全 文 ：· 82 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (1): 82−86



Minor new constituents from Heteroplexis micocephala
FAN Xiao-na, LIN Sheng, ZHU Cheng-gen, YANG Yong-chun, SHI Jian-gong*
(Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education of PRC,
Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China)
Abstract: By using a combination of various chromatographic techniques including column chromatography
over silica gel and Pharmadex LH-20 and reversed-phase HPLC, two minor new compounds, labda-12, 14-dien-
6β, 7α, 8β, 17-tetraol (1), 2, 3-cis-6-acetyl-5-hydroxy-2-(hydroxymethylvinyl)-2, 3-dihydrobenzofuran-3-ol angelate
(2), and a minor new natural product 6-methoxy-4-methyl-3, 4-dihydro-2H-naphthalen-1-one (3) have been isolated
from an ethanolic extract of Heteroplexis micocephala. Their structures were elucidated with spectroscopic
data analysis including 2D NMR experiments.
Key words: Heteroplexis micocephala; minor constituent; diterpene; benzofuran derivative; 3, 4-dihydro-
2H-naphthalen-1-one derivative
CLC number: R284.1 Document code: A Article ID: 0513-4870 (2010) 01-0082-05
小花异裂菊中的微量新成分
樊晓娜, 林 生, 朱承根, 杨永春, 石建功*
(中国医学科学院、北京协和医学院药物研究所, 中草药物质基础与资源利用教育部重点实验室, 北京 100050)

摘要: 通过硅胶和 Pharmadex LH-20 凝胶柱色谱以及反相 HPLC 等多种分离技术的组合应用, 从小花异裂菊
全草乙醇提取物中分离得到了 2 个微量新化合物: 半日花烷-12, 14-二烯-6β, 7α, 8β, 17-四醇 (1) 和 2, 3-顺式-6-
乙酰基-5-羟基-2-(羟甲基乙烯基)-2, 3-二氢苯并呋喃-3-醇当归酸酯 (2), 以及 1 个微量新天然产物: 6-甲氧基-4-甲
基-3, 4-二氢-2H-1-萘酮 (3)。运用包括二维核磁共振实验的波谱学数据解析确定了它们的结构。
关键词: 小花异裂菊; 微量成分; 二萜; 苯并呋喃衍生物; 3, 4-二氢-2H-萘-1-酮衍生物

Heteroplexis (Compositae) is an unique genus
divided from the genus Aster L. This genus consists
of only five species distributed in the limestone terrains
of Longzhou and Yangshuo, Guangxi Province,
mainland China. H. micocephala Y. L. Chen is a member
planted and used as a folk medicine for treatment of
indigestion and dropsy[1]. As part of a program to
assess the chemical and biological diversity of traditional
Chinese medicines[2], we carried out an investigation of

Received 2009-09-29.
Project supported by the National Natural Sciences Foundation of
China (30825044 and 20432030); the Program for
Changjiang Scholars and Innovative Research Team
in University (IRT0514); the national “973” program
of China (2004CB13518906 and 2006CB504701).
*Corresponding author Tel: 86-10-83154789, E-mail: shijg@imm.ac.cn
an ethanolic extract of this plant. In the previous
paper, we reported the isolation, structural elucidation
and in vitro bioassays of 11 new compounds including
two sesquiterpenes with an unusual 2, 2, 5, 9-tetra-
methylbicyclo[6.3.0] undecane carbon skeleton, five
phytane-type diterpene dilactones, an ent-clerodane
diterpene dilactone, and three phenylpropenol esters,
together with a diacylphenol and 38 known compounds[3].
This paper deals with the isolation and structure
characterization of three minor new compounds, labda-
12, 14-dien-6β, 7α, 8β, 17-tetraol (1), 2, 3-cis-6-acetyl-5-
hydroxy-2-(hydroxymethylvinyl)-2, 3-dihydrobenzofuran-
3-ol angelate (2) and 6-methoxy-4-methyl-3, 4-dihydro-
2H-naphthalen-1-one (3), from a continues investigation
on the same material (Figure 1).
DOI:10.16438/j.0513-4870.2010.01.008
FAN Xiao-na, et al: Minor new constituents from Heteroplexis micocephala · 83 ·


Figure 1 Structures of compounds 1−3

Results and discussion
Compound 1, a white amorphous powder, [α] 20D
+11.0 (c 0.17, MeOH), showed the presence of hydroxy
groups (3 356 cm−1) in its IR spectrum. The (+)-ESI-
MS of 1 exhibited quasi-molecular ion peaks at m/z 361
[M+Na]+ and 377 [M+K]+, and the (+)-HR-ESI-MS at
m/z 361.236 9 [M+Na]+ suggested a molecular formula
of C20H34O4 (calcd. for C20H34O4Na, 361.235 5) for
1, with four degrees of unsaturation. The 1H NMR
spectrum of 1 displayed signals (Table 1) attributed to a
mono-substituted vinyl unit at δ 5.01 (1H, d, J = 17.0
Hz, H-15a), 4.83 (1H, d, J = 10.5 Hz, H-15b), and 6.34
(1H, dd, J = 17.0, 10.5 Hz, H-14), a tri-substituted
double bond at δ 5.58 (1H, t, J = 7.0 Hz, H-12), an
olefinic methyl at δ 1.74 (3H, s, H3-16), and an olefinic
methylene at δ 2.55 (1H, m, H-11a) and 2.17 (1H, m,
H-11b). These data indicated the presence of a 13-
methylpenta-12, 14-dien-11-yl unit in 1. In addition,
the 1H NMR spectrum showed signals assignable to an
isolated hydroxymethylene unit at δ 4.55 (1H, dd, J =
11.0, 4.0 Hz, H-17a) and 3.53 (1H, m, H-17b), two
oxymethines at δ 4.35 (1H, br s, H-6) and 3.50 (1H, br s,
H-7), and three tertiary methyls at δ 1.24 (3H, s, H3-19),
1.18 (3H, s, H3-20), and 0.97 (3H, s, H3-18), as well as
partially overlapped multiplets integrating for eight
protons attributable to three methylenes and two
methines between δ 1.50 and 0.83. Four exchangeable
broadened singlets at δ 4.74 (1H, br s), 4.06 (1H, br s),
3.83 (1H, br s), and 3.61 (1H, br s) indicated the
presence of four hydroxy groups in 1. The 13C NMR
and DEPT spectra of 1 showed 20 carbon resonances
(Table 1) corresponding to the above units and three
additional quaternary carbons (an oxygen-bearing).
These spectroscopic data suggested that 1 was a
bicyclic diterpene containing the 13-methylpenta-12, 14-
dien-11-yl unit and four hydroxy groups.
The structure of 1 was finally elucidated from the
2D NMR spectroscopic data. Analysis of the 1H-1H
COSY and HSQC spectroscopic data provided an
unambiguous assignment of the proton and carbon
Table 1 1H and 13C NMR data of compounds 1 and 3a
1 3
Position
δH δC

δH δC
1a 1.48 (m) 42.8 196.2
1b 0.89 (m)
2a 1.32 (m) 19.4 2.66 (m) 36.4
2b 2.46 (m)
3a 1.29 (m) 44.3 2.20 (m) 31.4
3b 1.85 (m)
4 34.7 3.08 (m) 33.8
4a 152.3
5 1.01 (br s) 56.1 6.89 (s) 112.6
6 4.35 (br s) 72.2 164.7
7 3.50 (br s) 83.3 6.88 (d, J = 8.5 Hz) 113.5
8 76.3 7.89 (d, J = 8.5 Hz) 129.9
8a 126.4
9 1.41 (m) 60.4
10 39.8
11a 2.55 (m) 23.9
11b 2.17 (m)
12 5.58 (t, J = 7.0 Hz) 138.5
13 132.1
14 6.34 (dd, J = 17.0, 10.5 Hz) 142.9
15a 5.01 (d, J = 17.0 Hz) 109.8
15b 4.83 (d, J = 10.5 Hz)
16 1.74 (s) 11.9
17a 4.55 (dd, J = 11.0, 4.0 Hz) 65.0
17b 3.53 (m)
18 0.97 (s) 24.1
19 1.24 (s) 33.5
20 1.18 (s) 17.4
HO 4.74, 4.06, 3.83, 3.61 (br s)
OMe-6 3.87 (s) 55.8
Me-4 1.38 (d, J = 7.0 Hz) 20.8
aData were measured in acetone-d6 at 500 MHz for 1H NMR and
125 MHz for 13C NMR. Proton coupling constants (J) in Hz are
given in parentheses. The assignments are based on DEPT,
1H-1H COSY, HSQC and HMBC experiments

resonances in the NMR spectra of 1 (Table 1). COSY
cross-peaks (Figure 2, thick lines) for H2-11/H-12 and
H-14/H2-15 and HMBC correlations (Figure 2, blue
single arrows) from H3-16 to C-12, C-13 and C-14,
from H2-15 to C-13 and C-14, and from H2-11 to C-12
and C-13, in combination with the chemical shifts of
these protons and carbons, confirmed the presence of
the 13-methylpenta-12, 14-dien-11-yl unit in 1. Cross-
peaks of H2-2 with both H2-1 and H2-3 and H-6 with
both H-5 and H-7 in the 1H-1H COSY spectrum and
HMBC correlations from H-5 to C-6, C-7, C-9, and
C-10, from H-6 to C-8 and C-10, from H-7 to C-5 and
C-8, from H-9 to C-8 and C-17, from H2-17 to C-7 and
C-8, from both H3-18 and H3-19 to C-3, C-4, and
· 84 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (1): 82−86

C-5, and from H3-20 to C-1, C-5, C-9, and C-10,
together with the coupling patterns and chemical shift
of these protons and carbons, indicated unambiguously
the presence of a bicyclic 8-hydroxymethyl-4, 4, 10-
trimethyl-decahydronaphthalene-6, 7, 8-triol moiety in
1. In addition, a COSY cross-peak for H-9/H-11 and
HMBC correlations from H2-11 to C-8, C-9 and C-10
indicated that the 13-methylpenta-12, 14-dien-11-yl unit
located at C-9 of the bicyclic ring moiety. This
suggested a labdane diterpene planner structure of
labda-12, 14-dien-6, 7, 8, 17-tetraol for 1.


Figure 2 Main 1H-1H COSY (thick lines) and selected NOE
enhancements (red double arrows ) observed for compound 1,
and HMBC correlations (blue single arrows) for compounds 1
and 2

The relative stereochemistry of 1 was elucidated
with a combination analysis of the NOE difference data,
vicinal coupling constants and chemical shifts. In the
NOE difference spectrum of 1, irradiation of H-12
enhanced H-14 (Figure 2, red double arrows), indicating
that the double bond between C-12 and C-13 had a trans-
configuration. This was supported by the chemical shift
of H-14[3, 4]. Irradiation of H-11b or H-17a enhanced
H-20, H-11a and H-6 were enhanced by irradiation of
H-17b. H-17b and H3-18 were enhanced by irradiation
of H-6. These NOE enhancements indicated that H-6,
H2-11, H2-17, H3-18, and H3-20 were oriented on the
same side of the bicyclic ring system. In addition,
H-5, H-9, and H3-19 were enhanced by irradiation of
H-7, indicating these protons were oriented on another
side of the bicyclic ring system. The positive specific
rotation of 1 suggested that it possesses the absolute
stereochemistry identical to that of austroinulin[4−6].
Therefore, the structure of 1 was determined as labda-
12, 14-dien- 6β, 7α, 8β,17-tetraol.
Compound 2, a yellowish oil, [α] 20D +11.9 (c 0.52,
MeOH), showed the presence of hydroxy (3 455 cm−1),
ketone (1 649 and 1 632 cm−1) and conjugated carbonyl
(1 714 cm−1) groups in its IR spectrum. The ESI-MS
of 2 gave a quasi-molecular ion peak at m/z 355
[M+Na]+, and HR-ESI-MS at m/z 355.116 2 [M+Na]+
indicated a molecular formula of C18H20O6 (calcd. for
C18H20O6Na, 355.115 2) for 2. The 1H NMR spectrum
of 2 (Table 2) displayed characteristic signals attributed
to a 1, 2, 4, 5-tetrasubstituted phenyl moiety at δ 7.43
(1H, s, H-7) and 7.06 (1H, s, H-4), an aromatic acetyl at
δ 2.68 (s, H3-12), and a phenolic proton at δ 12.13 (s,
HO-5), as well as signals assignable to two oxymethines
at δ 6.32 (1H, d, J = 2.8 Hz, H-3) and 5.26 (1H, d, J =
2.8 Hz, H-2). In addition, it showed signals attributed
to a terminal double bond at δ 5.23 (1H, s, H-9a) and
5.17 (1H, s, H-9b), a hydroxymethylene unit at δ 4.22
(2H, d, J = 5.6 Hz, H2-10) and 4.02 (1H, t, J = 5.6 Hz,
exchangeable, HO-10), and an angeloyl unit at δ 6.18
(1H, qd, J = 7.2, 1.2 Hz, H-3), 1.94 (3H, dd, J = 7.2, 1.2
Hz, H3-4), and 1.84 (3H, br s, H3-5). The 13C NMR
spectrum of 2 showed 18 carbon resonances (Table 2)
corresponding to the above units. These spectroscopic
data are similar to those of 3-hydroxy-2, 3-dihydro-euparin
derivatives[5], suggesting that 2 is a tetrasubstituted
dihydrobenzofuran derivative with phenolic hydroxy
and acetyl groups, and hydroxymethylene, terminal
double bond, and angeloyloxy units as substituents.

Table 2 1H and 13C NMR data of compound 2a
2 (acetone-d6) 2 (benzene-d6)
Position
δH δC

δH
2 5.26 (d, J = 2.8 Hz) 88.6 5.26 (br s)
3 6.32 (d, J = 2.8 Hz) 78.2 6.19 (d, J = 1.8 Hz)
3a 134.9
4 7.06 (s) 116.9 6.76 (s)
5 158.1
6 121.3
7 7.43 (s) 110.9 7.15 (s)
7a 153.9
8 146.7
9a 5.23 (s) 112.2 5.20 (s)
9b 5.17 (s) 5.04 (s)
10a 4.22 (d, J = 5.6 Hz) 62.5 4.08 (d, J = 13.2 Hz)
10b 4.22 (d, J = 5.6 Hz) 62.5 4.03 (d, J = 13.2 Hz)
11 206.1
12 2.68 (s) 27.3 1.78 (s)
1 167.6
2 128.0
3 6.18 (qd, J = 7.2, 1.2 Hz) 139.8 5.65 (qd, J = 7.2, 1.2 Hz)
4 1.94 (dd, J = 7.2, 1.2 Hz) 16.0 1.84 (dd, J = 7.2, 1.2 Hz)
5 1.84 (br s) 20.5 1.70 (br s)
HO-5 12.13 (s) 12.54 (s)
HO-10 4.02 (t, J = 5.6 Hz)
aData were measured in acetone-d6 and benzene-d6 at 500 MHz
for 1H NMR, and in acetone-d6 at 125 MHz for 13C NMR. Proton
coupling constants (J) in Hz are given in parentheses. The
assignments are based on DEPT, HSQC and HMBC experiments
FAN Xiao-na, et al: Minor new constituents from Heteroplexis micocephala · 85 ·

The structure of 2 was further deduced from the
2D NMR spectroscopic data. The HSQC spectroscopic
data analysis provided an unambiguous assignment of
the proton and protonated carbon resonances in the
NMR spectra of 2. In the HMBC spectrum of 2, two-
and three-bond heteronuclear correlations (Figure 2,
blue single arrows) from H-2 to C-3 and C-3a, from
H-3 to C-3a and C-7a, from H-4 to C-3, C-5, C-6, and
C-7a, from H-7 to C-3a, C-5, C-7a, from HO-5 to C-4,
C-5, and C-6, and from H3-12 to C-6, in combination
with chemical shifts of these protons and carbons, indi-
cated unambiguously the presence of a 2-substituted and
3-oxygenated 6-acetyl-5-hydroxybenzofuran moiety in
2. In addition, HMBC correlations from H-2 to C-8
and C-9, from H-3 to C-8, from H2-9 to C-2 and C-10,
and from H2-10 to C-8 and C-9, together with chemical
shifts of these protons and carbons, indicated
unequivocally that there was a hydroxymethylvinyl unit
located at C-2 of the benzofuran moiety to form a
parent structure of 2. Although the HMBC spectrum
did not show a correlation from H-3 to the carbonyl of
the angeloyl unit due to a limitation of the sample
amount available, the chemical shift of H-3 and the
coupling patterns of the exchangeable hydroxy protons
in the 1H NMR in Me2CO-d6 indicated that the angeloyl
must be located at C-3 of the parent structure in 2.
Furthermore, the coupling constant between H-2 and
H-3 (1.8 Hz) in the 1H NMR spectrum of 2 in C6D6,
together with the positive specific rotation data of 2,
suggested that the two protons are cis-oriented[5]. The
relative stereochemistry of 2 was further confirmed by
the NOESY spectrum that showed cross-peaks between
H-2 and H-3 and between H-3 and H3-5. Therefore,
the structure of 2 was determined as 2, 3-cis-6-acetyl-5-
hydroxy-2-(hydroxymethylvinyl)-2,3-dihydrobenzofuran-3-
ol angelate. Its absolute configuration was not deter-
mined yet.
Compound 3 was obtained as a yellowish oil, [α] 20D
−0.2 (c 0.18, MeOH), showed IR absorption bands for
conjugated carbonyl (1 677 cm−1) and aromatic (1 598
cm−1) groups. Its EI-MS exhibited a molecular ion
peak at m/z 190 [M]+, and the HR-EI-MS at m/z
190.097 7 [M]+ suggested a molecular formula of
C12H14O2 (cacld for C12H14O2, 190.099 4). The 1H NMR
spectrum of 3 (Table 1) displayed characteristic signals
of an ABX spin system assignable to a trisubstituted
phenyl moiety at δ 7.89 (1H, d, J = 8.5 Hz, H-8), 6.89
(1H, s, H-5) and 6.88 (1H, d, J = 8.5 Hz, H-7), and
an aromatic methoxy group at δ 3.87 (3H, s, OMe-6).
In addition, the 1H NMR spectrum showed signals
attributed to a methyl at δ 1.38 (3H, d, J = 7.0 Hz, Me-4),
a methine at δ 3.08 (1H, m, H-4), and two methylenes
at δ 2.66 (1H, m, H-2a), 2.46 (1H, m, H-2b), 2.20 (1H,
m, H-3a), and 1.85 (1H, m, H-3b). The 13C NMR and
DEPT spectra of 3 showed 12 carbon resonances (Table
1) corresponding to the above structural units and a
conjugated ketone carbonyl at δC 196.2. These data
indicated that the structure of 3 was 6-methoxy-4-
methyl-3, 4-dihydro-2H-naphthalen-1-one reported as an
intermediate in the synthesis of trans-6α, 8β-dimethyl-
1β-hydroxy-4, 5-(4-methoxy-benzo) hydrindane[7] and
3-(2-hydroxy-isopropyl)-5, 8-dimethyl-2-naphtholmethyl
ether (emmotin-G methyl ether)[8]. The data were well
in agreement with those reported in the literature, and the
structure of 3, as a new natural product, was confirmed
by 2D NMR spectroscopic data. The specific rotation
of 3 is approximately zero, suggesting that it may be
obtained as a meso-mixture.

Experimental
General experimental procedures Optical rota-
tions were measured on a PE model 343 polarimeter.
IR spectra were recorded on a Nicolet 5700 FT-IR
microscope spectrometer (FT-IR microscope transmission).
1D- and 2D-NMR spectra were obtained at 500 MHz
for 1H and 125 MHz for 13C, respectively, on INOVA
500 MHz spectrometers in acetone-d6 with solvent
peaks as references. ESI-MS data were measured with
a Q-Trap LC/MS/MS (Turbo Ionspray source) spec-
trometer. EI-MS and HR-EI-MS data were measured
with a Micromass Autospec-Ultima ETOF spectrometer.
HR-ESI-MS data were measured using JMS-T100CS
AccuToF CS spectrometer. Column chromatography
was performed with silica gel (200−300 mesh, Qingdao
Marine Chemical Inc. Qingdao, People’s Republic of
China) and Pharmadex LH-20 (Amersham Biosciences
Inc. Shanghai, People’s Republic of China). HPLC
separation was performed on an instrument consisting
of a Waters 600 controller, a Waters 600 pump, and a
Waters 2 487 dual λ absorbance detector, with a Prevail
(250 mm × 10 mm ID) column packed with C18 (5 μm).
TLC was carried out with glass precoated silica gel
GF254 plates. Spots were visualized under UV light
or by spraying with 7% H2SO4 in 95% EtOH followed
by heating.
Plant material The herbs of H. micocephala
were collected at Dayao mountain, Guangxi Province,
People’s Republic of China, in 2003. The plant was
· 86 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (1): 82−86

identified by Mr. Guang-ri Long (Guangxi Forest
Administration, Guangxi 545005, China). A voucher
specimen (no. YG 01025) was deposited at the Herbarium
of the Department of Medicinal Plants, Institute of
Materia Medica.
Extraction and isolation The air-dried plant
material of H. micocephala (2.56 kg) was powdered
and extracted with 95% EtOH at room temperature.
The EtOH extract was evaporated under reduced pres-
sure below 40 ℃ to yield a dark green residue (270.0
g). The residue was suspended in H2O (1 500 mL)
and then partitioned with EtOAc (4 × 1 500 mL). After
removal of solvent, the EtOAc extract (125.0 g) was
applied to a normal-phase silica gel column. Successive
elution of the column with a gradient of increasing
EtOAc concentration (2%−100%) in petroleum ether,
afforded 12 fractions (A1−A12) on the basis of TLC
analysis. Fraction A5 (15.3 g), eluted by 20% EtOAc in
petroleum ether, was chromatographed over Pharmadex
LH-20 with CHCl3-MeOH (2∶1) as a mobile phase to
give four subfractions (A5-1−A5-4). Fraction A5-2
(3.4 g) was separated by reverse-phase preparative
HPLC using 46% MeOH in H2O as a mobile phase to
yield 1 (1.3 mg). Fraction A7 (30.2 g), eluted by 60%
EtOAc in petroleum ether, was subjected to CC over
normal-phase silica gel with a gradient of increasing
MeOH (0−100%) in CHCl3, to yield eight subfractions
(A7-1−A7-8). A7-2 (2.5 g) was separated by reverse-
phase preparative HPLC, using a mobile phase of 45%
MeOH in H2O, to yield 2 (1.5 mg). A7-5 (4.3 g) was
separated by reverse-phase preparative HPLC, using a
mobile phase of 40% MeOH in H2O, to yield 3 (0.9 mg).
Identification
Labda-12, 14-dien-6β, 7α, 8β, 17-tetraol (1) white,
amorphous powder; [α] 20D +11.0 (c 0.17, MeOH); UV
(MeOH) λmax (log ε): 195 (4.69), 232 (5.06) nm; IR νmax:
3 356, 2 927, 1 465, 1 442, 1 385, 1 365 cm−1; 1H NMR
(acetone-d6, 500 MHz) and 13C NMR (acetone-d6, 125
MHz) data see Table 1; ESI-MS m/z 361 [M+Na]+, 377
[M+K]+, 699 [2M+Na]+; HR-ESI-MS m/z 361.236 9
[M+Na]+ (cacld for C20H34O4Na, 361.235 5).
2,3-cis-6-Acetyl-5-hydroxy-2-(hydroxymethylvinyl)-
2, 3-dihydrobenzofuran-3-ol angelate (2) yellowish
oil; [α] 20D +11.9 (c 0.52, MeOH); IR νmax: 3 455, 2 954,
2 927, 2 868, 1 714, 1 649, 1 632, 1 593, 1 485, 1 429,
1 374, 1 325, 1 226, 1 148, 1 040 cm−1; 1H NMR
(acetone-d6, 500 MHz) and 13C NMR (acetone-d6, 125
MHz) data see Table 2; ESI-MS m/z 355 [M+Na]+, 331
[M−H]−; HR-ESI-MS m/z 355.116 2 [M+Na]+ (cacld
for C18H20O6Na, 355.115 2).
6-Methoxy-4-methyl-3, 4-dihydro-2H-naphthalen-
1-one (3) yellowish oil; [α] 20D −0.2 (c 0.18, MeOH);
IR νmax: 1 677, 1 598 cm−1; 1H NMR (acetone-d6, 500
MHz) and 13C NMR (acetone-d6, 125 MHz) data see
Table 1; EI-MS m/z 190 [M]+; HR-EI-MS m/z 190.0977
[M]+ (cacld for C12H14O2, 190.099 4).
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