Fitoterapia 83 (2012) 1430–1434

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Fitoterapia
journal homepage: www.elsevier.com/locate/fitote

Antibacterial dihydrobenzopyran and xanthone derivatives from Garcinia

cowa stem barks
Ittipon Siridechakorn a, Wong Phakhodee a, Thunwadee Ritthiwigrom b, Trinop Promgool a,
Suwanna Deachathai a, Sarot Cheenpracha c, Uma Prawat d, Surat Laphookhieo a,⁎
a
Natural Products Research Laboratory, School of Science, Mae Fah Luang University, Tasud, Muang, Chiang Rai 57100, Thailand
b
Department of Chemistry, Faculty of Science, Chiang Mai University, Sutep, Muang, Chiang Mai 50200, Thailand
c
School of Science, University of Phayao, Maeka, Muang, Phayao 56000, Thailand
d
Department of Chemistry, Faculty of Science and Technology, Phuket Rajabhat University, Rassada, Muang, Phuket 83000, Thailand

a r t i c l e i n f o a b s t r a c t

Article history: Two new compounds, garciniacowol (1) and garciniacowone (2) along with 15 known
Received 2 May 2012 compounds were isolated from the stem barks of Garcinia cowa. Their structures were
Accepted in revised form 10 August 2012 determined by intensive spectroscopic methods. The structure of 1 was a symmetrical dimeric
Available online 21 August 2012 dihydrobenzopyran derivative, whereas the framework of 2 was a triprenyl caged-xanthone
precursor. The antibacterial activities against Escherichia coli TISTR 780, Salmonella
Keywords: typhimurium TISTR 292, Staphylococcus aureus TISTR 1466, and methicillin-resistant S. aureus
Garcinia cowa (MRSA) SK1 of the isolated compounds were also evaluated. Compounds 2 and 9 exhibited
Clusiaceae good antibacterial activity against MRSA SK1 with the same minimum inhibitory concentra-
Dimeric chroman
tion (MIC) value of 2 μg/mL. Moreover, compound 2 also showed good antibacterial activity
Rearranged triprenylxanthone
against S. aureus with an MIC value of 2 μg/mL.
Antibacterial activity
© 2012 Elsevier B.V. All rights reserved.

1. Introduction
Garcinia (Clusiaceae), a large genus of polygamous trees or
shrubs containing more than 300 species, is commonly found in
tropical Asia, Africa, and Polynesia. This genus is a rich source of
molecules exhibiting a wide range of pharmacological activities,
such as antimicrobial, anti-HIV, antitumor, antioxidant, and
cytotoxic activities [1–5]. Garcinia cowa Roxb., found in several
parts of Thailand, is a tree with edible fruits and young leaves,
whose barks have been used in Thai folk medicine for its
antipyretic property [6]. Its chemical constituents have been
investigated, which included xanthones, flavanones, and
acylphloroglucinol derivatives [7–9]. As part of our continuing
studies on bioactive compounds from Thai medicinal plants, we
report herein the isolation and structural elucidation of two
novel compounds, a dimeric dihydrobenzopyran, garciniacowol
(1) and a rearranged triprenylxanthone, garciniacowone (2),
⁎ Corresponding author. Tel.: +66 53916238; fax: +66 53916776.
E-mail address: s.laphookhieo@sci.mfu.ac.th (S. Laphookhieo).
along with 15 known compounds (3–17) from the stem barks of
G. cowa as well as their antibacterial activities.
2. Experimental
2.1. General
Melting points were measured with a Buchi melting point
B-540. The UV spectra were recorded with a Perkin-Elmer UV–
Vis spectrophotometer. The IR spectra were recorded with a
Perkin-Elmer FTS FT-IR spectrophotometer. The NMR spectra
were recorded using 400 MHz Bruker spectrometer. Chemical
shifts are recorded in parts per million (δ) in CDCl3 with TMS as
an internal reference. The ESI-TOF-MS data were measured
from a MicroTOF, Bruker Daltonics mass spectrometer. Quick
column chromatography (QCC) and column chromatography
(CC) were carried out on Si gel 60 H (Merck, 5–40 μm) and Si
gel 100 (Merck, 63–200 μm), respectively. Precoated plates of
Si gel 60 F254 were used for analytical purposes.

0367-326X/$ – see front matter © 2012 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.fitote.2012.08.006
 I. Siridechakorn et al. / Fitoterapia 83 (2012) 1430–1434 1431

2.2. Plant material Table 1

NMR spectroscopic data (400 MHz, CDCl3) for garciniacowol (1) and
garciniacowone (2).
The stem barks of G. cowa were collected from Nong khai
Province of Thailand in April 2011. The plant was identified 1
by Mr. James Maxwell, Herbarium of Chiang Mai University
Position δH (J in Hz) δC HMBC
and the specimen (MFU-NPR0014) was deposited at Natural
2 75.1
Products Research Laboratory, School of Science, Mae Fah
3 1.71, m 31.2 2, 4, 9
Luang University. 4 2.35, m; 2.17, m 20.8 2, 3, 4a, 5, 8a
4a 120.3
5 115.8
2.3. Extraction and isolation
6 128.8
7 6.72, s 115.7 5, 7, 8, 8a, 26
The stem barks of G. cowa (4.70 kg) were extracted with 8 146.5
acetone over a period of 3 days at room temperature. Removal 8a 146.3
9 1.63, m; 1.53, m 39.9 3, 10, 11, 25
of the solvent under reduced pressure provided acetone extract
10 2.14, m 22.8 2, 9, 11, 12
(554.05 g) that was further separated by QCC over Si gel and 11 5.11, m 124.5 9, 13, 24
eluted with a gradient of hexanes-EtOAc (100% hexanes to 12 135.4
100% EtOAc) to give eight fractions (A–H). Fraction A (10.47 g) 13 1.97, m 39.8 11, 12, 14, 15
was further purified by QCC with 15% EtOAc-hexanes to 14 2.05, m 26.7 12, 13, 16, 23
15 5.11, m 124.3 13, 17, 23
produce compound 9 (19.8 mg) together with three
16 135.1
subfractions (A2–A4). Subfraction A4 (657.0 mg) was isolated 17 1.97, m 39.8 15, 16, 18, 19
by repeated CC with 50% CH2Cl2-hexanes, which yielded 18 2.03, m 26.9 16, 17, 20
compounds 1 (5.1 mg), 3 (5.7 mg), and 13 (6.0 mg). Fraction 19 5.11, m 124.3 17, 21, 22
20 135.4
B (30.1 g) was fractionated by QCC with a gradient of
21 1.60, s 17.8 20, 22
hexanes-EtOAc (100% hexanes to 100% EtOAc) that gave five 22 1.67, s 25.8 20, 21
subfractions (B1–B5). Compound 14 (1.7 mg) was derived 23 1.59, s 15.9 15, 16, 17
from subfraction B1 (189.9 mg) by repeated CC with 50% 24 1.58, s 16.1 11, 12, 13
CH2Cl2-hexanes. Fractionation of subfraction B4 (7.31 g) by 25 1.24, s 23.9 2, 3, 9
26 2.20, s 16.4 5, 6, 7
QCC with 5% acetone-hexanes gave ten subfractions (B4a–B4j).
8-OH 4.34, s 7, 8, 9
Subfractions B4d (20.4 mg) and B4h (213.7 mg) were further
purified by CC with 80% CH2Cl2-hexanes to give compounds 15 2
(2.0 mg) and 10 (34.5 mg), respectively, whereas compound 2 Position δH (J in Hz) δC HMBC
(6.2 mg) was derived from subfraction B5 (5.47 g) by repeated
1 159.1
CC with 75% CH2Cl2-hexanes. Fraction D (32.1 g) was subjected 2 110.2
to QCC and eluted with hexanes-CH2Cl2 (100% hexanes to 100% 3 161.5
CH2Cl2) to provide seven subfractions (D1–D7). Subfraction D2 4 6.44 (s) 94.0 2, 3, 4a, 9a
(90.2 mg) was further isolated by CC with 30% CH2Cl2-hexanes 4a 155.9
5 75.7
to yield compound 5 (30.2 mg). Compounds 6 (37.1 mg), 7
6 206.7
(15.7 mg), 12 (14.5 mg) and 16 (2.0 mg) were obtained by 7 3.35, m 31.8 6, 8a, 2″′
purification of subfraction D5 (1.28 g) by employing repeated 8 2.76,dd (15.2, 8.4); 2.79, dd (15.2, 7.2) 38.4 6, 8a, 10a, 1″′
CC with 55% CH2Cl2-hexanes. Fraction E (22.6 g) was subjected 8a 119.4
to QCC and eluted with a gradient of hexanes-EtOAc (100% 9 180.8
9a 104.6
hexanes-100% EtOAc) to produce five subfractions (E1–E5). 10a 160.5
Compounds 4 (13.1 mg) and 8 (1.5 mg) were isolated from 1′ 3.43, d (5.2) 21.4 1, 2, 3, 2′, 3′
subfractions E1 (752.2 mg) and E2 (4.4 mg), respectively, by 2′ 5.27, br t (5.2) 121.0 1′, 4′
CC with 20% EtOAc-hexanes. Finally, compounds 11 (6.2 mg) 3′ 135.4
4′ 1.76, s 26.0 2′, 3′
and 17 (1.0 mg) were isolated from subfraction E5 (150.0 mg)
5′ 1.83 (s) 17.9 2′, 3′, 4′
by CC using 50% CH2Cl2-hexanes. 1″ 2.92, dd (15.2, 7.2); 2.65, dd (15.2, 4.8) 36.1 5, 6, 10a, 2″, 3″
2″ 4.95, br t (6.4) 115.7 1″, 4″, 5″
3″ 137.7
2.3.1. Garciniacowol (1)
4″ 1.65, s 25.9 2″, 3″
Colorless viscous oil; [α]24D + 30.0 (c 0.015, CHCl3); UV 5″ 1.58, s 18.0 2″, 3″, 4″
(MeOH) λmax: 211 (6.02), 268 (5.19), 294 (5.29) nm; IR (neat) 1″′ 2.47, m; 2.23, m 32.5 7, 8
νmax: 3418 cm−1; 1H and 13C NMR (400 MHz, CDCl3) see 2″′ 5.11, br t (6.0) 120.4 1″′, 3″′, 4″′
Table 1; ESI-TOF-MS m/z 791.5978 [M+ H]+ (calcd for 3″′ 135.5
4″′ 1.71, s 25.8 2″′, 3″′
C54H79O4, 791.5978). 5″′ 1.60, s 18.0 2″′, 3″′, 4″′
1-OH 12.98, s 1, 2, 9a
3-OH 6.65, s
2.3.2. Garciniacowone (2)
Yellow viscous oil; [α]25D + 69.4 (c 0.043, MeOH); UV
(MeOH) λmax(log ε) 212 (5.44), 236 (5.18), 257 (5.21), 303
(4.91) nm; IR (neat) νmax: 3334, 2968, 2916, 1730, 1704 cm−1;
1
H NMR (400 MHz, CDCl3) and 13C NMR (100 MHz, CDCl3) see
1432 I. Siridechakorn et al. / Fitoterapia 83 (2012) 1430–1434
Table 1; ESI-TOF-MS m/z 467.2417 [M+ H]+ (calcd for
C28H35O6, 467.2434).
2.4. Antibacterial assay
Escherichia coli TISTR 780, Salmonella typhimurium TISTR
292, Staphylococcus aureus TISTR 1466 were derived from the
Microbiological Resources Center of the Thailand Institute of
Scientific and Technological Research whereas methicillin-
resistant S. aureus (MRSA) SK1 was derived from the Depart-
ment of Microbiology, Faculty of Science, Prince of Songkla
University, Thailand. The minimum inhibitory concentrations
(MICs) were determined by a two-fold serial dilution method
using Mueller Hinton broth according to the Clinical and
Laboratory Standards Institute recommendations [10]. The
test substances were dissolved in DMSO. Vancomycin and
gentamycin were used as standard drugs.
3. Results and discussion
Phytochemical investigation of acetone extract from the
stem barks of G. cowa led to the isolation of two new
compounds, garciniacowol (1) and garciniacowone (2),
together with 15 known compounds (Fig. 1): parvifoliol F
(3) [11], α-mangostin (4) [12], β-mangostin (5) [12],
cowaxanthone (6) [6], norcowanin (7) [6], cowanin (8) [6],
cowanol (9) [6], cowagarcinone B (10) [13], cowagarcinone D
(11) [13], cowagarcinone E (12) [13], fuscaxanthone A (13)
[3], fuscaxanthone C (14) [3], 6-O-methylmangostanin (15)
[7], cowaxanthone D (16) [7], and 1,7-dihydroxyxanthone
(17) [14]. All isolates were characterized by spectroscopic
methods and compared with those previously published
data.
Fig. 1. Compounds isolated from the stem barks of G. cowa.
Garciniacowol (1) was obtained as a colorless viscous oil.
Its molecular formula, C54H78O4, was deduced by ESI-TOF-MS
spectral data, which showed pseudo-molecular ion peak at
m/z 791.5978 [M + H] + (calcd 791.5978). The IR spectrum
showed the hydroxy functionality at 3418 cm −1, and the UV
spectrum revealed maxima absorption bands at λmax 211,
268, 294 nm, suggesting the presence of conjugated system
in the molecule. The 1H NMR spectrum displayed resonances
of a singlet aromatic proton at δ 6.72 (1H, s) and an aromatic
methyl group at δ 2.20 (3H, s), which were assigned as H-7
and Me-26, respectively. This is due to 2J and 3J HMBC
correlations of H-7 (δ 6.72) with C-5 (δ 115.8), C-6 (δ
128.8), C-8 (δ 146.5), C-8a (δ 146.3), and C-26 (δ 16.4), and
Me-26 (δ 2.20) with C-5 (δ 115.8), C-6 (δ 128.8), and C-7 (δ
115.7). Moreover, four methylene protons of a chroman
ring at δ 1.71 (2H, m, H-3), 2.17 (1H, m, H-4a), and 2.35
(1H, m, H-4b) were also observed in the 1H NMR spectrum.
The methylene protons H 2-4 (δ 2.17 and 2.35) showed
HMBC correlations with C-4a (δ 120.3) and C-8a (δ 146.3),
which confirmed the linked chroman ring at C-4a with an
ether linkage at C-8a (δ 146.3). Furthermore, the occurrence of a
linkage between an oxyquaternary methyl [δ 1.24 (3H, s)] and a
4,8,12-trimethyltrideca- 3,7,11-trienyl unit [δ 5.11 (3H, m), 2.14
(2H, m), 2.03 (2H, m), 2.05 (2H, m), 1.97 (4H, m), 1.63 (1H, m),
1.53 (1H, m), 1.67 (3H, s), 1.60 (3H, s), 1.59 (3H, s), and 1.58 (3H,
s)] was confirmed by COSY, HMQC, and HMBC correlations
(Table 1) located on C-2 of the chroman skeleton. The above
information on 1H NMR spectrum as well as NMR spectral data
in Table 1 suggested that the structure of 1 was similar to
the previously reported compound 3 [11]. However, 1H NMR of
H-5 of 1 was missing as well as the molecular formula of 1
(C54H78O4) was two-fold higher than that of 3. These
results implied that 1 was a highly symmetrical dimeric
dihydrobenzopyran derivative with carbon–carbon linkage at
 I. Siridechakorn et al. / Fitoterapia 83 (2012) 1430–1434 1433

C-5. The structure of 1 was, therefore, identified to be
garciniacowol. Detailed assignments of NMR spectral data are
shown in Table 1.
Garciniacowone (2) was obtained as a yellow viscous oil. Its
molecular formula was determined to be C28H34O6 by ESI-
TOF-MS, which showed [M+ H]+ ion peak at m/z 467.2417
(calcd 467.2434), suggesting the existence of 12 degree
unsaturations. The structure of 2, a xanthonoid derivative,
was established by a detailed comparison of its NMR spectral
data with those of the known compounds, 1,3-dihydroxy-5,7-
diprenyl caged xanthone [15], and oliganthin C [16], as well as
by its analysis on the basis of 2D NMR spectra. The 1H NMR
spectral data of 2 revealed a significant singlet aromatic proton
(δ 6.44, 1H, s, H-4), a chelated hydroxyl proton (δ 12.98, 1H, s,
1-OH), one methylene group [δ 2.76 (1H, dd, J = 15.2, 7.2 Hz)
and 2.79 (1H, dd, J = 15.2, 8.4 Hz, H-8)], and one methine
proton (δ 3.35, 1H, m, H-7). The latter two signals also showed
cross peaks with each other in the COSY spectrum. The protons
at δ 3.35 and 2.79 were syn-orientated due to NOE enhance-
ment of protons at δ 3.35 when irradiated at δ 2.79 in NOEDIFF
spectrum. In addition, three isoprenyl units were also observed
in 1H NMR spectrum with the combination of COSY and HMBC
spectral data (Table 1). The first set of isoprene appeared in the
1
H NMR signals at δ 5.11 (1H, br t, H-2″′), 2.47 (1H, m H-1″′a),
2.23 (1H, m, H-1″′b), 1.71 (3H, s, H-4″′), and 1.60 (3H, s, H-5″′).
This unit was located on C-7 of the xanthonoid skeleton due to
the methylene protons H-1″′ (δ 2.47 and 2.23), which showed
cross peaks with methine protons at δ 3.35 (1H, m, H-7) in the
COSY spectrum. Moreover, 2J and 3J HMBC also showed cross
peaks with C-6 (δ 206.7), C-7 (δ 31.8), and C-8 (δ 38.4)
(Table 2). The second unit of isoprenyl group [δ 5.27 (1H, br t,
H-2′), 3.43 (2H, d, J=5.2 Hz, H-1′), 1.83 (3H, s, H-5′), and 1.76
(3H, s, H-4′)] was placed on C-2 because methylene protons H-1′
(δ 3.43), a chelated hydroxy proton (δ 12.98), and H-4 (δ 6.44)
showed HMBC correlations with C-2 (δ 110.2). Finally, the last
unit of isoprenyl group [δ 4.95 (1H, br t, J=6.4 Hz, H-2″), 2.92
(1H, dd, J=15.2, 7.2 Hz, H-1″′a), 2.65 (1H, dd, J=15.2, 4.8 Hz,
H-1″b), 1.65 (3H, s, H-4″), and 1.58 (3H, s, H-5″)] was connected
with C-5 as the methylene protons H-1″ (δ 2.92 and 2.65)
showed 2J and 3J HMBC with quaternary carbon C-5 (δ 75.7)
and carbonyl carbon C-6 (δ 206.7), respectively. The relative
configurations at C-5 and C-7 were determined by the NOEDIFF
experiment. One methylene proton, H-1″ (δ 2.65), and methine
proton, H-7 (δ 3.35), gave NOE enhancements with proton at
δ2.79 (one of methylene proton H-8) implying syn orientation
of δ 2.65 (H-1″ of isoprenyl unit), 3.35 (H-7), and 2.79
(H-8). Therefore, the structure of 2 was identified to be
garciniacowone, a precursor of caged xanthone.
Garcinia species are well known to be a rich source of
xanthones [11–13,17–19] and benzophenones [20–22]; how-
ever, they are rare to produce dihydrobenzopyran derivatives.
To the best of our knowledge, compound 1 is the first example
of symmetrical dimeric dihydrobenzopyran isolated from
Garcinia species, and compound 3 was the first to be reported
from G. cowa. Also, compound 2 is the first example of
caged-xanthone precursor isolated from G. cowa.
Compounds 1–14 and 16 were further evaluated for their
antibacterial activity against Gram-negative bacteria: E. coli
TISTR 780 and S. typhimurium TISTR 292 and Gram positive
bacteria: S. aureus TISTR 1466 and methicillin-resistant
S. aureus (MRSA) SK1 (Table 2). Compounds 2, 8, 9, and 12
showed good activity against MRSA SK1 with MIC values of 2,
4, 2 and 8 μg/mL, respectively, whereas compounds 4–7
exhibited moderate activity with the same MIC value of
16 μg/mL. All the rest of the compounds were found to be
inactive or had weak activity (MIC value = 128 μg/mL). Only
five compounds: 2 and 6–9, were active against S. aureus
with MIC values of 2, 16, 8, 32, 8 μg/mL, respectively.
However, all compounds were found to have weak (128 μg/
mL) or inactive antibacterial activity against E. coli and S.
typhimurium except compound 7 that exhibited moderate
antibacterial activity (MIC value= 64 μg/mL) against E. coli. It
should be noted that structural difference between compounds
4 and 9 is only at C-8. Compound 4 possesses an isoprenyl
group at C-8 whereas 9 has a geranyl group, which plays an
important role in the antibacterial activity against MRSA SK1
and S. aureus. In case of cowanin derivatives, 7–9 and 12, C-7
demethylation of 8 produced 7, which has less antibacterial

Table 2
Antibacterial activity of compounds from the stem barks of G. cowa.

Compound MIC (μg/mL)

MRSA-SK1 S. aureus E. coli S. typhimurium

Garciniacowol (1) Inactive Inactive 128 128

Garciniacowone (2) 2 2 128 128
Parvifoliol F (3) 128 Inactive 128 128
α-Mangostine (4) 16 128 128 128
β-Mangostine (5) 16 Inactive Inactive 128
Cowaxanthone (6) 16 16 128 128
Norcowanin (7) 16 8 64 128
Cowanin (8) 4 32 128 128
Cowanol (9) 2 8 128 128
Cowagarcinone B (10) Inactive Inactive 128 128
Cowagarcinone D (11) 128 Inactive 128 128
Cowagarcinone E (12) 8 Inactive 128 128
Fuscaxanthone A (13) Inactive Inactive 128 128
Fuscaxanthone C (14) Inactive Inactive Inactive 128
Cowaxanthone D (16) 128 Inactive Not tested Not tested
Vancomycin 1 0.25 Not tested Not tested
Gentamycin Not tested Not tested 0.25 0.125

Data shown are from triplicate experiments and inactive at >128 μg/mL.
1434 I. Siridechakorn et al. / Fitoterapia 83 (2012) 1430–1434
activity against MRSA SK1 than that of compound 8. Oxidation
of 8 at C-5′ gave 9, which exhibited the best antibacterial
activity against MRSA SK1, whereas selective acetylation of 9 at
C-5′ yielded 12, which had reduced activity. From these results,
we can conclude that C-7 methoxyl group and C-5′ hydroxy
group are important for the enhancement of antibacterial
activity against MRSA SK1.
Acknowledgments
This work was supported by the Thailand Research Fund
(TRF Advanced Research Scholar) and Mae Fah Luang Univer-
sity. We are indebted to Mr. Nitirat Chimnoi, Chulabhorn
Research Institute, for recording the mass spectral data
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