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1014 Letters

6 Salatino A, Salatino MLF, Negri G. Traditional uses, chemistry and phar-


macology of Croton species (Euphorbiaceae). J Braz Chem Soc 2007; 18:
1133
7 Chi VV. Dictionary of Vietnamese medicinal plants. Ho Chi Minh City: New Cucurbitane-Type Triterpenoids
Medicine Press; 1997: 622
8 Giang PM, Jin HZ, Son PT, Lee JH, Hong YS, Lee JJ. ent-Kaurane diterpe-
from Bryonia aspera
noids from Croton tonkinesis inhibit LPS-induced NF-B activation and Shamim Sahranavard 1, 2, Farzaneh Naghibi 1, 2, Karsten Siems 3,
NO production. J Nat Prod 2003; 66: 12171220
Kristina Jenett-Siems 4
9 Giang PM, Phan TS, Hamada Y, Otsuka H. Cytotoxic diterpenoids from
1
Vietnamese medicinal plant Croton tonkinensis Gagnep. Chem Pharm Pharmacognosy Department, School of Pharmacy, Shaheed
Bull 2005; 53: 296300 Beheshti University of Medical Sciences, Tehran, Iran
10 Bitterman KJ, Anderson RM, Cohen HY, Latorre-Esteves M, Sinclair DA. 2
Traditional Medicine & Materia Medica Research Center,
Inhibition of silencing and accelerated aging by nicotinamide, a puta- Shaheed Beheshti University of Medical Sciences, Tehran, Iran
tive negative regulator of yeast Sir2 and human SIRT1. J Biol Chem 3
Analyticon Discovery GmbH, Potsdam, Germany
2002; 277: 45 09945 107
4
11 Giang PM, Son PT, Lee JJ, Otsuka H. Four ent-kaurane-type diterpenoids Institut fuer Pharmazie (Pharmazeutische Biologie),
from Croton tonkinensis Gagnep. Chem Pharm Bull 2004; 52: 879882 Freie Universitaet Berlin, Berlin, Germany
12 Perry NB, Burgess EJ, Baek SH, Weavers RT, Geis W, Mauger AB. 11-Oxy-
genated cytotoxic 8,9-secokauranes from a New Zealand liverwort,
Abstract
Lepidolaena taylorii. Phytochemistry 1999; 50: 423433
!
13 Minh PTH, Ngoc PH, Taylor WC, Cuong NM. A novel ent-kaurane diterpe-
noid from Croton tonkinensis leaves. Fitoterapia 2004; 75: 552556 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-
received August 17, 2009 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-


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
Fig. 1 Structures of compounds 14. 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
ta are similar to those of neocucurbitacin B isolated from Luffa angle of approximately 90, and led to the conclusion that the 7-
operculata [6], which in comparison to 1 possesses a double- 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 for column chromatography. HPLC analysis was performed on a
molecular formula was established as C9H11NO3 from its posi- Knauer instrument with Eurochrom 2000 using a Lichrospher
tive-mode HRESITOFMS (m/z = 204.0630 [M + Na]+). The 100-C18 (5 m, 250 16 mm) column.
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- Plant material
tons, suggesting the presence of a para-substituted aromatic ring. The roots of B. aspera Stev. ex Ledeb. were collected from the
Furthermore, two downfield methylene groups at = 3.66 (2H, t, Turkmen Sahra, Golestan Province, Iran, in July 2006 and were
J = 5.6 Hz) and = 3.47 (2H, q, J = 5.6 Hz) were observed. The identified by Mr. H. Moazeni and Mr. M. Kamalinejad, Traditional
13
CNMR spectrum revealed the presence of six aromatic car- Medicine & Materia Medica Research Center, Shaheed Beheshti
bons, one carbonyl carbon, and two methylene group carbons. University of Medical Sciences, Iran. Voucher specimens (TMRC
The HMBCs between the carbonyl group at = 170.0 and the aro- 252) of the plant have been deposited in the herbarium of the
matic protons at = 7.80 (H-2 and H-6) suggested that the car- Traditional Medicine and Materia Medica Research Center.
bonyl group is attached to the aromatic ring. The protons of the
methylene group at = 3.47 (H-8) also showed correlations with Extraction and isolation
the carbonyl carbon, whereas its chemical shift in the 13CNMR The dried and powdered roots of B. aspera (1.5 kg) were succes-
(C = 43.5) pointed to a nitrogen substitution. Therefore, the sively extracted with petroleum ether, chloroform, and methanol
structure of compound 3 (l " Fig. 1) was deduced as 4-hydroxy- (3 1 L each) at room temperature. The dried chloroform extract
N-(2-hydroxyethyl)-benzamide (bryonamide A). This compound (28.6 g) was separated by silica gel column chromatography
is known, for example, as an intermediate from the chemical syn- (68 6 cm) eluting with cyclohexane, a gradient of cyclohexane-
thesis of oxazoline derivatives [8], but it has never been described EtOAc (9 : 1, 8 : 2, 5 : 5, 3 : 7 to pure EtOAc), EtOAc-MeOH (5 : 5),
as a natural product before. and MeOH to give 10 fractions. Compound 5 (500 mg) was pre-

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Compound 4 was isolated as a yellowish amorphous solid, and its cipitated from fractions 3 and 4 eluting with cyclohexane-EtOAc
molecular formula was established to be C10H13NO4 based on 5 : 5. Fraction 4 (500 mg), which was eluted with cyclohexane-
positive-mode HRESITOFMS (m/z = 234.0739 [M + Na]+). Its EtOAc 5 : 5, was chromatographed on a silica gel column
1
H- and 13CNMR data were quite similar to that of 3, but instead (30 2 cm) eluting with CH2Cl2-EtOAc (85 : 15 to 80 : 20) to afford
of a para-substituted aromatic ring, characteristic signals for a 54 subfractions. Fractions 4550 (eluting with CH2Cl2-EtOAc
1,3,4-trisubstituted aromatic system were observed. Further- 80 : 20) were further purified by HPLC [MeCNH2O 30 : 70
more, the spectra revealed an additional methoxy group. There- (90 : 10 in 30 min)] to yield 6 (Rt = 16 min, 18 mg) and 7
fore, the structure of compound 4 (l " Fig. 1) was deduced as 4-hy- (Rt = 18 min, 8 mg). Fractions 3944 (eluting with CH2Cl2-EtOAc
droxy-3-methoxy-N-(2-hydroxyethyl)-benzamide (bryonamide 85 : 15) were further purified by HPLC [MeCNH2O 50 : 50 (100
B). This compound again represents a new natural product but MeCN in 50 min)] to yield 8 (Rt = 30 min, 3 mg). Fraction 5 (3.4 g),
has been obtained synthetically before [9]. A simple benzamide which was eluted with cyclohexane-EtOAc 3 : 7, was separated on
with the same substitution pattern in the aromatic ring was re- a silica gel column (40 4 cm) with a gradient of CH2Cl2-EtOAc
cently obtained from Naravelia zeylanica [10]. (85 : 15 to 40 : 60) to afford 44 subfractions. Further purification
The structures of the known compounds (see Supporting Infor- of fractions 4043 (eluting with CH2Cl2-EtOAc 40 : 60) by prepa-
mation) were identified as the pentacyclic triterpene bryonolic rative HPLC [MeCNH2O 30 : 70 (80 : 20 in 50 min)] yielded 9
acid (5) [11]; 23,24-dihydrocucurbitacin B (6) [12]; 23,24-dihy- (Rt = 20 min, 130 mg), 10 (Rt = 24 min, 114 mg), and 1 (Rt = 28 min,
dro-epi-isocucurbitacin B (7) [13, 14]; cucurbitacin E (8) [15 26 mg). Separation of fraction 7 (4.4 g), which was eluted with
17]; 23,24-dihydrocucurbitacin D (9) [15, 18]; cucurbitacin L pure EtOAc by preparative HPLC [MeCNH2O 20 : 80 (80 : 20 in
(10) [16, 19]; 23,24-dihydroisocucurbitacin D (11) [20]; 25-O-- 50 min)], yielded 11 (Rt = 23 min, 150 mg). Fraction 8 (4.7 g),
D-glucopyranosyl-23,24-dihydrocucurbitacin D (12) [21]; and 2- which was eluted with EtOAc-MeOH 5 : 5, was separated by silica
O--D-glucopyranosyl-23,24-dihydrocucurbitacin D (arvenin IV) gel CC (40 4 cm) using a gradient of CH2Cl2-MeOH [99 : 1
(13) [22] by comparison of their spectroscopic data with pub- (80 : 20)] to afford 45 subfractions. Isolation was continued by
lished values. preparative HPLC [MeOHH2O 40 : 60 (MeOH, in 50 min)] of frac-
Our results show that B. aspera is a rich source of cucurbitane- tions 3435 (eluting with CH2Cl2-MeOH 90 : 10) to afford 12
type triterpenoids, most of which are derivatives of 23,24-dihy- (Rt = 30 min, 43 mg) and of fractions 3740 (eluting with CH2Cl2-
drocucurbitacin D, whereas 23,24-unsaturated congeners were MeOH 85 : 15) to afford 13 (Rt = 2 min, 73 mg) and 3 (Rt = 8 min,
obtained only as minor constituents. Because bryonolic acid (5) 5 mg). Purification of fractions 3033 (eluting with CH2Cl2-MeOH
as well as several cucurbitacin derivatives are known to possess 90 : 10) by HPLC [MeOHH2O 40 : 60 (MeOH, in 50 min)] yielded 2
strong antiproliferative activity [14, 23, 24], these compounds (Rt = 16 min, 14 mg) and 4 (Rt = 10 min, 7 mg). Spectroscopic data
might be responsible for the traditional use of B. aspera as an of the known compounds are available as Supporting Informa-
anticancer remedy. tion.
Neocucurbitacin C (1): Yellowish amorphous solid; []20 D : + 12.05

Materials and Methods (c 0.2, MeOH); 1H- (400 MHz) and 13CNMR (125 MHz) data: see
! l" Table 1; HRESITOFMS (positive): m/z = 525.2827 [M + Na]+

General experimental procedures (calcd. for C29H42O7Na: 525.2823); ESITOFMS (negative): m/z =
Optical rotations were measured on a Perkin-Elmer 241 MC po- 501.2827 [M H].
larimeter. NMR spectra were recorded on Bruker DPX 400 and 7-Hydroxy-23,24-dihydrocucurbitacin D (2): White amorphous
Bruker DRX 500 spectrometers. Chemical shifts are given relative solid; []20 1
D : + 9.86 (c 0.15, MeOH); H- (400 MHz) and
13
CNMR
to TMS as an internal standard. EIMS were recorded on a Varian (125 MHz) data: see l Table 1; HRESITOFMS (positive): m/
"

MAT CH7A, and ESITOF spectra were obtained on an Agilent z = 557.3493 [M + Na]+ (calcd. for C30H45O8Na: 557.3085).
6210 spectrometer. Silica gel 60 (70230 mesh; Merck) was used

Sahranavard S et al. New Cucurbitane-Type Triterpenoids Planta Med 2010; 76: 10141017
Letters 1017

4-Hydroxy-N-(2-hydroxyethyl)-benzamide (bryonamide A) (3): 13 Kitajima J, Mukai A, Masuda Y, Tanaka Y. Studies on the constituents of
trichosanthes root. III Constiuents of roots of Trichosanthes bracteata
Yellowish amorphous solid; 1HNMR (400 MHz, acetone-d6):
Voigt. Yakugaku Zasshi (J Pharm Soc Jpn) 1989; 109: 265270
= 7.80 (2H, d, J = 8.7 Hz, H-2,6); 6.88 (2H, d, J = 8.7 Hz, H-3,5), 14 Galindo A, Villegas N, Mansilla H. Cucurbitacins from Bryonia verrucosa.
3.66 (2H, t, J = 5.6 Hz, H-9), 3.47 (2H, q, J = 5.6 Hz, H-8); 13CNMR Isomerization of 2-hydroxy-3-keto-cucurbitacins. Nat Prod Lett 1999;
(125 MHz, CD3OD): = 170.0 (s, C-7), 162.5 (s, C-4), 129.8 (d, C- 13: 285292
2,6), 126.8 (s, C-1), 115.8 (d, C-3,5), 61.7 (t, C-9), 43.5 (t, C-8); 15 Vande Velde V, Lavie D. 13CNMR spectroscopy of cucurbitacins. Tetra-
hedron 1983; 39: 317321
HRESITOFMS (positive): m/z = 204.0630 [M + Na]+ (calcd. for
16 Seger C, Sturm S, Mair M, Ellmerer E, Stuppner H. 1H- and 13CNMR sig-
C9H11NO3Na: 204.0637); EIMS (80 eV): m/z (rel. int.) = 181 [M]+ nal assignment of cucurbitacin derivatives from Citrullus colocynthis
(10), 163 (9), 121 (100). (L.) Schrader and Ecballium elaterium L. (Cucurbitaceae). Magn Reson
4-Hydroxy-3-methoxy-N-(2-hydroxyethyl)-benzamide (bryona- Chem 2005; 43: 489491
mide B) (4): Yellowish amorphous solid; 1HNMR (400 MHz, 17 Yamada Y, Hagiwara K, Iguchi K, Takahashi Y. Carbon-13 NMR spectral
assignments of cucurbitacin aglycones. Chem Lett 1978; 319322
CDCl3): = 7.49 (1H, d, J = 1.8 Hz, H-2), 7.25 (1H, dd, J = 1.8,
18 Jacobs H, Singh T. Isolation and 13CNMR assignments of cucurbitacins
8.2 Hz, H-6), 6.96 (1H, d, J = 8.2 Hz, H-5), 6.56 (1H, brs, NH), 3.88 from Cayaponia angustiloba, Cayaponia racemosa and Gurania subum-
(2H, q, J = 4.8 Hz, H-9), 3.67 (2H, q, J = 4.8 Hz, H-8), 2.67 (1H, t, bellata. J Nat Prod 1990; 53: 16001605
J = 4.8 Hz, OH); 13CNMR (125 MHz, CD3OD): = 170.0 (s, C-7), 19 Isaev M. Bryonia isoprenes. II. Cucurbitacin L. and bryoamaride from
Bryonia melanocarpa. Chem Nat Prod 2000; 36: 292294
150.5 (s, C-4), 148.8 (s, C-3), 127.0 (s, C-1), 121.8 (d, C-6), 115.7
20 Hussein HA, Abdel-Halim OB, Marwan EM, El-Gamal AA, Mosana R.
(d, C-5), 111.2 (d, C-2), 61.7 (t, C-9), 43.5 (t, C-8), 56.5 (q, OMe); Dendrocyin: an isocucurbitacin with novel cyclic side chain from Den-
HRESITOFMS (positive): m/z = 234.0739 [M + Na]+ (calcd. for drosicyos socotrana. Phytochemistry 2004; 65: 25512556
C10H13NO4Na: 234.0743); EIMS (80 eV): m/z (rel. int.) = 211 [M] 21 Panosyan AG, Nikishchenko MN, Mnatsakanyan VA, Sadovskaya VL. New
+
(18), 193 (2), 167 (26), 151 (100), 123 (17). cucurbitacin glucosides from the roots of Bryonia alba L. Bioorg Khim
1979; 5: 721729
22 Yamada Y, Hagiwara K, Iguchi K, Suzuki S, Hsu H. Isolation and structure

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Supporting information of arvenins from Anagallis arvensis L. (Primulaceae). New cucurbitacin
The structures and spectroscopic data for compounds 513 are glucosides. Chem Pharm Bull 1978; 26: 31073112
available as Supporting Information. 23 Baek NI, Lee DW, Lee YH, Kim SI, Aprikian GV. Cytotoxic constituents
from the roots of Bryonia alba L. Nat Prod Sci 1995; 1: 4349
24 Kondo T, Inoue M, Mizukami H, Ogihara Y. Cytotoxic activity of bryonolic
Acknowledgements acid isolated from transformed hairy roots of Trichosanthes kirilowii
! 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. received September 25, 2009
revised December 16, 2009
References accepted January 4, 2010
1 Ghorbani A. Studies on pharmaceutical ethnobotany in the region of
Turkmen Sahra, north of Iran. J Ethnopharmacol 2005; 102: 5868 Bibliography
2 Hylands P, Kosugi J. Bryonoside and bryoside new triterpene glyco- DOI http://dx.doi.org/10.1055/s-0029-1240840
sides from Bryonia dioica. Phytochemistry 1982; 21: 13791384 Published online January 27, 2010
3 Pohlmann J. Die Cucurbitacine in Bryonia alba und Bryonia dioica. Phy- Planta Med 2010; 76: 10141017
tochemistry 1975; 14: 15871589 Georg Thieme Verlag KG Stuttgart New York
4 Oobayashi K, Yoshikawa K, Arihara S. Structure revision of bryonoside ISSN 00320943
and structure elucidation of minor saponins from Bryonia dioica. Phy-
tochemistry 1992; 31: 943946 Correspondence
5 Hylands P, Salama A. Cucurbitacin S, a new cucurbitacin from Bryonia Shamim Sahranavard
dioica. Phytochemistry 1976; 15: 559560 Traditional Medicine & Materia Medica Research Center
6 Kawahara N, Kurata A, Hakamatsuka T, Sekita S, Satake M. Two novel Shaheed Beheshti University of Medical Sciences
cucurbitacins, neocucurbitacin A and B from the Brazilian folk medi- No. 8 Shams Alley, Valiassr Avenue
cine Buchinh (Luffa operculata) and their effect on PEBP2A and OCIF P. O. Box 1516745811
gene expression in a human osteoblast-like Saos-2 cell line. Chem Tehran
Iran
Pharm Bull 2001; 49: 13771379
Phone: + 98 21 88 77 60 27
7 Chen C, Qiang S, Lou L, Zhao W. Cucurbitacin-type triterpenoids from
Fax: + 98 21 88 77 60 27
the stems of Cucumis melo. J Nat Prod 2009; 72: 824829 ssahranavard@itmrc.org
8 Fiocca L, Po R, Giannotta G, Gleria M, Venzo A, Milani R, Depaoli G. Oxa-
zoline-containing phosphazene derivatives, part III: synthesis and
characterization of novel cyclophosphazenes functionalized with chi-
ral 2-oxazoline groups. Des Monomers Polym 2008; 11: 243260
9 Claus P, Klein E, Grosch W, Bertl H, Kratzl K. Phenolcarboxylic acid deriv-
atives yielding formaldehyde on cleavage. Monatsh Chem 1966; 97:
271280
10 Jaroszewski JW, Staerk D, Holm-Moller SB, Hogh Jensen T, Franzyk H, So-
manadhan B. Naravelia zeylanica: occurrence of primary benzamides
in flowering plants. Nat Prod Res 2005; 19: 291294
11 Akiyama K, Hayashi H. Arbuscular mycorrhizal fungus-promoted accu-
mulation of two new triterpenoids in cucumber roots. Biosci Biotech-
nol Biochem 2002; 66: 762769
12 Wu P, Lin F, Wu T, Kuoh C, Lee K, Lee S. Cytotoxic and anti-HIV priciples
from the rhizomes of Begonia nantoensis. Chem Pharm Bull 2004; 68:
12481254

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