Benzyl and phenylethanoid glycosides from the leaves of Magnolia sirindhorniae

Article abstract of DOI:10.1016/j.phytol.2019.02.021

A new benzyl triglycoside, benzyl O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside (1) together with two diastereomer phenylethanoid glycosides, (7R) and (7S)-campneoside I (10, 11) were isolated from the leaves of Magnolia sirindhorniae in addition to 20 known compounds. The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments.

Full text of DOI:10.1016/j.phytol.2019.02.021

PhytochemistryLetters30(2019)205–209
Contents lists available at ScienceDirect
Phytochemistry Letters
journal homepage: www.elsevier.com/locate/phytol
Benzyl and phenylethanoid glycosides from the leaves of Magnolia
sirindhorniae
Chutima Srinrocha, Poolsak Sahakitpichana, Supanna Techasakula, Nitirat Chimnoia,
⁎
Somsak Ruchirawata, Tripetch Kanchanapooma,b,
a Chulabhorn Research Institute, Kamphaeng Phet 6, Talat Bang Khen, Lak Si, Bangkok, 10210, Thailand
b Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen, 40002, Thailand
A R T I C L E I N F O
A B S T R A C T
Keywords:
A new benzyl triglycoside, benzyl O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyr-
anoside (1) together with two diastereomer phenylethanoid glycosides, (7R) and (7S)-campneoside I (10, 11)
were isolated from the leaves of Magnolia sirindhorniae in addition to 20 known compounds. The structure
elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D
NMR experiments.
Magnolia sirindhorniae
Magnoli aceae
Benzyl triglycoside
Phenethanoid glycoside
Campneoside I
1. Introduction
3)]-β-D-glucopyranoside (8) verbascoside (9) (Kanchanapoom et al.,
2002; 2018), isosyringalide 3′-α-L-rhamnopyranoside (12) (Yoshizawa
Magnolia sirindhorniae (Thai name: Champi-Si-Rin-Dhorn) is an ev-
erygreen tree up to 25 m high with sweet smelling flowers, endemic to
Thailand (Nooteboom and Chalermglin, 2000). In the course of our
ongoing study on plants of family Magnoliaceae (Sahakitpichan et al.,
2017; Kanchanapoom et al., 2018; Srinroch et al., 2019a,b), we in-
vestigated the secondary metabolites from this species, collected from
Lopburi Province, Thailand. The chemical constituent has not been
reported from this plant. This present paper deals with the isolation and
structure determination of 22 compounds including a new benzyl tri-
glycoside (1), two diastereomer phenylethanoid glycosides (10, 11)
(Fig. 1), as well as 20 known compounds from the water soluble frac-
tion of the MeOH extract of the leaves of this plant.
et al., 1990). crassifolioside (13) (Andary et al., 1989), echinacoside
(14) (Kobayashi et al., 1984), (+)-pinoresinol-4,4'-di-O-β-D-glucopyr-
anoside (15) (Deyama, 1983), (+)-syringaresinol O-β-D-glucopyrano-
side (16) (Kobayashi et al., 1985), rutin (17), kaempferol 3-O-neohe-
speridoside (18), quercetin 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-
rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (19), kaempferol 3-O-α-
L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-gluco-
pyranoside (20) (Agrawal and Bansal, 1989; Kazuma et al., 2003),
(6R,9R)-3-oxo-α-ionol-β-D-glucopyranoside (21) (Pabst et al., 1992)
and (6S,9R)-roseoside (22) (Yamano and Ito, 2005). All known com-
pounds were identified by comparison of physical data with literature
values and from spectroscopic evidence.
Compound 1 was isolated as an amorphous powder. Its molecular
formula was determined to be C25H38O15 by high resolution electro-
spray time-of-flight (HR-ESI-TOF) mass spectrometric analysis.
Inspection of the 1H NMR spectroscopic data indicated that this com-
pound was a benzyl triglycoside from the presence of the signals of a
mono-substituted aromatic ring, two methylene proton signals at δH
4.62 and 4.93 (each d, J = 11.0 Hz) in addition to three anomeric sugar
signals at δH 4.45 (d, J = 7.8 Hz), 4.47 (d, J = 7.8 Hz) and 5.21 (d,
J = 1.7 Hz). This compound was an analogous to benzyl O-β-D-gluco-
pyranoside (2). Acid hydrolysis provided D-glucose and L-rhamnose,
which was identified by HPLC analysis using the optical rotation de-
tector (Sahakitpichan et al., 2014). Positive HR-ESI-MS of 1 exhibited
2. Results and discussion
The methanolic extract of the leaves of M. sirindhorniae was parti-
tioned between Et2O and H2O. The water soluble fraction was separated
by combination of chromatographic methods to provide a new benzyl
triglycoside (1) and two diastereomer phenylethanoid glycosides (10,
11). The known compounds were identified as benzyl O-β-D-glucopyr-
anoside (2), β-D-glucopyranosyl syringate (3) (Inoshiri et al., 1987),
syringin (4) (Yang et al., 2007), icariside D2 (5) (Miyase et al., 1989),
tyrosol
4-O-β-D-xylopyranosyl-(1→6)-O-β-D-glucopyranoside
(6)
(Sawasdee et al., 2010), decaffeoylverbascoside (7), 3,4-dihydrox-
yphenethyl O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→
the significant fragment ions at m/z 455.1517 [M + Na-Rha]+
,
⁎ Corresponding author at: Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen, 40002, Thailand.
E-mail address: trikan@kku.ac.th (T. Kanchanapoom).
https://doi.org/10.1016/j.phytol.2019.02.021
Received 20 December 2018; Received in revised form 7 February 2019; Accepted 14 February 2019
1874-3900/©2019PhytochemicalSocietyofEurope.PublishedbyElsevierLtd.Allrightsreserved.

C. Srinroch, et al.
PhytochemistryLetters30(2019)205–209
Fig. 1. Structures of compounds 1, 10 and 11.
compounds had the same molecular formula, C30H36O16, based on HR-
ESI-TOF mass spectrometric analysis. The 1H and 13C NMR spectra were
compatible with those of campneoside I, which was firstly isolated from
Campsis chinensis and reported as a pair of epimers at C-7. (Imakura
et al., 1985). Campneoside I was isolated from several plant families
such as Acanthaceae (Wu et al., 2004), Bignoniaceae (Imakura et al.,
1985), Labiatae (Murata et al., 2008), Lentibulariaceae (Grevenstuk
et al., 2009), Orobanchaceae (Morikawa et al., 2010), Scrophulariaceae
(Abreu et al., 2009) and Verbenaceae (Zhang et al., 2015); however the
determination of the structure was based on the spectroscopic data of
the diasteromeric mixtures. In this study, two diastereomers 10 and 11
were successfully separated; therefore the configuration at C-7 of each
compound should be established. The absolute configuration at C-7 for
this compound type could be determined by using the chemical shift
difference of the neighboring methylene protons [ΔδH (H8a-H8b)]. It has
been reported that a large chemical shift difference corresponded to R,
in contrast to S with a small chemical shift difference for 2-alkoxy
phenylethanoid glycoside (Shao et al., 2016). In case of compound 10,
the absolute configuration of C-7 position was determined to be R by a
large chemical shift difference (ΔδH 0.41) and in compound 11 was S by
a small chemical shift difference (ΔδH 0.17). Consequently, compounds
10 and 11 were identified to be (7R) and (7S)-campneoside I, respec-
tively.
Fig. 2. HMBC correlations of compound 1.
439.1590 [M + Na-Glc]+
,
and 293.1002 [M + Na-Rha-Glc]+
, in-
dicating that these two sugars were bound to the hydroxyl groups of the
core β-D-glucopyranosyl unit. The assignment of the structure was
based on the results from the proton splitting and 2D NMR experiments
including COSY, HMQC and HMBC. The COSY spectrum showed the
proton connectivity of the core sugar moiety from H-1′ (δH 4.45, d,
J = 7.8 Hz)/ H-2′ (δH 3.56, dd, J = 8.9, 7.8 Hz)/ H-3′ (δH 3.67, dd,
J = 8.9, 8.8 Hz)/ H-4′ (δH 3.43, dd, J = 9.6, 8.8 Hz)/ H-5′ (δH 3.29, m)/
and H2-6′ [(δH 3.71, dd, J = 12.2, 5.9 Hz) and (δH 3.91, dd, J = 12.2,
2.0 Hz)], corresponding to the carbon atoms at δC 101.6 (C-1′)/ 79.2 (C-
2′)/ 88.3 (C-3′)/ 70.1(C-4′)/ 77.5 (C-5′) and 62.7 (C-6′), respectively.
The terminal α-L-rhamnopyranosyl and β-D-glucopyranosyl moieties
were placed at C-2′ and C-3′, respectively, assignable by the HMBC
correlations from i) H-1″ Rha (δH 5.21, d, J = 1.7 Hz) to C-2′ (δC 79.2),
ii) H-1″' Glc (δH 4.47) to C-3′ (δC 88.3), as shown in Fig. 2. Conse-
quently, the structure of compound 1 was identified as benzyl O-α-L-
rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyr-
anoside.
The presence of simple aromatic glycosides (1-6), phenylethanoid
glycosides (7-14), lignan glycosides (15-16), flavonol glycosides (17-
20) and megastigmane glycosides (21-22) from M. sirindhorniae was
related to our previous works on this family (Sahakitpichan et al., 2017;
Kanchanapoom et al., 2018; Srinroch et al., 2019a,b). This work added
the typical profile of the secondary metabolites for further chemo-
taxonomic studies of this family.
Compounds 10 and 11 were isolated as amorphous powders. Both
206

C. Srinroch, et al.
PhytochemistryLetters30(2019)205–209
3. Experimental
Table 1
1H and 13C NMR spectroscopic data of compound 1 (in CD3OD).
3.1. General procedures
Position
1
δH
δC
NMR spectra were recorded in CD3OD using a Bruker AV-400
(400 MHz for 1H-NMR and 100 MHz for 13C-NMR) spectrometer. The
MS data was obtained on a Bruker Micro TOF-LC mass spectrometer.
Optical rotations were measured with a Jasco P-1020 digital polari-
meter. For column chromatography, Diaion HP-20 (Mitsubishi
Chemical Industries Co. Ltd.), silica gel 60 (230–400 mesh, Merck), and
RP-18 (50 μm, YMC) were used. HPLC (Shimadzu LC-10AT pump) was
carried out on an ODS column (21.2 x 250 mm i.d., Vertisep™UPS) with
a Jasco UV-970 detector at 210 nm. The flow rates were 6 ml/min. The
spraying reagent used for TLC was 10% H2SO4 in H2O-EtOH (1:1, v/v).
Aglycone
1
138.5
130.0
129.3
128.9
71.9
2, 6
3, 5
4
7.41 (2H, dd, J = 8.3, 1.3 Hz)
7.33 (2H, td, J = 8.3, 1.3 Hz)
7.28 (1H, dd, J = 7.2, 1.3 Hz)
4.93(1H, d, J = 11.0 Hz)
7
4.62 (1H, d, J = 11.0 Hz)
Glc
1'
4.45 (1H, d, J = 7.8 Hz)
101.6
79.2
88.3
70.1
77.5
62.7
2'
3.56 (1H, dd, J = 8.9, 7.8 Hz)
3.67 (1H, dd, J = 8.9, 8.8 Hz)
3.43 (1H, dd, J = 9.6, 8.8 Hz)
3.29 (1H, m)
3'
4'
3.2. Plant material
5'
6'
3.91 (1H, dd, J = 12.2, 2.0 Hz)
3.71 (1H, dd, J = 12.2, 5.9 Hz)
The leaves of Magnolia sirindhorniae Noot. & Chalermglin were
collected from Lopburi Province, Thailand, in December 2017. Plant
specimen was identified by one of us (TK). Voucher specimens (TK-
PSKKU-0084) are on files in the Herbarium of the Faculty of
Pharmaceutical Sciences, Khon Kaen University.
Rha
1"
5.21 (1H, d, J = 1.7 Hz)
3.97 (1H, dd, J = 3.3, 1.7 Hz)
3.63 (1H, dd, J = 9.4, 3.3 Hz)
3.32 (1 H)a
102.7
72.2
72.0
73.9
70.1
17.7
2"
3"
4"
5"
3.93 (1H, m)
6"
0.92 (3H, d, J = 6.2 Hz)
3.3. Extraction and isolation
Glc
1'"
2'"
3'"
4'"
5'"
6'"
4.47 (1H, d, J = 7.8 Hz)
3.25 (1H, dd, J = 8.9, 7.8 Hz)
3.35 (1H, dd, J = 8.9, 8.8 Hz)
3.28 (1 H)a
104.6
75.0
78.2
71.5
78.1
62.5
The air dried leaves of M. sirindhorniae (2.3 kg) were extracted three
times with MeOH, and concentrated to dryness. The greenish residue
(331.4 g) was suspended in H2O and partitioned with Et2O. The water
soluble part (173.8) was subjected to a Diaion HP-20 column, and
eluted with H2O, and MeOH, successively. The fraction eluted with
MeOH (75.2 g) was applied to a silica gel column using solvent systems
EtOAc (4.0 L), EtOAc-MeOH (9:1, 12.0 L), EtOAc-MeOH-H2O (40:10:1,
12.0 L), EtOAc-MeOH-H2O (70:30:3, 8.0 L) and EtOAc-MeOH-H2O
(6:4:1, 7.0 L), respectively to provide six fractions (A to F).
3.32 (1H, m)
3.89 (1H, dd, J = 11.9, 1.8 Hz)
3.64 (1H, dd, J = 11.9, 5.0 Hz)
a
Chemical shifts were assigned by HMQC.
solvent system, H2O-MeOH (90:10 → 20:80, v/v) to provide 14 sub-
fractions. Sub-fraction E-8 was purified by preparative HPLC-ODS using
solvent system H2O-MeCN (85:15, v/v) to provide compounds 1
(18.9 mg) and 15 (44.6 mg). Finally, sub-fraction E-12 was purified by
preparative HPLC-ODS with solvent system H2O-MeCN (80:20, v/v) to
yield compounds 13 (35.9 mg) and 16 (21.9 mg).
Fraction B (4.9 g) was applies to a RP-18 column using a gradient
solvent system, H2O-MeOH (90:10 → 20:80, v/v) to provide 12 sub-
fractions. Sub-fraction B-5 was purified by preparative HPLC-ODS using
solvent system H2O-MeCN (83:17, v/v) to yield compound 9 (92.8 mg).
Sub-fraction B-7 was purified by preparative HPLC-ODS with solvent
system H2O-MeCN (77:23, v/v) to give compound 12 (47.7 mg).
Fraction C (22.5 g) was separated on a RP-18 column using solvent
system, H2O-MeOH (90:10 → 20:80, v/v) to provide 14 sub-fractions.
Sub-fraction C-1 was purified by preparative HPLC-ODS with solvent
system H2O-MeCN (90:10, v/v) to provide compounds 3 (17.7 mg), 5
(63.6 mg) and 7 (127.5 mg). Sub-fraction C-3 was purified by pre-
parative HPLC-ODS with solvent system H2O-MeCN (85:15, v/v) to
afford compounds 4 (81.5 mg) and 22 (389.8 mg). Sub-fraction C-4 was
purified by preparative HPLC-ODS with solvent system H2O-MeCN
(88:12, v/v) to obtain compound 2 (6.3 mg). Sub-fraction C-5 was
purified by preparative HPLC-ODS with solvent system H2O-MeCN
(83:17, v/v) to afford compound 10 (11.3 mg) and 11 (9.3 mg). Sub-
fraction C-8 was purified by preparative HPLC-ODS with solvent system
H2O-MeCN (80:20, v/v) to obtain compounds 18 (31.6 mg) and 21
(24.2 mg).
3.4. Benzyl O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-
β-D-glucopyranoside (1)
27
Amorphous powder, [α]D −39.3 (MeOH, c 0.25); 1H and 13C
NMR (CD3OD): Table 1; Positive HRESITOFMS, m/z: 601.2104 [M
+Na]+ (C25H38NaO15 required 601.2103).
3.5. (7R)-campneoside I (10)
27
Amorphous powder, [α]D −36.2 (MeOH, c 0.16); 1H and 13C
NMR (CD3OD): Table 2; Positive HRESITOFMS, m/z: 653.2078 [M
+H]+ (C30H37O16 required 653.2087).
3.6. (7S)-campneoside I (11)
Fraction D (11.8 g) was applied to a RP-18 column using solvent
system, H2O-MeOH (90:10 → 20:80, v/v) to give 13 sub-fractions. Sub-
fraction D-1 was purified by preparative HPLC-ODS with solvent system
H2O-MeCN (92:8, v/v) to obtain compound 6 (161.2 mg). Sub-fraction
D-3 was purified by preparative HPLC-ODS with solvent system H2O-
MeCN (88:12, v/v) to provide compound 8 (50.8 mg). Sub-fraction D-5
was purified by preparative HPLC-ODS with solvent system H2O-MeCN
(83:17, v/v) to give compounds 14 (148.3 mg), 19 (44.9 mg) and 20
(27.6 mg). Sub-fraction D-7 was purified by preparative HPLC-ODS with
solvent system H2O-MeCN (83:17, v/v) to provide compound 17
(34.8 mg).
Amorphous powder, [α]D −16.2 (MeOH, c 0.13); 1H and 13C
27
NMR (CD3OD): Table 2; Positive HRESITOFMS, m/z: 653.2075 [M
+H]+ (C30H37O16 required 653.2087).
3.7. Determination of the absolute configuration of sugars of compound 1
Compound 1 (ca 3 mg) in 2 N HCl-dioxane (1:1, 3.0 mL) was heated
at 80 °C for 6 h. After cooling, each reaction was diluted with H2O and
extracted with EtOAc. The aqueous layer was concentrated to dryness
providing the sugar fraction. This fraction was dissolved in H2O
(1.0 mL), and analysed by HPLC (Jasco OR-2090 plus chiral detector;
Fraction E (23.5 g) was applies to a RP-18 column using a gradient
207

C. Srinroch, et al.
PhytochemistryLetters30(2019)205–209
Table 2
NMR spectroscopic data of compounds 10 and 11 (in CD3OD).
Position
10
11
δH
δH
δC
δC
Aglycone
1
131.0
115.1
146.5
146.5
116.2
120.0
83.6
130.6
115.0
146.6
146.6
116.3
119.9
84.4
2
6.79 (1H, d, J = 2.0 Hz)
6.77 (1H, d, J = 2.0 Hz)
3
4
5
6.76 (1H, d, J = 8.0 Hz)
6.76 (1H, d, J = 8.1 Hz)
6
6.67 (1H, dd, J = 8.0, 2.0 Hz)
6.68 (1H, dd, J = 8.1, 2.0 Hz)
4.37 (1H, dd, J = 9.2, 2.4 Hz)
7
4.35 (1H, dd, J = 8.2, 3.4 Hz)
8a
8b
Glc
1'
2'
3'
4'
5'
6'
4.02 (1H, dd, J = 11.0, 8.2 Hz) 3.61 (1H, dd, J = 11.0, 3.4 Hz)
74.6
3.87 (1H, dd, J = 10.8, 2.4 Hz) 3.70(1H, dd, J = 10.8, 9.2 Hz)
75.0
4.39 (1H, d, J = 7.9 Hz)
3.43 (1H, dd, J = 9.1, 7.9 Hz)
3.82 (1H, dd, J = 9.5, 9.1 Hz)
4.93 (1H, dd, J = 9.5, 9.5 Hz)
3.56 (1H, m)
104.0
76.1
81.5
70.5
76.0
62.4
4.42 (1H, d, J = 7.9 Hz)
3.43 (1H, dd, J = 9.0, 7.9 Hz)
3.83 (1 H)a
104.5
76.3
81.4
70.5
76.1
62.4
4.92 (1H, dd, J = 9.5, 9.5 Hz)
3.53 (1H, m)
3.57 (1 H)a
3.54 (1 H)a
3.82 (1 H)a
3.87 (1 H)a
Rha
1"
5.19 (1H, d, J = 1.7 Hz)
3.92 (1H, dd, J = 3.1, 1.7 Hz)
3.57 (1H, dd, J = 9.6, 3.1 Hz)
3.30 (1 H)a
103.0
72.3
72.0
73.8
70.4
18.4
5.22 (1H, d, J = 1.7 Hz)
3.92 (1H, dd, J = 3.2, 1.7 Hz)
3.57 (1H, dd, J = 9.7, 3.2 Hz)
3.30 (1 H)a
102.9
72.4
72.0
73.8
70.4
18.4
2"
3"
4"
5"
3.56 (1 H)a
3.56 (1 H)a
6"
1.09 (3H, d, J = 6.2 Hz)
1.10 (3H, d, J = 6.2 Hz)
Caffoyl moiety
1'"
2'"
3'"
4'"
5'"
6'"
7'"
8'"
9'"
127.6
115.2
146.8
149.8
116.5
123.2
148.0
114.7
168.2
127.6
115.2
146.8
149.8
116.5
123.2
148.0
114.6
168.3
7.05 (1H, d, J = 2.0 Hz)
7.05 (1H, d, J = 2.0 Hz)
6.78 (1H, d, J = 8.0 Hz)
6.95 (1H, dd, J = 8.0, 2.0 Hz)
7.56 (1H, d, J = 15.9 Hz)
6.28 (1H, d, J = 15.9 Hz)
6.79 (1H, d, J = 8.2 Hz)
6.96 (1H, dd, J = 8.2, 2.0 Hz)
7.59 (1H, d, J = 15.9 Hz)
6.28 (1H, d, J = 15.9 Hz)
a
Chemical shifts were assigned by HMQC.
Vertisep™ sugar LMP column, 7.8 x 300 mm i.d.; mobile phase water;
flow rate 0.4 ml/min; temperature 80 °C), comparison of the retention
times and the optical rotations with authentic samples. Hydrolysis of
compound 1 yielded peaks corresponding to D-glucose at 19.2 min and
L-rhamnose 23.1 min with positive optical rotations.
Kazuma, K., Noda, N., Suzuki, M., 2003. Malonylated flavonol glycosides from the petals
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This research work was supported by the grant from Chulabhorn
Research Institute, Thailand and Khon Kaen University, Thailand.
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