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Article history:
Received 11 November 2009
Accepted in revised form 30 December 2009
Available online 18 January 2010
Keywords:
Psidium guajava L.
Benzophenone glycosides
Spectroscopic methods
a b s t r a c t
The ripe edible fruits of Psidium guajava L. was phytochemically investigated, three benzophenone
glycosides, 2, 6-dihydroxy-3, 5-dimethyl-4-O--D-glucopyranosyl-benzophenone (1), 2, 6dihydroxy-3-methyl-4-O-(6-O-galloyl--D-glucopyranosyl)-benzophenone (2), 2, 6dihydroxy-3, 5-dimethyl-4-O-(6-O-galloyl--D-glucopyranosyl)-benzophenone (3) were
isolated by means of chromatography, and their structures were elucidated on the basis of mass
spectrometry, 1H NMR, 13C NMR, HSQC and HMBC data. Compounds 1 and 2 were new
benzophenone glycosides, and here we report the complete spectroscopic assignments for 3.
2010 Elsevier B.V. All rights reserved.
1. Introduction
Psidium guajava L. (Myrtaceae) is commonly known as
Guava, an important food crop and medicinal plant in tropical
and subtropical countries. Different parts of the plant are
reported for the treatment of skin ailments such as antidiarrhoeic, stomach ache, wounds, cold, cough and fever. The
ower buds are used as a tonic in diseases of digestive
function [1]. The decoction of leaves and shoots is viewed as a
febrifuge and spasmolytic [2]. The bark is prescribed as an
astringent and as an antidiarrhoeatic in children [3]. The
bark and leaves are reported for skin ailments [4]. The fruit
is a tonic and laxative and is good in bleeding gums [5].
533
Table 1
1
H, 13C NMR (DMSO-d6) data of compound 1, 2 and 3 (500 MHz and 125 MHz, J in Hz, in ppm).
C
1
2
3
4
5
6
7
8
9
1
2
3
4
5
6
1
2
3
4
5
6
1
2
3
4
5
6
7
1 (DMSO-d6)
2 (DMSO-d6)
3 (DMSO-d6)
113.0
152.1
111.0
156.2
111.0
152.1
197.0
9.9
9.9
138.9
128.7
128.2
132.4
128.2
128.7
104.2
74.1
76.4
69.9
76.8
61.1
2.10 (s)
2.10 (s)
108.3
156.7
104.7
159.2
94.8
156.0
197.2
8.1
139.6
128.5
128.0
132.0
128.0
128.5
101.1
73.2
76.3
69.0
73.8
62.6
112.9
156.6
111.9
159.9
111.9
156.6
201.5
10.2
10.2
142.0
130.2
129.3
133.2
129.3
130.2
105.8
75.8
78.1
71.8
76.1
64.6
2.15
2.15
7.59
7.35
7.48
7.35
7.59
4.74
3.58
3.54
3.48
3.45
4.42
4.38
7.15
7.15
119.3
108.6
145.5
138.5
145.5
108.6
165.8
6.20 (s)
1.97 (s)
7.15 (s)
7.15 (s)
121.7
110.5
146. 7
140.1
146.7
110.5
168.6
(s)
(s)
(dd, J = 1.2, 7.0)
(like t, J = 7.6, 8.9)
(like t, J = 7.5)
(like t, J = 7.6, 8.9)
(dd, J = 1.2, 7.0)
(d, 7.6)
(m)
(m)
(m)
(m)
(dd, 2.0, 11.9 )
(dd, 4.6, 11.9)
(s)
(s)
534
carbons at C 104.2, 76.8, 76.4, 74.1, 69.9, and 61.1 from HSQC
experiment were characteristic of a -glucopyranosyl residue
[10]. In HMBC spectrum of 1 (Fig. 2), the aromatic protons of
ring B at H 7.69 (H-2 and H-6) showed cross-peaks with the
carbonyl carbon (C 197.0), methyl protons at H 2.10 (6H, H8 and H-9) correlated with C-2, 3, 4, 5, 6 implied that the two
methyl groups were located at C-3 and C-5, while hydroxyl
groups at H 8.79 (2H, s) showed correlations with C-1, 2, 3, 5,
6 in ring A, which suggested the two hydroxyl groups was
placed at C-2 and C-6. The anomeric proton at H 4.56
exhibited HMBC cross-peaks with a C-4 quaternary carbon at
C 159.2, therefore C-4 was identied as the linkage position of
glucoside. Based on these ndings the structure of 1 was
established as 2, 6-dihydroxyl-3, 5-dimethyl-4-O--D-glucopyranosyl-benzophenone.
535
Acknowledgement
This research was supported by the National Natural
Science Foundation (Grant No. u0732004/C1905).
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