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Natural Product Research: Formerly Natural Product Letters
Natural Product Research: Formerly Natural Product Letters
Natural Product Research: Formerly Natural Product Letters
a
Natural Product and Medicinal Chemistry Lab, Faculty of
Chemistry, Ho Chi Minh City University of Science, 227 Nguyen Van
Cu, Ho Chi Minh City, Vietnam
b
Faculty of Pharmacy, University of Medicine and Pharmacy in Ho
Chi Minh City, 41 Dinh Tien Hoang, Ho Chi Minh City, Vietnam
Version of record first published: 01 May 2012.
To cite this article: Le-Thu Thi Nguyen , Duc Minh Nguyen & Lien-Hoa Dieu Nguyen (2013): A new
xanthone from the bark of Calophyllum thorelii , Natural Product Research: Formerly Natural
Product Letters, 27:6, 563-567
This article may be used for research, teaching, and private study purposes. Any
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Natural Product Research, 2013
Vol. 27, No. 6, 563–567, http://dx.doi.org/10.1080/14786419.2012.682992
1. Introduction
The genus Calophyllum (Guttiferae) is well known as a rich source of phenolic compounds
such as xanthones, coumarins and chromanones (Su et al., 2008). Xanthones have shown
to possess various biological activities, from antimicrobial, antitubercular, antitumour,
antileukaemic to antidepressant, antihepatotoxic and anti-inflammatory (Peres & Nagem,
1997; Peres, Nagem, & de Oliveira, 2000) as well as antioxidant properties (Hay et al.,
2004; Hiroyuki, Kuwayama, Yoshizawa, & Yoshiyasu, 1996). In the previous paper
(T.L.T. Nguyen, M.D. Nguyen, & D.L.H. Nguyen, 2010b), we have reported the isolation
of a new xanthone, thorexanthone (1), together with trans-cinnamic acid and two
polyisoprenylated benzophenones, guttiferone F and 30-epi-cambogin, from a petroleum
ether extract of the fruit of Calophyllum thorelii collected in central Vietnam. In addition,
five compounds, osajaxanthone, 1,4,8-trihydroxyxanthone, 1,3,5-trihydroxy-4-(3-methyl-
but-2-enyl)xanthone, 1,2,5-trihydroxyxanthone, 1,3,5,6-tetrahydroxyxanthone and proto-
catechuic acid, were obtained from an ethyl acetate extract of the bark (T.L.T. Nguyen,
M.D. Nguyen, & D.L.H. Nguyen, 2010a). In this article, we describe the isolation and
structure elucidation of a new and five known compounds from a petroleum ether extract
of the same bark. Antioxidant activity of the isolated compounds using DPPH free radical
scavenging assay was also reported.
O OH OH O OH
OH O OH 13
14
HO 1
O
8a 9a
H
O 7 11
O
12
O
OH O 4a 3 O 15
(1) 5
10a
OH (3)
(2)
O OH
OH
HO
O
O
OH
(5)
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(4)
H
OH O O 13
HO 8a 9a
1 14
7 11
15
H 10a O 4a 3 O
5
H H
(2)
O OH 13 14
1
9a
11 H
12
O 4a 3 O 15
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reported for mangoxanthone (Nilar, Nguyen, Venkatraman, Sim, & Harrison, 2005). The
xanthone B ring therefore carried the remaining two hydroxyl groups. The second chelated
hydroxyl proton (�H 11.80, 8-OH) correlated to one substituted aromatic carbon (�C 108.2)
and two oxygenated aromatic carbons (�C 147.9 and 141.4), revealing that C-7 and C-8
were hydroxylated. The two ortho-coupled protons were therefore attached to C-5 and
C-6. Other HMBC correlations (Figure 2) supported the structure of the subunit. The
relative configuration of 2 was determined using NOESY experiment. The NOE
correlation between the oxymethine H�-12 (�H 4.59) and the methyl H3(�)-14 (�H 1.50)
indicated that the proton and the methyl group were in the same side. C�-13 and C�-15
methyls (�H 1.26 and 1.40, respectively) therefore had the same orientation, and this
was confirmed by an NOE correlation between the corresponding protons (Figure 3).
The compound thus had structure 2, which is named calothorexanthone. The absolute
configuration of 2 remained undetermined.
Antioxidant capacity of the isolated compounds was tested using DPPH free radical
scavenging assay (Hatano, Kagawa, Yasuhara, & Okuda, 1988). The scavenging activities
of the isolated compounds and ascorbic acid as a positive control are shown in Table 1.
All test compounds showed remarkable antioxidant activities except for 1,7-dihydroxyx-
anthone, which exhibited a low scavenging effect of 14.2% at the concentration
of 200 mg mL�1 and its IC50 was therefore not measured. 1,4,8-Trihydroxyxanthone
showed the strongest activity and the antioxidant capacity followed the order of
1,4,8-trihydroxyxanthone 4 garboginol (3) 4 calothorexanthone (2) 4 �-tocotrienol (4) 4
globuxanthone (5).
566 L.-T.T. Nguyen et al.
3. Experimental
3.1. General experimental procedures
Optical rotations were measured on an A. Krüss Optronic polarimeter spectrophotometer.
Melting points were determined on a Wagner & Munz Polytherm A hot stage microscope
and were uncorrected. UV spectra were obtained with an Agilent 8453 spectrophotometer
and IR spectra were recorded in KBr using a Bruker Tensor 37 spectrophotometer.
HRESIMS was performed on a Bruker micrOTOF-QII (80 eV). NMR spectra were
measured using a Bruker AV 500 [500 MHz (1H) and 125 MHz (13C)] with TMS as an
internal standard and acetone-d6 as the solvent. Multiplicities were determined using the
DEPT pulse sequence. CC was run on silica gel (Merck, 40–63 mm), Diol (Merck,
Lichroprep, 40–63 mm), or RP18 (Merck, 40–63 mm) bonded phases. For gel permeation
chromatography (GPC), Sephadex LH-20 (GE Healthcare) with CHCl3–MeOH 1 : 1 as
eluent was used. TLC was carried out on precoated glass TLC plates normal phase
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(Merck, 250 mm) and RP18 (Merck, 200 mm). TLC plates were visualised using UV light,
staining with I2 or spraying with ethanolic FeCl3 for detection of phenolic compounds.
Petroleum ether refers to the fraction of b.p. 50–90� C.
C-10a; H-12 ! C-14; H-13 ! C-2, C-11, C-12, C-14; H-14 ! C-2, C-11, C-12, C-13;
H-15 ! C-11, C-12; 1-OH ! C-1, C-2, C-9a; 7-OH ! C-6, C-7, C-8 and 8-OH ! C-7,
C-8, C-8a. HRESIMS m/z: 329.1023 [M þ H]þ (Calcd for C18H17O6, 329.1025).
the positive control. All the tests were carried out in triplicate and averaged.
Supplementary material
Figure S1, showing the HMBC spectra, is available online.
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