110772-39-9Relevant academic research and scientific papers
A series of sesquiterpenes with a 7α-isopropyl side chain and related compounds isolated from Curcuma wenyujin
Harimaya,Gao,Ohkura,Kawamata,Iitaka,Guo,Inayama
, p. 843 - 853 (2007/10/02)
Sesquiterpenoids possessing a 7α-isopropyl group, such as curcumol (1a), curdione (2a), curcumalactone (3), and a new epoxy germacrane, (1R,10R)-epoxy-(-)-1,10-dihydrocurdione (5a), were isolated from the essential oil of Curcuma wenyujin. Other related new sesquiterpenes, neocurdione (4) and (1S,10S),(4S,5S)-germacrone-1(10),4-diepoxide (6) were also isolated from this plant. The stereostructures and absolute configurations of these sesquiterpenes were established on the basis of spectroscopic and chemical data as well as X-ray crystallographic analyses.
THE ABSOLUTE CONFIGURATION AND CONFORMATION OF NEOCURDIONE
Ohkura, Tamiko,Gao, Ji-Fu,Harimaya, Kenzo,Hikichi, Manabu,Iitaka, Yoichi,et al.
, p. 4435 - 4438 (2007/10/02)
The complete stereostructure of neocurdione (1a) from Curcuma wenyujin and C. aromatica was determined unequivocally on the basis of chemical transformation of curdione (2a) to 4-epicurdione (1b) as well as X-ray crystallography of the p-bromobenzoate (3b) of 8αH-dihydro-4-epicurdione (3a).The preferred conformation of 1a in solution was found to be A based on 1H-NMR spectrometry at various temperatures, and NOE measurements, especially at -60 deg C.In contrast, the preferred conformation of 1a in crystals (X-ray) was found to be B .A conformational analysis of 1a, 1b and 2a is also presented based on molecular dynamics calculations using MM2.KEYWORDS - neocurdione; Curcuma wenyujin; Curcuma aromatica; Zingiberaceae; germacranoid; absolute configuration; 1H-NMR (500 MHz); variable-temperature; NOE; X-ray diffraction
