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

Abstract

Eight new hydroperoxides and a new enone of germacrane-type sesquiterpenoids were isolated from the aerial parts of eight different samples of Eupatorium heterophyllum DC. (Asteraceae) collected in P. R. China. The structures were determined based on spectroscopic analyses. Seven of the eight samples produced hiyodorilactone A as a major constituent, while one afforded neither hiyodorilactone nor hydroperoxide. The results indicated the presence of diversity within this species.

New Benzofuran Oligomers from the Roots of Eupatorium heterophyllum Collected in China

“…Only our group has previously reported detailed phytochemical studies on this plant [6][7][8][9]. Sesquiterpene lactones were isolated as major constituents from several samples of the aerial parts of E. heterophyllum collected in northwestern Yunnan and southwestern Sichuan [7], and benzofurans were isolated from the roots of this species in northwestern Yunnan [6] and northern Sichuan [8]. The characteristics of the chemical compositions are similar to those of E. chinense [11][12][13], suggesting that E. heterophyllum and E. chinense are related chemotaxonomically.…”

“…Plants in the Hengduan mountains area are useful for studying plant diversity and evolution. We have been studying inter-and intra-specific diversity in chemical constituents of some Asteraceae plants growing in this area, including Ligularia [1,2], Cremanthodium [3], Saussurea [4,5], and Eupatorium [6][7][8][9]. To date, the presence of intra-specific diversity has been discovered at various levels in most species, affording numerous new compounds produced by limited populations within a species.…”

“…(Asteraceae) is a perennial herb widely distributed in the Hengduan Mountains, including in the Yunnan, Sichuan, and Gansu provinces and the Xizang Autonomous Region of China [10]. Only our group has previously reported detailed phytochemical studies on this plant [6][7][8][9]. Sesquiterpene lactones were isolated as major constituents from several samples of the aerial parts of E. heterophyllum collected in northwestern Yunnan and southwestern Sichuan [7], and benzofurans were isolated from the roots of this species in northwestern Yunnan [6] and northern Sichuan [8].…”

Chemical Compositions of Eupatorium heterophyllum Leaf Samples from Yunnan and Sichuan Provinces of China—Isolation of 13 New Sesquiterpene Lactones

“…It is widely distributed in grasslands and forest areas at altitudes of 1700–3000 m in Southwest China (Sichuan, Yunnan, and Guizhou provinces and Xizang Autonomous Region) and has not been artificially cultivated [ 1 ]. We have been studying the intra-specific diversity in leaf and root chemicals of E. heterophyllum native to Yunnan and Sichuan provinces [ 2 , 3 , 4 , 5 , 6 ] as part of our continuing research on the chemical diversity of Asteraceae plants for obtaining unique secondary metabolites produced by limited populations within a species and for getting an insight into a chemical aspect of adaptation/differentiation. To date, diversity was observed in the minor constituents of the root chemicals of E. heterophyllum samples taken from different locations, affording various heterocyclic aromatic compounds, such as benzofuran/dihydrobenzofuran derivatives and propynyl thiophenes, in addition to some common major constituents [ 2 , 3 , 4 ].…”

Cytotoxic sesquiterpene lactones from Campuloclinium macrocephalum (=Eupatorium macrocephalum)

“…However, to the best of our knowledge, no studies to date have reported the isolation of sesquiterpene lactones from this species. Sesquiterpene lactones (SLs) constitute an important group of specialized products widely distributed in various genus of Asteraceae, including Eupatorium (Huo et al, 2004;Shen et al, 2005;Zhang et al, 2008;Hensel et al, 2011;Saito et al, 2014;Liu et al, 2015;Wang et al, 2018;Yu et al, 2018), the genus to which belonged the species C. macrocephalum. Eupatorium species extracts and their isolated sesquiterpene lactones have been reported to exhibit cytotoxic activities against different cancer cell lines (Huo et al, 2004;Shen et al, 2005;Hensel et al, 2011;Saito et al, 2014;Yu et al, 2018).…”