The chemical composition and the DNA sequence of an evolutionarily neutral region were studied for three samples of L. tsangchanensis, three samples of L. muliensis, and one sample of a hybrid between L. tsangchanensis and L. vellerea. L. tsangchanensis and L. muliensis were indistinguishable in the chemical composition and the ITS sequence, supporting a recent taxonomic study that merged the two species into L. tsangchanensis. Cacalol (1) was isolated as the most major component from both L. tsangchanensis and L. muliensis, while 6-acetoxy-9-oxofuranoeremophilane (10), a putative cacalol precursor, was isolated from the hybrid.
The diversity in root chemicals and evolutionally neutral DNA regions in the complex of Ligularia duciformis, L. kongkalingensis, and L. nelumbifolia (the d/k/n complex) was studied using eight samples collected in central and northern Sichuan Province of China. Cacalol (14) and epicacalone (15), rearranged eremophilanes, were isolated from the complex for the first time. Two new phenylpropanoids were also obtained. Seven of the eight samples produced phenylpropanoids and the other produced lupeol alone. Two of the seven samples also produced furanoeremophilanes or their derivatives and one produced oplopanes. The geographical distribution of the sesquiterpene-producing populations suggests that the production of sesquiterpenes evolved independently in separate regions. L. limprichtii collected in northern Sichuan was also analyzed and its chemical composition and the sequence of internal transcribed spacers (ITSs) in the ribosomal RNA gene cluster were found to be similar to that in the d/k/n complex and L. yunnanensis, which are morphologically similar.
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