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

Published on Dec 1, 2012in Tetrahedron 2.38
· DOI :10.1016/j.tet.2012.09.042
Yoshinori Saito12
Estimated H-index: 12
(Tokushima Bunri University),
Yuriko Takashima4
Estimated H-index: 4
(Tokushima Bunri University)
+ 9 AuthorsChiaki Kuroda10
Estimated H-index: 10
(Rikkyo University)
Cite
Abstract
Root chemicals and DNA sequences were analyzed for Ligularia virgaurea collected in the northern Sichuan Province and adjacent areas of China. Thirty-eight samples were found to contain five chemotypes, two known and three new ones. From samples of the new chemotypes, 13 new compounds were isolated, including 3 sesquiterpene dimers and some rearranged eremophilanes. The DNA sequences suggested that the chemotype differentiation had a genetic origin. (C) 2012 Elsevier Ltd. All rights reserved.
  • References (49)
  • Citations (25)
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References49
Newest
Published on Apr 1, 2012in Natural Product Communications 0.55
Anna Shimizu4
Estimated H-index: 4
(Rikkyo University),
Yurika Suzuki4
Estimated H-index: 4
(Rikkyo University)
+ 5 AuthorsChiaki Kuroda17
Estimated H-index: 17
(Rikkyo University)
Two samples of Ligularia kanaitzensis collected in the Shizhongshan Mountain region of Yunnan Province, as well as one sample collected in Sichuan Province, were analyzed with regard to root constituents and neutral DNA sequences. The two Shizhongshan samples were found to be different from each other and from other samples analyzed previously, indicating that the intra-specific diversity in the species was highly complex.
Published on Apr 1, 2012in Natural Product Communications 0.55
Chiaki Kuroda17
Estimated H-index: 17
(Rikkyo University),
Ryo Hanai17
Estimated H-index: 17
(Rikkyo University)
+ 2 AuthorsXun Gong23
Estimated H-index: 23
(Kunming Institute of Botany)
The chemical and genetic diversity of Ligularia species in the Hengduan Mountains area of China is reviewed. A hypothesis that the production of furanoeremophilanes is ecologically advantageous is proposed.
Published on Oct 1, 2011in Molecular Biology and Evolution 14.80
Koichiro Tamura28
Estimated H-index: 28
(ASU: Arizona State University),
Daniel S. Peterson14
Estimated H-index: 14
(ASU: Arizona State University)
+ 3 AuthorsSudhir Kumar63
Estimated H-index: 63
(ASU: Arizona State University)
Comparative analysis of molecular sequence data is essential for reconstructing the evolutionary histories of species and inferring the nature and extent of selective forces shaping the evolution of genes and species. Here, we announce the release of Molecular Evolutionary Genetics Analysis version 5 (MEGA5), which is a user-friendly software for mining online databases, building sequence alignments and phylogenetic trees, and using methods of evolutionary bioinformatics in basic biology, biomed...
Published on Aug 1, 2011in Natural Products and Bioprospecting
Jun-Li Yang11
Estimated H-index: 11
(Lanzhou University),
Rui Wang9
Estimated H-index: 9
(CAS: Chinese Academy of Sciences),
Yan-Ping Shi27
Estimated H-index: 27
(CAS: Chinese Academy of Sciences)
Ligularia, an important genus of the Compositae family, has captured the interest of natural product chemists for years. Phytochemical investigations on the title genus have led to isolation of hundreds of secondary metabolites with various skeletons. Herein, we summarized the chemical constituents of this genus and their biological activities over the past few decades. Open image in new window
Published on Jun 1, 2011in Natural Product Communications 0.55
Yu Hasegawa1
Estimated H-index: 1
(Rikkyo University),
Xun Gong23
Estimated H-index: 23
(Kunming Institute of Botany),
Chiaki Kuroda10
Estimated H-index: 10
(Rikkyo University)
From Iris delavayi collected in the northwestern Yunnan Province of China, eight iridal-type triterpenoids were isolated, three of which were new. Both 2(7)Z- and 2(7)E-iridals were isolated in about equal amounts from the sample collected at Laojunshan, while only 2(7)Z-iridals were isolated from samples collected in Shangrila area, indicating the presence of chemical diversity in the species.
Published on Apr 1, 2011in Phytochemistry 2.90
Hong-Li Huang1
Estimated H-index: 1
(Lanzhou University),
Yang‐Jun Xu2
Estimated H-index: 2
(Lanzhou University)
+ 5 AuthorsCheng-Shan Yuan9
Estimated H-index: 9
(Lanzhou University)
A dimeric eremophilane sesquiterpene lactone with a cyclobutane ring, biliguhodgsonolide (1) and an uncommon seco-sesquiterpene derivative, (4S,5S,6R,10R)-8,9-seco-12-hydroxyeremophil-7(11)-en-14,6;12,8-diolid-9-al (2), were isolated from the roots and rhizomes of Ligularia hodgsonii Hook. Their structures, including the absolute stereochemistry, were elucidated by spectroscopic data and CD analysis. The cyclobutane ring was confirmed by single-crystal X-ray diffraction.
Published on Mar 1, 2011in Tetrahedron 2.38
Yoshinori Saito12
Estimated H-index: 12
(Tokushima Bunri University),
Masato Hattori2
Estimated H-index: 2
(Rikkyo University)
+ 11 AuthorsXun Chao2
Estimated H-index: 2
(Rikkyo University)
Root chemicals and DNA sequences were analyzed for Ligularia lamarum samples collected in Yunnan and Sichuan Provinces of China and the relationship between the plant and Ligularia subspicata, its taxonomically closest species, was examined. Both species produce furanoeremophilanes and eremophilan-8-one derivatives as the major components. Eleven new compounds, including a new seco-bakkane compound, were isolated. The two species were found to harbor overlapping intra-specific diversities with r...
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Ferdinand Bohlmann47
Estimated H-index: 47
(Technical University of Berlin),
J. Jakupovic38
Estimated H-index: 38
(Technical University of Berlin)
+ 4 AuthorsHarold Robinson35
Estimated H-index: 35
(Smithsonian Institution)
The investigation of ten further Senecio species afforded 24 new furanoeremophilanes, 18 eremophilanolides, seven seco- and two rearranged eremophilanolides, twelve bisabolone derivatives and six sesquiterpenes with new carbon skeletons which are most likely derived from the latter. Possible biogenetic pathways are discussed. Furthermore five new eremophilones, an eudesmane, four p-hydroxyacetophenone, a bis-coniferylalcohol derivative and five shikimic acid derivatives were isolated. The struct...
Published on Feb 26, 2010in Journal of Natural Products 4.26
Wen-Juan Zhang2
Estimated H-index: 2
,
Xue-Hu Li1
Estimated H-index: 1
,
Yan-Ping Shi27
Estimated H-index: 27
Two new highly oxygenated spirosesquiterpene lactones, ligulactones A (1) and B (2), and one known sesquiterpenoid, 1β,10β-epoxy-6β-isobutyryloxy-9-oxo-furanoeremophiJane (3), were isolated from the roots of Ligularia fischeri. Their structures and relative configurations were elucidated by 1D and 2D NMR and MS data and by comparison of their NMR data with those of related compounds. Single-crystal X-ray diffraction analyses confirmed their structures. Compounds 1 and 2 are C-7 epimers. A possib...
Published on Jan 1, 2010in Natural Product Communications 0.55
Hajime Nagano16
Estimated H-index: 16
(Ochanomizu University),
Mika Matsushima4
Estimated H-index: 4
(Ochanomizu University)
+ 3 AuthorsChiaki Kuroda17
Estimated H-index: 17
(Rikkyo University)
From the roots of Ligularia oligonema and an unidentified sample of Ligularia collected in Yunnan Province of China, two new sesquiterpenoids, 3 beta-acetoxy-6 beta-(2-methylbutyryloxy)furanoereinophilan-10 beta-ol and 3 beta-acetoxy-6 beta-isobutyryloxyfuranoeremophilan-10 beta-ol, were isolated. DNA sequencing showed that the unidentified sample was likely to be L. oligonema. In addition, the DNA data suggested that the chemical evolution among L. oligonema and related Ligularia species is rat...
Cited By25
Newest
Published on Aug 1, 2019in Phytochemistry Letters 1.34
Hossam M. Abdallah14
Estimated H-index: 14
(Cairo University),
Ali M. El-Halawany14
Estimated H-index: 14
(Cairo University),
Hany M. El-Bassossy15
Estimated H-index: 15
(KAU: King Abdulaziz University)
Published on Apr 1, 2019in Tetrahedron 2.38
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University),
Saori Iga1
Estimated H-index: 1
(Tokushima Bunri University)
+ 5 AuthorsMotoo Tori31
Estimated H-index: 31
(Tokushima Bunri University)
Abstract Secobakkane B (C-6/C-7 cleaved secobakkane type aldehyde), secovirgaurenols B and C (C-8/C-9 cleaved secoeremophilane type), a 1β,10β-epoxyfuranoeremophilane, two 1β,10β-epoxyeremophilanolides, and fukinospirolide C (bakkane-type lactone), as well as 33 known compounds were isolated from three samples of Ligularia virgaurea collected in China. Two of the three analyzed samples were grouped in the neoadenostylone (N) type, and the rest, a mixture of the 6-hydroxyeuryopsyn (H) and cacalol...
Published on Jan 1, 2019in Chemical Communications 6.16
Raju S. Thombal4
Estimated H-index: 4
(Yeungnam University),
Seoung-Tae Kim2
Estimated H-index: 2
(KAIST)
+ 1 AuthorsYong Rok Lee35
Estimated H-index: 35
(Yeungnam University)
Ruthenium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with β-ketoamides for chemo- and stereoselective construction of cyclohexanone-fused γ-butenolides are described. This study represents the first example of the addition of an enol substrate which is formed by the tautomerization of the β-ketoamides to the electrophilic carbene center for unusual cyclization through amide cleavage. The combined experimental and computational studies shed light on the mechanistic pathway favour...
Published on Dec 1, 2018in Phytochemistry Letters 1.34
Jing Zhang4
Estimated H-index: 4
(SEU: Southeast University),
Wei Jiang1
Estimated H-index: 1
(SEU: Southeast University)
+ 4 AuthorsJin-Yue Sun3
Estimated H-index: 3
Abstract A phytochemical study of the EtOAc extract of Ligularia rumicifolia (J.R.Drumm.) S.W.Liu led to the isolation of two new monoterpene lactones ( 1 - 2 ) named (2 S ,3 S ,5 R )-5-ethyl-2,3-dimethyl-6-oxoterahydro-2 H -pyran-2-carboxylic acid and (2 S ,3 S ,5 R )-5-ethyl-2,3-dimethyl-6-oxoterahydro-2 H -pyran-2-carboxylic acid methyl ester, along with nine known compounds ( 3 - 11 ). All compounds were isolated from this species for the first time. Their structures were established on the ...
Published on Jul 1, 2018in Natural Product Communications 0.55
Katsuyuki Nakashima14
Estimated H-index: 14
(Tokushima Bunri University),
Kie Hoshiyama (Tokushima Bunri University)+ 5 AuthorsMotoo Tori31
Estimated H-index: 31
(Tokushima Bunri University)
Four samples of Ligularia virgaurea collected in China afforded three new eremophilane sesquiterpenoids, one new norsesquiterpenoid, and two new dinorsesquiterpenoids as well as 28 known compounds. All the four samples belonged to the ligularol type (L type), one of the five chemotypes we have described for this species. The configuration of the previously reported eremophila-7(11),9-dien-12,8-olide is revised to be H-8 alpha. The absolute configuration of ethyl 8-oxoeremophila-7(11),9-dien-12-o...
Published on Apr 1, 2018in Natural Product Communications 0.55
Chiaki Kuroda17
Estimated H-index: 17
(Rikkyo University),
Taketo Itoh (Rikkyo University)+ 5 AuthorsXun Gong23
Estimated H-index: 23
(Kunming Institute of Botany)
Published on Dec 1, 2017in Nature Communications 11.88
Jun Murata16
Estimated H-index: 16
,
Eiichiro Ono18
Estimated H-index: 18
+ 11 AuthorsMasaru Nakayasu4
Estimated H-index: 4
(Kobe University)
(+)-Sesamin, (+)-sesamolin, and (+)-sesaminol glucosides are phenylpropanoid-derived specialized metabolites called lignans, and are rich in sesame (Sesamum indicum) seed. Despite their renowned anti-oxidative and health-promoting properties, the biosynthesis of (+)-sesamolin and (+)-sesaminol remained largely elusive. Here we show that (+)-sesamolin deficiency in sesame is genetically associated with the deletion of four C-terminal amino acids (Del4C) in a P450 enzyme CYP92B14 that constitutes ...
Published on Nov 25, 2017in Molecules 3.06
Chiaki Kuroda10
Estimated H-index: 10
,
Ryohei Kobayashi + 6 AuthorsXun Gong2
Estimated H-index: 2
The diversity in root chemicals and evolutionally neutral DNA regions in the complex of Ligularia duciformis, L. kongkalingensis, and L. nelumbifolia (the d/k/n complex) was studied using eight samples collected in central and northern Sichuan Province of China. Cacalol (14) and epicacalone (15), rearranged eremophilanes, were isolated from the complex for the first time. Two new phenylpropanoids were also obtained. Seven of the eight samples produced phenylpropanoids and the other produced lupe...
Published on Aug 1, 2017in Phytochemistry 2.90
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University),
Mayu Ichihara5
Estimated H-index: 5
(Tokushima Bunri University)
+ 5 AuthorsMotoo Tori31
Estimated H-index: 31
(Tokushima Bunri University)
Abstract Three natural hybrids and an introgressed individual of Ligularia were evaluated based on a combination of morphology, root chemicals, and nucleotide sequences of evolutionally neutral regions to understand the chemical outcomes of hybridization and introgression. Six previously undescribed eremophilane sesquiterpenes were isolated from hybrids between L. cyathiceps and L. lamarum / L. subspicata , and benzofurans were isolated from L. subspicata for the first time. Their structures wer...
Published on Jun 1, 2017in Phytochemistry Letters 1.34
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University),
Motoki Hidaka (Nagasaki University)+ 7 AuthorsChiaki Kuroda10
Estimated H-index: 10
(Rikkyo University)
Chemical compositions and internal transcribed spacer (ITS) sequences of five samples of Ligularia lamarum collected in Sichuan Province, China, were analyzed. Fourteen compounds, including four new eremophilanes and one new seco-eremophilane, were isolated and their structures were elucidated by spectroscopic methods. Intra-specific diversity in the chemical composition was found to be higher than previously known. The result of DNA analysis suggested that one of the samples was introgressed, a...