriko Takashima, Kanako Mihara, Yoko Sasaki, Miho Fujiwara, Misato Sakaoku, Anna Shimizu, Xun Chao, Chiaki Kuroda, Xun Gong, Ryo Hanai, Motoo Tori

Tetrahedron 2011 67(12) pp: 2220-2231

Publication Date(Web):

DOI:10.1016/j.tet.2011.01.082

Direct MS measurement of the extract of Ligularia virgaurea collected in Yunnan and Sichuan provinces of China

Co-reporter:Yasuko Okamoto;Yoshinori Saito;Chiaki Kuroda;Ryo Hanai;Xun Gong

Phytochemical Analysis 2010 Volume 21( Issue 6) pp:513-523

Publication Date(Web):

DOI:10.1002/pca.1219

Abstract

Introduction – There are numerous Ligularia species in the eastern Qinghai–Tibet Plateau and adjacent areas. L. virgaurea has been used as a traditional folk medicine for the treatment of stomachache and nausea.

Objective – To analyse chemical constituents of L. virgaurea, grown in Yunnan and Sichuan provinces of China.

Methodology – The direct MS measurement of the crude extract of plant samples was used for grouping of this species. As the main compounds were available in pure form, the main peaks were analysed by LCMS.

Results – An easy and speedy method of analysis using MS spectra was developed. On the basis of the findings, L. virgaurea could be divided into two groups. The genetic studies also supported this grouping. Type 1 mainly includes virgaurenones and virgaurenolides. The MS of type 2 is quite different because it includes mainly ligularol and its congeners. Both MS were easily distinguished.

Conclusion – The crude extracts of 11 L. virgaurea samples already collected in recent years were analysed and it was possible to identify them as type 1 or 2. This method was applied to three samples collected in 2009 to successfully classify them as either type 1 or 2. Copyright © 2010 John Wiley & Sons, Ltd.

New eremophilanes from Farfugium japonicum

Co-reporter:Motoo Tori, Kanako Otose, Hiroko Fukuyama, Junko Murata, Yasuko Shiotani, Shigeru Takaoka, Katsuyuki Nakashima, Masakazu Sono, Masami Tanaka

Tetrahedron 2010 66(27–28) pp: 5235-5243

Publication Date(Web):

DOI:10.1016/j.tet.2010.04.079

Chemical and Genetic Study of Ligularia cyathiceps in Yunnan Province of China

Co-reporter:Hajime Nagano;Atsushi Torihata;Mika Matsushima;Ryo Hanai;Yoshinori Saito;Makiko Baba;Yui Tanio;Yasuko Okamoto;Yuriko Takashima;Mayu Ichihara;Xun Gong;Chiaki Kuroda

Helvetica Chimica Acta 2009 Volume 92( Issue 10) pp:2071-2081

Publication Date(Web):

DOI:10.1002/hlca.200900270

Abstract

Root chemicals and evolutionarily neutral DNA regions in L. cyathiceps samples collected in the Zhongdian (Shangrila) County of Yunnan, P. R. China, were examined. Twenty compounds were isolated, including three new ones, 1β,10β-epoxy-6β-(propionyloxy)furanoeremophilan-9-one (6), 1β,10β-epoxy-8α-ethoxyeremophila-6,11-diene (14), and 11αH-6β-isobutyryloxy-1β,10β,7β,8β-diepoxyeremophilan-12,8α-olide (15). The chemical diversity was found to be limited, with cacalol (1) and 6-(acyloxy)furanoeremophilan-9-ones (4 and/or 5) being major components in all the samples. The nuclear ribosomal RNA gene was also found to harbor little variation, although two distinct sequence types were found for the plastid atpB-rbcL intergenic region.

Studies toward the total synthesis of YW3699, a sesterterpenoid GPI biosynthesis inhibitor: preparation of the tri-substituted cyclooctene ring using the RCM reaction

Co-reporter:Reiko Mizutani, Katsuyuki Nakashima, Yoshinori Saito, Masakazu Sono, Motoo Tori

Tetrahedron Letters 2009 50(19) pp: 2225-2227

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.02.163

Chemical and genetic diversity of Ligularia vellerea in Yunnan, China

Co-reporter:Motoo Tori, Hiromi Nakamizo, Kanako Mihara, Masahiko Sato, Yasuko Okamoto, Katsuyuki Nakashima, Masami Tanaka, Yoshinori Saito, Masakazu Sono, Xun Gong, Yuemao Shen, Ryo Hanai, Chiaki Kuroda

Phytochemistry 2008 Volume 69(Issue 5) pp:1158-1165

Publication Date(Web):March 2008

DOI:10.1016/j.phytochem.2007.12.001

Intra-specific diversity in Liularia vellerea growing in the northwestern to central Yunnan province of China was studied by chemical and genetic approaches. Samples collected in the Jianchuan, Lijiang, and Zhongdian areas contained 6,15-dioxygenated furanoeremophilanes as their major components (type A); whereas samples from the Luguhu area accumulated 1,6-dioxygenated furanoeremophilanes (type B); a sample from near Kunming, however, contained 6,15-dioxygenated eremophilanolides (type C). 11βH- and 11αH-6β-angeloyloxy-15-carboxyeremophil-7-en-12,8-olides (eremofarfugins D and E) were also isolated and their structures were determined. A correlation between the composition and the DNA sequence was observed in the ITSs.L. vellerea of Zhongdian, Luguhu, and Kunming areas in Yunnan Province of China could be distinguished on the basis of chemical constituents and DNA sequences.

Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone

Co-reporter:Motoo Tori, Chiho Makino, Kenji Hisazumi, Masakazu Sono, Katsuyuki Nakashima

Tetrahedron: Asymmetry 2001 Volume 12(Issue 2) pp:301-307

Publication Date(Web):19 February 2001

DOI:10.1016/S0957-4166(01)00041-6

A homochiral bicyclic ketone having a pinguisane skeleton has been synthesised starting from homochiral methyl 3-[(1′S,6′R)-1′,6′-dimethyl-2′-oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi–Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone.The chiral ketone 14 was synthesised from 2, which is considered a formal total synthesis of deoxopinguisone.(1S,5R,6S,9R)-1,5,6,9-Tetramethylbicyclo[4.3.0]nonan-3-oneC13H22OEe=99.5%[α]D25=−22.6 (c 0.15, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,5R,6S,9R)(1S,5R,6S,9S)-1,5,6-Trimethyl-9-vinylbicyclo[4.3.0]nonan-3-oneC14H22OEe=99.5%[α]D20=−18.0 (c 1.18, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,5R,6S,9S)(4S,5R)-3,4,5-Trimethyl-4-[3′Z-5′-trimethylsilyl-3′-pentenyl]cyclohex-2-en-1-oneC17H30OSiEe=99.5%[α]D21=+8.9 (c 0.66, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,5R)(3S,4R)-2,3,4-Trimethyl-3-[3′Z-5′-trimethylsilyl-3′-pentenyl]cyclohexeneC17H32SiEe=99.5%[α]D21=+43.0 (c 0.86, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,4R)

Four alkaloids, lucidine B, oxolucidine A, lucidine A, and lucidulinone from Lycopodium lucidulum

Co-reporter:Motoo Tori, Tatsue Shimoji, Emi Shimura, Shigeru Takaoka, Katsuyuki Nakashima, Masakazu Sono, William A. Ayer

Phytochemistry 2000 Volume 53(Issue 4) pp:503-509

Publication Date(Web):9 February 2000

DOI:10.1016/S0031-9422(99)00592-0

The structures of four alkaloids extracted from Lycopodium lucidulum (Lycopodiaceae) were established by X-ray and 2D NMR spectroscopic analyses. The dihydro-derivative of oxolucidine A, which was obtained by NaBH4 reduction of oxolucidine A, was treated with p-bromobenzoyl chloride to afford crystals, whose X-ray crystallographic analysis established the stereostructure, including the absolute configuration. The 2D NMR spectra of tetrahydrodeoxylucidine B were fully analyzed to establish the full structure of lucidine B, and the hitherto unknown stereochemistry at the C-14 position was established as β-H. The structure of a new alkaloid, lucidulinone, was determined by spectroscopic analysis to be luciduline lactam.

Nine new clerodane diterpenoids from rhizomes of Solidago altissima

Co-reporter:Motoo Tori, Akiko Katto, Masakazu Sono

Phytochemistry 1999 Volume 52(Issue 3) pp:487-493

Publication Date(Web):October 1999

DOI:10.1016/S0031-9422(99)00273-3

Nine new clerodane- and abeoclerodane-type diterpenoids have been isolated from rhizomes of Solidago altissima L. and their structures established mainly based on 2D NMR spectral data as well as X-ray analysis. Ten known compounds have also been isolated and some of their 13C NMR data are listed.