Polyol Monoterpenes and Sesquiterpene Lactones from the Pacific Northwest Plant Artemisia suksdorfii

Abstract

Five new polyol monoterpenes (1-5) and seven new sesquiterpene lactones (6-12), along with five previously identified compounds, were isolated from the aerial parts of Artemisia suksdorfii. The structures of the new compounds were established by high-field NMR techniques (1H, 13C, 1H-1H DEPT, COSY, HMQC, and HMBC) and in case of 6 confirmed by X-ray analysis.

Secondary Metabolites of Phomopsis sp. XZ‐26, an Endophytic Fungus from Camptothecaacuminate

“…The 1D ( 1 H, 13 C and DEPT) and 2D (COSY, HMQC and HMBC) NMR spectra of 7 were similar to those of 6 except for changes at C-4 and C-5 due to the opening of the epoxide to form a vicinal diol moiety. We determined the relative configurations of these two hydroxy groups by analysis of NOESY spectra (Figure 3), and they were supported by the coupling patterns of H-4 and H-5 (Table 2).…”

“…Therefore, we determined the structure of 1 to be 8α-hydroxyoblongolide C or 3a,8α-dihydroxyoblongolide A and named it as oblongolide N for consistency with the literature. [12] We obtained 2 as a white powder and determined it to have the molecular formula C 14 13 C NMR (Table 1). We determined the structure of 2 to be a 6-hydroxy derivative of oblongolide A by a compari- son of its NMR spectra with those of oblongolides B (3), C (4), P (5) and N (1) ( Tables 1 and 2).…”

“…We obtained 9 as a white powder and determined it to have the molecular formula C 16 13 C NMR (Table 3). Its IR absorption at 1715 cm -1 and 13 C NMR signal at δ C = 208.9 (C-2) ppm indicated the presence of a ketone carbonyl group.…”

“…Continuous research on the secondary metabolites from Phomopsis sp. XZ-26, an endophytic fungal strain isolated from the surface-sterilized twig tissues of Camptotheca acuminate whose extract showed inhibitory activities against human pathogenic microorganisms (data not shown), led to the discovery of 11 lovastatin-analogous oblongolides N-V (1-2 and 5-11), oblongolides B (3) and C (4), [11,12] [10,12] one new monoterpene dihydroxysabinane (14) [13] and the sesterterpene terpestacin (15). [14] In this paper, we report the isolation and structural characterization of 1-15 and the antimicrobial activities of 1-5, 8, 10 and 13-15.…”

Loliolide - the most ubiquitous lactone

“…A common feature of their structure is oxygen, both in the form of hydroxyl groups and lactone rings. The simplest structural molecules containing both the lactone ring and the hydroxy group are called monoterpenoid lactones (Ragas et al 2005, Ahmed et al 2004, Garg & Agarwal 1994, Fukushima et al 1998, Wong & Bron 2002, Chen et al 2010.…”