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

Nagano, Hajime; Torihata, Atsushi; Matsushima, Mika; Hanai, Ryo; Saito, Yoshinori; Baba, Makiko; Tanio, Yui; Okamoto, Yasuko; Takashima, Yuriko; Ichihara, Mayu; Gong, Xun; Kuroda, Chiaki; Tori, Motoo

doi:10.1002/hlca.200900270

Cited by 41 publications

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References 34 publications

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“…We are interested in biologically active terpenoids from Asteraceae plants and have studied the chemical constituents of Ligularia, [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Saussurea, 22,23) Cremanthodium, [24][25][26][27] and Eupatorium. [28][29][30][31] In our previous study on E. glehnii growing in Japan, especially in Obihiro (Hokkaido), Fujimi-cho (Nagano), and Tokushima, a large diversity in the chemical constituents was found, while there was no diversity in DNA sequences (atpB-rbcL intergenic region).…”

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Germacranolides and Their Diversity of Eupatorium heterophyllum Collected in P. R. China

et al. 2014

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Eight new hydroperoxides and a new enone of germacrane-type sesquiterpenoids were isolated from the aerial parts of eight different samples of Eupatorium heterophyllum DC. (Asteraceae) collected in P. R. China. The structures were determined based on spectroscopic analyses. Seven of the eight samples produced hiyodorilactone A as a major constituent, while one afforded neither hiyodorilactone nor hydroperoxide. The results indicated the presence of diversity within this species.

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Germacranolides and Their Diversity of Eupatorium heterophyllum Collected in P. R. China

et al. 2014

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“…8 and Ligularia cyathiceps Hand.-Mazz. 6 The production of these compounds represents one of the major lineages among furanoeremophilane-producing species.…”

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Structures of six new compounds from Ligularia brassicoides

et al. 2014

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“…c ) DQ272328. In contrast, 9-oxofuranoeremophilanes 1 -3 are characteristic of L. cyathiceps [9] and have not been found in L. subspicata. e ) Two sequences with and without an A were present.…”

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“…The major diagnostic difference between the two species is the presence (L. lamarum) or the lack (L. subspicata) of ligulate florets. L. cyathiceps produces cacalol as the major component of the root chemicals [9]. In addition, we have found that L. subspicata and L. lamarum are indistinguishable in terms of both the chemical composition in the root and the nucleotide sequence of the internal transcribed spacers (ITSs) of the ribosomal RNA gene cluster [14] [15].…”

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“…In addition, we have found that L. subspicata and L. lamarum are indistinguishable in terms of both the chemical composition in the root and the nucleotide sequence of the internal transcribed spacers (ITSs) of the ribosomal RNA gene cluster [14] [15]. L. cyathiceps has been found to be distinct from L. lamarum/ L. subspicata with respect to the DNA sequence and the chemical composition [9] [14] [15]. Isolation of alkaloids from L. subspicata has also been reported [16].…”

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ChemInform Abstract: Chemical and Genetic Studies on Hybrid of Ligularia subspicata and Ligularia cyathiceps Collected in Yunnan Province of China.

et al. 2015

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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. subspicata. Although the morphology of sample A suggested that it was also a hybrid, the ITS sequence of sample A was that of L. cyathiceps. Twenty compounds were isolated from the five samples, and the structures of two new compounds 7 and 14 were determined. Furanoeremophilanes typical of L. lamarum/L. subspicata were detected not only in samples C and D, but also in samples A and B. These results indicate that the ability to produce root chemicals can spread through introgression. Introduction. -The genus Ligularia (Asteraceae) is highly diversified in the Hengduan Mountains area of China [1]. We have been studying the chemical diversity of Ligularia by combining two different approaches: analyses of the chemical composition in the root and the nucleotide sequences of evolutionarily neutral DNA regions. To date, we have reported that many Ligularia species harbor intraspecific diversity at various levels [2]. For example, Ligularia virgaurea (Maxim.) Mattf. [3] [4] contains five distinct chemotypes, Ligularia dictyoneura (Franch.) Hand.-Mazz. [5] and Ligularia kanaitzensis (Franch.) Hand.-Mazz. [6] [7] harbor complex diversity, while Ligularia cymbulifera [8] and Ligularia cyathiceps [9] are uniform. Sesquiterpenoids with the eremophilane skeleton have been isolated from most of the Ligularia species.

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

Cited by 41 publications

References 34 publications

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

Structures of six new compounds from Ligularia brassicoides

ChemInform Abstract: Chemical and Genetic Studies on Hybrid of Ligularia subspicata and Ligularia cyathiceps Collected in Yunnan Province of China.

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