Conformational Assignments of Thujopsene and Related Compounds

Abstract

Conformational analysis suggests that thujopsene (1) can exist as 2 possible conformations, steroidal and nonsteroidal. The conformation of 1 has been investigated using a NMR spectroscopic method. Analyses of the 1H NMR, ROESY, and long-range 1H-1H COSY spectra indicate that 1 exists in a steroidal conformation. Although the conformations of related compounds 2 and 3 were originally assigned as nonsteroidal, careful reexamination of the published NMR data indicates that both compounds exist in a steroidal conformation.

Evaporated fraction of thujopsene from Thujopsis dolabrata starves cancer cells via PKM2 Anti-tumor effect of the volatile components of Thujopsis dolabrata

“…Each terpene has a peculiar odor and evaporates. More than 1,000 terpenes have been identi ed to date, and most of them are classi ed into one of three groups, namely, monoterpene, sesquiterpene, or diterpene, based on their structural characteristics [5]. The scent and functional characteristics of each essential oil are formed depending on the type and composition of the terpenes it contains.…”

“…In addition, it is known to have antibacterial and antitumor effects [9]. Regarding the antitumor mechanism of thujopsene, previous studies have shown that mTOR (mechanistic target of rapamycin) and AKT (protein kinase B) expression and the growth of tumor cells are suppressed when thujopsene blocks the PI3K (phosphatidylinositol-3-kinase) pathway [5].…”

“…A portion of hexane-soluble fraction (610 mg) was subjected to silica gel column chromatography (80 g, 38 × 3 cm, hexane-ethyl acetate = 9:1) to give thujopsene (282 mg). Isolated thujopsene showed a molecular ion peak at m/z 204 (EIMS) and was identi ed by comparing their 1 H and 13 C NMR data with those in the literature [5].…”

Evaporated fraction of thujopsene from Thujopsis dolabrata starves cancer cells via PKM2

“…A portion of hexane-soluble fraction (610 mg) was subjected to silica gel column chromatography (80 g, 38 × 3 cm, hexane-ethyl acetate = 9:1) to give thujopsene (282 mg). Isolated thujopsene showed a molecular ion peak at m/z 204 (EIMS) and was identi ed by comparing their 1 H and 13 C NMR data with those in the literature [29].…”