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13 Minh PTH, Ngoc PH, Taylor WC, Cuong NM. A novel ent-kaurane diterpe-
noid from Croton tonkinensis leaves. Fitoterapia 2004; 75: 552556
received August 17, 2009
New Cucurbitane-Type Triterpenoids
from Bryonia aspera
Shamim Sahranavard 1, 2, Farzaneh Naghibi 1, 2, Karsten Siems 3,
Kristina Jenett-Siems 4
1
Pharmacognosy Department, School of Pharmacy, Shaheed
Beheshti University of Medical Sciences, Tehran, Iran
2
Traditional Medicine & Materia Medica Research Center,
Shaheed Beheshti University of Medical Sciences, Tehran, Iran
3
Analyticon Discovery GmbH, Potsdam, Germany
4
Institut fuer Pharmazie (Pharmazeutische Biologie),
Freie Universitaet Berlin, Berlin, Germany
Abstract
!
Phytochemical investigation of the chloroform extract of Bryonia
aspera roots resulted in the isolation and structure elucidation of
two new cucurbitacins (1, 2) together with eight known cucurbi-
tane derivatives (613), the pentacyclic triterpene bryonolic acid

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revised December 30, 2009 (5) and two hydroxybenzoic acid amides (3, 4). Their structures
accepted January 10, 2010 were elucidated by spectroscopic analysis, including 2D NMR
techniques.
Bibliography
DOI http://dx.doi.org/10.1055/s-0029-1240863
Published online February 22, 2010 Key words
Planta Med 2010; 76: 10111014 Bryonia aspera Cucurbitaceae cucurbitacins hydroxyben-
Georg Thieme Verlag KG Stuttgart New York zoic acid amides
ISSN 00320943
Supporting information available online at
Correspondence
http://www.thieme-connect.de/ejournals/toc/plantamedica
Won Keun Oh
College of Pharmacy
Chosun University
375 Seosuk-dong, Dong-gu
In the northeastern parts of Iran, the roots of Bryonia aspera Stev.
Gwangju 501759
Republic of Korea ex Ledeb. (Cucurbitaceae) are used traditionally for the treatment
Phone: + 82 6 22 30 63 70 of cancer, digestive disorders, liver problems, stomachache, and
Fax: + 82 6 22 30 63 70
cardiac disorders [1]. Several reports deal with the isolation of
wkoh@chosun.ac.kr
phytochemicals of different species of the genus Bryonia [25].
Nevertheless, this is the first time that B. aspera has been studied
for its chemical composition. In our search for bioactive metabo-
lites from medicinal plants, we investigated the chloroform ex-
tract from the roots of this plant and isolated and structurally
identified 13 compounds, two of which are new cucurbitane de-
rivatives
Compound 1 was obtained as a yellowish amorphous solid and
displayed a quasi-molecular ion peak at m/z = 525.2827 [M + Na]+
in its HRESITOFMS, corresponding to the formula C29H42O7.
The 1HNMR spectrum (l " Table 1) showed eight methyl groups,

two olefinic protons, and one hydroxymethine signal at = 4.28

(1H, t, J = 7.5 Hz). The 13CNMR spectrum (l " Table 1) showed 29

carbon signals, including eight methyl groups and three carbonyl

carbons at = 215.0, 212.7, and 172.5, the chemical shift of the
latter suggesting an ester moiety. Furthermore, the spectrum dis-
played four olefinic carbons, five methylenes, three methines,
and six quaternary carbons. These data showed a similar signal
pattern with those of 23,24-dihydrocucurbitacin D (9) except for
the A-ring. The HMBC data revealed the structure of ring A since
the olefinic proton at = 6.00 was correlated to the ester carbonyl
carbon at = 172.5 (C-3) which was further correlated to two
methyl groups at = 29.0 and 22.5 (C-28 and C-29) and three qua-
ternary carbons at = 47.9 (C-9), 117.0 (C-10) and 132.8 (C-5).
These results indicated a lactone-type structure of ring A. The da-

Sahranavard S et al. New Cucurbitane-Type Triterpenoids Planta Med 2010; 76: 10141017
 Letters 1015

Position 1 2 Table 1 1HNMR [400 MHz,

1
H 13
C 1
H 13
C CDCl3, m, J (Hz)] and 13CNMR
1 6.00 s 134.3 1.28 m 34.9 (125 MHz, CDCl3) spectroscopic
2.34 m data for compounds 1 and 2.
2 4.42 m 71.2
3 172.5 211.7
4 43.0 51.0
5 132.8 145.5
6 5.84 m 123.0 5.98 brd (4.0) 121.7
7 2.21 dd (5.0, 20.0) 25.1 4.13 brd (4.0) 66.2
2.47 ddd (2.0, 7.5, 20.0)
8 2.12 d (8.0) 42.4 2.15 s 51.8
9 47.9 48.0
10 117.0 2.73 m 34.5
11 212.7 210.9
12 2.75 d (14.5) 50.3 2.72 d (15.0) 48.9
3.10 d (14.5) 3.18 d (15.0)
13 51.0 50.5
14 49.2 47.5
15 1.88 m 45.2 1.50 d (15.0) 45.1
1.39 m 2.07 m
16 4.28 t (7.5) 71.2 4.35 t (7.5) 70. 8
17 2.60 d (7.0) 58.2 2.58 d (7.0) 57.5

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18 1.00 s 20.0 1.02 s 19.8
19 1.30 s 25.7 1.22 s 21.2
20 79.8 79.0
21 1.43 s 24.7 1.44 s 24.4
22 215.0 214.5
23 2.95 ddd (7.0, 8.0, 18.0) 31.2 2.93 ddd (6.7, 8.0, 18.0) 30.5
2.65 m 2.65 m
24 1.85 m 37.3 1.83 m 36.5
25 70.5 70.1
26 1.23 s 28.9 1.25 s 29.8
27 1.26 s 30.1 1.21 s 28.8
28 1.34 s 29.0 1.29 s 29.7
29 1.48 s 22.5 1.41 s 21.1
30 1.23 s 18.2 1.28 s 18.9
20-OH 4.39 s 4.38 s

lated neocucurbitacins, we named compound 1 which repre-

sents only the third example of a lactone-type norcucurbitacin
neocucurbitacin C (l" Fig. 1).

Compound 2 was obtained as a white amorphous solid. Its HRE-

Fig. 1 Structures of compounds 14.
ta are similar to those of neocucurbitacin B isolated from Luffa
operculata [6], which in comparison to 1 possesses a double-
SITOFMS showed a quasi-molecular ion peak at m/z = 557.3493
[M + Na]+, which corresponded to the molecular formula
C30H45O8. The 1HNMR data exhibited eight methyl signals and
one olefinic proton signal, as well as three hydroxymethine sig-
nals at = 4.13 (1H, br d, J = 4.0 Hz), = 4.35 (1H, t, J = 7.5 Hz),
and = 4.42 (1H, m). The 13CNMR spectrum showed 30 carbon
signals due to eight methyl groups and two olefinic carbons. In
addition, three carbonyl groups, five methylenes, six methines,
and six quaternary carbons were observed. These data again
showed signal patterns quite similar to those of 23,24-dihydro-
cucurbitacin D (9) except for one additional hydroxylated meth-
ine carbon at = 66.2, whereas the methylene carbon at = 23.5
(C-7) was missing. HMBCs between the downfield proton signal
at H = 4.13 and C-14 (C = 47.5), C-6 (C = 121.7), and C-5
(C = 145.5) suggested that the hydroxy group was attached to C-
7. The appearance of H-8 (H = 2.15) as a singlet provided no cou-
pling constant between H-7 and H-8, corresponding to a dihedral
angle of approximately 90, and led to the conclusion that the 7-
OH was -oriented [7]. Therefore, compound 2 (l " Fig. 1) was de-

bond between C-23 and C-24. In analogy to the previously iso- termined to be 7-hydroxy-23,24-dihydrocucurbitacin D.

Sahranavard S et al. New Cucurbitane-Type Triterpenoids Planta Med 2010; 76: 10141017
1016 Letters
Compound 3 was obtained as a yellowish amorphous solid. Its
molecular formula was established as C9H11NO3 from its posi-
tive-mode HRESITOFMS (m/z = 204.0630 [M + Na]+). The
1
HNMR data showed two pairs of doublets ( = 7.80, J = 8.7 Hz
and = 6.88, J = 8.7 Hz) where each signal integrated as two pro-
tons, suggesting the presence of a para-substituted aromatic ring.
Furthermore, two downfield methylene groups at = 3.66 (2H, t,
J = 5.6 Hz) and = 3.47 (2H, q, J = 5.6 Hz) were observed. The
13
CNMR spectrum revealed the presence of six aromatic car-
bons, one carbonyl carbon, and two methylene group carbons.
The HMBCs between the carbonyl group at = 170.0 and the aro-
matic protons at = 7.80 (H-2 and H-6) suggested that the car-
bonyl group is attached to the aromatic ring. The protons of the
methylene group at = 3.47 (H-8) also showed correlations with
the carbonyl carbon, whereas its chemical shift in the 13CNMR
(C = 43.5) pointed to a nitrogen substitution. Therefore, the
structure of compound 3 (l " Fig. 1) was deduced as 4-hydroxy-
N-(2-hydroxyethyl)-benzamide (bryonamide A). This compound
is known, for example, as an intermediate from the chemical syn-
thesis of oxazoline derivatives [8], but it has never been described
as a natural product before.
Compound 4 was isolated as a yellowish amorphous solid, and its
molecular formula was established to be C10H13NO4 based on
positive-mode HRESITOFMS (m/z = 234.0739 [M + Na]+). Its
1
H- and 13CNMR data were quite similar to that of 3, but instead
of a para-substituted aromatic ring, characteristic signals for a
1,3,4-trisubstituted aromatic system were observed. Further-
more, the spectra revealed an additional methoxy group. There-
fore, the structure of compound 4 (l " Fig. 1) was deduced as 4-hy-
droxy-3-methoxy-N-(2-hydroxyethyl)-benzamide (bryonamide
B). This compound again represents a new natural product but
has been obtained synthetically before [9]. A simple benzamide
with the same substitution pattern in the aromatic ring was re-
cently obtained from Naravelia zeylanica [10].
The structures of the known compounds (see Supporting Infor-
mation) were identified as the pentacyclic triterpene bryonolic
acid (5) [11]; 23,24-dihydrocucurbitacin B (6) [12]; 23,24-dihy-
dro-epi-isocucurbitacin B (7) [13, 14]; cucurbitacin E (8) [15
17]; 23,24-dihydrocucurbitacin D (9) [15, 18]; cucurbitacin L
(10) [16, 19]; 23,24-dihydroisocucurbitacin D (11) [20]; 25-O--
D-glucopyranosyl-23,24-dihydrocucurbitacin D (12) [21]; and 2-
O--D-glucopyranosyl-23,24-dihydrocucurbitacin D (arvenin IV)
(13) [22] by comparison of their spectroscopic data with pub-
lished values.
Our results show that B. aspera is a rich source of cucurbitane-
type triterpenoids, most of which are derivatives of 23,24-dihy-
drocucurbitacin D, whereas 23,24-unsaturated congeners were
obtained only as minor constituents. Because bryonolic acid (5)
as well as several cucurbitacin derivatives are known to possess
strong antiproliferative activity [14, 23, 24], these compounds
might be responsible for the traditional use of B. aspera as an
anticancer remedy.
Materials and Methods
! l" Table 1; HRESITOFMS (positive): m/z = 525.2827 [M + Na]+
General experimental procedures
Optical rotations were measured on a Perkin-Elmer 241 MC po-
larimeter. NMR spectra were recorded on Bruker DPX 400 and
Bruker DRX 500 spectrometers. Chemical shifts are given relative
to TMS as an internal standard. EIMS were recorded on a Varian
MAT CH7A, and ESITOF spectra were obtained on an Agilent
6210 spectrometer. Silica gel 60 (70230 mesh; Merck) was used
Sahranavard S et al. New Cucurbitane-Type Triterpenoids Planta Med 2010; 76: 10141017
for column chromatography. HPLC analysis was performed on a
Knauer instrument with Eurochrom 2000 using a Lichrospher
100-C18 (5 m, 250 16 mm) column.
Plant material
The roots of B. aspera Stev. ex Ledeb. were collected from the
Turkmen Sahra, Golestan Province, Iran, in July 2006 and were
identified by Mr. H. Moazeni and Mr. M. Kamalinejad, Traditional
Medicine & Materia Medica Research Center, Shaheed Beheshti
University of Medical Sciences, Iran. Voucher specimens (TMRC
252) of the plant have been deposited in the herbarium of the
Traditional Medicine and Materia Medica Research Center.
Extraction and isolation
The dried and powdered roots of B. aspera (1.5 kg) were succes-
sively extracted with petroleum ether, chloroform, and methanol
(3 1 L each) at room temperature. The dried chloroform extract
(28.6 g) was separated by silica gel column chromatography
(68 6 cm) eluting with cyclohexane, a gradient of cyclohexane-
EtOAc (9 : 1, 8 : 2, 5 : 5, 3 : 7 to pure EtOAc), EtOAc-MeOH (5 : 5),
and MeOH to give 10 fractions. Compound 5 (500 mg) was pre-
Downloaded by: University of Pittsburgh. Copyrighted material.
cipitated from fractions 3 and 4 eluting with cyclohexane-EtOAc
5 : 5. Fraction 4 (500 mg), which was eluted with cyclohexane-
EtOAc 5 : 5, was chromatographed on a silica gel column
(30 2 cm) eluting with CH2Cl2-EtOAc (85 : 15 to 80 : 20) to afford
54 subfractions. Fractions 4550 (eluting with CH2Cl2-EtOAc
80 : 20) were further purified by HPLC [MeCNH2O 30 : 70
(90 : 10 in 30 min)] to yield 6 (Rt = 16 min, 18 mg) and 7
(Rt = 18 min, 8 mg). Fractions 3944 (eluting with CH2Cl2-EtOAc
85 : 15) were further purified by HPLC [MeCNH2O 50 : 50 (100
MeCN in 50 min)] to yield 8 (Rt = 30 min, 3 mg). Fraction 5 (3.4 g),
which was eluted with cyclohexane-EtOAc 3 : 7, was separated on
a silica gel column (40 4 cm) with a gradient of CH2Cl2-EtOAc
(85 : 15 to 40 : 60) to afford 44 subfractions. Further purification
of fractions 4043 (eluting with CH2Cl2-EtOAc 40 : 60) by prepa-
rative HPLC [MeCNH2O 30 : 70 (80 : 20 in 50 min)] yielded 9
(Rt = 20 min, 130 mg), 10 (Rt = 24 min, 114 mg), and 1 (Rt = 28 min,
26 mg). Separation of fraction 7 (4.4 g), which was eluted with
pure EtOAc by preparative HPLC [MeCNH2O 20 : 80 (80 : 20 in
50 min)], yielded 11 (Rt = 23 min, 150 mg). Fraction 8 (4.7 g),
which was eluted with EtOAc-MeOH 5 : 5, was separated by silica
gel CC (40 4 cm) using a gradient of CH2Cl2-MeOH [99 : 1
(80 : 20)] to afford 45 subfractions. Isolation was continued by
preparative HPLC [MeOHH2O 40 : 60 (MeOH, in 50 min)] of frac-
tions 3435 (eluting with CH2Cl2-MeOH 90 : 10) to afford 12
(Rt = 30 min, 43 mg) and of fractions 3740 (eluting with CH2Cl2-
MeOH 85 : 15) to afford 13 (Rt = 2 min, 73 mg) and 3 (Rt = 8 min,
5 mg). Purification of fractions 3033 (eluting with CH2Cl2-MeOH
90 : 10) by HPLC [MeOHH2O 40 : 60 (MeOH, in 50 min)] yielded 2
(Rt = 16 min, 14 mg) and 4 (Rt = 10 min, 7 mg). Spectroscopic data
of the known compounds are available as Supporting Informa-
tion.
Neocucurbitacin C (1): Yellowish amorphous solid; []20 D : + 12.05
(c 0.2, MeOH); 1H- (400 MHz) and 13CNMR (125 MHz) data: see
(calcd. for C29H42O7Na: 525.2823); ESITOFMS (negative): m/z =
501.2827 [M H].
7-Hydroxy-23,24-dihydrocucurbitacin D (2): White amorphous
solid; []20 1
D : + 9.86 (c 0.15, MeOH); H- (400 MHz) and
13
CNMR
(125 MHz) data: see l Table 1; HRESITOFMS (positive): m/
"
z = 557.3493 [M + Na]+ (calcd. for C30H45O8Na: 557.3085).

4-Hydroxy-N-(2-hydroxyethyl)-benzamide (bryonamide A) (3):
Yellowish amorphous solid; 1HNMR (400 MHz, acetone-d6):
= 7.80 (2H, d, J = 8.7 Hz, H-2,6); 6.88 (2H, d, J = 8.7 Hz, H-3,5),
3.66 (2H, t, J = 5.6 Hz, H-9), 3.47 (2H, q, J = 5.6 Hz, H-8); 13CNMR
(125 MHz, CD3OD): = 170.0 (s, C-7), 162.5 (s, C-4), 129.8 (d, C-
2,6), 126.8 (s, C-1), 115.8 (d, C-3,5), 61.7 (t, C-9), 43.5 (t, C-8);
HRESITOFMS (positive): m/z = 204.0630 [M + Na]+ (calcd. for
C9H11NO3Na: 204.0637); EIMS (80 eV): m/z (rel. int.) = 181 [M]+
(10), 163 (9), 121 (100).
4-Hydroxy-3-methoxy-N-(2-hydroxyethyl)-benzamide (bryona-
mide B) (4): Yellowish amorphous solid; 1HNMR (400 MHz,
CDCl3): = 7.49 (1H, d, J = 1.8 Hz, H-2), 7.25 (1H, dd, J = 1.8,
8.2 Hz, H-6), 6.96 (1H, d, J = 8.2 Hz, H-5), 6.56 (1H, brs, NH), 3.88
(2H, q, J = 4.8 Hz, H-9), 3.67 (2H, q, J = 4.8 Hz, H-8), 2.67 (1H, t,
J = 4.8 Hz, OH); 13CNMR (125 MHz, CD3OD): = 170.0 (s, C-7),
150.5 (s, C-4), 148.8 (s, C-3), 127.0 (s, C-1), 121.8 (d, C-6), 115.7
(d, C-5), 111.2 (d, C-2), 61.7 (t, C-9), 43.5 (t, C-8), 56.5 (q, OMe);
HRESITOFMS (positive): m/z = 234.0739 [M + Na]+ (calcd. for
C10H13NO4Na: 234.0743); EIMS (80 eV): m/z (rel. int.) = 211 [M]
+
(18), 193 (2), 167 (26), 151 (100), 123 (17).
Supporting information
The structures and spectroscopic data for compounds 513 are
available as Supporting Information.
Acknowledgements
! var. japonica. Biol Pharm Bull 1995; 18: 726729
The authors would like to thank Mr. Mohammad Kamalinejad
and Mr. Hamid Moazeni for the plant collection and identifica-
tion.
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Bibliography
DOI http://dx.doi.org/10.1055/s-0029-1240840
Published online January 27, 2010
Planta Med 2010; 76: 10141017
Georg Thieme Verlag KG Stuttgart New York
ISSN 00320943
Correspondence
Shamim Sahranavard
Traditional Medicine & Materia Medica Research Center
Shaheed Beheshti University of Medical Sciences
No. 8 Shams Alley, Valiassr Avenue
P. O. Box 1516745811
Tehran
Iran
Phone: + 98 21 88 77 60 27
Fax: + 98 21 88 77 60 27
ssahranavard@itmrc.org
Planta Med 2010; 76: 10141017