Isocedrene and Guaiane Derivatives from Pleocarphus revolutus

Oleodaphnoic Acid and Coriaceol, Two New Natural Products from the Stem Bark of Wikstroemia coriacea

“…Further analysis of the other significant long-range 1 H- 13 C correlations (Figure 2) suggested that NMR data were typical of a guaiane-type skeleton [21]. NMR data close similarity regarding the C-7 carbons of oleodaphnal ( 3 ) [22], indicanone ( 4 ) [6] and (5 R ,8 R ,8a R )-3,8-dimethyl-4,5,6,7,8,8a-hexahydro-5-(1-methylethenyl)-2(1 H )-azulenone ( 5 ) [23], respectively, allowed to infer the R stereochemistry of C-7. Finally, the carboxylic group was assigned to be at the C-10 position based on the HMBC relationship between H-9 and C-14.…”

“…In addition to these two new structures, we isolated three sesquiterpenoids: oleodaphnal ( 3 ) [22], indicanone ( 4 ) [6], (5 R ,8 R ,8a R )-3,8-dimethyl-4,5,6,7,8,8a-hexahydro-5-(1-methylethenyl)-2(1 H )-azulenone, ( 5 ) [23]; two phenylphenalenones: 1,5-diphenyl-1-pentanone ( 6 ) [25], (+)-3-hydroxy-1,5-diphenyl-1-pentanone ( 7 ) [26]; two coumarins: umbelliferone ( 8 ) [27], daphnoretin ( 9 ) [28]; one triterpenoid: β-sitostenone ( 10 ) [29] and one lignan: (−)-hinokinin ( 11 ) [30] (Figure 1). The identifications of these nine known compounds were confirmed by comparison of their physical and spectroscopic data (UV, 1 H, 13 C-NMR, MS and [α]) with the corresponding authentic samples or with values described in the literature.…”

5-Methylcoumarin derivatives from Aphyllocladus denticulatus

“…Colourless gum; IR v$$, cm-': 1730 (GO), 1720, 1630, 1605 (coumarin); MS Table 1. 'H NMR spectral data of Za, 3,4,4a,5,7,9,11 12a,13a and 14 (400 MHz,CDCI,, LHz]: 6:7-7,8=8; 3',15'= 11',12'= 11'.13'-7; compound 2a: l',? '= 11.5; 10',11'=5.5; compound 3, 4and 4a: 1;,1;=14;compound 3: 10',,10;=14; 10',11'=5; compounds4and4a:…”

Bioactive Isocedrenes from Perezia multiflora

“…Isocedrenes are sesquiterpenes first described in P. multiflora and Proustia pyrifolia [3] by Bohlman, and then also in Trixis wrightii and Trixis inula [4]. Further studies have confirmed the occurrence of this group of sesquiterpenes in various genera, like Jungia [5], Moscharia [6], Pleocarphus [7], and Acourtia [8], all belonging to the tribe Nassauviineae, subfamily Mutisioidaea, in the Asteraceae family [9]. The name isocedrene was first proposed by Bohlman because of the similarity of this skeleton with α-cedrene, from which it differs by the shift of a methyl group from C-3 to C-5 [3].…”