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Isolation of Pyranocoumarins from Angelica gigas
V.L. Niranjan Reddya, Atul N. Jadhava, Bharathi Avulaa and Ikhlas A. Khana,b*
aNational Center for Natural Products Research, Research Institute of Pharmaceutical Sciences,
The University of Mississippi, University, MS-38677, USA
bDepartment of Pharmacognosy, School of Pharmacy, The University of Mississippi,
University, MS-38677, USA
ikhan@olemiss.edu
Received: November 5th, 2007; Accepted: March 9th, 2008
A mixture of diastereomers of the coumarin glycoside 3′-O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (1), along with six
known pyranocoumarins, columbianoside (4), marmesin (5), 3′-hydroxy-3′,4′-dihydroxanthyletin (6), decursin (7), decursinol
angelate (8), and isoimperatorin (9), were isolated from the roots of Angelica gigas Nakai. The racemic compound 1 was
successfully separated by preparative HPLC to obtain a new isomer 3′(S)-O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (2),
and a known isomer 3′(R)-O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (3). The absolute configuration of compounds 2 and
3 was determined by comparison of optical rotation and NMR data of their acid hydrolysis products.
Keywords: Angelica gigas, Umbelliferae, coumarins.
The plant Angelica gigas Nakai (Umbelliferae) grows
in Korea on moist soils at altitudes of above 200 m
[1]. The roots, also known as Korean angelica (‘Zam
Dang Gui’), are used in traditional medicine as a
sedative, anodyne, tonic and in the treatment of
anemia [1]. A. gigas has been studied extensively
and reported to contain different classes of
chemical constituents that include coumarins,
triterpenoids, essential oils, and polyacetylenes [2].
Pharmacological evaluations of this plant report
antibacterial and antiamnestic effects, depression of
cardiac contraction, activation of protein kinase C,
and antitumor activity [3-5]. A. gigas is known to be
a rich source of coumarins, some of which have been
found to possess neuroprotective activity and shown
to inhibit acetyl cholinesterase [6,7]. Extract of
A. gigas has also been found to possess
antinociceptive effects in various pain models [8].
Recently, we have reported the bioavailability and
blood-brain barrier transport of these compounds [9].
In the present study, we are reporting the isolation
and structural elucidation of six known
pyranocoumarins 4-9, and separation of the mixture
of diastereomers 1 by preparative HPLC to yield a
new compound 2 and a known compound 3, being
reported for the first time from the plant. In addition,
compound 1 was separated into R and S isomers
(2a and 3a) by acetylation (Scheme-1), followed by
purification using reverse phase (RP-18) column
chromatography.
Compound 1 was isolated from the methanolic
extract of roots of A. gigas. This compound showed a
characteristic 1H NMR spectrum for coumarin
compounds with low intensity signals indicating the
presence of isomers. These were successfully
separated into compounds 2 and 3 by reverse phase
HPLC, as detailed in the experimental section.
Compound 2 was a white solid, [α]D25 21.24 (c 0.37,
pyridine), and showed a quasi-molecular ion peak
[M+H+] at m/z 409.1667 in HR-ESIMS, indicating
the molecular formula to be C20H24O9. Signals at
1711 and 1619 cm-1 in the IR spectrum were assigned
to a carbonyl group and an aromatic system of a
coumarin skeleton, respectively. The aromatic region
of the 1H NMR spectrum of 2 revealed a pair of
doublets at δ 6.31 (1H, d, J = 10.0 Hz) and 7.68
(1H, d, J = 9.6 Hz), which were attributed to the
H-3 and H-4 signals of the α-pyrone ring system. It
also revealed a pair of singlets at δ 7.13 (1H, s) and
NPC Natural Product Communications 2008
Vol. 3
No. 5
785 - 790
786 Natural Product Communications Vol. 3 (5) 2008 Niranjan Reddy et al.
*
Ac
2
O/Py
R
+
O O O
HO
R
15% HCl
MeOH, ref lux
Mp: 194-195ºC
[α]
D
= -26.67 (CH Cl
3
,c,0.195)
Mp: 174-175ºC
[α]
D25
=-15.36(CHCl
3
,c,0.155)
Reported [12], Mp. 176-178ºC; [α]
D25
=-13.9(CHCl
3
,c,0.05)
3'(R)-Hydroxy-3',4'-dihydroxanthyletin (11)
3'-O-β-D-glucopyranosyl-3',4'-dihydroxanthyletin (1)
3a
S
O O O
HO
S
15% HCl
MeOH, ref lux
Mp: 194-195ºC
[α]
D
= +29.77 (CHCl
3
, c, 0.04)
3'(S)-Hydroxy-3',4'-dihydroxanthyletin (10)
2a
Mp: 174-175ºC
[α]
D25
= +12.17 (CH Cl
3
,c,0.06)
Reported [12], Mp. 178ºC; [α]
D22
=+10.8(CHCl
3
,c,0.65)
3' 3'
3'
O O O
O
O
OH
OH
HO
HO
O O O
O
O
OAc
OAc
AcO
AcO
3'
O O O
O
O
OAc
OAc
AcO
AcO
Scheme 1: Acetylation and subsequent hydrolysis of compound 1.
Table 1: 1H (400 MHz) and 13C NMR (100 MHz) data of
coumarins 2 and 3 (pyridine-d5, in δ ppm).
3′-(S)-O-β-D-
glucopyranosyl-3′, 4′-
dihydroxanthyletin (2)
3′-(R)-O-β-D-
glucopyranosyl-3′, 4′-
dihydroxanthyletin (3)
Position
1H 13C 13C 1H
2 - 161.5 161.5 -
3 6.31 (d, 10.0 Hz) 112.2 112.4 6.30 (d, 8.4 Hz)
4 7.68 (d, 9.6 Hz) 144.6 144.6 7.62 (d, 9.6 Hz)
5 7.13 (s) 124.1 124.4 7.05 (s)
6 - 126.1 126.1 -
7 - 164.1 164.2 -
8 6.76 (s) 97.7 97.8 6.76 (s)
9 - 156.2 156.3 -
10 - 113.1 113.2 -
2’ - 78.2 78.2 -
3’ 5.00 (t, 7.6 Hz) 91.2 91.1 5.12 (t, 7.6 Hz)
4’ 3.18 (dd, 16.0,
9.2 Hz)
3.56 (dd, 16.0,
8.0 Hz)
30.0 30.3 3.27 (dd, 16.0,
8.8 Hz)
3.48 (dd, 16.0,
7.6 Hz)
Gem
(CH3)2 1.56 (s)
23.8
22.5 24.2
21.8 1.59 (s)
1.44 (s)
1” 5.14 (overlap)* 99.1 99.2 5.09 (d, 8.0 Hz)
2” 3.98(t, 8.0) 75.4 75.5 3.97(overlap)
3” 3.88.-3.91 78.3 78.6 3.97(overlap)
4” 4.20-4.25 71.8 72.0 4.17-4.22
5” 4.25-4.29 78.8 79.0 4.21-4.24
6” 4.30-4.34
62.8 63.1 4.35 (dd, 12.0,
5.7 Hz)
4.56
(br d,11.2 Hz)
6.76 (1H, s), which corresponded to the signals of H-
5 and H-8 of a benzene ring. Together, this indicated
that 2 was a coumarin substituted at C-6 and C-7.
Furthermore, the 1H NMR spectrum revealed signals
at δ 5.00 (1H, t, J = 7.6 Hz, H-3′), δ 3.18 (1H, dd,
J =16.0, 9.2 Hz, Ha-4′), and 3.56 (1H, dd, J =16.0,
8.0 Hz, Hb-4′), which indicated the presence of a
Table 2: 1H (400 MHz) and 13C NMR (100 MHz) data of
coumarins 2a and 3a (CDCl3, in δ ppm).
3′-(S)-(2, 3, 4, 6-tetra-O-acetyl-
β-D-glucopyranosyloxy)-3′, 4′-
dihydroxanthyletin (2a)
3′-(R)-(2, 3, 4, 6-tetra-O-
acetyl-β-D-
glucopyranosyloxy)-3′, 4′-
dihydroxanthyletin (3a)
Position
1H 13C 13C 1H
2 -- 163.2 163.1 --
3 6.21 (1H, d, 9.5 Hz) 112.3 112.4 6.21 (1H, d, 9.5 Hz)
4 7.60 (1H, d, 9.5 Hz) 143.6 143.7 7.60 (1H, d, 9.5 Hz)
5 7.21 (1H, s) 123.3 123.4 7.25 (1H, s)
6 -- 124.9 125.2 --
7 -- 161.4 161.3 --
8 6.69 (1H, s) 97.7 97.6 6.69 (1H, s)
9 -- 155.7 155.6 --
10 -- 112.7 112.8 --
2’ -- 78.5 78.4 --
3’ 4.76 (1H, t, 8.4 Hz) 89.9 90.1 4.69 (1H, t, 8.0 Hz)
4’ 3.18
(1H, dd, 16.8, 10.0 Hz)
3.24
(1H, dd, 16.8, 8.4 Hz)
29.4 29.6 3.13 (1H, dd, 16.8,
9.6 Hz)
3.32 (1H, dd, 16.8,
8.4 Hz)
Gem
(CH3)2 1.37 (3H, s)
1.28 (3H, s) 24.0
20.9 23.9
22.0 1.32 (3H, s)
1.27 (3H, s)
1” 4.79 (1H, d, 8.0 Hz) 95.6 95.6 4.82 (1H, d, 8.0 Hz)
2” 4.92
(1H, dd, 9.6, 8.0 Hz) 71.3 71.6 4.91 (1H, dd, 9.6,
8.0 Hz)
3” 5.21 (1H, t, 9.6 Hz) 72.8 72.9 5.19 (1H, t, 9.6 Hz)
4” 5.02 (1H, t, 9.6 Hz) 68.8 68.7 5.01 (1H, t, 9.6 Hz)
5” 3.72 (1H, m) 71.7 71.6 3.48 (1H, m)
6” 4.21 (1H, dd, 12.0,
2.4 Hz)
4.14 (1H. dd, 12.4,
6.0 Hz)
62.3 61.8 3.83 (1H. dd, 12.4,
4.4 Hz)
3.54 (1H, dd, 12.0,
2.4 Hz)
2”-OAc 1.83 (3H, s) 20.4
169.1 20.5
169.1 1.99 (3H, s)
3”-OAc 1.99 (3H, s) 20.6
169.4 20.6
169.4 1.99 (3H, s)
4”-OAc 2.04 (3H, s) 20.6
170.2 20.6
170.2 1.99 (3H, s)
6”-OAc 2.06 (3H, s) 20.7
170.3 20.7
170.3 2.05 (3H, s)
CH2-CHOH substituted moiety in the molecule.
Comparison with the chemical shifts [12]
and coupling patterns of the skeleton of smyrinol also
Coumarins from Angelica gigas Natural Product Communications Vol. 3 (5) 2008 787
OO O
S
OO O
R
OO O
HO
OO
HO
O
*
OO
O
O
OOO
O
O
O
OO O
O
45
78
9
2.R=H
2a.R=Ac 3.R=H
3a.R=Ac
6
3' 3'
4'
2'
5
6
789
10
2
3
4
1''
2''
3''
4'' 5''
6''
O
O
OR
OR
RO
RO
O
O
OR
OR
RO
RO
O
OO
O
O
OH
OH
HO
HO
H H
Key HMBC Correlations
Figure 1: Pyranocoumarins from Angelica gigas.
also showed an attached group at C-3′. In the HMQC
spectrum (Figure 1), the two proton signals at δ 3.18
and 3.56 correlated with the carbon signal at δ 30.0,
showing a lack of substitution at C-4′. These same
signals (δ 3.18, 3.56) also correlated with the carbon
signals at δ 124.1 (C-5) and 126.1 (C-6) in the
HMBC spectrum, confirming the lack of substitution.
The signals at δ 99.1 (C-1′′), 75.4 (C-2′′), 78.3
(C-3′′), 71.8 (C-4′′), 78.9 (C-5′′), and 62.8 (C-6′′) in
the 13C NMR spectrum were due to the presence of a
glucose moiety, as confirmed by hydrolysis and TLC
with a standard. In the HMBC spectrum, the proton
signal at δ 5.14 (C1′′ -H) correlated with the carbon
signal at δ 91.2 (C-3′), which indicated that the
glucose moiety is attached to C-3′. Thus, compound
2 was elucidated as 3′-(S)-O-β-D-glucopyranosyl-
3′,4′-dihydroxanthyletin. Using optical rotation in
addition to 1D and 2D NMR data, compound 3 was
elucidated as 3′-(R)-O-β-D-glucopyranosyl-3′,4′-
dihydroxanthyletin, earlier reported from
Peucedanum dissolutum with the same sign of optical
rotation [12].
In order to prove this, we re-investigated the obtained
racemic compound 1 by acetylation (Ac2O/Py),
followed by chromatography on a reverse phase
(RP-18) column to obtain 3′(S)-(2,3,4,6-tetra-O-
acetyl-β-D-glucopyranosyloxy)-3′,4′-dihydroxanthy-
letin (2a) [[α]D25 +29.76º (c 0.04, CHCl3)] and 3′(R)-
(2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3′,
4′-dihydroxanthyletin (3a) [[α]D25 -26.66º (c 0.195,
CHCl3)]. The signals in the 1H NMR and 13C NMR
spectra were assigned by HMQC and HMBC
correlations and are listed in the experimental
section. Acid hydrolysis of 2a and 3a gave products
that were identified as 3′-(S)-hydroxy-3′, 4′-
dihydroxanthyletin (10) and 3′-(R)-hydroxy-3′, 4′-
dihydroxanthyletin (11), respectively, by comparison
of spectral data and optical rotations with those
reported in the literature [11-12]. Optical rotation was
used to assign the absolute configuration of C-3′ in 2
and 3 as S and R, respectively. Thus, these chemical
structures were elucidated as 3′-(S)-O-β-D-
glucopyranosyl-3′,4′-dihydroxanthyletin (2) and 3′-
(R)-O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin
(3).
Compound 2 is a new natural product, whereas
compound 3 is being reported for the first time from
A. gigas.
788 Natural Product Communications Vol. 3 (5) 2008 Niranjan Reddy et al.
Experimental
General procedures: Melting points were taken on a
Thomas Hoover Unimelt capillary-melting-point
apparatus, and UV spectra were recorded on a Varian
Cary 50 Bio UV-visible spectrophotometer. Optical
rotations were measured on an Autopol-IV
polarimeter. IR spectra were recorded on a Bruker
Tensor-27 FT-IR spectrometer. NMR spectra
(1H, 13C, COSY, HMQC, and HMBC) were recorded
in CDCl3 or DMSO-d6 on a Bruker DRX 400
spectrometer operating at 400 MHz for 1H and 100
MHz for 13C, running gradients and using residual
solvent peaks as internal references. For compound 2
and 3, the NMR spectra were recorded on a Varian
400 NMR spectrometer in pyridine-d5. The high-
resolution mass spectrum of 2 was acquired on an
Agilent Series 1100 SL spectrometer. Column
chromatography was performed using silica gel
(40 μm, J. T. Baker) and reversed-phase silica gel
(RP-18, 40 μm, J. T. Baker). Preparative HPLC was
performed on a Waters LC Module-I-Plus with a
Synergy Max RP-18, 80 Å column (250 X 10 mm,
4μ).
Plant materials: Roots of A. gigas were obtained
from Korea (Jinbo Kangwondo) and a voucher
specimen (No. 2994 ANGIA) has been deposited at
the NCNPR repository, University of Mississippi,
Mississippi, USA.
Extraction and isolation: The dried powdered roots
(1.0 kg) of A. gigas were extracted with CHCl3 (4 ×
3L) and MeOH (3 × 3L) using an ultrasonic bath.
After the removal of solvent in vacuo, the CHCl3 and
MeOH extracts yielded 117.7 g and 40.2 g,
respectively. The CHCl3 extract was subjected to
silica gel column chromatography using gradient
elution with mixtures of n-hexane-EtOAc-MeOH to
afford seven fractions (Fraction 1-7). Fraction 2 (1.23
g) was subjected to silica gel column chromatography
with n-hexane: EtOAc (97:3) yielding compound 9
(6 mg). Fraction 3 (76.25 g) yielded a mixture of
structural isomers 7 and 8 [9]. Fraction 5 (4.34 g)
was subjected to C18 RP silica gel column
chromatography with n-hexane:EtOAC:acetone
(5:4:1) and yielded compound 5 (3.2 mg) and
crude compound 6 (11.0 mg). The pure compound 6
(3.1 mg) was obtained by silica gel column
chromatography eluting with n-hexane:EtOAc (1:1).
Fraction 6 (1.73 g) was subjected to silica gel column
chromatography eluting with CHCl3:MeOH (9:1) and
yielded compounds 4 (8 mg) and 1 (40 mg). Fraction-
7 (2.3 g) was subjected to Sephadex LH-20 column
chromatography eluting with DCM:MeOH (1:1) to
obtain compound 4 (80 mg).
The MeOH extract (30.1 g) was suspended in
aqueous methanol and partitioned with n-hexane and
CHCl3. After concentrating the aqueous fraction,
24.3 g of crude extract was obtained. A portion of
this (20.4 g) was subjected to C18 RP silica gel
column chromatography using MeOH:H2O (7:3).
This yielded compound 1 (3.2 g), which was further
purified on silica gel column chromatography eluting
with CHCl3:MeOH (9:1) to afford a mixture of
diastereomers (1) (1.8 g). This mixture (25 mg) was
purified by preparative HPLC on a Synergy Max RP-
18, 80 Å column (250 X 10 mm, 4μ), eluting with
H2O-Reagent alcohol-ACN (83:15:2) at 3 mL/min to
obtain compounds 2 (5 mg, tR 48.0 min) and 3 (12
mg, tR 52.0 min).
3′(S)-O-β-D-Glucopyranosyl-3′, 4′-dihydroxanthy-
letin (2)
White solid.
MP: 212-214ºC.
[α]D25: 21.52 (c 0.37, pyridine).
IR
ν
max: 3254, 2875, 1711, 1619, 1565, 1445, 1390,
1260, 1076, 1033, 893, 849 cm-1.
UV λmax: 334 nm.
1H NMR (400 MHz, pyridine-d5): Table 1.
13C NMR: (100 MHz, pyridine-d5): Table 1.
HR ESIMS: m/z: 409.1667 (C20H24O9 calcd.
409.1500 for [M + H]+).
3′(R)-O-β-D-Glucopyranosyl-3′, 4′-dihydroxanthy-
letin (3)
White solid.
MP: 212-214ºC.
[α]D25: -21.24 (c 0.37, pyridine).
IR
ν
max: 2874, 1713, 1621, 1563, 1447, 1390, 1256,
1073, 1028, 849 cm-1.
UV λmax: 334 nm.
1H NMR (400 MHz, pyridine-d5): Table 1.
13C NMR: (100 MHz, pyridine-d5): Table 1.
HR ESIMS: m/z: 409.1658 (C20H24O9 calcd.
409.1500 for [M + H]+).
Acetylation of 3′-O-
β
-D-glucopyranosyl-3′, 4′-
dihydroxanthyletin (1): Compound 1 (200 mg) was
dissolved in pyridine (1 mL) and acetic anhydride (4
mL). The solution was warmed in a hot-water bath
for 1 h and then left overnight in the dark. The crude
Coumarins from Angelica gigas Natural Product Communications Vol. 3 (5) 2008 789
product was washed with water followed by 10%
HCl and then extracted with EtOAc. The EtOAc
layer was concentrated under reduced pressure to
give a crude product, which was purified by C18 RP
silica gel column chromatography using the non-
protic solvent n-hexane: EtOAc (1:1). This gave pure
compounds 3′-(S)-(2, 3, 4, 6-tetra-O-acetyl-β-D-
glucopyranosyloxy)-3′,4′-dihydroxanthyletin (2a, 55
mg) and 3′-(R)-(2, 3, 4, 6-tetra-O-acetyl-β-D-
glucopyranosyloxy)-3′,4′-dihydroxanthyletin (3a, 45
mg).
3′-(S)-(2, 3, 4, 6-Tetra-O-acetyl-β-D-glucopyrano-
syloxy)-3′,4′-dihydroxanthyletin (2a)
White solid.
MP:194-195ºC.
[α]D25: +29.77 (c 0.04, CHCl3).
IR
ν
max: 1743, 1719, 1625, 1564, 1487, 1366, 1257,
1229, 1121, 1088, 1040, 959, 909, 851, 719 cm-1.
UV λmax: 335, 195 nm.
1H NMR (400 MHz, CDCl3): Table 2.
13C NMR: (100 MHz, CDCl3): Table 2.
HR ESIMS: m/z: 577.1901 (C28H32O13 calcd
577.1923 for [M + H]+).
3′-(R)-(2, 3, 4, 6-Tetra-O-acetyl-β-D-glucopyrano-
syloxy)-3′,4′-dihydroxanthyletin (3a)
White solid.
MP: 194-195ºC.
[α]D25: -26.66 (c 0.195, CHCl3).
IR
ν
max: 2922, 1738, 1714, 1628, 1566, 1490, 1446,
1398, 1363, 1259, 1214, 1088, 1178, 1146, 1124,
1092, 1048, 964, 908, 856, 825 cm-1.
UV λmax: 335, 195 nm.
1H NMR (400 MHz, CDCl3): Table 2.
13C NMR: (100 MHz, CDCl3): Table 2.
HR ESIMS: m/z: 577.1889 (C28H32O13 calcd
577.1923 for [M + H]+).
Acid hydrolysis of 3′-(S)-(2, 3, 4, 6-tetra-O-acetyl-
β-D-glucopyranosyloxy)-3′,4′-dihydroxanthyletin
(2a): Compound 2a (15 mg) was dissolved in MeOH
(5 mL), 15% HCl (2 mL) was added, and the reaction
mixture refluxed for 1 h. The solution was
neutralized with 10% NaOH, and extracted with
CHCl3. The CHCl3 layer was dried with Na2SO4 and
concentrated under reduced pressure. The residue
was purified by silica gel column chromatography
with n-hexane:EtOAc (2:3) to give 3′(S)-hydroxy-
3′,4′-dihydroxanthyletin (10, 3.1 mg).
3′(S)-Hydroxy-3′,4′-dihydroxanthyletin (10)
White solid.
MP: 174-175ºC; 178ºC [2].
[α]D25: +12.17 (c 0.06, CHCl3); +10.8 (c 0.65,
CHCl3) [2].
IR
ν
max: 3583, 3493, 3250, 2925, 2854, 2394, 1712,
1632, 1370, 1261, 1117, 952 cm-1.
1H NMR (400 MHz, CDCl3): δ 6.19 (1H, d, J = 9.2
Hz, H-3), 7.57 (1H, d, J = 9.2 Hz, H-4), 7.19 (1H, s,
H-5), 6.72 (1H, s, H-8), 4.71 (1H, t, J = 8.2 Hz, H-3′),
3.62 (1H, bs, 3′-OH), 3.19 (2H, dd, J = 12.0, 10.0 Hz,
H-4′), 1.35 (3H, s, C-2′-CH3), 1.23 (3H, s, C-2′-CH3).
HR ESIMS: m/z: 247.1002 (C14H14O4 calcd 247.0992
for [M + H]+).
Acid hydrolysis of 3′-(R)-(2, 3, 4, 6-tetra-O-acetyl-
β-D-glucopyranosyloxy)-3′,4′-dihydroxanthyletin
(3a): Compound 3a (10 mg) was dissolved in MeOH
(5 mL), 15% HCl (2 mL) was added, and the reaction
mixture refluxed for 1 h. The solution was
neutralized with 10% NaOH, and extracted with
CHCl3. The CHCl3 layer was dried with Na2SO4 and
concentrated under reduced pressure. The residue
was purified by preparative TLC, developed with
n-hexane:EtOAc (2:3) to give 3′(R)-hydroxy-3′,4′-
dihydroxanthyletin (11, 2.1 mg).
3′-(R)-Hydroxy-3′, 4′-dihydroxanthyletin (11)
White solid.
MP: 174-175ºC; 176-178ºC [2].
[α]D25: -15.36 (c 0.155, CHCl3); -13.9 (c 0.05,
CHCl3) [2].
IR
ν
max: 3488, 2923, 2852, 2392, 2348, 2283, 1709,
1631, 1461, 1400, 1269, 1139, 950, 818 cm-1.
1H NMR (400 MHz, CDCl3): δ 6.21 (1H, d, J = 9.6
Hz, H-3), 7.59 (1H, d, J = 9.6 Hz, H-4), 7.21 (1H, s,
H-5), 6.74 (1H, s, H-8), 4.73 (1H, t, J = 8.4 Hz, H-3′),
3.64 ((1H, bs, 3′-OH), 3.21 (2H, dd, J = 12.4, 9.2 Hz,
H-4′), 1.37 (3H, s, C-2′-CH3), 1.23 (3H, s, C-2′-CH3).
HR-ESIMS: m/z: 247.0989 (C14H14O4 calcd
247.0992 for [M + H]+).
Acknowledgments - Authors are thankful to Dr
Young-Whan Choi for the plant material and
Christina Coleman for reading the manuscript. This
research was funded in part by “Botanical Dietary
Supplements: Science-Base for Authentication”
funded by the Food and Drug Administration grant
number FD-U-002071-06.
790 Natural Product Communications Vol. 3 (5) 2008 Niranjan Reddy et al.
References
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