Phytochemistry Letters 4 (2011) 48–51

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Phytochemistry Letters
journal homepage: www.elsevier.com/locate/phytol

Xanthones from the twigs of Cratoxylum cochinchinense

Hiep D. Nguyen a, Binh T.D. Trinh a, Nam K. Nguyen a, Son V. Dang b,
Hung D. Pham a, Lien-Hoa D. Nguyen a,*
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, Viet nam
b
Department of Biological Resources, Institute of Tropical Biology, 85 Tran Quoc Toan, Ho Chi Minh City, Viet nam

A R T I C L E I N F O A B S T R A C T

Article history: Three new xanthones, 1,3,7-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-4-(3-methylbut-2-enyl)-

Received 6 October 2010 xanthone (1), 8-hydroxy-1,2,3-trimethoxyxanthone (2), and 3-O-methylmangostenone D (3), together
Received in revised form 11 November 2010 with (13E,17E)-polypoda-8(26),13,17,21-tetraene-3b-ol, d-tocotrienol, cochinchinone A, b-mangostin,
Accepted 13 November 2010
1,6-dihydroxy-5-methoxyxanthone, 1-hydroxy-5,6-dimethoxyxanthone, and blancoic acid, were
Available online 26 November 2010
isolated from the twigs of Cratoxylum cochinchinense. Their structures were determined using mainly
2-D NMR techniques.
Keywords:
ß 2010 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
Cratoxylum cochinchinense
Guttiferae
Xanthones
Isolation
Structure elucidation

1. Introduction (Bennett et al., 1993), cochinchinone A (Mahabusarakam et al., 2006),

b-mangostin (Mahabusarakam et al., 1987), 1,6-dihydroxy-5-
Cratoxylum cochinchinense has been long used in Vietnamese methoxyxanthone (Dharmaratne et al., 2009), 1-hydroxy-5,6-
folk medicine. The bark, roots and leaves are used for the treatment dimethoxyxanthone (Dharmaratne et al., 2009), and blancoic acid
of fevers, coughs, flatulence, diarrhoea, bellyaches, scabies and (Nguyen et al., 2009).
eczema whilst the twigs is used to treat scabies, burns and injuries 1,3,7-Trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-4-(3-
(Pham, 2006; Vo, 1997). Previous research on chemical constitu- methylbut -2-enyl)xanthone (1) was obtained as yellow needles, mp.
ents of the species reveals it to be a rich source of xanthones 197–198 8C, ½a27 D ¼ 21:0, giving a positive test with ethanolic ferric
(Boonnak et al., 2009; Laphookhieo et al., 2008; Mahabusarakam chloride. HR-ESIMS showed a [M+H]+ ion peak at m/z 397.1688,
et al., 2006), triterpenoids (Bennett et al., 1993; Nguyen and corresponding to the molecular formula of C23H24O6. The IR
Harrison, 1998), tocotrienols (Bennett et al., 1993), benzophenones spectrum exhibited absorption bands for hydroxyl (3422 cm1),
(Yu et al., 2009), and flavonoids (Hoang et al., 2006), in which chelated carbonyl (1651 cm1) and aromatic ring (1568 cm1)
xanthones are the most abundant. In this work we describe the whilst the UV spectrum revealed four maxima at 236, 269, 319 and
isolation and structure elucidation of three new xanthones, along 384 nm. The 1H NMR spectrum (Table 1) had signals due to a chelated
with seven known compounds, from the twigs of C. cochinchinense hydroxyl [dH 13.14 (1H, s, 1-OH)], a 1,2,4-trisubstituted benzene ring
collected in south Vietnam. [dH 7.58 (1H, d, J = 3.1 Hz, H-8), 7.49 (1H, d, J = 9.0 Hz, H-5), and 7.36
(1H, dd, J = 9.0 and 3.1 Hz, H-6)], a 3-methylbut-2-enyl group [dH
5.28 (1H, m, H-17), 3.53 (2H, d, J = 7.0 Hz, H2-16), 1.88 (3H, s, H3-19),
2. Results and discussion and 1.65 (3H, s, H3-20)], and a 2-oxygenated-3-methylbut-3-enyl
side chain [dH 5.03 and 4.82 (1H each, s, H2-14), 4.42 (1H, d, J = 8.3 Hz,
An ethyl acetate extract of the dried and ground twigs of C. H-12), 3.16 (1H, dd, J = 15.0 and 2.0 Hz, Ha-11) and 2.91 (1H, d,
cochinchinense was subjected to column chromatographic separation J = 15.0 and 8.3 Hz, Hb-11), and 1.85 (3H, s, H3-15)]. The 13C NMR
to afford 1,3,7-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-4-(3- spectrum (Table 1) contained resonances for a conjugated carbonyl
methylbut-2-enyl)xanthone (1), 8-hydroxy-1,2,3-trimethoxyx- carbon [dC 181.5 (C-9)], two benzene rings, an isoprenyl and a 2-
anthone (2), 3-O-methylmangostenone D (3), (13E,17E)-polypoda- oxygenated-3-methylbut-3-enyl group. Of the 12 aromatic carbons,
8(26),13,17,21-tetraene-3b-ol (Bennett et al., 1993), d-tocotrienol five were oxygenated, indicating that the compound was a
trioxygenated xanthone derivative. Since the molecular formula of
1 was C23H24O6, the 2-oxygenated-3-methylbut-3-enyl group was
* Corresponding author. Tel.: +84 8 38355270; fax: +84 8 38350096.
confirmed to be 2-hydroxy-3-methylbut-3-enyl.
E-mail address: [email protected] (L.D. Nguyen).

1874-3900/$ – see front matter ß 2010 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
doi:10.1016/j.phytol.2010.11.006
 H.D. Nguyen et al. / Phytochemistry Letters 4 (2011) 48–51 49

Table 1
1 13
H (500 MHz) and C (125 MHz) NMR data for 1–3 (J in Hz in parentheses).

Position 1a 2a 3b

dH dC dH dC dH dC
1 159.6 153.5 159.6
2 108.6 139.8 111.3
3 163.5 159.6 163.3
4 107.8 6.71 s 96.0 6.35 s 88.8
4a 154.6 154.6 155.4
5 7.49 d (9.0) 119.7 6.81 dd (8.3, 0.8) 106.1 6.80 s 100.3
6 7.36 dd (9.0, 3.1) 125.0 7.50 t (8.3) 135.8 151.5
7 154.8 6.75 dd (8.3, 0.8) 110.7 138.0
8 7.58 d (3.1) 109.3 162.2 121.4
8a 121.6 109.4 111.5
9 181.5 181.4 182.6
9a 103.2 109.0 104.0
10a 150.8 155.5 153.1
11 3.16 dd (15.0, 2.0) 29.4 3.35 d (7.0) 21.4
2.91 dd (15.0, 8.3)
12 4.42 d (8.3) 77.3 5.23 m 122.4
13 147.8 131.7
14 5.03 s 4.82 s 110.5 1.80 s 17.8
15 1.85 s 18.6 1.68 s 25.8
16 3.53 d (7.0) 22.5 3.51 t (6.5) 22.4
17 5.28 m 123.5 1.89 t (6.5) 32.9
18 131.4 75.6
19 1.88 s 18.0 1.39 s 26.5
20 1.65 s 25.8 1.39 s 26.5
1-OH 13.14 s 13.44 s
6-OH 6.40 s
8-OH 13.13 s
1-OCH3 4.03 s 62.1
2-OCH3 3.91 s 61.5
3-OCH3 3.99 s 56.4 3.90 s 55.8
a
Measured in acetone-d6.
b
Measured in CDCl3.

In the HMBC plot (Fig. 1), the chelated hydroxyl proton (dC 108.6) indicated that the side chain was attached to C-2. The
correlated to an oxygenated aromatic carbon (dC 159.6, C-1), and protons also gave a cross-peak to another oxygenated carbon (dC
two substituted aromatic carbons (dC 108.6 and 103.2) which were 163.5) which had to be C-3. The isoprenyl group was identified to
C-2 and C-9a. Correlations of the benzylic methylene protons of the be bonded to C-2 based on HMBC correlations of its benzylic
2-hydroxy-3-methylbut-3-enyl side chain (H2-11) to C-1 and C-2 methylene protons (H2-16) to C-3. The xanthone B ring therefore
[()TD$FIG]
14 15
O OH
11 19
HO 7 8a 9a
1 12
17
12
15 OH O OCH3 20
16
O OH 14

3
OH 8a 9a
1
OCH3 O 8a 9a
1
11
10a O 4a
OH 7
5 7
3 3
16
1 17 10a O 4a
OCH3 HO 10a O 4a OCH3
5 5

19 20 2 3

H
H O O
H
HO OH O OCH3 O O
H OCH3 O
OH
H O OH
H O OCH3 HO O OCH3
H
1 H H
2 H H
3

Fig. 1. HMBC correlations for 1–3.

50 H.D. Nguyen et al. / Phytochemistry Letters 4 (2011) 48–51

contained the last hydroxyl group. The most deshielded aromatic H3-19 and H3-20); dC 75.6 (C-18), 32.9 (C-17), 26.5 (C-19 and C-20)
proton (dH 7.58) showed a correlation to the carbonyl carbon, and 22.4 (C-16)], and 12 aromatic carbons including six
revealing its attachment to C-8. In the 1H NMR spectrum, H-8 oxygenated ones, were also observed. The compound was
appeared as a doublet with a meta-coupling constant (J = 3.1 Hz), therefore a tetraoxygenated xanthone carrying two C5 units and
indicating that the hydroxyl group was bonded to C-7. This is a methoxyl group. The 3-oxygenated-3-methylbutyl unit had to
confirmed by HMBC correlations of H-8 with two oxygenated form a 2,2-dimethyl-3,4-dihydropyran ring to be consistent with
aromatic carbons [dC 154.8 and 150.8, C-7 and C-10a] and a the molecular formula of C24H26O6. Comparison of the 1H and 13C
protonated aromatic carbon [dC 125.0, C-6] which carried its meta NMR spectra of 3 with those of mangostenone D previously
coupling partner. However, HMBC correlations could not help to isolated from the young fruit of Garcinia mangostana (Suksamrarn
differentiate the 13C shifts of C-7 and C-10a and this is solved by et al., 2006) clearly indicated that 3 was an O-methylated
comparison of the carbon resonances with those of 2-geranyl- derivative of mangostenone D, and this is confirmed by HMBC
1,3,7-trihydroxy-4-(3-methylbut-2-enyl)xanthone (Bennett et al., correlations (Fig. 1). In the HMBC plot, a correlation observed
1993) which suggested that C-7 should be the more deshielded between the methoxyl protons (dH 3.90) and C-3 (dC 163.3)
carbon. The remaining substituted aromatic carbon [dC 121.6] was revealed that C-3 carried the group. The structure of 3-O-
thus assigned to C-8a. The compound was therefore 1,3,7- methylmangostenone D was consequently established as 3.
trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-4-(3-methylbut- Chromanone acids have been considered a marker of the genus
2-enyl)xanthone (1) which has not been previously isolated. Its Calophyllum (Cottiglia et al., 2004; Samaraweera et al., 1983) and it
absolute configuration has not been determined. is interesting to note that blancoic acid reported in this paper is the
8-Hydroxy-1,2,3-trimethoxyxanthone (2) was obtained as first example of a chromanone acid found in another genus.
yellow needles, mp. 126–127 8C, giving a positive test with
FeCl3/EtOH, UV (lmax 268, 300 and 362 nm), and IR (3464, 1643, 3. Experimental
1601 cm1). Its molecular formula C16H14O6 was deduced from the
HR-ESIMS spectrum which exhibited an [M+Na]+ ion peak at m/z 3.1. General experimental procedures
325.0701. The 1H and 13C NMR spectra (Table 1) contained
resonances for a chelated hydroxyl group [dH 13.13 (1H, s, 8-OH)], a Melting points were determined on a Wagner & Munz
1,2,3-trisubstituted benzene ring [dH 7.50 (1H, t, J = 8.3 Hz, H-6), Polytherm A hot stage microscope and were uncorrected. UV
6.81 (1H, dd, J = 8.3 and 0.8 Hz, H-5) and 6.75 (1H, dd, J = 8.3 and spectra were obtained with an Agilent 8453 spectrophotometer
0.8 Hz, H-7); dC 135.8 (C-6), 110.7 (C-7) and 106.1 (C-5)], an and IR spectra were recorded in KBr using a Bruker Tensor 37
isolated aromatic proton [dH 6.71 (1H, s, H-4); dC 96.0 (C-4)] and spectrophotometer. HR-ESIMS was performed on a Bruker micrO-
three methoxyl groups [dH 4.03 (3H, s, 1-OCH3), 3.99 (3H, s, 3- TOF-QII (80 eV). NMR spectra were measured using a Bruker AV
OCH3) and 3.91 (3H, s, 2-OCH3); dC 62.1 (1-OCH3), 61.5 (2-OCH3) 500 spectrometer [500 MHz (1H) and 125 MHz (13C)] with TMS as
and 56.4 (3-OCH3)]. There were also signals due to a conjugated an internal standard. Multiplicities were determined using the
carbonyl [dC 181.4 (C-9)] and eight substituted aromatic carbons, DEPT pulse sequence.
six of which were oxygenated. Column chromatography (CC) was run on silica gel (Merck, 40–
In the HMBC spectrum, the chelated hydroxyl proton correlated 63 mm) or RP18 (Merck, 40–63 mm) bonded phases. For gel
to three aromatic carbons which were assigned to C-8 (dC 162.2, s), permeation chromatography (GPC), Sephadex LH-20 (GE Health-
C-7 (dC 110.7, d) and C-8a (dC 109.4, s). Proton H-7 appeared as a care) with CHCl3–MeOH 1:1 as eluent was used. TLC was carried
doublet of doublets (J = 8.3 and 0.8 Hz), indicating that C-5 and C-6 out on precoated glass TLC plates normal phase (Merck, 250 mm)
were protonated and this was confirmed by HMBC correlations and RP18 (Merck, 200 mm). TLC plates were visualized using UV
(Fig. 1). The xanthone A ring therefore carried three methoxyl light, staining with I2 or spraying with ethanolic FeCl3 for the
groups which had to be at the position 1,2,3- or 2,3,4- since two of detection of phenolic compounds.
them were ortho-disubstituted (dC 61.5 and 62.1) (Silva and Pinto,
2005). The upfield shift of the isolated aromatic proton (dH 6.71) in 3.2. Plant material
the 1H NMR spectrum revealed that the proton was located at C-4
rather than at C-1. The three methoxyl groups hence had to take The twigs of C. cochinchinense was collected in Lo Go-Xa Mat
the first three positions. The methoxyl group at dC 56.4 was not National Park, Tay Ninh Province and was identified by Mr. Dang
ortho-disubstituted, it therefore had to attach to C-3 (dC 159.6). Van Son, Institute of Tropical Biology, Ho Chi Minh City. Voucher
Chemical shifts of the remaining carbons were established by specimens (TNN-Logo Xamat-01) are deposited at Natural
HMBC correlations of H-4 to C-2 (dC 111.3), C-4a (dC 155.4) and C- Products and Medicinal Chemistry Lab, Ho Chi Minh City
9a (dC 104.0). The compound was thus 8-hydroxy-1,2,3-trimethox- University of Science.
yxanthone (2). Although 2 was previously synthesized (Gil et al.,
1990), this is the first report of its finding in nature. 3.3. Extraction and isolation
3-O-methylmangostenone D (3) was isolated as yellow crystals
(mp. 195–196 8C) with a molecular formula of C24H26O6 (m/z The dried and ground twigs of C. cochinchinense (1.2 kg) were
433.1594 [M+Na]+). Its IR and UV spectra (see Section 3) were also exhaustively extracted with EtOAc. Concentration of the solvent
indicative of a xanthone derivative. The 1H and 13C NMR spectra produced an EtOAc extract (47.6 g), which was fractionated over a
(Table 1) had signals due to a chelated hydroxyl and the column of silica gel (0–100% EtOAc in hexane) to give eight
corresponding carbonyl carbon [dH 13.44 (1H, s, 1-OH); dC 182.6 fractions (F1–F8).
(C-9)], a free hydroxyl [dH 6.40 (1H, s, 6-OH)], two isolated Fraction F2 (3.2 g) was subjected to CC (silica gel, 0–50%
aromatic protons [dH 6.80 (1H, s, H-5) and 6.35 (1H, s, H-4)], and a acetone in hexane and 5–50% EtOAc in hexane, respectively) and
methoxyl group [dH 3.90 (3H, s, 3-OCH3); dC 55.8 (3-OCH3)]. Signals further purified using GPC to furnish (13E,17E)-polypoda-
for an isoprenyl side chain [dH 5.23 (1H, m, H-12), 3.35 (2H, d, 8(26),13,17,21-tetraene-3b-ol (830 mg). Fraction F5 (5.3 g) was
J = 7.0 Hz, H2-11), 1.80 (3H, s, H3-14) and 1.68 (3H, s, H3-15); dC separated using CC (silica gel, 0–100% acetone in hexane and 0–
131.7 (C-13), 122.4 (C-12), 25.8 (C-15), 21.4 (C-11) and 17.8 (C- 100% EtOAc in hexane, respectively) followed by CC on RP18 (70%
14)], a 3-oxygenated-3-methylbutyl group [dH 3.51 (2H, t, MeOH in H2O) to afford 1-hydroxy-5,6-dimethoxyxanthone
J = 6.5 Hz, H2-16), 1.89 (2H, t, J = 6.5 Hz, H2-17) and 1.39 (6H, s, (5.1 mg). Fraction F6 (11.2 g) was subjected to CC (silica gel, 0–
 H.D. Nguyen et al. / Phytochemistry Letters 4 (2011) 48–51 51

100% EtOAc in hexane) to give four fractions (F6.1–4). Fraction 3.3.3. 3-O-Methylmangostenone D (3)
F6.3 (6.28 g) was further purified by CC (silica gel, 5–50% EtOAc in Yellow crystals, mp. 195–196 8C (acetone–hexane); UV (MeOH)
hexane) to yield nine fractions (F6.3.1–9). Fraction F6.3.3 (1.54 g) lmax 245, 262, 317 and 363 nm; IR (KBr) nmax 3482, 2923, 2857,
was fractionated by CC (silica gel, 40–100% CHCl3 in hexane) to 1642, 1602, 1462, 1289, 1163 cm1; 1H and 13C NMR: see Table 1;
afford six fractions (F6.3.3.1–6). Fraction F6.3.3.2 (182 mg) was HMBC: see Fig. 1; HR-ESIMS m/z 433.1594 [M+Na]+ (calcd. for
purified using GPC followed by CC on silica gel (60–100% CHCl3 in C24H26O6Na 433.1621).
hexane) to afford b-mangostin (12.6 mg) and 8-hydroxy-1,2,3-
trimethoxyxanthone (2) (5.8 mg). Fraction F6.3.3.3.3 (135.6 mg) References
was subjected to CC (RP18, 60–90% MeOH in H2O) to give 1,6-
dihydroxy-5-methoxyxanthone (60.2 mg). Fraction F6.3.5 Bennett, J.G., Harrison, L.J., Sia, G.L., Sim, K.Y., 1993. Triterpenoids, tocotrienols and
(283 mg) was repeatedly purified by CC (silica gel, 0–100% EtOAc xanthones from the bark of Cratoxylum cochinchinense. Phytochemistry 32,
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in hexane) to produce 1,3,7-trihydroxy-2-(2-hydroxy-3-methylbut- Boonnak, N., Karalai, C., Chantrapromma, S., Ponglimanont, C., Fun, H.-K., Kanjana-
3-enyl)-4-(3-methylbut-2-enyl)xanthone (1) (5.6 mg). Fraction Opas, A., Chantrapromma, K., Kato, S., 2009. Anti-Pseudomonas aeruginosa
F6.4 (1.48 g) was fractionated using CC (0–100% acetone in xanthones from the resin and green fruits of Cratoxylum cochinchinense. Tetra-
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was separated by CC (silica gel, 10–100% acetone in hexane) to antibacterial activity from Calophyllum brasiliense. J. Nat. Prod. 67, 537–541.
give 7 fractions (F6.4.2.1–7). Fraction F6.4.2.3 (301 mg) was Dharmaratne, H.R.W., Napagoda, M.T., Tennakoon, S.B., 2009. Xanthones from roots
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(35.1 mg). Similarly, fraction F7 (2.5 g) was subjected to CC (silica Laphookhieo, S., Maneerat, W., Buatip, T., Syers, J.K., 2008. New xanthones from
gel, 10–100% acetone in hexane and then 0–30% MeOH in CHCl3) Cratoxylum cochinchinense. Can. J. Chem. 86, 757–760.
followed by GPC to yield d-tocotrienol (6.3 mg). Furthermore, CC Mahabusarakam, W., Wiriyachitra, P., Taylor, W.C., 1987. Chemical constituents of
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