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Three New Eremophilanes from a Ligularia Hybrid Collected in China

Published on Jul 1, 2016in Natural Product Communications0.554
· DOI :10.1177/1934578x1601100709
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University),
Yuriko Takashima4
Estimated H-index: 4
(Tokushima Bunri University)
+ 4 AuthorsMotoo Tori12
Estimated H-index: 12
(Tokushima Bunri University)
Abstract
  • References (16)
  • Citations (1)
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References16
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#1Anna Shimizu (Rikkyo University)H-Index: 4
#2Shizuka Watanabe (Rikkyo University)H-Index: 1
Last. Chiaki Kuroda (Rikkyo University)H-Index: 20
view all 7 authors...
Two morphologically ambiguous Ligularia samples (samples A and B), and samples with morphology of Ligularia subspicata (sample C), Ligularia lamarum (sample D), or Ligularia cyathiceps (sample E), were collected at Tianchi Pond, Shangrila County, Yunnan Province, China. Analysis of the nucleotide sequence of the internal transcribed spacers (ITSs) in the nuclear ribosomal RNA gene cluster indicated that not only sample B but also sample D was a hybrid of L. cyathiceps and L. lamarum/ L. subspica...
11 CitationsSource
#1Chiaki KurodaH-Index: 20
#2Ryo HanaiH-Index: 22
Last. Xun GongH-Index: 23
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18 CitationsSource
#1Chiaki Kuroda (Rikkyo University)H-Index: 20
#2Ryo Hanai (Rikkyo University)H-Index: 22
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 Saito (Tokushima Bunri University)H-Index: 12
#2Mayu Ichihara (Tokushima Bunri University)H-Index: 5
Last. Motoo Tori (Tokushima Bunri University)H-Index: 30
view all 6 authors...
Five new 1 beta-angeloyloxyeremophilanolides (subspicatins H-L) and 1 beta-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. (C) 2011 Elsevier Ltd. All rights reserved.
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: 30
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
#1Ferdinand Bohlmann (Technical University of Berlin)H-Index: 48
#2Jasmin Jakupovic (Technical University of Berlin)H-Index: 39
Last. Harold Robinson (Smithsonian Institution)H-Index: 38
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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...
19 CitationsSource
#1Hajime Nagano (Ochanomizu University)H-Index: 17
#2Mika Matsushima (Ochanomizu University)H-Index: 4
Last. Chiaki Kuroda (Rikkyo University)H-Index: 20
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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...
33 CitationsSource
#1Hajime Nagano (Ochanomizu University)H-Index: 17
#2Atsushi Torihata (Rikkyo University)H-Index: 6
Last. Motoo Tori (Tokushima Bunri University)H-Index: 30
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 Tori (Tokushima Bunri University)H-Index: 30
#2Yasuko Okamoto (Tokushima Bunri University)H-Index: 12
Last. Ryo Hanai (Rikkyo University)H-Index: 22
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New C-1 oxidized eremophilane-type sesquiterpenoids, subspicatins A, B, C, and D, and subspicatolide, were isolated from the root of Ligularia subspicata and their structures were established by spectroscopic and X-ray analyses. Subspicatins A and B were the major components. The species were found to be diverse both in the composition of the root chemicals and in the nucleotide sequences of the internal transcribed spacers (ITS) of the ribosomal RNA gene and the atpB-rbcL intergenic region, but...
36 CitationsSource
#1D. Lee Taylor (UAF: University of Alaska Fairbanks)H-Index: 30
#2Michael G. Booth (UAF: University of Alaska Fairbanks)H-Index: 6
Last. Thomas G. Marr (UAF: University of Alaska Fairbanks)H-Index: 6
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High throughput sequencing methods are widely used in analyses of microbial diversity, but are generally applied to small numbers of samples, which precludes characterization of patterns of microbial diversity across space and time. We have designed a primer-tagging approach that allows pooling and subsequent sorting of numerous samples, which is directed to amplification of a region spanning the nuclear ribosomal internal transcribed spacers and partial large subunit from fungi in environmental...
50 CitationsSource
Cited By1
Newest
#1Yoshinori Saito (Nagasaki University)H-Index: 12
#2Mayu Ichihara (Tokushima Bunri University)H-Index: 5
Last. Motoo Tori (Tokushima Bunri University)H-Index: 30
view all 8 authors...
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...
4 CitationsSource
#1Rye Hanai (Rikkyo University)H-Index: 1
#2Sayako Tanabe (Rikkyo University)H-Index: 1
Last. Chiaki Kuroda (Rikkyo University)H-Index: 20
view all 8 authors...
The composition of root chemicals was examined for samples of L. cyathiceps x L. duciformis, L. duciformis x L. yunnanensis, and L. yunnanensis. Various furanoeremophilanes were isolated from a sample of L. cyathiceps x L. duciformis and found to be very similar to those isolated from L. cyathiceps. Lupeol and docosyl ferulate were isolated from L. yunnanensis, L. duciformis, and L. duciformis x L. yunnanensis.
1 CitationsSource