SUPPLEMENTARY MATERIAL
Geissoschizine methyl ether N-oxide, a new alkaloid with antiacetylcholinesterase activity from Uncaria rhynchophylla
Wei-Wei Jing a,b , Jia Su a , Xing-De Wu a , JuanHe a , Li-Yan Peng a , Xiao Cheng a , Qin-Shi Zhao a, * a
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People’s Republic of China b University of the Chinese Academy of Sciences, Beijing 100049, People’s Republic of China
Abstract
Geissoschizine methyl ether N -oxide, a new oxindole alkaloid, along with 14 known alkaloids, was isolated from the aerial part of Uncaria rhynchophylla . Their structures were identified by comprehensive spectral methods, including 2D NMR experiments, and confirmed by comparing with the literature data. In vitro acetylcholinesterase
(AChE) inhibitory activity assay showed that the new compound exhibited anti-AChE activity with IC
50
value of 23.4
µ
M.
Key words : Uncaria rhynchophylla ; Rubiaceae; Alkaloids; Geissoschizine methyl ether N -oxide; Anti-AChE activity.

Contents of supplementary data
Figure S1 1 H-NMR spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S2 13 C-NMR spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S3 HSQC spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S4 HMBC spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S5 1 H1 H COSY spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S6 ROESY spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S7 UV spectrum of geissoschizine methyl ether N -oxide ( 1 ).
Figure S8 IR spectrum of geissoschizine methyl ether N -oxide ( 1 ).
Figure S9 ESIMS spectrum of geissoschizine methyl ether N -oxide ( 1 ).
Figure S10 HRESIMS spectrum of geissoschizine methyl ether N -oxide ( 1 ).

Figure S1
1
H-NMR spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.
Figure S2
13
C-NMR spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.

Figure S3 HSQC spectrum of geissoschizine methyl ether N-oxide ( 1 ) in CD
3
OD.
Figure S4 HMBC spectrum of geissoschizine methyl ether N-oxide ( 1 ) in CD
3
OD.

Figure S5
1
H-
1
H COSY spectrum of geissoschizine methyl ether N -oxide ( 1 ) in
CD
3
OD.
Figure S6 ROESY spectrum of geissoschizine methyl ether N -oxide ( 1 ) in CD
3
OD.

Figure S7 UV spectrum of geissoschizine methyl ether N -oxide ( 1 ).
Figure S8 IR spectrum of geissoschizine methyl ether N -oxide ( 1 ).
Figure S9 ESIMS spectrum of geissoschizine methyl ether N -oxide ( 1 ).

Figure S10 HRESIMS spectrum of geissoschizine methyl ether N -oxide ( 1 ).