Eudesmanolides, trichomatolides B–E, and A heliangolide from Calea trichomata

Two New Cytotoxic Sesquiterpenoids from Eupatorium lindleyanum DC.

“…The relative stereochemistry of compound 1 was resolved through extensive analysis of the NOESY spectrum ( Figure 2B). The NOESY correlations of H-7/H-5 and H-7/H-8 indicated that H-5, H-7, and H-8 were on the same side and were designated as α-orientation on the basis of the biogenetic assumption that H-7 adopted an α-orientation (Ober et al 1984). Moreover, the correlation between H-5 and H-1 indicated that H-1 was also αoriented.…”

“…The NOESY correlations of H-7/H-8 indicated that H-7 and H-8 were on the same side and H-8 was designated as α-orientation on the basis of the biogenetic assumption that H-7 adopted an α-orientation (Ober et al 1984). Thus, the structure of compound 2 was assigned as 8β-tigloyloxy-3β,10β-epoxy-15-hydroxy-3α-methoxy-6βH,7αH-germacra-4Z,11(13)-dien-6,12-olide.…”

“…The relative stereochemistry of compound 2 was demonstrated by the NOESY experiment ( Figure 3B), in which the H 3 -14 (δ H 1.53, s) correlated with the methoxyl and H'-4 (δ H 1.74, d, J=7.0 Hz) correlated with H'-5 (δ H 1.72, d, J=1.3 Hz). The NOESY correlations of H-7/H-8 indicated that H-7 and H-8 were on the same side and H-8 was designated as α-orientation on the basis of the biogenetic assumption that H-7 adopted an α-orientation (Ober et al 1984). Thus, the structure of compound 2 was assigned as 8β-tigloyloxy-3β,10β-epoxy-15-hydroxy-3α-methoxy-6βH,7αHgermacra-4Z,11(13)-dien-6,12-olide.…”

Potential Anti-inflammatory Sesquiterpene Lactones from Eupatorium lindleyanum

“…2). The ROESY correlations of H-3 and H-15, H-15 and H-5, H-5 and H-7, and H-7 and H-8 indicated that H-3, H-7 and H-8 were on the same side and were assumed to be in α-orientation on the basis of the biogenetic assumption [14]. The strong ROESY correlation between H-5 and H-15 indicated that the configuration of the double bond (Δ 4, 5 ) should be elucidated as cis.…”

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

“…sp., C. pilosa, C. urticifolia Romo, de Vivar, and Ortega (1973); Bohlmann, Fritz, et al (1981); ; Bohlmann and Jakupovic (1979) 2 11,13-Dihydroxy-calaxin C. pinnatifida Lima et al (2017) 3 9α-Hydroxy-11,13-dihydro-11α,13-epoxyatripliciolide-8β-O-methylacrylate C. crocinervosa, C. zacatechichi, C. pilosa, C. nelsonni, C. ternifolia Bohlmann, Fritz, et al (1981); Lee, Fronczek, Malcolm, Fischer, and Urbatsch (1982); Fischer, Lee, Fronczek, Chiari, and Urbatsch (1984); ; Martinez et al (1988); Ortega et al (1989) 120 Subcortalide C C. subcordata Ober, Fronczek, and Fischer (1984b) 121 Trichomatolide A C. trichomata ; Ober et al (1984) 122 Trichomatolide B C. trichomata Ober et al (1984) 123 Trichomatolide D C. trichomata Ober et al (1984) 124 Trichomatolide E C. trichomata Ober et al (1984) 125 8β-Tyglinoyloxyreynosin C. trichomata, ; Ober et al (1984) 126 (2015) 193 α-Hydroxy-butein C. uniflora 194 Yomogi alcohol…”