Chemical Constituents of Ligularia Nelumbifolia and L. Subspicata Hybrid Collected in Shangrila County, Yunnan Province of China

Abstract

Four Ligularia individuals possessing morphological characters of both L. nelumbifolia and L. subspicata were discovered in Shangrila County, Yunnan Province, China. DNA sequencing showed that the specimens were hybrids of the two species and their maternal parent was L. subspicata. The chemical composition of the root extract was examined for three of them as well as L. nelumbifolia and L. subspicata collected sympatrically. Nelumol was isolated from L. nelumbifolia, and furanoeremophilanes from L. subspicata. While nelumol and furanoeremophilanes were detected in two of the hybrid samples, only furanoeremophilanes were detected in the others.

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

“…The 1 H-and 13 C-NMR spectra indicated the presence of two EtO groups, in addition to three Me groups of eremophilanolides. The IR spectrum evidenced the presence of an OH and an ester C¼O group.…”

“…The 1 H-and 13 C-NMR spectra indicated the presence of two EtO groups, in addition to three Me groups of eremophilanolides. This compound may be an artifact generated from 11 or 12 during EtOH extraction [6] [13]. 4).…”

“…A study on Ligularia duciformis and related species suggested that the ability to produce sesquiterpenoids was acquired through hybridization [12]. We recently reported that three hybrid individuals of Ligularia nelumbifolia and Ligularia subspicata produced furanoeremophilanes [13], which were produced by the latter species but not by the former.…”

“…We recently reported that hybrids of L. subspicata and L. nelumbifolia also produced furanoeremophilanes of L. subspicata origin [13]. -Five Ligularia samples, including two morphologically ambiguous ones, collected at Tianchi, Yunnan Province, were analyzed.…”

“…Compounds eluted with hexane/AcOEt 97 : 3 were further purified by CC and HPLC to give 20 (4.6 mg), 16 (31.5 mg), and 17 (2)); 2.34 (sept., J ¼ 6.9, HÀC(2')); 2.45 -2.52 (m, H b ÀC(9)); 2.52 (br. 13 C-NMR (C 6 D 6 ) 2 ): 8.2 (C(13)); 14.7 (C(15)); 19.1 (C(3')); 19.1 (C(4')); 21.4 (C(9)); 24.8 (C(14)); 26.7 (C(2)); 27.2 (C(3)); 30.1 (C(6)); 34.4 (C(2')); 37.4 (C(4)); 37.4 (C(5)); 40.4 (C(10)); 72.3 (C(1)); 115.8 (C(7)); 119.8 (C(11)); 138.2 (C(12)); 147.8 (C (8) d, J ¼ 17.0, H a ÀC(9)); 4.76 (td, J ¼ 11.0, 4.6, H a ÀC(1)); 7.01 (s, HÀC (12)).…”