Diversity of Furanoeremophilane Composition in Ligularia tongolensis

Abstract

The composition of root chemicals was studied for 7 samples of Ligularia tongolensis collected in Yunnan and Sichuan Provinces of China. The structures of 2 new 3β-angeloyloxy-6β-acyloxyfuranoeremophilan-15-oic acids were determined. It was found that the plant harbors chemical diversity in the acyloxy groups in 3,6-bis(acyloxy)eremophilan-15-oic acids. The presence of a 3-methylpentanoate moiety at C-3 appears geographically differentiated to a degree. Consistent with this low diversity, results of DNA analysis indicated little genetic differentiation, although introgression was inferred for one of the samples.

Cumulative Data of 1H and 13C NMR Signals and Specific Rotations of Eremophilane Sesquiterpenoids. 4. 10H-3-O-Furanoeremophilanes

“…Table 35 tabulates the data of 2 diacyloxy acids, 161 and 162 , 59,60 a methyl ester 163 , 61 and an acid 164 62 (Figure 13). All have 10βH and 3β,6β-substituents.…”

“…Table 33 presents the data of three diacyloxy 15-oic acids, 152 , 153 , and 155 , 15,57,59 and methyl ester 154 (Figure 13). 57 Compound 154 is the methyl ester of 153 .…”

“…All have 3β-angeloyloxy groups, and among them 155 has one more angeloyloxy group at C-6β. Compound 152 is a mixture with 161 , 59 153 with 155 and 159 , 57 154 with 157 and 160 , 57 and 155 with 154 and 158 . 57 The 13 C NMR signals of C-1, 9, and 2' of compound 152 were broad.…”

“…57 Table 32 compiles the data of four 15-oic acids, 148, 150, and 151, 15,58 and two methyl esters, 147 and 149 (Figure 13). 15 The Table 33 presents the data of three diacyloxy 15-oic acids, 152, 153, and 155, 15,57,59 and methyl ester 154 (Figure 13). 57 Compound 154 is the methyl ester of 153.…”

“…Compound 161 is a mixture with 151, and the 13 C NMR peaks of C-1, 9, and 2' were broad. 59 Compound 163 was derived from the natural product, the corresponding acid. 61 Both 1 H and 13 C NMR signals are tentatively assigned for compound 164.…”