70 Letters
rhamnopyranosyl) (1–6) β-D-galactopyranoside (2), along with
Novel Flavonoids from the Leaves
of Actinidia valvata Dunn: Structural
Elucidation and Antioxidant Activity
Hai-Liang Xin 1, 2, Ying-Chun Wu 2*, Yong-Hua Su 1, Jia-Yu
Sheng 1, Chang-Quan Ling 1
1
Department of Traditional Chinese Medicine, Changhai Hospital,
The Second Military Medical University, Shanghai, P. R. China
2
School of Chinese Materia Medica, Shanghai University
of Traditional Chinese Medicine, Shanghai, P. R. China
Abstract
! The 13C‑NMR (see Supporting Information, Fig. 5S) and DEPT
Two novel flavonoids, kaempferol 3-O-α-L-rhamnopyranosyl (1–
3) (2,4-di-O-acetyl-α-L-rhamnopyranosyl) (1–6) β-D-galactopy-
ranoside (1) and kaempferol 3-O-α-L-rhamnopyranosyl (1–3)
(4-O-acetyl-α-L-rhamnopyranosyl) (1–6) β-D-galactopyranoside
(2), along with three known ones, kaempferol-3-O-β-D-galacto-
pyranoside (3), kaempferol (4), and 7-hydroxychromone (5),
have been isolated from the leaves of Actinidia valvata Dunn,
and their structures were elucidated based on spectroscopic
methods. Compounds 1–3 exhibited dose-dependent activity in
scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals,
superoxide anion radicals, and hydroxyl radicals, and inhibited
lipid peroxidation of mouse liver homogenate in vitro.
Key words
Actinidia valvata · Actinidiaceae · flavonoid glycosides
Abbreviations
! Information, Fig. 9S), two acetyl groups were evidenced by the
DPPH: 1,1-diphenyl-2-picrylhydrazyl
ESI: electrospray ionization
TCM: traditional Chinese medicine
Supporting information available online at
http://www.thieme-connect.de/ejournals/toc/plantamedica
There are nearly sixty species in the genus Actinidia, family Acti-
nidiceae, and some of them are well-known for the delicious kiwi
fruit worldwide [1]. It has been reported that the taxa in genus
Actinidia were characterized by the presence of mono-, di-, and
in some cases, triglycosides with isorhamnetin, kaempferol, myr-
icetin, or quercetin as aglycone. Besides, the unique flavonoid
patterns in most Actinidia species may be widely used in chemo-
taxonomic studies [2]. As an important medicinal plant, Actinidia
valvata Dunn grows mainly in eastern China. Its root is known as
“mao ren shen” in traditional Chinese medicine (TCM) exhibiting
antitumor and anti-inflammatory activity and has been used for
the treatment of hepatoma, lung carcinoma, and myeloma for a
long time [3, 4]. In the present study, we reported two novel fla-
vonoids, kaempferol 3-O-α-L-rhamnopyranosyl (1–3) (2′′′, 4′′′-di-
O-acetyl-α-L-rhamnosyl) (1–6) β-D-galactopyranoside (1) and
kaempferol 3-O-α-L-rhamnopyranosyl (1–3) (4′′′-O-acetyl-α-L-
* Co-first author
Xin H-L et al. Novel Flavonoids from … Planta Med 2011; 77: 70–73
three known flavonoids, kaempferol-3-O-β-D-galactopyranoside
(3), kaempferol (4), and 7-hydroxychromone (5) isolated from
leaves of A. valvata. The antioxidant activity of compounds 1–3
was also evaluated in scavenging 1,1-diphenyl-2-picrylhydrazyl
(DPPH) free radicals, superoxide anion radicals, and hydroxyl
radicals as well as in inhibiting lipid peroxidation in vitro.
Compound 1 was isolated as a pale yellow powder and gave a
positive Molischʼs test. It exhibited an HR‑ESI‑MS (see Support-
ing Information, Fig. 3S) ion at m/z 847.2279 [M + Na]+ indicating
a molecular formula of C37H44O21. The UV spectrum showed the
maximum at 265 and 348 nm, which suggested that compound 1
was a flavone. IR spectrum (see Supporting Information, Fig. 1S)
exhibited strong bands for hydroxyl (3431 cm−1), carbonyl
(1656 cm−1), and a double bond (1609, 1510, and 1451 cm−1).
spectra (see Supporting Information, Fig. 6S) showed thirty-sev-
en carbon signals, including four CH3, one oxygenated CH2,
twenty-two CH, and ten quaternary C-atoms (including three
C = O groups). One carbonyl signal at δ179.41 was characteristic
of a flavone skeleton and could be assigned to C-5. In the aromatic
region of the 1H‑NMR spectrum (see Supporting Information,
Fig. 4S), two singlets at δ 6.20 and δ 6.40 could be assigned to H-
6 and H-8, respectively, and two doublets at δ 8.14 (2H, dd, J = 9,
2 Hz) and 6.88 (2H, dd, J = 9, 2 Hz) were assigned to H-2′, H-6′, and
H-3′, H-5′, respectively. As for the identification of the sugar moi-
ety, compound 1 was decomposed with trifluoroacetic acid (TFA),
derivatized with 1-phenyl-3-methyl-5-pyrazolone (PMP) and
analyzed with the HPLC method described previously [5] (see
Supporting Information, Fig. 23S for HPLC chromatogram of hy-
drolyzed and derivatized monosaccharides). The results showed
that the sugar moiety of compound 1 was composed of rhamnose
and galactose. By analysis of 1H- and 13C‑NMR, HMQC (see Sup-
porting Information, Fig. 8S), and HMBC spectra (see Supporting
signals of two carbonyl carbons at δ171.62 and δ171.72 and two
methyls (δH2.04/δC20.77 and δH2.04/δC20.87, respectively; as-
signments might be interchanged). In the HMBC spectrum, the
correlations of δH2.04/δC73.06 and δH2.04/δC73.93, revealed that
the two acetyls were connected to C-2′′′ and C-4′′′ of the inner
rhamnose. The anomeric protons of galactose, 2′′′,4′′′-di-O-ace-
tylrhamnose, and rhamnose showed strong HMBC correlations
with δ135.68 (C-3), δ68.50 (C-6′′), and δ76.26 (C-3′′′), respectively
(l" Fig. 2). Therefore, the sugar linkage could be inferred as rham-
nose (1–3) (2′′′,4′′′-di-O-acetylrhamnose) (1–6) galactose, and
the galactose was connected to C-3 of the C-ring. Assuming D-
configuration, the β-configuration of the galactose moiety was
evidenced by the size of the coupling constant between Gal H-1
and H-2. The relative and absolute configuration of the rhamnose
moieties were confirmed by comparison with those reported in
the literature [6] and based on biogenetic consideration. Hence,
the structure of compound 1 was identified as kaempferol 3-O-
α-L-rhamnopyranosyl (1–3) (2′′′,4′′′-di-O-acetyl-α-L-rhamno-
pyranosyl) (1–6) β-D-galactopyranoside (l " Fig. 1).
Compound 2 was also isolated as a pale yellow powder and gave a
positive Molischʼs test. The HR‑ESI‑MS spectrum (see Supporting
Information, Fig. 14S), showed a [M + Na]+ ion at m/z 805.2166,
compatible with the molecular formula of C35H42O20. The UV
and IR spectra (see Supporting Information, Fig. 12S) showed a
similar pattern to compound 1. Both 1H- and 13C‑NMR (see Sup-
porting Information, Fig. 15S, 16S) spectra were also closely re-
lated to those of compound 1 except that the C-2′′′ of the internal
 Letters 71

Fig. 3 Antioxidative
activity of compounds
1–3 and positive con-
trol. (The values were
expressed as mean ± SD
of three determina-
tions.) A Scavenging
effect on DPPH radicals.
B Scavenging effect on
superoxide anion radi-
cals. C Scavenging ef-
fect on hydroxyl radi-
cals. D Inhibitory effect
on lipid peroxidation in
mouse liver homoge-
nate.

Fig. 1 Structures of compounds 1–5.

respectively (l" Fig. 1) [7, 8]. They all were structurally deter-

mined for the first time in material extracted from this plant.
Furthermore, antioxidant activties of compounds 1–3 were eval-
uated in this work by measuring their ability to scavenge DPPH,
superoxide anion, and hydroxide radicals, and to inhibit lipid per-
oxidation. As presented in l " Fig. 3 A – C, they all exhibited dose-

Fig. 2 Key HMBC correlations of compounds 1 and 2. dependent activity in scavenging DPPH, superoxide anion, and
hydroxide radicals. In addition, compounds 1–3 potently inhib-
ited the lipid peroxidation initiated by Fe2+ and ascorbic acid in
mouse liver homogenates (l " Fig. 3 D). Previous structure/activity

rhamnose of the sugar moieties was not acetylated. This was evi-
denced by ESI‑MS (see Supporting Information, Fig. 13S) spec-
trum (42 mass units less than compound 1) and the 1H- and
13
C‑NMR spectroscopic data of the internal rhamnose (see Sup-
porting Information, Fig. 15S, 16S). Thus, the structure of com-
pound 2 was identified as kaempferol 3-O-α-L-rhamnopyranosyl
(1–3) (4′′′-O-acetyl-α-L-rhamnopyranosyl) (1–6) β-D-galacto-
pyranoside (l" Fig. 1).
Compounds 3–5 were identified by comparison of their spectro-
scopic data with the literature values as kaempferol-3-O-β-D-ga-
lactopyranoside (3), kaempferol (4), and 7-hydroxychromone (5),
studies of flavonoids with the same structural features as com-
pounds 1–3 showed antioxidant activity at similar levels [9–11].
(See Supporting Information for antioxidant experiments.)
Materials and Methods
!
Vit C (purity > 98%) and Vit E (purity > 98%) were purchased from
Sigma Aldrich. The leaves of A. valvata (2.5 kg) were collected in
Changshan County, Zhejiang Province, P. R. China, in June 2007,
and identified by Professor Han-Chen Zheng. A voucher specimen
(No. 20070612) was deposited at the Department of TCM, the
Second Military Medical University. The powdered leaves were

Xin H-L et al. Novel Flavonoids from … Planta Med 2011; 77: 70–73
72 Letters

1
Table 1 H- and 13C‑NMR spectroscopic data of compounds 1 and 2 in DMSO-d6.

Position 1 2
δH a δC b HMBC δH a δC b HMBC
1 / / / / / /
2 / 159.14 (s) C-3, C-4, C-9, C-1′, C-2′, C-6′ / 159.31 (s) C-3, C-4, C-9, C-1′, C-2′, C-6′
3 / 135.68 (s) C-2, C-4, C-10,C‑1′ / 135.80 (s) C-2, C-4, C-10, C-1′
4 / 179.41 (s) / / 179.52 (s)
5 / 162.91 (s) / / 162.97 (s)
6 6.20 (1H, s) 99.97 (d) C-4, C-5, C-7, C-8, C-10 6.20 (1H, s) 100.10 (d) C-4, C-5, C-7, C-8, C-10
7 / 166.00 (d) / / 166.12 (d) /
8 6.40 (1H, s) 94.86 (d) C-6, C-7, C-9, C-10 6.40 (1H, s) 94.93 (d) C-6, C-7, C-9, C-10
9 / 158.39 (s) / / 158.46 (s) /
10 / 105.51 (s) / / 105.56 (s) /
1′ / 122.41 (s) / / 122.55 (s) /
2′ 8.14 (1H, dd, 9, 2) 132.40 (d) C-2, C-1′, C-3′, C-4′, C-6′ 8.14 132.47 (d) C-2, C-1′, C-3′, C-4′, C-6′
(1H, dd, 9, 2)
3′ 6.88 (1H, dd, 9, 2) 116.11 (d) C-1′, C-2′, C-4′, C-5′ 6.88 116.15 (d) C-1′, C-2′, C-4′, C-5′
(1H, dd, 9, 2)
4′ / 161.62 (s) / / 161.64 (s) /
5′ 6.88 (1H, dd, 9, 2) 116.11 (d) C-1′, C-3′, C-4′, C-6′ 6.88 116.15 (d) C-1′, C-3′, C-4′, C-6′
(1H, dd, 9, 2)
6′ 8.14 (1H, dd, 9, 2) 132.40 (d) C-2, C-1′, C-2′, C-4′, C-5′ 8.14 132.47 (d) C-2, C-1′, C-2′, C-4′, C-5′
(1H, dd, 9, 2)
gal-1′′ 5.06 (1H, d, 8) 105.51 (d) C-3, C-2′′, C-3′′, C-5′′ 5.05 (1H, d, 8) 105.71 (d) C-3, C-2′′, C-3′′, C-5′′
gal-2′′ 3.60 (1H, m) 74.88 (d) C-1′′, C-3′′, C-4′′ 3.66 (1H, m) 75.08 (d) C-1′′, C-3′′, C-4′′
gal-3′′ 3.81 (1H, m) 72.93 (d) C-1′′, C-2′′, C-4′′, C-5′′ 3.82 (1H, m) 73.01 (d) C-1′′, C-2′′, C-4′′, C-5′′
gal-4′′ 3.66 (1H, m) 70.35 (d) C-2′′, C-3′′, C-5′′, C-6′′ 3.62 (1H, m) 70.21 (d) C-2′′, C-3′′,C‑5′′, C-6′′
gal-5′′ 3.61 (1H, m) 75.53 (d) C-1′′, C-3′′, C-4′′, C-6′′ 3.74 (1H, m) 75.33 (d) C-1′′, C-3′′, C-4′′, C-6′′
gal-6′′ 3.61 (1H, m), 68.50 (t) C-1′′′, C-4′′, C-5′′ 3.58 (1H, m), 68.77 (t) C-1′′′, C-4′′, C-5′′
3.70 (1H, m) 3.70 (1H, m)
rha-1′′′ 4.62 (1H, d, 2) 98.94 (d) C-6′′, C-2′′′, C-3′′′, C-5′′′ 4.56 (1H, s) 102.28 (d) C-6′′, C-2′′′, C-3′′′, C-5′′′
rha-2′′′ 4.98 (1H, m) 73.06 (d) = C = O′, C-1′′′, C-3′′′, C-4′′′ 3.68 (1H, m) 72.02 (d) C-1′′′, C-3′′′, C-4′′′
rha-3′′′ 3.85 (1H, m) 76.26 (d) C-1′′′, C-2′′′, C-4′′′, C-5′′′ 3.75 (1H, m) 78.01 (d) C-1′′′,C‑2′′′,C‑4′′′, C-5′′′
rha-4′′′ 4.93 (1H, m) 73.93 (d) = C = O′′, C-2′′′, C-3′′′, 4.96 (1H, m) 74.20 (d) = C = O′′, C-2′′′,C‑3′′′, C-5′′′,
C-5′′′, C-6′′′ C-6′′′
rha-5′′′ 3.76 (1H, m) 67.63 (d) C-1′′′, C-3′′′, C-4′′′, C-6′′′ 3.77 (1H, m) 67.87 (d) C-1′′′, C-3′′′, C-4′′′, C-6′′′
rha-6′′′ 0.99 (1H, d, 6) 17.67 (q) C-4′′′, C-5′′′ 0.99 (1H, d, 7) 17.71 (t) C-4′′′, C-5′′′
rha-1′′′′ 4.67 (1H, d, 1) 104.01 (d) C-4′′′, C-2′′′′, C-3′′′′, C-5′′′′ 4.69 (1H, s) 103.83 (d) C-4′′′, C-2′′′′, C-3′′′′, C-5′′′′
rha-2′′′′ 3.46 (1H, m) 71.95 (d) C-1′′′′, C-3′′′′, C-4′′′′ 3.74 (1H, m) 71.84 (d) C-1′′′′, C-3′′′′, C-4′′′′
rha-3′′′′ 3.60 (1H, m) 72.30 (d) C-1′′′′, C-2′′′′, C-4′′′′, C-5′′′′ 3.76 (1H, m) 72.38 (d) C-1′′′′, C-2′′′′, C-4′′′′, C-5′′′′
rha-4′′′′ 3.32 (1H, m) 73.49 (d) C-2′′′′, C-3′′′′, C-5′′′′, C-6′′′′ 3.38 (1H, m) 73.87 (d) C-2′′′′, C-3′′′′, C-5′′′′, C-6′′′′
rha-5′′′′ 3.46 (1H, m) 70.52 (d) C-1′′′′, C-3′′′′, C-4′′′′, C-6′′′′ 3.81 (1H, m) 70.36 (d) C-1′′′′, C-3′′′′, C-4′′′′, C-6′′′′
rha-6′′′′ 1.01 (1H, d, 6) 17.80 (q) C-4′′′′, C-5′′′′ 1.13 (1H, d, 6) 17.94 (q) C-4′′′′, C-5′′′′
= C = O′(rha-2′′′) / 171.62 (s)c / / / /
= C = O′′(rha-4′′′) / 171.7 (s)c / / 171.90 (s) /
-CH3′(= C = O′) 2.04 (3H, s) 20.77 (q)d = C = O′ / / /
-CH3′′(= C = O′′) 2.04 (3H, s) 20.87 (q)d = C = O′′ 2.04 (3H, s) 20.93 (q) = C = O′′
a
Chemical shifts in ppm recorded at 500 MHz; integral, splitting pattern, and coupling constants (Hz) in parenthesis; b recorded at 125 MHz, multiplicity by DEPT;
c, d
assignments might be interchanged

extracted in 80 % EtOH (3 × 25 L, 24 h each time) under soak. The
EtOH extract was suspended in water and then successively par-
titioned with petroleum ether (PE, 60–90 °C), CHCl3, and n-BuOH.
The CHCl3 extract (85 g) was subjected to silica gel (200–300
mesh, 3000 g, 8 × 120 cm) column chromatography eluted with
PE–EtOAC (20 : 1, 10 : 1, 5 : 1, 1 : 1, each 15 L) to give fractions 1–7
and CHCl3-MeOH (10 : 1, 7 : 1, 5 : 1, 3 : 1, each 15 L) to give frac-
tions 8–14. Fractions 6 and 8 were chromatographed on a silica
gel column (200–300 mesh, 450 g, 5 × 80 cm) eluted with CHCl3-
MeOH (20 : 1, 10 : 1, 7 : 1, 5 : 1, 3 : 1, each 2 L) to yield fraction 6.1–
6.8 and fractions 8.1–8.8, respectively. Fraction 6.3–6.7 and frac-
tion 8.3–8.5 were both subjected to Sephadex LH-20 column
(2 × 120 cm) and eluted with MeOH‑H2O (1 : 1) repeatedly to
yield compound 4 (11.5 mg) and compound 5 (6.8 mg). The n-
BuOH extract (103 g) was loaded on a silica gel column chroma-
tography (200–300 mesh, 3000 g, 8 × 120 cm) eluted with CHCl3-
MeOH (20 : 1, 10 : 1, 5 : 1, 3 : 1, 1 : 1, each 15 L) to give 11 fractions.
Fraction 7 was subjected to a silica gel column (200–300 mesh,
400 g, 5 × 80 cm) using CHCl3-MeOH (20 : 1, 10 : 1, 7 : 1, 5 : 1, 3 : 1,
each 2 L) as a solvent to give 9 fractions. Fractions 4–7 were incor-
porated and chromatographed on a Sephadex LH-20 column
(2 × 120 cm) eluted with MeOH‑H2O (1 : 1) repeatedly to yield
compound 1 (623 mg, 98.2%), 2 (481 mg, 97.5 %), and 3 (348 mg,
99.1 %).
The identification of the sugar moiety of compounds 1 and 2 was
carried out as described previously with proper modifications
[5]. 5 mg of each compound was dissolved in 1 mL of 2 M TFA in
an ampoule (5 mL). The ampoule was sealed under a nitrogen at-

Xin H-L et al. Novel Flavonoids from … Planta Med 2011; 77: 70–73

mosphere and kept in a heating oven at 120 °C to hydrolyze the
sugar linkage into its component monosaccharides for 2 h. After
being cooled to room temperature, the reaction mixture was cen-
trifugated at 1000 rpm for 5 min. The supernatant was collected
and extracted with dichlormethane (1 mL × 3 times), and the
aqueous layer was collected and dried under a reduced pressure.
The hydrolyzed and dried sample was added to 1 mL distilled
water, then 0.3 M aqueous NaOH (50 µL), and 0.5 M methanol so-
lution (50 µL) of PMP was added to both. Each mixture was al-
lowed to react for 60 min at 70 °C, then cooled to the room tem-
perature and neutralized with 50 µL of 0.3 M HCl. The resulting
solution was extracted with chloroform (1 mL × 3 times) and the
aqueous layer was filtered through a 0.45 µm membrane. The
analysis of PMP-labeled monosaccharides was carried out on a
Shimadzu LC-20AD HPLC system equipped with a quaternary
gradient pump unit, a UV‑Vis detector (190–700 nm), and an au-
tosampler (0.1–100 µL); the column oven temperature was set at
26 °C. The analytical column was a RP‑C18 column (4.6 mm,
i. d. × 250 mm, 5 µm; DIKMA, INC.). The wavelengths for UV detec-
tion were 250 nm and 270 nm. Elution was carried out at a flow
rate of 1.0 mL/min. The mobile phase A consisted of acetonitrile
and the mobile phase B of 0.68 % KH2PO4–0.095 % NaOH buffer
(pH 6.9), using a gradient elution of 85 % –82 % – 75 % B by a linear
decrease from 0–10–30 min. The injection volume was 20 µL.
Kaempferol 3-O-α-L-rhamnopyranosyl (1–3) (2,4-di-O-acetyl-α-
L-rhamnopyranosyl) (1–6) β-D-galactopyranoside (1): Pale yel-
low powder, m. p. 183–185 °C; [α]25 D = − 21.8 (c 0.1, MeOH). UV
λmax (MeOH): 265, 348 nm. FT‑IR (KBr) νmax = 3431, 2979, 2936,
1656, 1609, 1510, 1451, 1359 cm−1. ESI‑MS: m/z = 825.28 [M + 1]+,
847.28 [M + Na]+ (see Supporting Information Fig. 2S);
HR‑ESI‑MS: m/z = 847.2279 (calcd. for C37H44O21Na+ 847.2273)
(see Supporting Information Fig. 3S). For 1H- (DMSO-d6,
500 MHz) and 13C‑NMR (DMSO-d6, 125 MHz) data, see l " Table 1.
Kaempferol 3-O-α-L-rhamnopyranosyl (1–3) (4-O-acetyl-α-L-
rhamnopyranosyl) (1–6) β-D-galactopyranoside (2): Pale yellow
powder, m. p. 203–205 °C; [α]25D = − 35.7 (c 0.1, MeOH). UV λmax
(MeOH) = 265, 348 nm. FT‑IR (KBr) νmax = 3411, 2978, 2935, 1656,
1609, 1510, 1451, 1359 cm−1. ESI‑MS: m/z = 783.28 [M + 1]+,
805.28 [M + Na]+ (see Supporting Information Fig. 3S);
HR‑ESI‑MS: m/z = 805.2166 (calcd. for C35H42O20Na+ 805.2167)
(see Supporting Information Fig. 14S). For 1H- (DMSO-d6,
500 MHz) and 13C‑NMR (DMSO-d6, 125 MHz) data, see l " Table 1.
The activity of scavenging DPPH, superoxide anion, and hydroxyl
radicals was assayed according to the methods described previ-
ously [12–14]. Lipid peroxidation was initiated by Fe2+ (10 µM)
and ascorbic acid (100 µM) in mouse liver homogenates, and the
inhibitory activity was assayed according to a previous report [15].
Supporting information
Detailed experimental protocols and original spectra of com-
pounds 1 and 2 are available as Supporting Information.
Acknowledgements
! P. R. China
This work was supported by the National Natural Science Fund of
China (Grant No.: 30572360) and Special Project of TCM Modern-
ization of Science and Technology Commission of the Shanghai
Municipality (Grant No.: 04DZ19808).
Letters 73
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revised June 2, 2010
accepted June 10, 2010
Bibliography
DOI http://dx.doi.org/10.1055/s-0030-1250113
Published online July 21, 2010
Planta Med 2011; 77: 70–73
© Georg Thieme Verlag KG Stuttgart · New York ·
ISSN 0032‑0943
Correspondence
Chang-Quan Ling
Department of Traditional Chinese Medicine
Changhai Hospital
The Second Military Medical University
No. 800, Xiangyin Road
200433 Shanghai
Phone: + 86 21 81 87 15 51
Fax: + 86 21 81 87 15 59
lingchangquan@hotmail.com
Xin H-L et al. Novel Flavonoids from … Planta Med 2011; 77: 70–73