Furanoeremophilan-10β-ol, a major component of Ligularia cymbulifera growing in northwestern Yunnan Province of China, reacted with pyridoxal or its 5′-phosphate at room temperature in aqueous solution to afford condensation products. It is plausible that the reaction also occurs in nature.
HanaiR, GongX, ToriM, KondoS, OtoseK, OkamotoY, NishihamaT, MurotaA, ShenY, WuS, KurodaC. (2005) Chemical and genetic study of Ligularia tongolensis, Ligularia cymbulifera, and Ligularia atroviolacea in the Hengduan Mountains of China. Bulletin of the Chemical Society of Japan, 78, 1302–1308.
3.
NaganoH, IwazakiY, GongX, ShenY, KurodaC, HanaiR. (2006) Chemical and genetic differentiation of Ligularia pleurocaulis in northwestern Yunnan and southwestern Sichuan Provinces of China. Bulletin of the Chemical Society of Japan, 79, 300–304.
4.
ToriM, HondaK, NakamizoH, OkamotoY, SakaokuM, TakaokaS, GongX, ShenY, KurodaC, HanaiR. (2006) Chemical constituents of Ligularia virgaurea and its diversity in southwestern Sichuan of China. Tetrahedron, 62, 4988–4995.
5.
ToriM, NakamizoH, MiharaK, SatoM, OkamotoY, NakashimaK, TanakaM, SaitoY, SonoM, GongX, ShenY, HanaiR, KurodaC. (2008) Chemical and genetic diversity of Ligularia vellerea in Yunnan, China. Phytochemistry, 69, 1158–1165.
6.
NaganoH, IwazakiY, MatsushimaM, SatoM, GongX, ShenY, HirotaH, KurodaC, HanaiR. (2007) High diversity of Ligularia dictyoneura in chemical composition and DNA sequence, Chemistry & Biodiversity, 4, 2874–2888.
7.
ToriM, WatanabeA, MatsuoS, OkamotoY, TachikawaK, TakaokaS, GongX, KurodaC, HanaiR. (2008) Diversity of Ligularia kanaitzensis in sesquiterpenoid composition and neutral DNA sequences. Tetrahedron, 64, 4486–4495.
8.
GaikwadNW, MadyasthaKM. (2002) Biosynthesis of β-substituted furan skeleton in the lower furanoterpenoids: A model study. Biochemical Biophysical Research Communications, 290, 589–594.
9.
SchulerMA. (1996) The role of cytochrome P450 monooxygenases in plant-insect interactions. Plant Physiology, 112, 1411–1419.
10.
IidaK, MitaniM, KurodaC. (2007) Fixation of natural furanoeremophilane by Diels-Alder reaction. Bulletin of the Chemical Society of Japan, 80, 966–971.
11.
JenningsPW, ReederSK, HurleyJC, CaughlanCN, SmithGD. (1974) Isolation and structure determination of one of the toxic constituents from Tetradymia glabrata. Journal of Organic Chemistry, 39, 3390–3398.
12.
KurodaC, UeshinoT, NaganoH. (2004) Ehrlich's reaction of furanoeremophilanes. Bulletin of the Chemical Society of Japan, 77, 1737–1740.
13.
KurodaC, NishioE. (2007) Substituent effect in color of Ehrlich's test of tetrahydrobenzofuran. Natural Product Communications, 2, 581–585.
14.
IshiiH, TozyoT, MinatoH. (1965) Studies on sesquiterpenoids-IX. Tetrahedron, 21, 2605–2610.
