TY - JOUR
T1 - New 19(10 → 9)abeo-euphane-type triterpenoids from Trichilia dregeana leaves and NO production inhibitory activities
AU - Mba Nguekeu, Yves M.
AU - Kodama, Takeshi
AU - Tsepeupon Matchide, Marie G.
AU - Do, Kiep Minh
AU - Nghokeng, Josker
AU - Tabakam, Gaétan T.
AU - Tsuge, Kiyoshi
AU - Ngouela, Silvère A.
AU - Mathieu, Tene
AU - Awouafack, Maurice Ducret
AU - Morita, Hiroyuki
N1 - Publisher Copyright:
© 2023
PY - 2024/7
Y1 - 2024/7
N2 - Phytochemical investigation of the EtOAc soluble fraction from leaves of Trichilia dregeana Sond. (Meliaceae) afforded naturally rare four new pentacyclic triterpenoids (1–4), together with five known pentacyclic analogs (5–8, and 11) and two steroids (9 and 10). Their structures were elucidated by extensive spectroscopic techniques such as 1D and 2D NMR and HRESIMS data analyses. The absolute configuration of 1 was determined by using the single-crystal X-ray diffraction analysis. The nitric oxide (NO) production inhibitory assay indicated that the EtOAc fraction as well as 4 and 7 inhibited the NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with the IC50 values of 83.53 μg/mL and 81.31 and 85.71 μM, respectively. Compounds 1–4 are rare 19(10 → 9)abeo-euphane-type triterpenoids bearing a 3,10-ether bridge. To the best of our knowledge, this study is the first isolation of triterpenoids with the 3,10-ether bridge in their skeleton from the genus Trichilia, providing new insights into the chemodiversity of the terpenoids in T. dregeana.
AB - Phytochemical investigation of the EtOAc soluble fraction from leaves of Trichilia dregeana Sond. (Meliaceae) afforded naturally rare four new pentacyclic triterpenoids (1–4), together with five known pentacyclic analogs (5–8, and 11) and two steroids (9 and 10). Their structures were elucidated by extensive spectroscopic techniques such as 1D and 2D NMR and HRESIMS data analyses. The absolute configuration of 1 was determined by using the single-crystal X-ray diffraction analysis. The nitric oxide (NO) production inhibitory assay indicated that the EtOAc fraction as well as 4 and 7 inhibited the NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with the IC50 values of 83.53 μg/mL and 81.31 and 85.71 μM, respectively. Compounds 1–4 are rare 19(10 → 9)abeo-euphane-type triterpenoids bearing a 3,10-ether bridge. To the best of our knowledge, this study is the first isolation of triterpenoids with the 3,10-ether bridge in their skeleton from the genus Trichilia, providing new insights into the chemodiversity of the terpenoids in T. dregeana.
KW - 19(10 → 9)abeo-Euphane triterpenoids
KW - Meliaceae
KW - NO production inhibitory activity
KW - Trichilia dregeana
UR - http://www.scopus.com/inward/record.url?scp=85192725728&partnerID=8YFLogxK
U2 - 10.1016/j.fitote.2024.106001
DO - 10.1016/j.fitote.2024.106001
M3 - 学術論文
C2 - 38729246
AN - SCOPUS:85192725728
SN - 0367-326X
VL - 176
JO - Fitoterapia
JF - Fitoterapia
M1 - 106001
ER -