69010-39-5Relevant academic research and scientific papers
BIOTRANSFORMATION OF GERMACRONE BY SUSPENSION CULTURED CELLS
Sakamoto, Shiho,Tsuchiya, Naoko,Kuroyanagi, Masanori,Ueno, Akira
, p. 1215 - 1220 (2007/10/02)
The transformation of germacrone, a 10-membered ring sesquiterpene, by suspension cultured cells of Lonicera japonica, Bupleurum falcatum, Polygonum tinctorium and Solidago altissima, was investigated.Germacrone was converted into several types of sesquiterpenes, such as guaiane, eudesman and seco-guaiane and their structures were determined from spectral and chemical evidence.The configurations of some of the products were determined by CD spectroscopy.The differences of the kinds of products among the four suspension cultured cells is discussed.
BIOTRANSFORMATION OF SESQUITERPENES BY CULTURED CELLS OF CURCUMA ZEDOARIA
Sakui, Norihiro,Kuroyanagi, Masanori,Ishitobi, Yoko,Sato, Makoto,Ueno, Akira
, p. 143 - 148 (2007/10/02)
The transformation of a 10-membered ring sesquiterpene, germacrone, into guaiane-type sesquiterpenes by suspension cultured cells of Curcuma zedoaria was investigated.Germacrone was converted into several sesquiterpenes, some of which were isolated from the Curcuma spp. plants through the key intermediate, (4R,5R)-germacrone 4,5-epoxide, and their structures were determined by spectral and chemical evidence.The configurations of some of the derivatives were opposite to those of the sesquiterpenes isolated from the Curcuma sp plants, C. aromatica, C. longa and C. zedoaria.An eudesmane-type product was also isolated and its structur e was determined.From the structure, the transformation of germacrone through the intermediate, (1S,10S)-germacrone 1,10-epoxide, was supposed and further confirmed by the transformation of germacrone 1,10-epoxide into the same product by acid treatment.The structures of two new products were also determined and their transformation mechanism through curcumenone and dihydrocurcumenone was deduced. Key Word Index - Curcuma zedoaria; Zingiberaceae; cell suspension culture; biotransformation; sesquiterpene; germacrone; guaiane; eudesmane.
