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Original Article
CHEMICAL PROFILE OF TWO JASMINUM SAMBAC L. (AIT) CULTIVARS CULTIVATED IN
EGYPT–THEIR MEDIATED SILVER NANOPARTICLES SYNTHESIS AND SELECTIVE
CYTOTOXICITY
SEHAM S. EL-HAWARY
1
, HALA M. EL-HEFNAWY
1
, SAMIR M. OSMAN
2
, EMAN S. MOSTAFA
3
, FATMA ALZAHRAA
MOKHTAR
1*
, MOHAMED A. EL-RAEY
4
1, 2
Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, Egypt,
3
Department of Pharmacognosy, Faculty of
Pharmacy, October University for Modern Sciences and Arts (MSA), 6
th
October City, Giza, Egypt,
4
Phytochemistry and Plant Systematic
Department, National Research Centre, Dokki, Cairo, Egypt
Email: drfatmaalzahraa1950@gmail.com
Received: 17 Apr 2019, Revised and Accepted: 23 Sep 2019
ABSTRACT
Objective: Evaluation of two Jasminum sambac L. (Ait) cultivars; Arabian Nights (JSA) and Grand Duke of Tuscany (JSG) ethanolic leaves extracts as
reducing agents for the green synthesis of silver nanoparticles (AgNPs) and evaluation of their cytotoxicity against MCF-7 breast cancer and 5637
bladder cancer cell lines and chemical profiling of the two cultivars.
Methods: The synthesis of silver nanoparticles (AgNPs) by the two cultivars and characterization of AgNPs by ultraviolet (UV)–visible
spectroscopy, Transmission electron microscopy (TEM) and Fourier Transform Infrared Spectroscopy (FTIR). Additionally, the use of The high-
performance liquid chromatography coupled with photodiode array-mass-mass-spectroscopy (HPLC-PDA-MS/MS) for chemical profiling of both
cultivars and evaluation of total leaves extracts and corresponding nanoparticles towards MCF-7 and 5637 cell lines compared to aneuploidy
immortal keratinocyte (Ha Cat) normal cells by neutral cell assay.
Results: The green synthesized AgNPs (of an average size range of 8.83 and 11.24 nm for JSA and JSG, respectively) exhibited cytotoxicity against
MCF-7 and 5637 cell lines. The IC
50
was determined for each total extract JSA (15.29±2.16 μg/ml) and JSG (20.28±1.20 μg/ml) and corresponding
AgNPs 17.32±2.22 μg/ml and 6.32±1.01μg/ml for JSA and JSG, respectively. The IC
50
of JSA and JSG against 5637 bladder cancer cell line were
13.76±1.11 μg/ml and 50.69±3.75 μg/ml, while the corresponding AgNPs showed IC
50
of 5.54±0.88 μg/ml and 27.89±2.84 μg/ml, respectively. The
HPLC-PDA-MS/MS allowed the identification of 59 compounds; 10 simple phenols, 17 flavonoids; quercetin and kaempferol glycosides, 2 lignans,
and 30 secoiridoids; oleuropein, molihauside, and sambacoside.
Conclusion: This study proved that JSA is an excellent source for the synthesis of AgNPs with optimum characters and enhanced activities toward
MCF-7 and 5637 cell lines in correlation to identified compounds.
Keywords: Jasminum sambac, AgNPs, HPLC-PDA-MS/MS, cytotoxicity, green synthesis
© 2019 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/)
DOI: http://dx.doi.org/10.22159/ijap.2019v11i6.33646
INTRODUCTION
Cancer is the second leading death cause 9.6 million death cases
worldwide in 2018, most death cases are in low-and-middle-income
countries. The most common cancers are breast cancer around 2.09
million cases [1]. Precancerous lesions convert normal cells to
malignant tumors due to several factors as exposure to ultraviolet
(UV) and infrared (IR) radiation, chemical carcinogens such as
tobacco smoke, aflatoxin and arsenic and biological carcinogens due
to infectious diseases: viruses, parasites and bacteria and may be
due to genetic causes Bladder cancer is the second prominent cancer
in males, this type of cancer is resistant for most medical treatments,
with the highest incidence in developing countries, most cases of
bladder tumor are subjected to tumor recurrence after radical
cystectomy [2]. In the early stages, medication therapies are
involved in the form of hormonal therapy, targeted therapy [3] or
chemotherapy. Several studies have been devoted to the discoveries
of new natural therapies that can fight the cancerous cell
progression with limited effect on normal cells to achieve the
maximum healing properties of breast cancer that can overcome the
side effects of previous treatment protocols [4].
Nanoparticle sciences involve recently considerable interest from both
academic and industrial fields and spreading of their application
practically in medicinal [5-7], electrical [8], agriculture, environment
[9] and aquaculture fields due to spontaneous discoveries of their
diverse and interesting properties. Development of biologically based
and inspired processes for the optimization of nanoparticles
characters to target specific diseases or drug delivery pathway is an
important branch of nanoscience and nanotechnology. In recent
tendency, silver nanoparticles are introduced in medical researches as
antimicrobial [10], antifungal, antiviral and cytotoxicity against many
cell lines as NIH 3T3 cells and Hela cells [11].
Synthesis of nanoparticles is achieved using chemical, thermal or
biological synthesis using bacteria or natural plant extracts [12, 13].
The biological green pathway involves using of natural plants
extracts as reducing agents is more favorable for the development of
nanoparticles of optimized characters excluding the effects of
chemicals which could alter the nanoparticles characters, toxicity
and biological activity [14].
Jasminum sambac L. (Ait), Oleaceae is also known as Arabian Jasmine
is native to Middle east and Asia. The two cultivars Jasminum sambac
L.” Arabian Nights”; (JSA) and Jasminum sambac L.”Grand duke of
Tuscany”; (JSG) are cultivated in Egypt for thousands of years [15].
Both cultivars are characterized by the high scent aroma of the shiny
white composite flowers. They differ from each other by the shape of
leaves and the structure of the corolla. They are extensively used in the
perfume industry and as a flavoring agent in jasmine tea and
aromatherapy [16]. Considerable attention has been gained to
Jasminum sambac cultivars and their pharmacological activity[17].
Several studies were performed on its antidiabetic [18], anti-
inflammatory [19], vasodilator activity [20] and effect on morphine
withdrawal symptoms [21]. Additionally, extracts of the flowers were
reported to exhibit cytotoxic activity towards brine shrimp Artemia
[22], Hep-G2 [23] and Dalton’s ascites lymphoma [24].
High-performance liquid chromatography coupled to photodiode
array–mass spectroscopy-mass spectroscopy (HPLC-PDA-MS/MS) is
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ISSN- 0975-7058
Vol 11, Issue 6, 2019
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
155
a type of liquid chromatography-mass spectroscopy used for
tentative identification and profiling of the chemical composition
and the fragmentation pattern of base peaks of selected plant
species [25-27]. This chromatographic technique is used for
complete qualitative profiling of secondary metabolites with link to
the library for tentative identification.
The current research aims to evaluate the silver nanoparticles
(AgNPs) synthesized by the JGA and JSG total ethanolic extracts
towards MCF-7 breast cancer cell line and 5637 bladder cancer
cell line in compariso n to t he leaves total e xtracts. Also, the
identific atio n o f t he chemical composi tion of the total extracts o f
leaves was pe rformed using HPL C-PDA-MS/MS technique .
MATERIALS AND METHODS
Plant material
The plant leaves were collected in March 2016 from fully mature
non flowering stage plants from Keram Farms-Moderayat Al-Tahrir,
Behaira, Egypt. Voucher specimens (# 3.10.16.2), (#3.10.16.6) for
Jasminum sambac L. (Ait) Arabian Nights cultivar and Jasminum
sambac L. (Ait) Grand Duke of Tuscany cultivar, respectively are
kept at the Department of Pharmacognosy, Faculty of Pharmacy,
Cairo University.
Preparation of extracts
The dry leaves (100) g of each of JSA and JSG were extracted
with 9 9% ethanol by perco lation (4 x 1 L), filtere d through
Whatmann No.1 filter paper (pore size 0.6 m), each filtrate was
conce ntrated under vacuum using rotary evaporator at 45° C and
lyophilized to yield 24% and 20% dry extract, respecti vely. One
hundred mg of each lyophili zed extract was used for HPLC-PDA-
MS/MS ana lysis, nanoparticles synthesis, cha racterization, and
cytotoxicity study.
Green synthesis of silver nanoparticles (AgNPs)
AgNPs were synthesized as in the following protocol: 1 Mm aqueous
solution of silver nitrate (AgNO3) was prepared and kept in a cool
and dark place to use in the synthesis of 1 mmol aqueous solution of
silver nitrate (AgNO3) was prepared and used for the synthesis of
silver nanoparticles. 10 ml of each ethanolic extract of leaves of JSA
and JSG added separately into 90 ml of an aqueous solution of 1
mmol silver nitrate for reduction of Ag+ions and incubated
overnight at room temperature in dark place. The resultant
yellowish brown solutions were the indication for the formation of
silver nanoparticles. The formed solutions were used directly for
TEM and UV quantifications [12, 13]. Centrifugation at 4000 rpm for
30 min. followed by a series of washing by dist. H2O, filtration to
obtain pure AgNPs. The pure AgNPs were used for cytotoxicity
study.
Characterization of AgNPs
The UV–Vis spectroscopy of AgNPs were monitored as a function of
time in 10 mm optical path-length-quartz-cuvettes with UV–Vis
range 3600 spectrophotometer (Shimadzu, Japan). Samples were
diluted 5 times with distilled water before being measured. The
morphology of the particles (shape and dimensions) was examined
by Transmission electron microscope (TEM). (JEOL-JEM-1011,
Japan). Sample for TEM analysis were prepared by placing 3 ml of
the sample on the copper grid and kept for drying at room
temperature for 15 min. The different functional groups of the
prepared nanomaterials in the range of 4000–400 cm_1 were
measured by Fourier transform infrared spectroscopy (FTIR) 6100
spectrometer (Jasco, Japan).
Cytotoxicity assay
Cells of breast cancer cell line (MCF-7) and colon cancer cell line
(5637) were obtained from the CLS Cell Lines Service (Eppelheim,
Germany). Cells were cultured in RPMI 1640 medium (BioWhittaker,
Lonza, Belgium) supplemented with 8 % fetal bovine serum (Sigma
Aldrich, Germany) and a ntibiotics (100 U/ml penicillin/100
µg/ml streptomycin; Sigma Aldrich, Germany) at 95% humi dity,
5% CO2 and 37.5 ◦C. MCF-7 and 5637 cells were sub-cultured
twice a week and regularly tested for mycoplasma
conta mination . Cytotoxicity of test sample s investig ated cell li ne
using the neutral red uptake (NRU) assay [2 8]. Statistical
analy sis of the data was expressed as mea n±SD for tr iplicate
trials of each measurement.
Therapeutic index
The therapeutic index is calculated as the ratio between the IC
50
of
the extract or nanoparticles on the normal keratinocyte cells and the
IC
50
on the cancer cell line. The drug or extract is considered
effective with low cellular toxicity if the therapeutic index (TI) is
high [29].
TI =IC50 on normal cells/IC50 on cancer cells
HPLC-PDA-MS/MS
HPLC-PDA-MS/MS using A Thermo Finnigan LC system (Thermo
Electron Corporation, Austin, TX, USA). A Zorbax Eclipse XDB-C18;
Rapid resolution, 4.6 × 150 mm, 3.5 µm column was used (Agilent,
Santa Clara, CA, USA). A gradient consisting of water, 0.1% formic
acid and acetonitrile, acetonitrile was increased to 30% within 60
min with a flow rate1 ml/min and a 1:1 split before the ESI source
[30]. The sample was injected using autosampler. LCQ-Duo ion trap
having a Thermo Quest ESI source was used for MS analysis.
Xcalibur software (Xcalibur™ 2.0.7, Thermo Scientific, Waltham, MA,
USA) was used to control the system. MS operating parameters in
the negative mode were used as described in [31].
RESULTS AND DISCUSSION
Nanoparticles characterization
UV-vis spectroscopy
UV-vis spectroscopy is a reliable, accurate, simple, selective
technique for monitoring the synthesis and stability of AgNPs.
AgNPs have unique optical properties, which make them strongly
interact with specific wavelengths of light. The conduction band and
valence band lie close to each other in which electrons move freely.
These free electrons give rise to a surface plasmon resonance (SPR)
absorption band due to the collective oscillation of electrons of
AgNPs [32]. The absorption of AgNPs depends on the dielectric
medium, and chemical surroundings, particles dimensions, and
particle size. Observation UV measurements of the formed
nanoparticles showed absorbance at 443 nm for JSA AgNPs and 447
nm for JSG AgNPs.
Transmission electron microscopy (TEM)
TEM photography fig. (1) Showed biosynthesized AgNPs were
predominantly spherical in shape with an average size ranging of
8.83 and 11.24 nm for JSA AgNPs and JSG AgNPs, respectively.
Fourier transform infrared spectroscopy (FTIR)
The FTIR spectroscopy analysis was performed to investigate plant
metabolites acting as reducing agents for the metal ions to form
nanoparticles and supporting their subsequent stability [33, 34]. For
JSA and JSG FIG (2A, 2B) The peaks near 3280, 2942 and
1648 cm
−1
could be due to the O-H, aliphatic C-H and C=O stretching
vibration of flavonoids and phenolic groups. The peak
1408 cm
−1
corresponds for polyphenol OH and confirms the presence
of an aromatic group, while the absorption peaks at 1012 cm
−1
were
assigned for C-O-C and secondary OH group. (In fig. 2 C, D), there is a
deviation at 3280 and 1648 cm
−1
of peak observed for JSA AgNPs and
JSG AgNPs fig. (2 C, D). It suggests that the O-H and C=O groups were
adsorbed on the surface of AgNPs have a deterministic role in the
reduction of silver nitrate for AgNPs formation. These functional
groups are attributed to flavonoids and secoiridoids the main
components of the extracts.
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
156
Fig. 1: TEM of silver nanoparticles biosynthesized using JSA; a (100 nm), b (200 nm) and JSG; c (100 nm), d (200 nm)
Fig. 2: FTIR spectra of a; total ethanolic leaves extract of JSA, b; JSA AgNPs, c; total ethanolic leaves extract of JSG, d; JSG AgNPs
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
157
Cytotoxicity results
Both ethanolic extracts of cultivars of Jasminum sambac possessed
cytotoxic activities against MCF-7 cell lines JSA (IC
50
= 15.29±2.16
µg/ml), while JSG showed lower (IC
50
= 20.28±1.20 µg/ml)
indicating both Jasminum sambac cultivars show cytotoxicity with a
higher cytotoxic effect of the total ethanolic extract of JSA than JSG.
The corresponding synthesized AgNPs showed higher cytotoxicity
toward the MCF-7 breast cancer cell line with (IC
50
= 6.32±1.01
µg/ml) for JSA AgNPs and (IC
50
=17.32±2.22 µg/ml) for JSG AgNPs.
JSA AgNPs were more effective than the standard drug etoposide.
IC
50
are arranged in the following order JSA AgNPs>etoposide>
JSA>JSG AgNPs>JSG. Table (1), fig. 3.
The cytotoxicity of ethanolic extract of JSA against 5637 bladder
cancer cell line (IC
50
= 13.76±1.11µg/ml) while ethanolic extract of
JSG (IC
50
= 50.69±3.75 µg/ml), meanwhile corresponding AgNPs
exhibited better cytotoxicity on 5637 cell line with (IC
50
= 5.54±0.88
µg/ml) and (IC
50
27.89±2.84 µg/ml) for JSA AgNPs and JSG AgNPs,
respectively. Both extracts and their corresponding AgNPs have very
low toxicity toward normal cell line (Ha CaT)>300 µg/ml as
illustrated in table (1), fig. (2, 3).
Table 1: IC
50
of JSA and JSG ethanolic extracts and their corresponding AgNPs on cell lines; MCF-7 breast cancer and 5637 bladder cancer
and normal keratinocyte (Ha CaT) using selective standard drugs etoposide for (MCF-7) and Vincristine for (5673) cell lines
IC
50
µg
/ml±
standard
deviation
MCF
-
7
5637 cells
Ha CaT
JSA
15.29±2.16
13.76±1.11
500±7.90
JSA
AgNPs
6.32±1.01
5.54±0.88
490±4.90
J
SG
20.28±1.20
50.69±3.75
400±6.33
JSG
AgNPs
17.32±2.22
27.89±2.84
300±4.56
e
toposide (standard)
10.90±1.06
-------
444.14±1.59
v
incristine (standard
)
-
------
43
.0
±3.21
520±5.76
Values are expressed as mean±SD (N=3)
Fig. 3: IC
50
of ethanolic extracts of leaves of JSA and JSG ethanolic extracts and their corresponding synthesized AgNPs on MCF-7 breast
cancer and 5637 bladder cancer cell lines (Values are expressed as mean±SD)
Fig. 4: Therapeutic index of ethanolic extracts of leaves of JSA and JSG and their corresponding synthesized AgNPs on MCF-7 breast cancer
and 5637 bladder cancer cell lines
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
158
By calculating the therapeutic indices of JSA and JSG and their
corresponding AgNPs, all the tested extracts and AgNPS have a good
TI but a very high TI of JSA AgNPs toward both cell lines: MCF-7
breast cancer cell line (93.5) and the 5637 bladdetr cell line (81.3).
Indicating the effectiveness of JSA AgNPs toward the two cell lines
with very low cellular toxicity.
HPLC-PDA-MS/MS
Phytoconstituents of the two Jasminum sambac cultivars were
identified via HPLC-PDA-MS/MS, a total of 59 compounds were
identified as listed in table (2) and fig. (4), assignments were done
by comparing retention times data and UV-vis spectral data for the
screening and qualitative determination of phenolic acids,
secoiridoids glycosides and flavonoids in plants has been
illustrated with the ethanolic leaves extracts of Jasminum sambac
(Ait.) cultivars. In this paper, it has been shown that parent ion
scan and base peaks are powerful tools to identify the presence of
certain compounds often occurring in genus Jasminum,
interpretation of HPLC-PDA-MS/MS of JSA and JSG showed some
variations among these 2 cultivars, JSA result in tentative
identification of 42 compounds the main class is the secoiridoid
glycosides 23 compounds and 2 lignans in addition to simple
phenols and flavonoids. While in JSG cultivar a total of 26
compounds were tentatively identified composed of 9
secoiridoids, 7 phenolic acids derivatives, and 9 flavonoid
glycosides and one lignan. Table (2), fig. 4
Identification of simple phenols and phenolic acids
Simple phenols i.e. free hydroxytyrosol (2) and hydroxytyrosol
hexoside (1) with molecular ion peaks at [M-H]
-
of m/z 315, 153
were identified in JSA, while not identified in JSG. Phenolic acids and
derivatives; caftaric acid, caftaric acid rhamnoside, ethyl cinnamate,
syringic acid, and salvianolic acid were determined in JSG, and
coumaroyl hexoside has been detected in JSA only.
Protocatechualdehyde and sinapoyl hexoside were detected in both
cultivars.
Fig. 4: Total ion chromatogram of ethanolic extracts of leaves of a; JSA and b; JSG
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
159
Table 2: Tentative identification of the chemical profile of ethanolic extracts of leaves of JSA and JSG using HPLC-PDA-MS/MS in the
negative ion mode
No.
t
r.(min)
JSA
JSG
[M
-
H]
-
MS/M
S
UV (nm)
Identified compound
Ref.
1
9.65
+
-
315
153,
123
278
hydroxy tyrosol
hexoside
[35]
2
11.27
-
+
153
123
277
hydroxy tyrosol
[35]
3
12.2
+
+
137
109
277
P
rotocatechualdehyde
[36]
4
12.39
-
+
447
311
276
caftaric acid rhamnoside
5
14.05
+
-
325
163
260,282
coumaroyl hexoside
[36, 37]
6
15.4
-
+
175
147
268
ethyl cinnamate
[38]
7
18.39
-
+
567
405
229, 278
oleoside 11methy ester hexoside
[39]
8
19.02
+
+
565
403
229, 278
10
-
hydroxy oleoside hexoside
[40]
9
20.59
-
+
311
267, 249
276
caftaric acid
[41, 42]
10
21.44
+
-
755
593, 285
342
kaempferol rutinoside hexoside
[43]
11
22.42
+
+
537
375
n
. d
.
cycloolivil hexoside
[44]
12
22.73
+
-
403
223
227, 277
oleoside 11 methyl ester
[45]
13
22.94
+
+
385
223
269, 282
sinapoyl hexoside
[46]
14
24.92
-
+
197
171, 153
266, 281
syringic acid
[47, 48]
15
25.02
-
+
491
293, 191
265, 290
salvianolic acid
[49]
16
25.32
-
+
755
593, 447
n
. d
.
quercetin
hexosyl dirhamnoside
[50]
17
25.63
-
+
521
389
224, 280
oleoside pentoside
[51]
18
27.48
+
-
625
463,301
346
quercetin dihexoside
[52]
19
28.44
+
-
393
311, 179
233
jasmolactone B
[53]
20
28.59
+
+
609
463, 301
352
quercetin rutinoside
[54, 55]
21
30.23
-
739
285
344
kaempferol hexoside
dirhamnoside
[43]
22
30.56
-
+
771
609,285
345
kaempferol trihexoside
[56]
23
30.81
+
-
609
447, 285
344
kaempferol
dihexoside
[56]
24
30.86
+
-
589
353, 209
n
. d
.
hydroxy jasmesosidic acid methyl ester
[39]
25
31.27
+
-
913
895, 209
n
. d
.
jasmosidic acid
[57]
26
31.44
-
+
609
447, 301
353
quercetin
hexosyl rhamnoside
[38]
27
31.96
-
+
593
447, 285
342
kaempferol rutinoside
[50]
28
32.76
+
-
463
301, 179
350
quercetin hexoside
[38]
29
33.97
+
+
623
461, 315
336
isorhamnetin hexosyl rhamnoside
[58]
30
34.15
+
-
555
389, 345
231, 280
Jaspolinaloside
[59]
31
34.25
+
-
579
433, 301
n
. d
.
quercetin rhamnosyl pentoside
[38]
32
35.37
+
-
579
417,285
342
kaempferol
pentosyl hexoside
[56]
33
35.69
-
-
433
301
348
quercetin pentoside
[38]
34
36.22
+
-
499
315
n
. d
.
jasmolactone C
[60]
35
36.65
+
+
447
285
344
kaempferol hexoside
[61]
36
37.01
+
-
701
539
232, 277
oleuropein
hexoside
[62]
37
38.49
+
-
685
523
230, 277
ligstroside hexoside
[63]
38
42.36
+
-
403
241,223
226, 280
elenoic acid hexoside
[64]
39
43.32
+
-
677
515
231, 277
Multifloroside
[65]
40
43.88
+
-
839
667
231,282
caffeoyl multifloroside
[65]
41
44.15
+
-
539
377
233, 277
Oleuropein
[66]
42
44.78
-
+
593
447, 301
282, 339
caffeoyl kaempferol rhamnosyl
[67]
43
45.87
+
-
975
813
233
d
eacylsambacoside
A
isomer
[68]
44
46.02
+
-
1071
839
234
P
olyanoside
[69]
45
46.66
-
+
975
813,589
234
m
olihuaside A
[68]
Table 2: Tentative identification of the chemical profile of ethanolic extracts of leaves of JSA and JSG using HPLC-PDA-MS/MS in the
negative ion mode
No tr (min) JSA JSG [M-H]
-
MS/MS UV(nm) Identified compound Ref.
46 47.13 + - 945 783, 421 229 jasnudifloside H [70]
47 48.69 - + 1347 589 231 dihydrojasuroside A [62]
48 49.51 + - 1347 1183, 961 222, 276 dihydro jasnudifloside B [71]
49 50.37 + - 975 813, 589 226 deacylsambacoside A isomer [68]
50 51.45 + - 523 377 231, 277 Ligstroside [63]
51 51.58 - + 921 759, 389 235 sambacolignoside [72]
52 51.69 - + 965 921, 759 233 carboxy sambacolignoside [72]
53 52.12 + - 375 195, 179 n. d. Cycloolivil [71]
54 53.31 + - 819 539 226, 278 jaspolyanthoside [73]
55 53.42 + + 1361 961, 589 229 sambacoside A [74]
56 53.75 - + 945 713, 559 233 jasnudifloside H [70]
57 59.19 + - 285 267, 251 341 Kaempferol [75]
58 59.62 + - 909 523 229 Jaspolyanoside [76]
59 63.15 + - 943 727,595 227 jaspogeranoside B [59]
No: compound number tr (min): retention time in minutes Ref: reference, *compounds are numbered according to elution from the column
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
160
Identification of secoiridoids
Secoiridoids are the characteristic key elements in the Oleaceae
family[77]. Secoiridoid glycosides are secoiridoids attached to
phenolic compound: ligstroside and oleuropein or secoiridoids
attached to tetraol structure as sambacoside A or secoiridoids
attached to lignans; sambacolignoside. In this study 30 secoiridoids
were identified via HPLC-PDA-MS/MS (peaks 7, 8, 12, 17, 19, 24, 25,
30, 34, 36-41, 43-51, 53-56, 58 and 59). Oleuropein derivatives are
the major secoiridoid class in this plant family were assigned in
peaks 39, 40, 41 and 44 with a corresponding molecular ion [M-H]-
of m/z 677, 839, 539 and 1071, respectively. A major abundance of
tetraol dimeric and trimeric secoiridoid hexosides was detected,
dimeric secoiridoids peaks 25, 43, 45, 49, 54 and 58 with a
corresponding molecular ion [M-H]
-
of m/z 913, 975, 975, 975, 819
and 909 respectively, compounds with the same mass distinguished
from each other by the fragmentation pattern, tetraol trimeric
secoiridoid glycosides was represented in peaks 47, 48 and 55 and
with a corresponding molecular ion [M-H]
-
of m/z 1347, 1347, and
1361 respectively. Peak 55 (sambacoside A) is the characteristic
compound in both Jasminum sambac cultivars, secoiridoids lactones
were determined and represented by the peaks 19, 34 with a
corresponding molecular ion [M-H]
-
of m/z 393 and 499
respectively. Secoiridoid gconjugated to lignin was assigned in the
peak 51 (sambacolignoside) with molecular ion [M-H]
-
of m/z 921.
Most other secoiridoids identified are classified as oleoside
derivatives with different substitutions at 7, 11 and 10 positions of
the secoiridoid nucleus to give the peaks 7, 8, 30, 37 and 38 with a
corresponding molecular ion [M-H]
-
of m/z 567, 565, 555, 685 and
403 respectively.
Identification of flavonoids
MS/MS spectral analysis allowed the tentative identification of
sixteen flavonoid glycosides peaks 10, 16, 18, 20-23, 26-29, 31-33,
35 and 42, in addition to one aglycone peak 57 (kaempferol),
identified flavonoids were tri, di and monoglycosides of kaempferol,
quercetin and isorhamnetin flavonoids based on their masses and
UV-spectral data analysis. Structure identification was confirmed by
MS/MS indicating the fragmentation pathway of each compound,
quercetin rutinoside (20), kaempferol rutinoside (27), isorhamnetin
hexosyl rhamnoside (29) and kaempferol hexoside (35) were
identified in both JSA and JSG with a corresponding molecular ion
[M-H]
-
of m/z 609, 593, 623 and 447, respectively with aglycone
daughter ions 285, 301 and 315 for kaempferol, quercetin and
isorhamnetin in the same order. Other kaempferol derivatives were
identified peaks 10, 21, 22, 23 42 with a corresponding molecular
ion [M-H]
-
of m/z 755, 739, 771, 609 and 593, quercetin glycosides
were identified in peaks 16, 18, 26, 28, 31 and 33 with a
corresponding molecular ion [M-H]
-
of m/z 755, 625, 609, 463, 579,
433 respectively, peaks 20, 23 and 26 have the same molecular ion
peaks [M-H]
-
of m/z 609 and differentiated through MS/MS
fragmentation peak 23 give base peaks [M-H]
-
of m/z 447 and 285
with identify the compound to be a kaempferol derivative with
dihexoside substitution confirmed by the presence of 447 peak,
while MS/MS fragmentation peak 26 give base peaks [M-H]
-
of m/z
447 and 301 with identify the compound to be a quercetin
derivative with rutinoside substitution confirmed by the presence of
447 peak which indicates rhamnose substitution direct to the
quercetin flavonoid which differs from peak 20 which give base
peaks [M-H]
-
of m/z 463 and 301 that show the direct attachment of
hexose to the quercetin nucleus.
Identification of lignans
MS spectral interpretation allowed for the identification of 2 lignans,
cycloolivil hexoside and cycloolivil peaks 11 and 53 with a
corresponding molecular ion [M-H]
-
of m/z 537 and 375 with their
characteristic daughter ions of m/z 195, 179.
R
R1
R2
R3
OH
H
H
CH3
Oleuropein
OH
H
Hex
CH3
Oleuropein hexoside
H
H
H
CH3
Ligstroside
H
H
Hex
CH3
Ligstroside hexoside
R
OHcycloolivil
O-HexCycloolivil hexoside
Polyanoside
Jaspolyanoside
Jaspolinaloside
Jaspolyanthoside
Sambacoside A
Deacylsambacoside A
Jasmolactone B
Fig. 5: Chemical structures of some secoiridoid glycosides tentatively identified in the ethanolic extract of JSA and JSG leaves
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
161
Fig. 6: MS/MS fragmentation pattern of some identified secoiridoid glycosides; a (oleuropein hexoside), b (oleuropein), c (deacyl
sambacoside), d (sambacoside A)
Mokhtar et al.
Int J App Pharm, Vol 11, Issue 6, 2019, 154-164
162
DISCUSSION
Jasminum sambac L. (Arabian Nights) possessed cytotoxicity against
both MCF-7 breast cancer and 5637 bladder cancer, with lower IC
50
of 15.29±2.16 and 13.76±1.11 µg/ml while Jasminum sambac L.
(Grand duke of Tuscany) show mild cytotoxicity toward MCF-7
breast cancer and no cytotoxicity toward 5637 bladder cancer, JSA
AgNPs give high cytotoxicity with IC
50
values (6.32±1.01 µg/ml and
5.54±0.88 µg/ml) toward both MCF-7 and 5637 cell lines, while JSG
AgNPs show lower cytotoxicity toward MCF-7 cell line 17.32±2.22
µg/ml and lower cytotoxicity toward 5637 cell line (27.89±2.84)
µg/ml. These results showed that a plant with higher cytotoxic
results produces silver nanoparticles with higher characteristics
(less particle size and better cytotoxic activities toward the same cell
lines). The chemical profile of the JSA cultivar differs from the JSG
cultivar. HPLC-PDA-MS/MS of JSA showed the abundance of
secoiridoids and secoiridoids glycosides different from JSG like
oleoside methyl ester, oleoside dimethyl ester, jasmolactone B,
polyanoside, jaspolyanoside, polyanthoside, oleuropein, oleuropein
hexoside, ligstroside, and ligstroside hexoside, while common
secoiridoids in the two cultivars is sambacoside. Both cultivars
showed secoiridoid as a major metabolite, but JSA cultivar possessed
a higher abundance of secoiridoid derivatives than JSG.
Flavonoid glycosides were derivatives of kaempferol and quercetin
in both cultivars with slight differences among them. From the
above fig 3 and table 2, the main components of JSA were; deacyl
sambacoside, sambacoside A, quercetin dihexoside, jaspolyanoside,
and elonolic acid hexoside, while major compounds in JSG were
sambacoside A, sambacolignoside, jasnudifloside H, molihauside A,
kaempferol hexoside, kaempferol rutinoside, and oleoside
pentoside. These results are in accordance with a previous report on
Chinese Jasminum sambac flowers which identified molihauside A,
sambacoside A and quercetin hexosides as major constituents[78].
The silver nanoparticles green synthesis with the optimum
characters by JSA and their selective cytotoxicity may be attributed
to the presence of secoiridoids in this cultivar. Additionally, the
chemical profile could be used to distinguish the two cultivars of
Egyptian Jasminum sambac (Arabian Nights and Grand Duke of
Tuscany)
CONCLUSION
Jasminum sambac (Arabian Nights) cultivar is an excellent source for
the synthesis of green biofriendly silver nanoparticles with
selectivity to MCF-7 breast cancer and 5637 bladder cancer cell lines
and limited toxicity towards the normal cells, thus offering a high
safety margin when used as a cytotoxic agent.
FUNDING
This research did not receive any specific grant from funding
agencies in the public, commercial, or not-for-profit sectors.
AUTHORS CONTRIBUTIONS
All the authors have contributed equally
CONFLICT OF INTERESTS
Declared none
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