A novel phloroglucinol and two new phenolic glycosides from Psidium littorale

Article abstract of DOI:10.1080/10286020.2016.1271792

One novel phloroglucinol, psidosone A (1), and two new phenolic glycosides, psidoside A (2), and psidoside B (3), together with nine known phenol compounds (4–12), were isolated from the fruits of Psidium littorale Raddi. Their structures were elucidated using data obtained from MS, ¹H and ¹³C NMR spectra, and correlation experiments (HMQC and HMBC), as well as by comparison with published data.

Full text of DOI:10.1080/10286020.2016.1271792

Journal of Asian Natural Products Research
ISSN: 1028-6020 (Print) 1477-2213 (Online) Journal homepage: http://www.tandfonline.com/loi/ganp20
A novel phloroglucinol and two new phenolic
glycosides from Psidium littorale
Ji-Cheng Shu, Hang-Qing Cui, Yin-Zheng Huang, Jian-Qun Liu & Hui-Lian
Huang
To cite this article: Ji-Cheng Shu, Hang-Qing Cui, Yin-Zheng Huang, Jian-Qun Liu & Hui-Lian
Huang (2016): A novel phloroglucinol and two new phenolic glycosides from Psidium littorale,
Journal of Asian Natural Products Research, DOI: 10.1080/10286020.2016.1271792
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Date: 03 January 2017, At: 03:10

Journal of asian natural Products research, 2016
http://dx.doi.org/10.1080/10286020.2016.1271792
A novel phloroglucinol and two new phenolic glycosides from
Psidium littorale
Ji-Cheng Shu, Hang-Qing Cui, Yin-Zheng Huang, Jian-Qun Liu and Hui-Lian Huang
Key laboratory of Modern Preparation oftcM, Ministry of education, Jiangxi university of traditional chinese
Medicine, nanchang 330004, china
ABSTRACT
ARTICLE HISTORY
received 1 september 2016
accepted 6 december 2016
One novel phloroglucinol, psidosone A (1), and two new phenolic
glycosides, psidoside A (2), and psidoside B (3), together with nine
known phenol compounds (4–12), were isolated from the fruits
of Psidium littorale Raddi. Their structures were elucidated using
KEYWORDS
Myrtaceae; Psidium littorale;
phenols; spectroscopic
methods
1
data obtained from MS, H and 13C NMR spectra, and correlation
experiments (HMQC and HMBC), as well as by comparison with
published data.
1. Introduction
e genus Psidium (Myrtaceae) includes approximately 150 species, which are widespread
in tropical America [1]. Due to both its medicinal importance and good edible quality,
guava varieties have been cultivated in various parts of the world, such as tropical and
subtropical regions, including China. Two species of the genus, Psidium littorale Raddi,
and Psidium guajava L.,were distributed mainly over southern provinces of China, such as
Fujian, Guangdong, and Guangxi [1]. P. littorale Raddi. (P. littorale) is commonly known as
strawberry guava and Chinese guava, and Psidium cattleianum Sabine var. littorale (Raddi)
Mattos is a synonym for it [2,3]. In recent years, some literatures have been reported about
pharmacology and phytochemistry of P. littorale [4–7]. Pharmacological investigations
showed that this plant had antioxidant, antimicrobial, analgesic, and anticancer activi-
ties [4,5]. Phytochemical studies indicated that its major secondary metabolites were fla-
vonoids, benzophenone, and some volatiles [4,6,7]. As a part of our ongoing search for
potentially bioactive components from plants in the genus Psidium, we have systematically
investigated the constituents of P. littorale, and reported the isolation of four benzophe-
none glycosides, four megastigmane glycosides, and three lignans from the leaves of this
plant [6,8]. In a continuation of our investigation on the plant, we have examined the
chemical constituents of the fruits of P. littorale. is paper describes the isolation and
structural elucidation of one novel phloroglucinol, psidosone A (1), and two new phenolic
glycosides, psidosides A (2) and B (3), along with nine known phenols, glochierioside F
(4), ethyl brevifolin carboxylate (5) [9], methoxyellagic acid 4-O-α-L-rhamnopyranoside
(6) [10], benzyl-β-D-glucopyranoside (7) [11], gallic acid (8) [12], ethyl gallate (9) [13],
CONTACT hui-lian huang
huilianh@163.com
© 2016 informa uK limited, trading as taylor & francis Group

2
J.-C. SHU ET AL.
benzyl 2-O-β-D-glucopyranosyl-2,6-dihydroxybenzoate (10) [14], schumanniofioside A
(11) [15,16], 2-hydroyl-benzoic acid 5-O-β-D-glucopyranoside (12) [17] (Figure 1). Up
1
13
to now, the H and C NMR data of 4 are unavailable. Here, we reported the complete
spectroscopic assignment for 4.
2. Results and discussion
e fruits of P. littorale were extracted with MeOH. e MeOH extract was fractionated
among petroleum ether (60–90 °C), ethyl acetate, and H2O. e ethyl acetate and H2O-
soluble fractions were subjected to separation by a combination of silica gel column chro-
matography, Sephadex LH-20 column chromatography, and preparative HPLC to give one
novel phloroglucinol psidosone A (1), two new phenolic glycosides psidoside A (2), and
psidoside B (3), and nine known phenols (Figure 1).
Compound 1 was obtained as yellowy oil. 1 showed a quasi-molecular ion at m/z 349.1270
[M + Na]+ in its HR-ESI-MS, compatible with the molecular formula C16H22O7, suggesting
six degrees of unsaturation. 1H, 13C NMR and HSQC spectra (Table 1) showed four methyl
groups (δH /δC 1.31/24.6, 1.31/24.6, 1.41/25.3, and 1.43/25.2), two carbonyl groups (δC 213.8
and 196.9), and a double bond (δC 183.0 and 111.7). Two sets of methyl protons (δH 1.41,
1.43) showed long-range correlations to the carbonyl (δC 213.8) and vinylic oxycarbon
(δC 183.0), while the other two sets of methyl protons (δH 1.31*2) showed HMBC correlations
to two carbonyls (δC 213.8 and 196.9), indicated 1 possessed a β-triketone moiety, which
was characteristic structure of phloroglucinol compounds isolated from Myrtaceae plants
[18,19]. e low field chemical shif of C-5 (δC 183.0) indicated that the β-triketone moiety
was connected to the oxygen of a furan ring [20,21]. H-1′ (δH 5.66) showed cross-peaks
with C-1 (δC 196.9), C-5 (δC 183.0), C-3′ (δC 75.2), and C-4′ (δC 80.0) in HMBC spectrum.
H-2′ (δH 5.12) also displayed cross-peaks with C-5 (δC 183.0), C-6 (δC 111.7), and C-4′ (δC
80.0) in HMBC spectrum. ese revealed a benzo[b]furo[23-d]-furan structural moiety. It
could be also confirmed by 1H–1H COSY spectrum (Figure 2) and the coupling constant of
protons. H-1′ (δH 5.66, d, J = 6.0 Hz) showed a correlation to H-2′ (δH 5.12, d, J = 6.0 Hz);
H-2′ had correlations with H-1′ and H-3′ (δH 4.41, d, J = 2.5 Hz). H-3′ displayed correlations
with H-2′ and H-4′ (δH 3.44, dd, J = 2.5, 8.2 Hz). In addition, H-1″ (δH 3.95, ddd, J = 3.2,
1
5.6, 8.2 Hz) showed H–1H COSY correlations with H-4′ and H-2″ (δH 3.73, dd, J = 3.2,
11.5 Hz and 3.56 (dd, J = 5.6, 11.5 Hz), which implied that 1 had an ethylene glycol moiety,
and it was located at C-4′. e same conclusion can be drawn with the HMBC experiment.
H-2″ showed a cross-peak with C-4′ (δC 80.0) by 3J correlations, and H-1″ has correlation
to C-3″ (δC 75.1). In the NOESY experiment (Figure 2), the correlation of the methine
proton (H-1′) with H-2′ provided the assignment of a cis relative stereochemistry, and
β-configuration for H-1′ and H-2′ [18]. In addition, the NOESY spectrum displayed the
correlation between H-1′ and H-4′, but was not observed between H-1′ and H-3′, indicated
the β-configuration for H-4′, and α-configuration for H-3′. e same conclusion can be
drawn with the coupling constant of H-3′ in 1H NMR spectrum. e coupling constant was
not observed between H-3′ and H-2′, but the coupling constant was 2.5 Hz between H-3′
and H-4′, indicating the assignments of same ring-side position (cis) and trans orientations
for H-2′/H-4′ and H-2′/H-3′, respectively [22]. e absolute configuration at C-1″ of 1
was not known according to the present evidence. erefore, 1 was confirmed as 2, 2, 4,
4-tetramethyl-3′-hydroxy-4′-(12-dihydroxyethyl)-4H-benzo[b]furo[23-d]-furan-13-dione,
named psidosone A.

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
3
Figure 1. structures of compounds 1–4.
Table 1. 1h nMr (Meoh-d4, 600 Mhz) and 13c nMr (Meoh-d4, 150 Mhz) spectral data of 1.
1H
13C
C
1
2
3
4
5
6
1′
2′
3′
4′
1″
2″
–
–
–
–
–
196.9 (s)
56.9 (s)
213.8 (s)
46.8 (s)
183.0 (s)
111.7 (s)
81.4 (d)
94.5 (d)
75.2 (d)
80.0 (d)
70.3 (d)
65.3 (t)
–
5.66 (d, J=6.0 hz)
5.12 (d, J=6.0 hz)
4.41 (d, J=2.5 hz)
3.44 (dd, J=2.5, 8.2 hz)
3.95 (ddd, J=3.2, 5.6, 8.2 hz)
3.73 (dd, J=3.2, 11.5 hz)
3.56 (dd, J=5.6, 11.5 hz)
1.31 (s)
2a
2b
4a
4b
24.6 (q)
24.6 (q)
25.2 (q)
25.3 (q)
1.31 (s)
1.43 (s)
1.41 (s)
Compound 2 was obtained as an amorphous powder. A molecular formula C26H32O14
was determined by HR-ESI-MS at m/z 591.1681 [M + Na]+, and confirmed by 1H and 13C
NMR experiments. e structure of 2 was elucidated by detailed analyses of 1H and 13C NMR
chemical shif (Table 2), and by HSQC and HMBC experiments (Figure 2). e 1H NMR
spectrum of 2 showed the signals due to one 1, 2, 6-trisubstituted aromatic ring at δH 6.57
(1H, br. d, J = 8.4 Hz, H-5), 6.68 (1H, br. d, J = 8.4 Hz, H-3) and 7.26 (1H, like t, J = 8.4 Hz,
H-4), one mono substituted aromatic ring at δH 7.51 (2H, br. d, J = 7.2 Hz, H-2′, 6′), 7.40
(2H, like t, J = 7.2 Hz, H-3′, 5′), and 7.34 (1H, like t, J = 7.2 Hz, H-4′), one methylene at δH
5.39 (2H, s, H-7′), and two anomeric protons at δH 5.28 (1H, d, J = 7.4 Hz, H-1″), 4.45 (1H,

4
J.-C. SHU ET AL.
Figure 2. Key 1h–1h cosY, noesY and hMBc correlations of compounds 1–3.
d, J = 7.8 Hz, H-1″′). On acid hydrolysis, 2 afforded only d-glucose, which was identified
by GC analysis [23]. e chemical shif and coupling constants of H-1″ (d, J = 7.4 Hz) and
of H-1″′ (d, J = 7.8 Hz) and the chemical shif of C-1″ (δC 99.7), and of C-1″′ (δC 104.4)
supported a β-configuration for the anomeric carbons [24]. ese spectral features were
very similar to those of a known compound, plicatumoside A [25], except for the aromatic
proton signals of the benzyl methanol moiety in 1H NMR spectrum. Plicatumoside A was
ortho-disubstituted aromatic ring, but 2 possessed one mono-substituted aromatic ring. is
conclusion was also confirmed by the molecular formula. By HSQC and HMBC experiments
(Figure 2), a total of 24 carbon signals were detected, including 12 signals assignable to 2
glucopyranosyl moieties. e low-field chemical shif of glucose C-2″ (δC 83.4) suggests the
connection of another glucose. e interglycosidic linkage was determined by the HMBC
correlation between H-2″ and C-1″′ (δC 104.4). e attachment of the sugar chain at C-2
of the aromatic ring was supported by the HMBC correlation between H-1″ at δH 5.28
and C-2 at δC 157.4. On the basis of above mention, the structure of 2 was determined to
be benzyl 2-(2-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)-6-hydroxybenzoate, and
named psidoside A.
Compound 3 was obtained as an amorphous powder. A molecular formula C26H32O14
was determined by HR-ESI-MS at m/z 569.18631 [M + H]+, and confirmed by 1H and 13C
1
NMR experiments. e molecular formula of 3 was the same as that of 2. e H NMR
and 13C NMR spectral features of 3 were very similar to those of 2, except for the 1H and
13C NMR chemical shifs of C-2″ and C-6″, which suggested that 3 was a position iso-
mer of 2. e chemical shif variations noted in both 2 and 3 could be explained by the

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
5
Table 2. 1h nMr (600 Mhz) and 13c nMr (150 Mhz) spectral data of 2 and 3.
2 (MeOH-d4)
3 (DMSO-d6)
1H
13C
1H
13C
C
1
2
3
4
5
6
7
1′
2′
3′
4′
5′
6′
7′
–
–
110.3
157.4
106.3
134.0
111.1
160.0
169.9
137.4
129.7
129.8
129.6
129.8
129.7
68.3
–
–
111.8
155.2
105.8
131.4
109.3
155.3
165.9
136.3
127.9
128.4
127.9
128.4
127.9
66.1
6.68 (br. d, J=8.4 hz)
7.26 (like t, J=8.4 hz)
6.57 (br. d, J=8.4 hz)
–
6.76 (br. d, J=8.3 hz)
7.18 (like t, J=8.3 hz)
6.54 (br. d, J=8.3 hz)
–
–
–
–
–
7.51 (br. d, J=7.2 hz)
7.40 (like t, J=7.2 hz)
7.34 (like t, J=7.2 hz)
7.40 (like t, J=7.2 hz)
7.51 (br. d, J=7.2 hz)
5.39 (2h, s)
7.46 (br. d, J=8.4 hz)
7.37 (like t, J=8.4 hz)
7.32 (like t, J=8.4 hz)
7.37 (like t, J=8.4 hz)
7.46 (br. d, J=8.4 hz)
5.32 (d, J=12.7 hz)
5.23 (d, J=12.7 hz)
4.87 (d, J=7.6 hz)
3.20–3.23 (m)
1″
2″
3″
4″
5″
6″
5.28 (d, J=7.4 hz)
3.47-.3.52 (m)
3.07–3.10 (m)
3.34–3.43 (m)
3.28–3.31 (m)
3.47–3.52 (m)
99.7
83.4
77.4
70.6
77.7
61.3
100.2
73.3
76.7
69.7
76.1
68.4
3.09–3.12 (m)
3.14–3.17 (m)
3.55–3.61 (m)
3.55–3.61 (m)
3.98 (d, J=10.4 hz)
3.15–3.19 (m)
4.45 (d, J=7.8 hz)
3.15–3.19 (m)
3.34–3.43 (m)
3.34–3.43 (m)
3.62–3.68 (m)
3.62–3.68 (m)
3.82–3.85 (m)
1″′
2″′
3″′
4″′
5″′
6″′
104.4
76.0
77.9
70.8
77.6
62.4
4.22 (d, J=7.8 hz)
2.95–2.98 (m)
2.99–3.05 (m)
2.99–3.05 (m)
3.26–3.29 (m)
103.3
73.7
77.0
70.1
76.8
61.1
3.65 (dd, J=1.4, 11.7 hz)
3.40 (dd, J=5.6, 11.7 hz)
difference of the interglycosidic linkage. e glycosyl linkage was at C-6″ of the inner β-D
glucopyranosyl group in 3, replacing C-2″ in 2, because the signal of C-6″ was markedly
downfield shifed at δC 68.4 (+7.1 ppm), while the signal of C-2″ was markedly upfield
shifed to δC 73.3 (–10.1 ppm), when comparing the 13C NMR spectrum of 2 with that of
3. is conclusion was confirmed by the HMBC experiments (Figure 2), which showed
the long-range correlation between H-1″′ (δH 4.22) and C-6″ (δC 68.4). On the basis of the
foregoing, the structure of 3 was determined to be benzyl 2-(6-O-β-D-glucopyranosyl-β-
D-glucopyranosyloxy)-6-hydroxybenzoate, and named psidoside B.
3. Experimental
3.1. General experimental procedures
Optical rotations were acquired on Shenguang SGW-1 digital polarimeter (Jingke, Shanghai,
1
13
China). H (600 MHz), C (150 MHz), and 2D NMR spectra were obtained on Bruker
AV-600 with TMS as internal reference, and methanol-d4 as solvent (Bruker, Fällanden,
Switzerland). ElectroSpray Ionisation (ESI) mass spectra were acquired in the positive ion
mode on a LCQ DECAXP instrument (ermo Finnigan, San Jose, CA, U.S.A.) equipped
with an ion trap mass analyzer. HR-ESI-MS were obtained in the positive ion mode on
Waters UPLC Premir Q-TOF (Waters Inc., Milford, MA, U.S.A.). GC-MS were obtained on
ermo Finnigan Trace DSQ with TR-5MS column 60 m × 0.25 mm × 2.5 μm (ermo

6
J.-C. SHU ET AL.
Finnigan, San Jose, CA, U.S.A.). TLC plates were HSGF254 SiO2 from Yantai Jiangyou
Silica Gel Development Co., Ltd., Yantai, China. Column chromatography (CC) silica gel
(SiO2; 200–300 mesh; Qingdao Haiyang Chemical Co., Ltd., Qingdao, China), MCI GEL
CHP20P (Mitsubishi Chemical corporation, Tosa, Japan), Sephadex LH-20 (GE-Healthcare
Bio-Sciences AB, Uppsala, Sweden), ODS (Grace C18, Grace Davison Discovery Sciences,
Columbia, MD, U.S.A.) were employed as packing materials. Semi-preparative HPLC was
Agilent 1200 (Agilent, Santa Clara, CA, U.S.A.). Semi-preparative column was Grace Prevail
C18 column (5 μm, 10.0 mm I.D × 250 mm, Grace Davison Discovery Sciences, Columbia,
MD, U.S.A.). All other chemicals were of analytical reagent grade.
3.2. Plant materials
Fruits of Psidium littorale were collected in the city of Liuzhou in Guangxi province of
China, and were identified by Prof. Xiaomei Fu of Jiangxi Traditional Chinese Medicine
University. A voucher specimen (No. 20140802) was deposited in Key Laboratory of Modern
Preparation of TCM, Ministry of Education, Jiangxi University of Traditional Chinese
Medicines.
3.3. Extraction and isolation
e dried fruits of P. littorale (3.2 kg) were macerated with MeOH at room temperature for
one month. e MeOH extract was concentrated under reduced pressure, and the residue
(309 g) was suspended in water. is suspension was successively extracted with petroleum
ether (60–90 °C), ethyl acetate, and H2O. e ethyl acetate-soluble fraction was concentrated
under reduced pressure to yield the EtOAc residue (52.8 g). is fraction was subjected to
silica gel column chromatography with gradient mixtures CH2Cl2/MeOH (100:0, 50:1, 25:1,
10:1, 5:1, 1:1, 0:100). Each 200 ml elution was collected and evaporated, and some elution
was combined by inspection of analytical TLC (CHCl3/MeOH 8:1). Finally, 16 fractions
(Fr.E-1→16) were obtained. Fr.E-8 (3.5 g) was further chromatographed on a silica gel
column using CHCl3-MeOH (18:1), and the elution was separated into 35 fractions (Fr.E-
8-1→35). Fr.E-8-3 (207 mg) was chromatographed on a Sephadex LH-20 column using
MeOH-CHCl3 (1:1) to give 1 (6.0 mg). Fr.E-8-9 (248 mg) was subjected to preparative
HPLC [column, Grace Prevail C18 column; mobile phase, MeOH-H2O (2:3); UV detector,
254 nm; flow rate, 1.0 ml/min; column temperature, 25 °C] to yield 2 (11.1 mg), 8 (9.5 mg),
and 11 (8.2 mg). Fr.E-8-21 (198 mg) was chromatographed on a Sephadex LH-20 column
using MeOH to give 3 (11.0 mg), and 6 (7.4 mg). Fr.E-8-32 (119 mg) was subjected to pre-
parative HPLC [column, Grace Prevail C18 column; mobile phase, MeOH-H2O (3:7); UV
detector, 254 nm; flow rate, 1.0 ml/min; column temperature, 25 °C] to yield 5 (8.6 mg),
and 7 (12.4 mg). Fr.E-11 (1.8 g) was further divided into five parts (Fr.E-11-1→5) by MCI
GEL CHP20P column chromatography using MeOH/H2O (20, 40, 60, 80, 100%). Fr.E-11-2
(79 mg) was further purified by Sephadex LH-20 (MeOH) to give 4 (6.9 mg). Fr.E-11-3
(152 mg) was subjected to preparative HPLC [column, Grace Prevail C18 column; mobile
phase, MeOH-H2O (3:7); UV detector, 254 nm; flow rate, 1.0 ml/min; column temperature,
25 °C] to yield 9 (12.6 mg), 10 (5.8 mg) and 12 (9.3 mg).

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
7
3.3.1. Psidosone A (1)
Yellowy oil; [ꢀ]2D5–79.5 (c 0.25, MeOH); UV λ (MeOH, logε): 262 (4.6) nm. H NMR
1
max
13
and C NMR spectral data see Table 1. HRESI-MS m/z: 349.1270 [M + Na]+ (calcd for
C16H22O7Na, 349.1263).
3.3.2. Psidoside A (2)
An amorphous powder; [ꢀ]2D5–38.2 (c 0.31, MeOH); UV λmax (MeOH, logε): 251 (3.8) nm.
1H NMR and 13C NMR spectral data see Table 2. HR-ESI-MS m/z: 591.16813 [M + Na]+
(calcd for C26H32O14Na, 591.16843).
3.3.3. Psidoside B (3)
An amorphous powder; [ꢀ]2D5–39.6 (c 0.30, MeOH); UV λmax (MeOH, logε): 251 (3.8) nm.
13
1H NMR and C NMR spectral data see Table 2. HR-ESI-MS m/z: 569.18631 [M + H]+
(calcd for C26H33O14, 569.18648).
3.3.4. Glochierioside F (4)
An amorphous powder; molecular formula C20H22O9; H NMR (CD3OD, 600 MHz) δH:
1
7.19 (1H, d, J = 3.1 Hz, H-2)，7.28 (1H, d, J = 8.9 Hz, H-5), 6.96 (1H, dd, J = 8.9, 3.1 Hz,
H-6), 4.72 (1H, d, J = 7.3 Hz, H-1′), 3.35–3.50 (4H, m, H-2′, 3′, 4′, 5′), 3.90 (1H, dd, J = 12.1,
1.8 Hz, H-6′a), 3.70 (1H, dd, J = 12.1, 5.0 Hz, H-6′b), 7.44 (2H, like d, J = 7.6 Hz, H-2″, 6″),
7.38 (2H, like t, J = 7.6 Hz, H-3″, 5″), 7.32 (1H, t, J = 7.6 Hz, H-4″), 5.34 (1H, d, J = 12.4 Hz,
13
H-7″a), 5.28 (1H, d, J = 12.4 Hz, H-7″b); C NMR (CD3OD, 150 MHz) δC: 123.4 (C-1),
117.8 (C-2), 154.2 (C-3), 152.0 (C-4), 121.7 (C-5), 122.1 (C-6), 167.9 (C-7), 105.4 (C-1′),
75.1 (C-2′), 77.6 (C-3′), 71.4 (C-4′), 78.5 (C-5′), 62.8 (C-6′), 137. 4 (C-1″), 129. 4 (C-2″,6
″), 129.8 (C-3″, 5″), 129.5 (C-4″), 68.2 (C-7″).
3.4. Acid hydrolysis of 2 and 3
e absolute configuration of glucose was determined as described by Lei et al. [25]. Each
compound (2 mg) was heated in 1 mol/L HCl (2 ml) for 4 h at 105 °C. e mixture was
cooled, neutralized, and partitioned between ethyl acetate (2 ml) and H2O (2 ml). e aq.
layer was evaporated and contained in a vial. e following solutions were added: (a) (2S)-1-
aminopropan-2-ol/MeOH 1:8 (20 μl); (b) AcOH/MeOH 1:4 (17 μl); (c) 3% Na[BH3CN] in
MeOH (13 μl). e vial was capped, and the mixture was allowed to react for 2 h at 65 °C.
Afer cooling, 3 mol/L aq. CF3COOH was added dropwise until the pH dropped to pH
1−2. e mixture was evaporated and co-evaporated with H2O (3 × 0.5 ml) and MeOH
(5 × 0.5 ml). e residue was dried overnight in a vacuum desiccator and treated with pyri-
dine/Ac2O 1:1 for 1 h at 100 °C. Afer cooling, the mixture was extracted with CHCl3 and
the extract washed with H2O (3 × 1 ml), and sat. NaHCO3 soln. (3 × 1 ml). e org. phase
was dried (Na2SO4) and subjected to GC/MS; derivatives of d-glucose eluted at tR 65.30 min.
Disclosure statement
No potential conflict of interest was reported by the authors.

8
J.-C. SHU ET AL.
Funding
is work was financially supported by the National Natural Science Foundation of China (NSFC)
[grant number 31370376], [grant number 81360630], [grant number 81360628]; Cultivated Talents
by Young Scientists Program of Jiangxi Province [grant number 20142BCB23023]; Natural Science
Foundation of Jiangxi Province [grant number 20161BAB205219].
References
[1] Flora republicae popularis sinicae [Flora of China], 53 vols. (Beijing Science Press, Beijing,
1979), p. 122.
[2] F.R. Fosberg, Pro. Biol. Soc. Wash. 54, 179 (1941).
[3] C. Wikler, Distribuição geográfica mundial de Psidium cattleianum Sabine e um cecidógeno
com possibilidades de utilização em controle biologico [Geographical distribution of psidium
cattleianum Sabine and possibilities of biological use], (Universidade Federal do Paraná,
Curitiba, P.R, Tese de doutorado, 1999).
[4] R. Ho, A. Violette, D. Cressend, P. Raharivelomanana, P.A. Carrupt, and K. Hostettmann,
Nat. Prod. Res. 26, 274 (2012).
[5] A. Medina, L. Haas, F. Chaves, M. Salvador, R. Zambiazi, W. Silva, L. Nora, and C. Rombaldi,
Food Chem. 128, 916 (2011).
[6] J.C. Shu, C.Y. Peng, J.Q. Liu, and R. Zhang, Chem. Nat. Compd. 51, 865 (2015).
[7] J. Pino, R. Marbot, and C. Vázquez, J. Agric. Food Chem. 49, 5883 (2001).
[8] C.Y. Peng, J.Q. Liu, J.C. Shu, and R. Zhang, J. Chin. Med. Mater. 37, 2201 (2014).
[9] H.P. Wang, F. Cao, and X.W. Yang, Chin. Tradit. Herb. Drugs 44, 24 (2013).
[10] X. Yang, R.J. Liang, A.H. Hong, Y.F. Wang, and Y.Z. Chen, Chin. Tradit. Herb. Drugs 45, 170
(2014).
[11] S. Marino, C. Festa, F. Zollo, and M. Iorizzi, Phytochem. Lett. 2, 130 (2009).
[12] Y.J. Huang, M. Zhao, Y.Y. Zong, C.Y. Chen, and Z.T. Che, China J. Chin. Mater. Med. 33, 1561
(2008).
[13] J.J. Tan, Q.C. Zhao, L. Yang, Z.P. Shang, Z.Q. Du, and M. Yan, Chin. Tradit. Herb. Drugs 41,
1245 (2010).
[14] F. Wang, Y.P. Jiang, X.L. Wang, S. Lin, P.B. Pu, C.G. Zhu, S.J. Wang, Y.C. Yang, and J.G. Shi,
China J. Chin. Mater. Med. 38, 1378 (2013).
[15] P. Tane, J. Ayafor, B. Sondengam, and J. Connolly, Phytochemistry 29, 1004 (1990).
[16] L.F. Han, F. Zheng, Y. Zhang, E.W. Liu, W. Li, M.H. Xia, T. Wang, and X.M. Gao, Nat. Prod.
Res. 29, 1703 (2015).
[17] J. Fayos, J. Bellés, M. Lóez-Gresa, J. Primo, and V. Conejero, Phytochemistry 67, 142 (2006).
[18] A. Hiranrat, and W. Mahabusarakam, Tetrahedron 64, 11193 (2008).
[19] D. Salni, M. Sargent, B. Skelton, I. Soediro, M. Sutisna, A. White, and E. Yulinah, Aust. J. Chem.
55, 229 (2002).
[20] F. Shaheen, M. Ahmad, S. Khan, S. Hussain, S. Anjum, B. Tashkhodjaev, K. Turgunov,
M. Sultankhodzhaev, M. Choudhary, and Atta-ur-Rahman. Eur. J. Org. Chem. 10, 2371 (2006).
[21] Y. Fukuyama, H. Minami, and A. Kuwayama, Phytochemistry 49, 853 (1998).
[22] D.Q. Yu, and J.S. Yang, Analytical Chemistry Handbook,7 vols. (Chemical industry Press, Beijing,
1999), p. 85
[23] Y. Lei, L.J. Wu, H.M. Shi, and P.F. Tu, Helv. Chem. Acta 91, 495 (2008).
[24] P. Agrawal, Phytochemistry 31, 3307 (1992).
[25] M. Kikuchi, R. Onoguchi, Y. Yaoita, and K. Machida, J. Nat. Med. 65, 202 (2011).