Chemical and Genetic Study of Ligularia tongolensis, Ligularia cymbulifera, and Ligularia atroviolacea in the Hengduan Mountains of China

Abstract

Three Ligularia species (L. tongolensis, L. cymbulifera, and L. atroviolacea) were examined with respect to the chemical composition and nucleotide sequence. Furanoeremophilanes were found to be produced in the root of all samples of the three species collected in northwest Yunnan and southwest Sichuan. Eight furanoeremophilanes were identified, two of which were new. Most of the identified furanoeremophilanes were oxygenated at 3, 6, and 15-positions. The nucleotide sequence of the atpB-rbcL intergenic region was found to be essentially the same in the three species. These similarities imply that the three Ligularia species, all belonging to the section Corymbosae, are close to one another. The intra-specific diversity in the two widely distributed species in the Hengduan Mountains area, L. tongolensis and L. cymbulifera, were in contrast. Four out of 19 L. tongolensis samples contained a strongly Ehrlich-positive compound besides a number of positive compounds, and five variants of the atpB-rbcL sequence were found in these samples. In contrast, no variation was observed in 13 L. cymbulifera samples with respect to the furanoeremophilane composition or the atpB-rbcL sequence. The lack of diversity in L. cymbulifera probably resulted from the uniformity of its habitat.

Eremophilanes from <i>Ligularia hookeri</i> Collected in China and Structural Revision of 3β-Acyloxyfuranoeremophilan-15,6-olide

“…Other compounds isolated were 3β-(3′-methylpentanoyloxy)-furanoeremophilan-15,6α-olide (3) 10) and furanoeremophil-3-en-15,6α-olide (4), 10) bisabola-2,10-dien-1-one (8), 11) and eudesm-4-en-11-ol (9). 12) Compounds 1 and 2 are different in the substituent of the 3β-acyloxy group from the previously reported compounds bearing 3β-angeloyloxy and 3β-(2′-methylpropenoyloxy) groups.…”

“…A year later, Hanai et al also isolated the compound from L. tongolensis and identified it to be 12, 10) citing Bohlmann and Knoll's report 5) erroneously. 16 10) are one and the same.…”

“…We believe that 11 should also be revised to 13 accordingly. Because no spectroscopic data have been published for 13, it is worth recording the data, measured on material isolated from L. tongolensis, 10) here (Table 2 and Experimental). The base sequence of the ITS1-5.8S-ITS2 region of the nuclear ribosomal RNA gene cluster was determined in order to assess the genetic diversity in the samples.…”

Sesquiterpenoids Isolated from Eupatorium glehnii. Isolation of Guaiaglehnin A, Structure Revision of Hiyodorilactone B, and Genetic Comparison

“…We then studied the DNA sequence of the atpB-rbcL region in the plastid genome and the internal transcribed spacers (ITSs) of the ribosomal RNA gene on the nuclear genome. 33) 678…”

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

“…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).…”