Anti-diabetic potential of ursolic acid stearoyl glucoside: A new triterpenic gycosidic ester from Lantana camara

Article abstract of DOI:10.1016/j.fitote.2011.10.004

A new stearoyl glucoside of ursolic acid, urs-12-en-3β-ol-28-oic acid 3β-d-glucopyranosyl-4′-octadecanoate and other compounds were isolated from the leaves of Lantana camara L. The structure of this new glycoside was elucidated and established by standard spectroscopic methods. In streptozotocin-induced diabetic rats it showed significant reduction in blood glucose level. Crown Copyright

Full text of DOI:10.1016/j.fitote.2011.10.004

Fitoterapia 83 (2012) 142–146
Contents lists available at SciVerse ScienceDirect
Fitoterapia
journal homepage: www.elsevier.com/locate/fitote
Anti-diabetic potential of ursolic acid stearoyl glucoside: A new triterpenic
gycosidic ester from Lantana camara
a
b
a
a
c
Imran Kazmi , Mahfoozur Rahman , Muhammad Afzal , Gaurav Gupta , Shakir Saleem ,
c
c
a
c
a,
Obaid Afzal , Md.Adil Shaharyar , Ujjwal Nautiyal , Sayeed Ahmed , Firoz Anwar ⁎
Siddhartha Institute of Pharmacy, Uttarakhand, India
Dreamz College of Pharmacy, Himachal Pradesh, India
Faculty of Pharmacy, Jamia Hamdard, New Delhi, India
a
b
c
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 27 June 2011
Accepted in revised form 10 October 2011
Available online 24 October 2011
A new stearoyl glucoside of ursolic acid, urs-12-en-3β-ol-28-oic acid 3β-D-glucopyranosyl-4′-
octadecanoate and other compounds were isolated from the leaves of Lantana camara L. The
structure of this new glycoside was elucidated and established by standard spectroscopic
methods. In streptozotocin-induced diabetic rats it showed significant reduction in blood
glucose level.
Keywords:
Lantana camara
Crown Copyright © 2011 Published by Elsevier B.V. All rights reserved.
Stearoyl glucoside of ursolic acid
Anti-diabetic
1
. Introduction
Lantana camara L. is regarded as a notorious weed; how-
plant is used in folk medicine for the treatment of cancers,
chicken pox, measles, asthma, ulcers, swellings, eczema, tu-
mors, high blood pressure, bilious fevers, catarrhal infections,
tetanus, rheumatism, malaria and ataxy of abdominal viscera
ever it is popular as an ornamental garden plant and is used
in folk medicine worldwide [1]. It is known as Red or Yellow
or Wild sage and has been used in many parts of the world to
treat a wide variety of disorders [2,3]. In spite of its medicinal
importance, it is an invasive plant species that has been
found in diverse geophysical environments, causing a threat
to the native flora. Various eradication programmes have
been attempted such as burning, chemical sprays, bio-
control agents and physical plugging mechanism to remove
such invasive species in India, Australia and many other
countries [4–6].
[
1,10]. The plant has displayed anticonvulsant [11], termici-
dal [12], wound healing [13,14], anticancer [15,16], antiulcer
17], antioxidant [16], anti-diabetic [18,19], analgesic and
[
anti-inflammatory [20], anti-motility [21], anti-feedant, lar-
val mortality/repellency [22–24], antifungal and antibacterial
[25–27] activities.
The leaves are found to contain various chemical constituents
such as monoterpenes; sesquiterpenes including germacrene-D,
γ-elemene, β-caryophyllene, β-elemene, α-copaene and α-
cadinene [28], zingiberene [29], b-curcumene, (E)-nuciferal,
Tea or decoction prepared from leaves and flowers is used
as a remedy and treatment for cough, fever, influenza, stom-
ach ache, tetanus, rheumatism, malaria and ataxy of abdom-
inal viscera [7,8]. Pounded leaves are applied to cuts, ulcers
and swellings for their healing properties [9]. Extract of this
(
Z)-nuciferol, (−)ar-curcumen-15-al, g-curcumene, ar-
curcumene, (−)-γ-epi-b-bisabolol and (−)-γ-curcumen-15-al
30, 31]; triterpenes including lantadenes [32–35], lantic acid
36], camarolic acid, lantrigloylic acid, camaric acid, lantanolic
[
[
acid, lantanilic acid, pomolic acid, camarinic acid, lantoic acid,
camarin, lantacin, camarinin, ursolic acid [37] and 28-
noroleanane [38]; glycosides including theveside, 3-methoxy-,
⁎
Corresponding author. Tel.: +91 9412937329; fax: +91 135 2607784.
E-mail address: firoz_anwar2000@yahoo.com (F. Anwar).
3,7-dimethoxy-
and
3,7,49-trimethoxyquercetin
[39],
0367-326X/$ – see front matter. Crown Copyright © 2011 Published by Elsevier B.V. All rights reserved.
doi:10.1016/j.fitote.2011.10.004

I. Kazmi et al. / Fitoterapia 83 (2012) 142–146
143
camaraside [40], verbacoside [41], martynoside [1], derhamno-
sylverbascoside, isonuomioside A and an iridoid glycoside
J=6.2 Hz, Me-18 ), 0.76 (3H, d, J=6.3 Hz, Me-30); MS m/z:
884 [M] (C54H O ).
92 9
+
[42,43]. The leaves are a rich source of fatty acids [44]; proteins
[45] and carbohydrates [46].
2.3. Anti-diabetic activity
2
. Materials and methods
2.3.1. Animals
Wistar albino rats (150–200 g) were obtained from Central
Animal Facility, Hamdard University and kept at 25± 1 °C,
2
.1. Plant material
5
5 ± 5% humidity along with 12 h light/dark cycle. The animals
L. camara Linn. leaves were collected from Hamdard Uni-
versity and identified by Dr. S. B. Singh, Scientist, NISCAIR,
New Delhi. A voucher specimen (NISCAIR/RHMD/consult/-
0-09-10/1322/125) was deposited in the herbarium of NIS-
CAIR, India.
were given standard pellet diet (Lipton rat feed, Ltd., Pune) and
water ad libitum throughout the experimental period. The ex-
periment was approved by the ‘Institutional Animal Ethics
Committee’. Extract of compound (1) and the standard drug
were administered orally.
2
2
.2. Extraction and isolation procedure
2.3.2. Chemicals
Only analytical grades chemicals and reagents were used.
Streptozotocin (Spectrochem Pvt. Ltd. Mumbai, India) was
obtained from Chopra chemicals (Delhi, India).
Dried powder of L. camara leaves (1.7 kg) was extracted
with methanol (4 L) at 50 °C for 1 day. Extract was concen-
trated to dryness under reduced pressure to obtain slurry
(
270 g). The slurry was dissolved in minimum amount of
2.3.3. Drugs
methanol and was adsorbed on silica gel (60–120 mesh).
The slurry was subjected to a silica gel column using a petro-
Standard drug: Glimepiride was prepared in Tween 80 so-
lution; Test drug: plant extract in CMC (1%) solution and
compound 1 in Tween 80 solution.
leum ether/CHCl
1
0
3
/MeOH gradient system (1:0:0, 3:1:0, 1:1:0,
:3:0, 0:1:0, 0:99:1, 0:49:1, 0:97:3, 0:19:1, 0:97:7, 0:91:9,
:89:11, 0:87:13 and 0:17:3; 2.0 L for each gradient system).
/MeOH (49:1) along
with two other known compounds, compound 2 from CHCl
2.3.4. Induction of diabetes
A new compound 1 (270 mg) from CHCl
3
The animals were fasted for 16 h prior to the induction of
diabetes. STZ freshly prepared in citrate buffer (pH 4.5) was
administered i.p. as a single dose of 50 mg/kg body weight.
The development of diabetes was confirmed by polydipsia,
polyurea and by measuring blood glucose concentrations
72 h after injection of STZ. The rats with blood glucose level
of 250 mg/dl or higher were considered to be diabetic and
were selected for the experiment. The animals were random-
ly assigned to various groups. Group I was the normal
untreated control rats and received distilled water daily for
21 days. Group 2, the diabetic control rats, received distilled
water during the experiment. Animals of Group III received
the reference standard drug Glimepiride (0.1 mg/kg), Groups
IV to V received the aqueous extracts of L. camara (250 mg/
kg, and 500 mg/kg) and Group VI received Compound 1
(0.3 mg/kg).
3
/
3
MeOH (97:3) and compound 3 from CHCl /MeOH (93:7)
were obtained as colourless crystals.
2
.2.1. urs-12-en-3β-ol-28-oic acid 3β-D-glucopyranosyl-4′-
octadecanoate (1)
f 3
Colourless crystal, mp 281–282 C; R : 0.28 (CHCl /MeOH,
9
3
1
5
4
9:1); UV λmax (MeOH): 220 nm (log ε 4.8); IR γmax (KBr):
424, 3392, 3150, 2930, 2855, 1721, 1703, 1635, 1447, 1379,
223, 1183, 1096, 1035, 994, 767 cm−1
1
3
; H NMR (CDCl ): δ
.35 (1H, d, J=6.0 Hz, H-12), 5.01 (1H, d, J=7.2 Hz, H-1′),
.67 (1H, m, H-5 ), 4.32 (1H, dd, J=7.2, 5.1 Hz, H-2′), 4.26
(
1H, m, H-3′), 4.15 (1H, m, H-4′), 3.62 (1H, dd, J=5.3, 9.6 Hz,
H-3α), 3.39 (1H, d, J=8.7 Hz, H -6′a), 3.25 (1H, d, J=9.3 Hz,
-6b′), 2.40 (1H, d, J=7.8 Hz, H -2a), 2.35 (1H, d , J=
.4 Hz, H -2b), 2.03 (2H, m, CH ), 1.61(4H, m, 2×CH ), 1.58
4H, m, 2×CH ), 1.28 (6H, brs, 3×CH ), 1.25 (14H, brs,
×CH ), 1.08 (3H, brs, Me-23), 1.03 (3H, brs, Me-27), 0.97
3H, brs, Me-25), 0.95 (3H, brs, Me-24), 0.92 (3H, d,
2
H
2
2
8
2
2
2
(
2
2
2.3.5. Estimation of blood glucose
7
2
The non fasting blood glucose level was determined just
before administering the drugs on 1st, 7th, 14th and 21st
day. The blood glucose level was estimated with One Touch
(
J=6.1 Hz, Me-29), 0.89 (3H, brs, Me-26), 0.85 (3H, t,
Table 1
Antidiabetic activity of compound 1 on Wister albino rat.
Groups
Treatment
Dose
Blood glucose level in mg/dl
1st day
8st day
14st day
21st day
I
II
III
IV
V
Normal
Normal saline
50 mg/kg
0.1 mg/kg
250 mg/kg
500 mg/kg
0.3 mg/kg
113.73± 4.69
370.33± 5.05
374.67± 5.06
366.67± 5.80
361.83± 14.72
366.45± 5.89
114.67± 1.02
374.50± 1.76
161.33± 2.21
183.83± 4.29
180.50± 3.07
183.56± 3.61
116.50± 1.56
368.33± 3.22
124.67± 1.80
165.50± 4.26
157.83± 5.28
143.43± 2.79
119.50± 1.15
375.33± 4.46
105.50± 3.12
136.83± 1.99
124.67± 2.40
118.67± 2.40
#
#
##
##
Diabetic control (streptozotocin)
Standard (Glimepiride)
Aq. extract of L. camara
Aq. extract of L. camara
Compound I
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
⁎⁎
VI
Values are given as mean± S.E.M. of six rats in each group. ## (Pb0.01) compared with the corresponding value for normal control animals (group I); ** (Pb0.01)
compared with the corresponding value for diabetic control animals (group II).

144
I. Kazmi et al. / Fitoterapia 83 (2012) 142–146
Basic Glucometer (Accu Chek Active, Roche, Germany), see
Table 1.
12-en-3β-ol-28-oic acid 3β-D-glucopyranosyl-4′-octade-
canoate (Fig. 1).
Compound 1 was evaluated for anti-diabetic activity [52–
5
4]. Many plant products can exert specific medicinal actions.
2
.3.6. Statistical analysis
All the data were expressed as mean± S.E.M., and analysis
The compounds in these plants have been explored for their
therapeutic potential to prevent and cure common and lethal
of variance (ANOVA) was used for the statistical analysis. The
values were considered to be significant when the P value
was b0.01.
3
. Result and discussion
The known compounds urs-12-en-3β-ol-28-oic acid (2)
[47] and oleane-12-en-3β-ol-28-oic acid 3β-D-glucopyrano-
side (3) [48], were identified by comparison of their spectro-
scopic data from the reported literature.
Compound 1, named stearoyl glucoside of ursolic acid was
obtained as colourless crystals using chloroform-methanol
(
49:1) elutant. Liebermann–Burchard, Salkowski and Anti-
mony trichloride tests [49] were positive for triterpenic gly-
coside. Carboxylic group in molecule was confirmed by
sodium bicarbonate effervescence test. The presence of acyl
group in the compound was confirmed by alkaline hydrolysis
which yielded triterpenic glycoside and stearic acid [50]. The
presence of acyl group was further confirmed by reaction of
compound 1 with potassium hydroxide, refluxed for 20 min
and distilled with ethyl alcohol. The presence of acyl group
was confirmed by Iodoform test with distillate [51]. IR
spectra showed the presence of hydroxyl group (3424,
1
−
1
−1
3
392 cm ), carbonyl group (3150, 1690 cm ), ester
−
1
−1
group (1721 cm ) and unsaturation (1635 cm ). The mo-
lecular weight of compound was established as 884 which
was found consistent with the molecular formula of penta-
92 9
cyclic triterpene glycosidic ester; C54H O . Nine degrees of
unsaturation, five of them adjusted in pentacyclic carbon
framework of the oleanene-type space triterpene and one of
each in the vinylic linkage, ester group, sugar unit and car-
boxylic group were found. The 1H NMR spectra displayed
two one–proton doublets at δ 5.35 (J=6.0 Hz) and 5.01
(
J=7.2 Hz) assigned to vinylic H-12 and anomeric H-1′ pro-
tons, respectively. Three one-proton multiplets at δ 4.67, 4.26
and 4.15 and a one-proton double doublet at δ 4.32 (J=7.2,
2
5
.1 Hz) were ascribed correspondingly to the carbinol proton
of sugar unit H-5′, H-3′, H-4′, and H-2′. The shifting of H-4
proton signal in the deshielded region suggested location of
the ester group at C-4′. Four one-proton doublet at δ 3.29
(
(
J=7.8 Hz), 3.25 (J=9.3 Hz), δ 2.40 (J=7.8 Hz) and at 2.35
J=8.4 Hz) were attributed to hydroxy methylene H -6 and
-2 protons adjacent to the ester group.
2
the methylene H
2
Five proton triplets at δ 1.08, 1.03, 0.94, 0.95, and 0.89 were
due to tertiary C-23, C-27 C-25, C-24, and C-26 methyl pro-
tons respectively, all attached to saturated carbons. Two
three-proton doublets at
δ 0.92 (J=6.1 Hz) and 0.76
(
J=6.3 Hz) and a three-proton triplet at δ 0.85 (J=6.2 Hz)
accounted for secondary C-29 and C-30 and primary C-18
methyl protons, respectively. The remaining methylene and
methane proton appeared between δ 2.83 and 1.25. Acid
hydrolysis of compound 1 yielded ursolic acid, D-glucose
and stearic acid, comparable with co-TLC. On the basis of
spectral data analysis and chemical reactions, the structure
of new triterpenic gycosidic ester was established as urs-
3
Fig. 1. Structures of compounds 1–3.

I. Kazmi et al. / Fitoterapia 83 (2012) 142–146
145
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