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@ A Novel Limonoid From The Seeds of Chisocheton Siamensis
@ A Novel Limonoid From The Seeds of Chisocheton Siamensis
@ A Novel Limonoid From The Seeds of Chisocheton Siamensis
Abstract: Analysis of an acetone/hexane (1:1) extract of the seeds of Chisocheton siamensis led to the isolation of a
novel limonoid, chisosiamensin (1), along with five known limonoids, dysobinin (2), azadiradione (3), mohinin (4),
epoxyazadiradione (5), and 6 -acetoxyepoxyazadiradione (6). Their structures were characterized by spectroscopic
methods, including UV, IR, NMR, and MS. All isolated limonoids were reported for the first time as secondary metabolites of C. siamensis.
Key words: Chisocheton siamensis, Meliaceae, chisosiamensin, limonoids.
Rsum : Lanalyse dun extrait par un mlange actone-hexane (1:1) de graines de Chisocheton siamensis a permis
dextraire un nouveau limonode, la chisosiamensine (1), aux cts de cinq limonodes connus, la dysobinine (2),
lazadiradione (3), la mohinine (4), lpoxyazadiradione (5) et la 6 -actoxypoxyazadiradione (6). On a caractris
leurs structures par des mthodes spectroscopiques, incluant lUV, lIR, la RMN et la SM. Tous les limonodes isols
ont t identifis pour la premire fois comme mtabolites secondaires du C. siamensis.
Mots-cls : Chisocheton siamensis, Meliaceae, chisosiamensine, limonodes.
[Traduit par la Rdaction]
Laphookhieo et al.
208
Introduction
H
O
H
O
Azadiradione (3)
Dysobinin (2)
Chisosiamensin (1)
O
O
H
O
O
H
H
O
O
O
O
O
O
O
O
Epoxyazadiradione (5)
Mohinin (4)
6 -Acetoxyepoxyazadiradione (6)
H
O
O
OH
Nimonol (7)
doi:10.1139/V07-155
206
Table 1. 1H,
Nimonol
C/H
H (J in Hz)
H (J in Hz)
DEPTa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
28
29
30
7-OCOCH3
7-OCOCH3
158.1
125.4
204.6
39.9
158.2
129.7
74.5
44.1
38.6
42.8
16.5
33.0
47.1
158.8
119.6
34.3
51.6
19.0
27.0
124.5
139.6
111.0
142.5
21.1
27.3
20.6
170.1
21.2
7.15
5.84
5.33
5.27
2.28
1.75
1.68
5.37
2.35
2.80
0.78
1.07
7.23
6.27
7.37
1.19
1.22
1.07
1.95
157.40
126.14
205.96
40.51
49.88
68.08
79.08
45.43
37.13
43.11
16.39
32.72
47.08
158.53
119.55
34.30
51.12
20.84
27.08
124.37
139.64
110.94
142.57
20.23
31.87
20.79
172.32
21.16
2.21 (m)
1.82 (m)
1.82 (m)
7.26 (m)
6.29 (m)
7.39 (m)
1.27 (s)
1.31 (s)
1.41 (s)
2.05 (s)
CH
CH
C
C
C
CH
CH
C
CH
C
CH2
CH2
C
C
CH
CH2
CH
CH3
CH3
C
CH
CH
CH
CH3
CH3
CH3
C
CH3
(d, J = 10.2)
(d, J = 10.2)
(m)
(br m)
(m)
(m), 2.03 (m)
(m), 1.95 (m)
(br m)
(m)
(dd, J = 7.8, 10.5)
(s)
(s)
(br s)
(br m)
(br m)
(s)
(s)
(s)
(s)
Laphookhieo et al.
207
Experimental section
General
Melting points were determined using a FisherJohn melting point apparatus. The optical rotation []D values were
determined with a JASCO P-1020 digital polarimeter. UV
spectra were measured with a UV-160A spectrophotometer
(Shimadzu). The IR spectra were measured with a
PerkinElmer FTS FT-IR spectrophotometer. The 1H NMR
and 13C NMR spectra were recorded using a 300 MHz
Bruker FTNMR Ultra Shield spectrometer. Chemical shifts
were recorded in parts per million () in CDCl3 with
tetramethylsilane (TMS) as the internal reference. The EIMS
was obtained from a MAT 95 XL mass spectrometer. Quick
column chromatography (QCC) and column chromatography
(CC) were carried out on silica gel 60 H (Merck, 540 m)
and silica gel 100 (Merck, 63200 m), respectively.
Precoated plates of silica gel 60 F254 were used for the analytical procedure.
Plant material
Seeds of C. siamensis were collected from Queen Sirikit
Garden, Mae Rim District, Chiang Mai Province, northern
Thailand, in February, 2006. The botanical identification
was made by Dr. Prachaya Srisanga, botanist at Queen
Sirikit Garden. Voucher specimens are deposited in the
Acknowledgments
Surat Laphookhieo thanks the Bioresources Research
Network, National Center for Genetic and Engineering and
Biotechnology (grant number BRN 003 G-49), and Mae Fah
Luang University for financial support.
2008 NRC Canada
208
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