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Diversity in Chemical Constituents of Ligularia longihastata Collected in China.

Published on Feb 1, 2016in Natural Product Communications0.554
· DOI :10.1177/1934578x1601100203
Yasuko Okamoto13
Estimated H-index: 13
(Tokushima Bunri University),
Mizuho Taniguchi2
Estimated H-index: 2
(Tokushima Bunri University)
+ 5 AuthorsChiaki Kuroda20
Estimated H-index: 20
(Rikkyo University)
Abstract
: Root constituents of Ligularia longihastata were examined for the first time. Fourteen eremophilane sesquiterpenes, including two new eremophilanes identified as 3α-isobutyroyloxy-7βH-eremophila-9,11-dien-8-one and 3β-angeloyloxy-1β,10β-epoxyfuranoeremophilan-9-one, and three eudesmanes were isolated. From samples collected in Baiyu County, Sichuan Province, furanoeremophilane derivatives were isolated, while various eremophilan-8-ones were isolated from samples collected in Kangding County, Sichuan. The results suggest chemical diversity in the species.
  • References (22)
  • Citations (1)
References22
Newest
#1Chiaki Kuroda (Rikkyo University)H-Index: 20
#2Chiemi Shibayama (Rikkyo University)H-Index: 1
Last. Xun Gong (Kunming Institute of Botany)H-Index: 23
view all 8 authors...
: Six Ligularia fischeri samples, two from Sichuan (samples 1 and 2) and four from Chongqing (samples 3-6), were examined for root chemicals and the DNA sequence of the internal transcribed spacers of the ribosomal RNA gene. Samples 2 and 3 contained benzofurans. The isolation of benzofurans shows that the chemical diversity in L. fischeri is higher than previously reported. Samples 1, 4, 5, and 6 contained eremophilanes. However, the compounds were different between sample 1 and samples 4-6, in...
4 CitationsSource
#1Yoshinori Saito (Tokushima Bunri University)H-Index: 12
#2Yoko Sasaki (Tokushima Bunri University)H-Index: 3
Last. Motoo Tori (Tokushima Bunri University)H-Index: 31
view all 7 authors...
Four new eremophilane type sesquiterpenoids, a new bakkane type sesquiterpenoid, and a new secoeremophilane type sesquiterpenoid were isolated from Ligularia brassicoides Hand.-Mass. (Asteraceae) collected in China, and were an epoxy lactone derived from 6-acyloxyeuryopsin 1, 6-acyloxy-9oxoeuryopsin 2, 6-acyloxy-9-oxofuranoeremophilane 3, 6-acyloxyeuryopsin 4, 6-acyloxy bakkane type epoxy lactone 5, and secovirgaurenol 6-O-(2'-hydroxymethyl)acrylate (6), respectively. All but one had a 2'-hydrox...
8 CitationsSource
#1Chiaki KurodaH-Index: 20
#2Ryo HanaiH-Index: 23
Last. Xun GongH-Index: 23
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18 CitationsSource
#1Chiaki Kuroda (Rikkyo University)H-Index: 20
#2Ryo Hanai (Rikkyo University)H-Index: 23
Last. Xun Gong (Kunming Institute of Botany)H-Index: 23
view all 5 authors...
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.
33 CitationsSource
#1Yoshinori SaitoH-Index: 12
#2Mayu IchiharaH-Index: 6
Last. Motoo ToriH-Index: 31
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Two samples of Cremanthodium stenactinium (Asteraceae) were collected in Sichuan Province, China. From the ethyl acetate extracts of the roots, three new eremophilane-type sesquiterpenoids and one new trinoreremophilane compound were isolated, together with other known eremophilanes. Their structures were determined based on the spectroscopic data. This is the first report of isolation of eremophilane-type compounds from the genus Cremanthodium.
9 CitationsSource
#1Yoshinori Saito (Tokushima Bunri University)H-Index: 12
#2Masato Hattori (Rikkyo University)H-Index: 2
Last. Motoo Tori (Tokushima Bunri University)H-Index: 31
view all 14 authors...
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...
40 CitationsSource
#1Wen-Juan ZhangH-Index: 2
#2Xue-Hu LiH-Index: 5
Last. Yan-Ping ShiH-Index: 30
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Two new highly oxygenated spirosesquiterpene lactones, ligulactones A (1) and B (2), and one known sesquiterpenoid, 1β,10β-epoxy-6β-isobutyryloxy-9-oxo-furanoeremophilane (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...
15 CitationsSource
#1Hajime Nagano (Ochanomizu University)H-Index: 17
#2Atsushi Torihata (Rikkyo University)H-Index: 6
Last. Motoo Tori (Tokushima Bunri University)H-Index: 31
view all 13 authors...
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, 1 beta,10 beta-epoxy-6 beta-(propionyloxy)furanoeremophilan-9-one (6), 1 beta,10 beta-epoxy-8 alpha-ethoxyeremophila-6,11-diene (14), and 11 alpha H-6 beta-isobutyryloxy-1 beta,10 beta,7 beta,8 beta-diepoxyeremophilan-12,8 alpha-olide (15). The chemical diversity was found to b...
34 CitationsSource
#1Motoo ToriH-Index: 13
#2Yui TanioH-Index: 3
Last. Ryo HanaiH-Index: 23
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Two new ketones, franchetianones A and B, were isolated from the root of Ligularia franchetiana collected in Yunnan province of China and their structures determined based on the spectroscopic analyses.
11 CitationsSource
#1Motoo Tori (Tokushima Bunri University)H-Index: 31
#2Aki Watanabe (Tokushima Bunri University)H-Index: 2
Last. Ryo Hanai (Rikkyo University)H-Index: 23
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Twenty-six eremophilane-type sesquiterpenoids, including six new compounds, were isolated from the title species. One of the new compounds, kanaitzensol, suggested the presence of an enzyme for the conversion of eremophil-7(11)-en-8-one derivative to furanoeremophilanes. The plant was collected at 15 locations in Yunnan Province of China and found to be diverse with respect to its sesquiterpenoid composition. DNA sequencing also revealed a large intraspecific diversity of the plant. (c) 2008 Els...
51 CitationsSource
Cited By1
Newest
#1Chiaki Kuroda (Rikkyo University)H-Index: 20
#2Kou Inagaki (Rikkyo University)H-Index: 1
Last. Xun Gong (Kunming Institute of Botany)H-Index: 23
view all 8 authors...
The chemical composition of a sample of the title species collected in Pianma, Lushui County, Yunnan Province of China, was examined. Two 3,6,10 oxygenated and two 3,6-oxygenated furanoeremophilanes were isolated. Structures of two new compounds were elucidated. The 3,6-oxygenated furanoeremophilanes were not detected in a sample of the same species previously collected in Laojunshan, Jianchuan County, Yunnan, indicating chemical diversity in the species.
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