Original Papers 893

Polyacetylenes and Flavonoids from the Aerial Parts

of Bidens pilosa

Authors Rui Wang 1, Quan-Xiang Wu 1, Yan-Ping Shi 1, 2

1
Affiliations State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University,
Lanzhou, P. R. China
2
Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of
Sciences, Lanzhou, P. R. China

Key words Abstract and one new chalcone glucoside (11). The molec-
l
" Bidens pilosa
! ular structures of the isolated compounds were

Downloaded by: UC Santa Barbara. Copyrighted material.

l
" Asteraceae
Bidens pilosa is used in various folk medicines elucidated by comprehensive spectroscopic anal-
l
" polyacetylene
such as antimalarial, antibacterial, blood pres- ysis.
l
" flavonoids

sure-lowering, and antihyperglycemic agents.

Phytochemical investigation of the aerial parts of Supporting information available online at
this plant yielded 10 polyacetylenes and 9 flavo- http://www.thieme-connect.de/ejournals/toc/
noids, including four new polyacetylenes (5, 7–9) plantamedica

Introduction Materials and Methods

! !
Bidens pilosa (family Asteraceae) is widely distrib-
uted in the subtropical and tropical regions of the
world. It is commonly known as hairy beggar
ticks, sticks tights, and Spanish needles. The plant
is used in various folk medicines such as antima-
larial, antibacterial, blood pressure-lowering, and
antihyperglycemic agents [1–5]. It has been
widely used in Taiwan as the major ingredient of
an herbal tea that is believed to prevent inflam-
mation and cancer [6].
received Sept. 14, 2009
Phytochemical investigation indicate that this
revised Dec. 1, 2009 plant is especially rich in polyacetylenes and fla-
accepted Dec. 29, 2009 vonoids, which have been shown to possess anti-
malarial, antimicrobial, antibacterial, and antioxi-
Bibliography
DOI http://dx.doi.org/ dant activities [7–13]. To the best of our knowl-
10.1055/s-0029-1240814 edge, there have been no previous phytochemical
Published online January 27, studies on B. pilosa derived from Hainan Province,
2010 P. R. China. We report herein the isolation and elu-
Planta Med 2010; 76: 893–896
cidation of 10 polyacetylenes and 9 flavonoids
© Georg Thieme Verlag KG
Stuttgart · New York · (l" Fig. 1), including four new polyacetylenes (5,
Apparatus
Optical rotations were measured on a Perkin-El-
mer model 341 polarimeter with a 1-dm cell. IR
spectra were obtained on a Nicolet NEXUS 670
FT‑IR spectrometer. UV spectra were measured
on a NewCentury PGeneral T6 spectrophotome-
ter. NMR spectra were recorded on Varian INO-
VA-300, Bruker AVANCE Ш-400, and Varian INO-
VA-600 spectrometers. Chemical shifts are given
on a δ (ppm) scale using TMS as an internal stan-
dard (s, singlet; d, doublet; t, triplet; m, multip-
let). HR‑ESI‑MS was carried out on a Bruker APEX
II mass spectrometer. Silica gel (200–300 mesh)
used for column chromatography and silica gel
GF254 (10–40 µm) for TLC were both supplied by
the Qingdao Marine Chemical Factory. TLC was
detected at 254 nm, and spots were visualized by
spraying with 5 % H2SO4 in C2H5OH (v/v) followed
by heating.

ISSN 0032‑0943
Correspondence
Prof. Yan-Ping Shi
Lanzhou Institute of Chemical
Physics
Chinese Academy of Sciences
Lanzhou University
730000 Lanzhou
Peopleʼs Republic of China
Phone: + 86 93 14 96 82 08
Fax: + 86 93 18 27 70 88
shiyp@lzb.ac.cn
7–9) and one new chalcone glucoside (11), from
the aerial parts of this plant. The molecular struc-
tures of these new compounds were elucidated by
comprehensive spectroscopic analysis.
Plant material
The air-dried aerial parts of Bidens pilosa were
collected in Wenchang Town, Hainan Province,
P. R. China, in August 2006, and were identified
by adjunct professor Huan-Yang Qi. A voucher
specimen (No. 2006001) has been deposited in
the State Key Laboratory of Applied Organic
Chemistry, Lanzhou University, P. R. China.

Wang R et al. Polyacetylenes and Flavonoids … Planta Med 2010; 76: 893–896
894 Original Papers
Extraction and isolation
The air-dried powder of the aerial parts of B. pilosa (5.5 kg) was
extracted with 95 % ethanol (3 × 7 d) at room temperature. After
concentration under reduced pressure, the crude extract (400 g)
was mixed with H2O (1 L) to form a suspension that was parti-
tioned successively with petroleum ether (PE) (60–90 °C), EtOAc,
and n-BuOH. The extraction of PE merged with that of EtOAc ac-
cording to the TLC analysis. The acquired fraction (121 g) was
subjected to silica gel column chromatography (CC) eluted with
a PE-EtOAc gradient system to give six main fractions (A1–A6).
Fraction A2 was further chromatographed on silica gel CC with a
PE-acetone gradient system to give several subfractions. Further
purification of each subfraction through repeated chromatogra-
phy with PE-EtOAc and PE-acetone as eluent yielded compounds
1 (54.0 mg), 2 (5.4 mg), 3 (5.0 mg), and 4 (4.3 mg). In the same
way, fractions A3–A5 were separated with PE-acetone, PE-EtOAc,
Wang R et al. Polyacetylenes and Flavonoids … Planta Med 2010; 76: 893–896
Fig. 1 Molecular structures of polyacetylenes and
flavonoids isolated from B. pilosa.
Downloaded by: UC Santa Barbara. Copyrighted material.
and CHCl3-acetone as eluent to give compounds 5 (4.1 mg), 6
(6.7 mg), 8 (3.2 mg), 9 (1.8 mg), 12 (14.0 mg), 13 (13.4 mg), and
15 (9.6 mg), respectively. A similar isolation procedure, along
with preparative TLC and recrystallization, was adopted for the
isolation of the extraction of n-BuOH (58 g) to afford compounds
7 (5.3 mg), 10 (32.0 mg), 11 (7.8 mg), 14 (7.2 mg), 16 (43.3 mg), 17
(11.0 mg), 18 (6.7 mg), and 19 (13.4 mg). The purities of these
compounds were determined by spectroscopic analysis. The de-
tailed procedure is given as Supporting Information.
7-Phenyl-hepta-4,6-diyn-1,2-diol (5): Pale yellow oil; Rf = ca. 0.50
(PE-acetone, 3 : 1); [α]20D : − 7 (c 0.4, acetone); UV (acetone):
λmax = 223 nm; IR (film): νmax = 3363, 2922, 2245, 2163, 1458,
1442, 1091, 1033, 755, 689 cm−1; 1H‑NMR (CDCl3, 300 MHz):
δ = 7.50–7.46 (2H, m, H-2′ and 6′), 7.36–7.26 (3H, m, H-3′, 4′, and
5′), 3.95 (1H, m, H-2), 3.79 (1H, dd, 11.1, 3.6 Hz, H-1a), 3.64 (1H,
dd, 11.1, 6.6 Hz, H-1b), 2.63 (2H, d, 6.6 Hz, H2-3); 13C‑NMR (CDCl3,

75 MHz): δ = 132.5 (C-2′), 132.5 (C-6′), 129.1 (C-4′), 128.4 (C-3′),
128.4 (C-5′), 121.2 (C-1′), 79.7 (C-4), 75.6 (C-7), 73.8 (C-5), 70.1
(C-2), 67.5 (C-6), 65.4 (C-1), 24.6 (C-3); HR‑ESI‑MS (positive): m/
z = 223.0729 [M + Na]+ (calcd. for C13H12O2Na: 223.0730).
5-(2-Phenylethynyl)-2-thiophene methanol (6): Pale yellow nee-
dles; Rf = ca. 0.67 (PE-acetone, 5 : 1); UV (CHCl3): λmax = 306 nm;
1
H‑NMR (CDCl3, 300 MHz): δ = 7.53–7.49 (2H, m, H-2′ and 6′),
7.35–7.31 (3H, m, H-3′, 4′, and 5′), 7.14 (1H, d, 3.3 Hz, H-4), 6.90
(1H, d, 3.6, 2.4 Hz, H-3), 4.80 (2H, d, 2.4 Hz, -OCH2-); 13C‑NMR
(CDCl3, 75 MHz): δ = 145.8 (C-2), 131.8 (C-4), 131.4 (C-2′), 131.4
(C-6′), 128.4 (C-4′), 128.3 (C-3′), 138.3 (C-5′), 125.2 (C-3), 123.4
(C-5), 122.8 (C-1′), 93.2 (C-7′), 82.6 (C-8′), 60.1 (-OCH2-).
5-(2-Phenylethynyl)-2-β-glucosylmethyl-thiophene (7): Pale yel-
low oil; Rf = ca. 0.60 (CHCl3-CH3OH, 5 : 1); UV (MeOH):
λmax = 304 nm; IR (film): νmax = 3382, 2926, 2875, 2204, 1075,
1030, 896 cm−1; 1H‑NMR (DMSO-d6, 300 MHz): δ = 7.52–7.50
(2H, m, H-2′ and 6′), 7.42–7.39 (3H, m, H-3′, 4′, and 5′), 7.28 (1H,
d, 3.6 Hz, H-4), 7.06 (1H, d, 3.6 Hz, H-3), 4.91 (1H, d, 12.9 Hz,
-OCH2-), 4.76 (1H, d, 13.5 Hz, -OCH2-), 4.22 (1H, d, 7.8 Hz, H-1′′);
13
C‑NMR (DMSO-d6, 75 MHz): δ = 143.8 (C-2), 133.1 (C-4), 131.8
(C-2′), 131.8 (C-6′), 129.6 (C-4′), 129.5 (C-3′), 129.5 (C-5′), 127.8
(C-3), 122.5 (C-5), 122.5 (C-1′), 102.1 (C-1′′), 93.6 (C-7′), 83.4
(C-8′), 77.6 (C-3′′), 77.2 (C-5′′), 73.9 (C-2′′), 70.1 (C-4′′), 64.7
(-OCH2-), 61.6 (C-6′′); HR‑ESI‑MS (positive): m/z = 394.1313 [M +
NH4]+ (calcd. for C19H24O6SN: 394.1319).
(6E,12E)-3-Oxo-tetradeca-6,12-dien-8,10-diyn-1-ol (8): Pale yel-
low oil; Rf = ca. 0.58 (PE-EtOAc, 5 : 1); [α]20D : − 11 (c 0.3, acetone);
UV (acetone): λmax = 241, 249, 263, 278, 295, 315 nm; IR (film):
νmax = 3390, 2923, 2853, 2202, 2128, 1710, 1653, 1620,
950 cm−1; 1H‑NMR (CDCl3, 300 MHz): δ = 6.31 (1H, m, H-13),
6.24 (1H, m, H-6), 5.59 (1H, m, H-7), 5.56 (1H, m, H-12), 3.86
(2H, m, H2-1), 2.66 (2H, m, H2-2), 2.56 (2H, t, 7.8 Hz, H-4), 2.43
(2H, ddd, 7.8, 6.6 Hz, H-5), 1.81 (3H, dd, 6.9, 1.8 Hz, H3-14);
13
C‑NMR (CDCl3, 75 MHz): δ = 209.8 (C-3), 145.6 (C-7), 143.6 (C-
13), 110.0 (C-6), 109.8 (C-12), 80.1 (C-11), 79.0 (C-8), 73.8 (C-10),
72.1 (C-9), 57.7 (C-1), 44.5 (C-2), 41.7 (C-4), 26.8 (C-5), 18.9 (C-14);
HR–ESI‑MS (positive): m/z = 234.1492 [M + NH4]+ (calcd. for
C14H20O2N: 234.1489).
(5E)-1,5-Tridecadiene-7,9-diyn-3,4,12-triol (9): Pale yellow oil;
Rf = ca. 0.50 (PE-acetone, 3 : 1); [α]20D : + 15 (c 0.1, acetone); UV
(acetone): λmax = 214, 241, 254, 268, 285 nm; IR (film):
νmax = 3373, 2922, 2233, 2142, 1626, 1456, 1113, 1080, 1043,
956, 943 cm−1; 1H‑NMR (CDCl3, 600 MHz): δ = 6.29 (1H, dd, 16.2,
6.0 Hz, H-5), 5.86 (1H, m, H-2), 5.84 (1H, d, 16.2 Hz, H-6), 5.38
(1H, m, H-1a), 5.31 (1H, m, H-1b), 4.29 (1H, m, H-3), 4.23 (1H,
m, H-4), 4.01 (1H, m, H-12), 2.51 (2H, m, H2-11), 1.28 (3H, d,
6.0 Hz, H3-13); 13C‑NMR (CDCl3, 150 MHz): δ = 143.7 (C-5), 135.4
(C-2), 118.1 (C-1), 111.0 (C-6), 80.8 (C-10), 75.3 (C-3), 75.1 (C-8),
74.3 (C-4), 73.4 (C-7), 67.3 (C-9), 66.3 (C-12), 30.1 (C-11), 22.5 (C-
13); HR–ESI‑MS (positive): m/z = 243.0096 [M + Na]+ (calcd. for
C13H16O3Na: 243.0092).
Okanin-4-methyl ether-3′,4′-di-O-β-(4′′,6′′,4′′′,6′′′-tetracetyl)-glu-
copyranoside (11): Pale yellow gum; Rf = ca. 0.67 (CHCl3-CH3OH,
D : − 98 (c 0.35, acetone); UV (acetone): λmax = 380 nm;
2 : 1); [α]20
IR (film): νmax = 3399, 1741, 1266, 1247, 1087, 1039, 986 cm−1;
1
H‑NMR (acetone-d6, 300 M): δ = 8.08 (1H, d, 9.3 Hz, H-6′), 7.82
(1H, d, 12.9 Hz, H-α), 7.79 (1H, d, 12.3 Hz, H-β), 7.38 (1H, d,
1.5 Hz, H-2), 7.27 (1H, dd, 8.4, 2.4 Hz, H-6), 7.02 (1H, d, 8.4 Hz,
H-5), 6.90 (1H, d, 9.3 Hz, H-5′), 5.17 (1H, d, 7.5 Hz, H-1′′), 5.13
(1H, d, 6.9 Hz, H-1′′′), 4.90 (2H, m, H-4′′ and 4′′′), 4.22 (2H, m, H-
6′′a and 6′′′a), 4.08 (2H, m, H-6′′b and 6′′′b), 3.89 (3H, s, -O‑CH3);
13
C‑NMR (acetone-d6, 75 MHz): δ = 193.6 (-C=O), 171.1 (2×-C = O,
Original Papers 895
OAc), 170.7 (2×-C = O, OAc), 158.4 (C-2′), 156.5 (C-4′), 151.5 (C-4),
147.8 (C-3), 146.4 (C-β), 134.8 (C-3′), 128.8 (C-1), 125.2 (C-6),
123.9 (C-6′), 119.1 (C-α), 117.8 (C-1′), 114.9 (C-5), 112.3 (C-2),
108.1 (C-5′), 104.3 (C-1′′), 102.3 (C-1′′′), 75.3 (C-3′′)*, 74.8 (C-3′′′)*,
74.5 (C-5′′)#, 74.3 (C-5′′′)#, 72.9 (C-4′′)†, 72.8 (C-4′′′)†, 71.7 (C-2′′)‡,
71.4 (C-2′′′)‡, 63.3 (C-6′′), 63.3 (C-6′′′), *, #, †, ‡: interchangeable;
HR–ESI‑MS (positive): m/z = 795.2348 [M + H]+ (calcd. for
C36H43O20: 795.2342).
Supporting information
NMR spectra (1H‑NMR, 13C‑NMR, and HMBC of all new com-
pounds and 6, 1H-1H COSY spectra of compounds 5 and 9), HR‑E-
SI‑MS of all new compounds, and detailed extraction and isola-
tion procedures are given as Supporting Information.
Results and Discussion
!
Compound 5, a pale yellow oil, had a molecular formula of
C13H12O2 based on its HR‑ESI‑MS and 13C‑NMR data. The IR spec-
trum showed absorptions of OH groups (3363 cm−1) and C‑C tri-
ple bonds (2245 and 2163 cm−1). The NMR data were similar to
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those of 7-phenyl-hepta-4,6-diyn-2-ol (pilosol A) [14], except
for an extra oxygenated methylene (δH = 3.64 and 3.79, δC = 65.4)
in 5, which was assigned at CH-2 by analysis of its HMBC and 1H-
1
H COSY correlations. Accordingly, the structure of 5 was deter-
mined to be 7-phenyl-hepta-4,6-diyn-1,2-diol. However, the ab-
solute configuration was not determined for the limited amount
of this compound available.
Compound 6 was obtained as pale yellow needles. Although this
compound has been reported previously [8], its NMR data were
never published. Therefore, these data were included in the
above section.
The IR spectrum of 7 displayed absorptions due to OH groups
(3382 cm−1) and C‑C triple bonds (2204 cm−1). The molecular for-
mula C19H20O6S was deduced by its HR‑ESI‑MS and 13C‑NMR
spectra. Comparison of the NMR data of 7 with those of 6 showed
the existence of an extra β-glucose unit (δH = 4.22, 1H, d,
J = 7.8 Hz; δC = 102.1, 77.6, 77.2, 73.9, 70.6, and 61.6) in 7. The sug-
ar moiety was assigned at the methylene, which was deduced
from its HMBC between the anomeric proton (δH = 4.22) and the
methylene carbon (δC = 64.7). The structure of 7 was thus estab-
lished to be 5-(2-phenylethynyl)-2-β-glucosylmethyl-thiophene.
The molecular formula of 8 was deduced as C14H16O2 from its
HR‑ESI‑MS and 13C‑NMR spectra. Its IR spectrum indicated the
presence of hydroxy groups (3390 cm−1), C‑C triple bonds (2202
and 2128 cm−1), and acetonyl groups (1710 cm−1). The UV spec-
trum revealed a typical ene-diyne-ene chromophore absorption
(λmax = 241, 249, 263, 278, 295, 315 nm) [7]. Comparison of the
NMR spectra of 8 with those of 3-oxo-tetradeca-6E,12E-dien-8,
10-diyn-1-ol isobutyrate [15] indicated the absence of the isobu-
tyryl group in 8, which was confirmed by the clearly upfield-
shifted H2-1 signal from δH = 4.33 in the isobutyrate to δH = 3.86
in 8. The conclusion was also consistent with its HMBCs and
HR‑ESI‑MS. Accordingly, the structure of 8 was determined to be
(6E,12E)-3-oxo-tetradeca-6,12-dien-8,10-diyn-1-ol.
The IR spectrum of 9 showed the presence of OH groups
(3363 cm−1) and C‑C triple bonds (2245 and 2163 cm−1). Its UV
spectrum indicated typical absorptions for a conjugated ene-
diyne chromophore (λmax = 214, 241, 254, 268, and 285 nm) [7].
The 1H‑NMR spectrum showed a methyl group (δ = 1.28), a meth-
ylene (δ = 2.51), three oxygenated methane (δ = 4.01, 4.23, and
Wang R et al. Polyacetylenes and Flavonoids … Planta Med 2010; 76: 893–896
896 Original Papers
4.29), and five olefinic protons (δ = 5.31, 5.38, 5.84, 5.86, and
6.29). The trans (E) configuration of the double bond at C-5 was
deduced by the large vicinal coupling constant (J = 16.2 Hz). Anal-
ysis of 1H-1H COSY data revealed a substructure (C11–C13) and
the connection of CH-4 and CH-3. In its HMBC spectrum, the cor-
relations (H11/C9, C10) indicated the connection of CH2-11 and
the ene-diyne chain. On the opposite side of the ene-diyne chain,
important HMBCs (H1/C3 and C4/H2, H5) were observed. Thus,
the structure of 9 was determined to be (5E)-1,5-tridecadiene-
7,9-diyn-3,4,12-triol. The absolute configuration was not deter-
mined because of the limited amount of this compound available.
Compound 11 exhibited a major UV absorption band at
λmax = 380 nm typical of a chalcone. Its NMR data closely re-
sembled those of okanin 3′,4′-di-O-β-D-glucoside (ODG) [10],
which revealed that 11 was also an acetylated okanin 3′,4′-di-O-
β-glucoside. This conclusion was confirmed by its HR‑ESI‑MS (m/
z = 795.2348 [C36H42O20 + H]+). Compared with ODG, an extra
methoxy (δH = 3.89) and four additional acetyl groups (δC = 20.9,
20.9, 20.8, and 20.7) in 11 were obtained. The methoxy was as-
signed at C-4 due to its HMBC. The sites of acetylation were read-
ily inferred at C-4′′, 6′′, 4′′′, and 6′′′ from the obviously downfield
shifts of H-4′′, 4′′′, 6′′, and 6′′′ (δH = 4.90, 4.22, and 4.08, each 2H)
[11], respectively. Thus, the structure of compound 11 was deter-
mined to be okanin-4-methyl ether-3′,4′-di-O-β-(4′′,6′′,4′′′,6′′′-
tetracetyl)-glucopyranoside.
Other known polyacetylenes and flavonoids isolated from this
plant were 1-phenyl-hepta-1,3,5-triyne (1) [16], 7-phenyl-hep-
ta-2,4,6-triyn-2-ol (2) [17], 7-phenyl-2-heptene-4,6-diyn-1-ol
(3) [18], 7-phenyl-hepta-4,6-diyn-2-ol (4) [14], 3-β-glucopyrano-
syloxy-1-hydroxy-6E-tetradecene-8,10,12-triyne (10) [19], api-
genin (12) [20], digitoflavone (13) [21], luteoside (14) [22], quer-
cetagetin 3,6,3′-trimethyl ether (15) [23], quercetagetin 3,6,3′-tri-
methyl ether-7-O-β-glucoside (16) [24], quercetagetin 3,7,3′-tri-
methyl ether-6-O-β-glucoside (17) [25], axillaroside (18) [26],
and rutin (19) [27]. Their structures were determined by compar-
ison of their spectroscopic data with literature values.
Acknowledgements
! chemical study of Isoplexis chalcantha. Planta Med 1985; 51: 9–11
This work was financially supported by the Foundation for the
National Natural Science Foundation of China (No. NSFC 20621
091), the National Key Technology Research and Development
Program of China (No. 2007BAI37B05), and the National 863 Pro-
gram of China (No. 2007AA09Z403).
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