ArticlePDF Available

Phenolic Composition of Leaf extracts of Ailanthus altissima (Simaroubaceae) with Antibacterial and Antifungal Activity Equivalent to Standard Antibiotics

Authors:
  • Institute of Agriculture and Tourism Porec, Croatia
  • Institut za poljoprivredu i turizam Porec

Abstract and Figures

Extracts of fresh and dry Ailanthus altissima leaves from Croatia were evaluated for their phenolic composition, antioxidant and antimicrobial activities. The methanolic extract had a higher concentration of total phenolics, flavonoids and non-flavonoids, as well as a higher antioxidant capacity than water extracts. Flavonoids identified in A. altissima leaves belong to two groups: Flavones (glycosides of apigenin and luteolin) and flavonols (glycosides of quercetin and kaempferol). They were mainly present as glycosides, quercetin-3-O-glucoside was the predominant flavonoid. Only traces of aglycones were detected even after extract hydrolysis. Caffeic acid was the predominant phenolic acid both before and after hydrolysis, followed by chlorogenic acid after hydrolysis. The concentration of chlorogenic acid significantly increased soon after tissue fragmentation suggesting this compound is involved in rapid response against mechanical wounding in A. altissima. Therefore, to increase the chlorogenic acid concentration, mechanical wounding could be applied. The acetone leaf extract was as active against Escherichia coli as the positive control gentamicin. Both acetone and methanol:dichloromethane extracts had a higher activity against Candida albicans than a standard drug amphotericin B. Therefore, A. altissima could serve as a valuable resource for antimicrobial activity, which makes this species interesting for further investigation and possible pharmaceutical application.
Content may be subject to copyright.
Volume 12. Issue 10. Pages 1529-1672. 2017
ISSN 1934-578X (printed); ISSN 1555-9475 (online)
www.naturalproduct.us
INFORMATION FOR AUTHORS
Full details of how to submit a manuscript for publication in Natural Product Communications are given in Information for Authors on our Web site
http://www.naturalproduct.us.
Authors may reproduce/republish portions of their published contribution without seeking permission from NPC, provided that any such republication is
accompanied by an acknowledgment (original citation)-Reproduced by permission of Natural Product Communications. Any unauthorized reproduction,
transmission or storage may result in either civil or criminal liability.
The publication of each of the articles contained herein is protected by copyright. Except as allowed under national “fair use” laws, copying is not permitted by
any means or for any purpose, such as for distribution to any third party (whether by sale, loan, gift, or otherwise); as agent (express or implied) of any third
party; for purposes of advertising or promotion; or to create collective or derivative works. Such permission requests, or other inquiries, should be addressed
to the Natural Product Inc. (NPI). A photocopy license is available from the NPI for institutional subscribers that need to make multiple copies of single
articles for internal study or research purposes.
To Subscribe: Natural Product Communications is a journal published monthly. 2017 subscription price: US$2,595 (Print, ISSN# 1934-578X); US$2,595
(Web edition, ISSN# 1555-9475); US$2,995 (Print + single site online); US$595 (Personal online). Orders should be addressed to Subscription Department,
Natural Product Communications, Natural Product Inc., 7963 Anderson Park Lane, Westerville, Ohio 43081, USA. Subscriptions are renewed on an annual
basis. Claims for nonreceipt of issues will be honored if made within three months of publication of the issue. All issues are dispatched by airmail throughout
the world, excluding the USA and Canada.
NPC Natural Product Communications
EDITOR-IN-CHIEF
DR. PAWAN K AGRAWAL
Natural Product Inc.
7963, Anderson Park Lane,
Westerville, Ohio 43081, USA
agrawal@naturalproduct.us
EDITORS
PROFESSOR ALEJANDRO F. BARRERO
Department of Organic Chemistry, University of Granada,
Campus de Fuente Nueva, s/n, 18071, Granada, Spain
afbarre@ugr.es
PROFESSOR MAURIZIO BRUNO
Department STEBICEF,
University of Palermo, Viale delle Scienze,
Parco d’Orleans II - 90128 Palermo, Italy
maurizio.bruno@unipa.it
PROFESSOR VLADIMIR I. KALININ
G.B. Elyakov Pacific Institute of Bioorganic Chemistry,
Far Eastern Branch, Russian Academy of Sciences,
Pr. 100-letya Vladivostoka 159, 690022,
Vladivostok, Russian Federation
kalininv@piboc.dvo.ru
PROFESSOR YOSHIHIRO MIMAKI
School of Pharmacy,
Tokyo University of Pharmacy and Life Sciences,
Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
mimakiy@ps.toyaku.ac.jp
PROFESSOR STEPHEN G. PYNE
Department of Chemistry, University of Wollongong,
Wollongong, New South Wales, 2522, Australia
spyne@uow.edu.au
PROFESSOR MANFRED G. REINECKE
Department of Chemistry, Texas Christian University,
Forts Worth, TX 76129, USA
m.reinecke@tcu.edu
PROFESSOR WILLIAM N. SETZER
Department of Chemistry, The University of Alabama in Huntsville,
Huntsville, AL 35809, USA
wsetzer@chemistry.uah.edu
PROFESSOR PING-JYUN SUNG
National Museum of Marine Biology and Aquarium
Checheng, Pingtung 944
Taiwan
pjsung@nmmba.gov.tw
PROFESSOR YASUHIRO TEZUKA
Faculty of Pharmaceutical Sciences, Hokuriku University,
Ho-3 Kanagawa-machi, Kanazawa 920-1181, Japan
y-tezuka@hokuriku-u.ac.jp
PROFESSOR DAVID E. THURSTON
Institute of Pharmaceutical Science
Faculty of Life Sciences & Medicine
King’s College London, Britannia House
7 Trinity Street, London SE1 1DB, UK
david.thurston
@
kcl.ac.uk
ADVISORY BOARD
Prof. Giovanni Appendino
Novara, Italy
Prof. Norbert Arnold
Halle, Germany
Prof. Yoshinori Asakawa
Tokushima, Japan
Prof. Vassaya Bankova
Sofia, Bulgaria
Prof. Roberto G. S. Berlinck
São Carlos, Brazil
Prof. Anna R. Bilia
Florence, Italy
Prof. Geoffrey Cordell
Chicago, IL, USA
Prof. Fatih Demirci
Eskişehir, Turkey
Prof. Francesco Epifano
Chieti Scalo, Italy
Prof. Ana Cristina Figueiredo
Lisbon, Portugal
Prof. Cristina Gracia-Viguera
Murcia, Spain
Dr. Christopher Gray
Saint John, NB, Canada
Prof. Dominique Guillaume
Reims, France
Prof. Duvvuru Gunasekar
Tirupati, India
Prof. Hisahiro Hagiwara
Niigata, Japan
Prof. Judith Hohmann
Szeged, Hungary
Prof. Tsukasa Iwashina
Tsukuba, Japan
Prof. Leopold Jirovetz
Vienna, Austria
Prof. Phan Van Kiem
Hanoi, Vietnam
Prof. Niel A. Koorbanally
Durban, South Africa
Prof. Chiaki Kuroda
Tokyo, Japan
Prof. Hartmut Laatsch
Gottingen, Germany
Prof. Marie Lacaille-Dubois
Dijon, France
Prof. Shoei-Sheng Lee
Taipei, Taiwan
Prof. M. Soledade C. Pedras
Saskatoon, Canada
Prof. Luc Pieters
Antwerp, Belgium
Prof. Peter Proksch
Düsseldorf, Germany
Prof. Phila Raharivelomanana
Tahiti, French Polynesia
Prof. Stefano Serra
Milano, Italy
Dr. Bikram Singh
Palampur, India
Prof. Leandros A. Skaltsounis
Zografou, Greece
Prof. John L. Sorensen
Manitoba, Canada
Prof. Johannes van Staden
Scottsville, South Africa
Prof. Valentin Stonik
Vladivostok, Russia
Prof. Winston F. Tinto
Barbados, West Indies
Prof. Sylvia Urban
Melbourne, Australia
Prof. Karen Valant-Vetschera
Vienna, Austria
HONORARY EDITOR
PROFESSOR GERALD BLUNDEN
The School of Pharmacy & Biomedical Sciences,
University of Portsmouth,
Portsmouth, PO1 2DT U.K.
axuf64@dsl.pipex.com
Phenolic Composition of Leaf extracts of Ailanthus altissima
(Simaroubaceae) with Antibacterial and Antifungal Activity
Equivalent to Standard Antibiotics
Danijela Poljuhaa, Barbara Sladonjaa, Ivana Šolab*, Slavica Dudašc, Josipa Bilićd, Gordana Rusakb,
Katlego E Motlhatlegoe and Jacobus N Eloffe
aDepartment of Agriculture and Nutrition, Institute of Agriculture and Tourism, Karla Huguesa 8, Poreč 52440,
Croatia
bDepartment of Biology, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000, Zagreb, Croatia
cPolytechnic of Rijeka, Agricultural Department Poreč, Karla Huguesa 6, 52440 Poreč, Croatia
dMaterials Research Centre METRIS, Zagrebačka 30, 52100 Pula, Croatia
ePhytomedicine Programme, Faculty of Veterinary Science, University of Pretoria, Private Bag X04,
Onderstepoort, South Africa 0110
ivana.sola@biol.pmf.hr
Received: March 28th, 2017; Accepted: May 25, 2017,
Extracts of fresh and dry Ailanthus altissima leaves from Croatia were evaluated for their phenolic composition, antioxidant and antimicrobial activities. The
methanolic extract had a higher concentration of total phenolics, flavonoids and non-flavonoids, as well as a higher antioxidant capacity than water extracts.
Flavonoids identified in A. altissima leaves belong to two groups: flavones (glycosides of apigenin and luteolin) and flavonols (glycosides of quercetin and
kaempferol). They were mainly present as glycosides, quercetin-3-O-glucoside was the predominant flavonoid. Only traces of aglycones were detected even
after extract hydrolysis. Caffeic acid was the predominant phenolic acid both before and after hydrolysis, followed by chlorogenic acid after hydrolysis. The
concentration of chlorogenic acid significantly increased soon after tissue fragmentation suggesting this compound is involved in rapid response against
mechanical wounding in A. altissima. Therefore, to increase the chlorogenic acid concentration, mechanical wounding could be applied. The acetone leaf
extract was as active against Escherichia coli as the positive control gentamicin. Both acetone and methanol:dichloromethane extracts had a higher activity
against Candida albicans than a standard drug amphotericin B. Therefore, A. altissima could serve as a valuable resource for antimicrobial activity, which
makes this species interesting for further investigation and possible pharmaceutical application.
Keywords: Antibacterial, Antimicotic, Antioxidant, Flavonoids, HPLC, Phenolic acids, Tree of Heaven.
Ailanthus altissima (Mill.) Swingle or Tree of Heaven
(Simaroubaceae) is an invasive deciduous tree. High production of
seeds dispersed by wind, extremely fast growth (2 m/y), and a high
regenerative capacity makes A. altissima easily dispersible and hard
to control and therefore is considered one of the worst invasive
plant species [1]. A. altissima contains a quassinoide ailanthone, 18
alkaloids, 62 terpenoids, 15 steroids, 30 aliphatic components, 7
flavonoids and several coumarins, organic acids and lignans [2, 3],
which are responsible for biological activities of its extracts. Luís et
al. [4] found highest phenolic content in A. altissima leaves,
followed by stalks and stems. It makes sense to investigate the
possible use of invasive plant species because it grows easily.
Pedersini et al. investigated its use as a herbicide [5].
The aim of this study was to provide new information on the
chemical composition and biological activity of different extracts of
A. altissima leaves. For that purpose we: a) analyzed total phenolic,
flavonoid and non-flavonoid compounds content, b) determined
antioxidant capacity of different extracts, c) developed a short RP-
HPLC (reversed phase-high performance liquid chromatography)
method for separation and identification of flavonoids and phenolic
acids in extracts, d) qualitatively and quantitatively compared
extracts on the level of flavonoids and phenolic acids, and f)
determined the antibacterial and antifungal activity.
Total phenolic (TP), flavonoids (TF) and non-flavonoids (TNF)
contents as well as antioxidant capacity (AC) were the highest
in the methanolic extract of fresh chopped leaves, followed by the
Figure 1: The total phenolics (TP), non-flavonoids (TNF) and flavonoids (TF) content
in water and methanolic extracts of Ailanthus altissima. Data are the mean values of
three replicates ± SE. Different letters indicate significant difference (Tukey's least
significant difference; p ≤ 0.01).
water extract of dry ground leaves, and water extracts of fresh
chopped and whole leaves (Figure 1, Table 1). The highest TP
(247±8.4 mg GAE/g dw), TF (57±1.1 mg CE/g dw) and TNF
(164±3.9 mg GAE/g dw) contents of methanolic extracts were
expected due to the ability of methanol to damage cell membranes
and dissolve highly polar compounds present in leaves [6]. There
was no significant difference in TP, TF and TNF content between
water extracts of intact and chopped leaves. The degree of tissue
damage therefore did not influence their content.
Antioxidant capacity (AC) was determined by ABTS, FRAP and
DPPH assays (Table 1). Both FRAP and DPPH assays revealed the
NPC Natural Product Communications 2017
Vol. 12
No. 10
1609 - 1612
1610 Natural Product Communications Vol. 12 (10) 2017 Poljuha et al.
Table 1: Antioxidant capacity of different Ailanthus altissima leaves extracts
determined by ABTS, DPPH and FRAP assays. Values are expressed in dry weight
(dw) and as mean values of three replicates ± SE. Different letters in the same column
indicate significant difference. (Tukey's least significant difference; p ≤ 0.05).
Extract ABTS
(mmol TE/100 g DW)
DPPH
(mmol TE/100 g DW)
FRAP mM
(FeSO4+/100 g DW)
H2O fresh whole leaves 16.5±0.5c 4.7±0.5d 5.0±0.0d
H2O fresh chopped leaves 24.1±0.0c 10.0±0.5c 16.5±0.5c
H2O dry ground leaves 51.8±0.5b 48.8±0.5b 94.0±0.5b
MeOH fresh chopped leaves 208.3±9.5a 173.1±2.1a 331.0±0.5a
Figure 2: RP-HPLC profiles of phenolic standards A) recorded at 360 nm, and C)
recorded at 310 nm. B) Glycosylated flavonoids recorded at 360 nm, and D) phenolic
acids recorded at 310 nm from methanolic extracts of Ailanthus altissima.
significant difference (p ≤ 0.05) between all extracts, while in the
case of ABTS assay, there was no significant difference between
the values obtained in water extracts of fresh tissue. We also found
a positive correlation between AC and TP, TF and TNF contents.
To separate and identify phenolic compounds, we developed a new
RP-HPLC method. Compared to the so far available [4, 7], ours is
significantly shorter, takes less time and solvents, therefore is more
economic. The highest amount of flavonoids and phenolic acids was
recorded in methanolic extracts. The RP-HPLC chromatograms of
standard phenolic compounds, flavonoid glycosides and phenolic
acids in methanolic extract are shown in Figure 2.
Flavonoid contents were quantified at 360 nm and phenolic acids at
310 nm. Three main peaks at 360 nm were identified based on their
retention times, UV spectra, co-injections with standard compounds
and previous reports [4, 7].
From the flavonoid composition of water and methanolic extracts of
A. altissima dry and fresh leaves, respectively it was clear that no
flavonoid could be identified in water extracts of fresh leaves
(Figure 3).
From dried leaves Q-3-O-glucoside (2.7 g/kg dw), kaempferol-3-O-
glucoside (0.5 g/kg dw) and luteolin-3,7-di-O-glucoside (0.1 g/kg
dw) were extracted with water. Methanol extraction of flavonoid-
glycosides from fresh chopped A. altissima leaves yielded Q-3-O-
glucoside as the predominant compound (2.7 g/kg fw), followed by
apigenin-8-C-glucoside (0.7 g/kg fw), kaempferol-3-O-glucoside
(0.6 g/kg fw), luteolin-3,7-di-O-glucoside (0.1 g/kg fw) and
kaempferol-3-O-rutinoside (0.0 g/kg fw). The total amount of
flavonoid-glycosides identified in water extract of dry leaves was
3.3 g/kg dw, while in methanolic extract of fresh leaves it was 4.17
g/kg fw. The predominant flavonoid in the extracts was quercetin-3-
O-glucoside with 80.5% and 64.8% of total identified flavonoids,
respectively. The relative percentage of kaempferol-3-O-glucoside
(around 15%) and luteolin-3,7-di-O-glucoside (around 3%) was
similar in methanolic and water extract. Two additional flavonoids
Figure 3: Composition of flavonoid-glycosides in water and methanolic extracts of
Ailanthus altissima dry ground and fresh chopped leaves, respectively. Data are the
means of three replicates ± SE. Different letters indicate significant difference (Tukey's
least significant difference; p ≤ 0.01). Lut-di-glc = luteolin-3,7-di-O-glucoside, Api-glc
= apigenin-8-C-glucoside, Q-glc = quercetin-3-O-glucoside, K-glc = kaempferol-3-O-
glucoside, K-rut = kaempferol-3-O-rutinoside. nd = not detected, it = in trace.
identified in methanolic extract of fresh leaves (apigenin-8-C-
glucoside with 17.6% and kaempferol-3-O-rutinoside with 0.2% of
total identified flavonoids) were extracted, but the content of the
main flavonoid quercetin-3-O-glucoside decreased. Analogue
flavonoid aglycones were found by Loizzo et al. [8] and Said et al.
[9] in methanolic extract of Egyptian A. excelsa leaves, however
they also identified other glycosides, which not surprising given that
they used different species. Quercetin- and kaempferol-glycosides
are also the main flavonoids in leaves of A. altissima from Tunisia
[7].
Among phenolic acids, before hydrolysis caffeic was predominant
both in methanolic extract of fresh leaves with 99.2%, and in water
extract of dry leaves with 96.2% (Figure 4). After hydrolysis,
caffeic acid was still predominant in both extracts with 64.4% in
methanolic and 72.3% in water extract, however a significant
amount of chlorogenic acid was also detected (33.0% in the
methanolic and 22.4% in the water extract), which suggests
chlorogenic acid was mainly present in bound forms in A. altissima
leaves. These results are different than those from Luís et al. [4]
who found ellagic and chlorogenic acid as predominant in A.
altissima from Portugal, and those from Albouchi et al. [7] who
found gallic and chlorogenic acid as dominant in A. altissima from
Tunisia. Since the biosynthesis of phenolics in plants depends on
numerous environmental factors [10], phenolic profiles of
populations from different geographical areas significantly differ.
Also, the extraction process of Luís et al. [4] differs from ours and
this could cause the discrepancy as well. In order to determine the
optimal state of leaves for the highest yield of bioactive compounds,
we compared the content of phenolic acids between water extracts
of fresh chopped and dry ground leaves; dry ground leaves
contained significantly higher amounts of caffeic, chlorogenic, p-
coumaric and ferulic acid (Figure 4). Finally, we compared the
water extraction efficiency between fresh whole and fresh chopped
leaves; no flavonoids could be detected in either of the samples, and
significantly higher amount of chlorogenic acid was present in cut
leaves. We presume chlorogenic acid has a protective effect and is
released after mechanical wounding of A. altissima leaves. Similar
tendency was observed on potato tubers, carrot and lettuce [11-13].
The application of abiotic stress in plant tissues has already been
proposed as a possible strategy to increase level of high value
phenolic compounds [12].
Many plant species have very good antimicrobial activities [14].
Even though the phytotoxic effect of A. altissima is the best studied
biological property of this species, there are a few papers on its
antimicrobial activity.
Phytochemical profiles of A. altissima extracts Natural Product Communications Vol. 12 (10) 2017 1611
Figure 4: Composition of phenolic acids in water and methanolic extract (non-hydrolyzed and hydrolyzed) of Ailanthus altissima leaves. Data are the means of three replicates ± SE.
Different letters indicate significant difference (Tukey's least significant difference; p ≤ 0.01). nd = not detected, it = in trace.
Balkan et al. [15] found an MIC of 1.3 for ethanol and 2.5 mg/mL
for methanol extract against some cereal plant pathogens. Albouchi
et al. [7] concluded that methanol extracts are not active against
Gram negative bacteria, however they used agar diffusion methods
that do not yield results which can properly be compared between
different laboratories [16]. Rahman et al. [17] found MICs of 0.13
to 0.5 mg/mL against several Listeria species, 0.13 to 0.3 mg/mL
against different Staphylococcus aureus isolates, 0.5 mg/mL against
Bacillus subtilis and Escherichia coli and 0.3 mg/mL against
Pseudomonas aeruginosa.
The activities we found (Table 2) were much higher than those
reported by previous authors. The MIC of positive control
gentamicin for antibacterial activity was 0.0 mg/mL in all cases, and
positive control B-amphotericin for antifungal was 0.1 mg/mL.
With P. aeruginosa as an exception, the acetone extracts showed a
higher or similar activity to that of methanol:dichloromethane
extracts. The results for the extracts against different
microorganisms varied from 0.0 to 0.6 mg/mL. We found that the
acetone leaf extract had an excellent MIC of 0.04 mg/mL against E.
coli. This value was as good as that of a generic drug gentamicin.
This discrepancy with the results of other authors may be due to the
extraction solvents or less sensitive bioassay methods used. The
result against the fungus C. albicans was also very promising. The
extracts had a higher activity than amphotericin B, a gold standard
in antifungal therapy. It may be worthwhile to determine the
cytotoxicity of the extracts and to isolate the antifungal compounds.
Table 2: Minimum inhibitory activities in mg/mL of Ailanthus altissima leaves acetone
and methanol:dichloromethane (MeOH:DCM, 1:1) extracts on different bacteria and
Candida albicans.
Microor
g
anism Acetone MeOH:DCM
Escherichia coli 0.0 0.2
Bacillus cereus 0.6 0.6
Enterococcus faecalis 0.6 0.6
Pseudomonas aeruginosa 0.3 0.2
Salmonella typhimurium 0.2 0.2
Staphylococcus aureus 0.2 0.6
Candida albicans 0.0 0.0
Experimental
Extracts preparation: Extracts for antioxidant properties, and for
phenolic composition analysis were prepared using water or 99.5 %
methanol. Water extracts were prepared using the modified method
of Lawrence et al. [18]. Whole and chopped fresh (200 g) and finely
ground air-dried (100 g) leaves were extracted by maceration in 1 l
of deionized water for 48 h and filtered through Whatman #4 filter
paper. Methanolic extract was prepared using the modified method
of Tsao et al. [6]. Chopped fresh leaves (327 g) were soaked in
1800 mL of methanol for 72 hours at room temperature. After
extraction the supernatant was filtered and evaporated to a volume
of 140 mL by rotary evaporator (< 40 °C), then the water was made
up to a volume of 500 mL. Extracts were stored at 4 °C until use.
For antimicrobial assays finely minced dried plant material was
extracted using acetone because this was shown to be the best
extraction solvent for antimicrobial activities [19, 20]. A 1:1
mixture of methanol and dichloromethane was also used. The
rationale is that dichloromethane would break cell membranes and
extract non-polar compounds and that methanol would extract polar
compounds. In both case a ratio of 10 mL of extractant per g dry
mass under vigorous shaking was used. The pellet obtained after
centrifugation was re-extracted two times more. The volatile
extraction solvents were removed from the extract at room
temperature over a current of cold air.
Total phenolics, flavonoids and non-flavonoids content and
antioxidant capacity: Total phenolics content (TP) was determined
using the method of Singleton and Rossi [21], while total non-
flavonoids (TNF) content was measured as described by Ough and
Amerine [22]. The results are expressed as mg of gallic acid
equivalents (GAE) per g of plant dry weight (dw). Total flavonoids
content (TF) was determined by method described in Martins et al.
[23]. The results are expressed as mg of (+)-catechin equivalents
(CE) per g of plant dw. All measurements were performed in
duplicates per treatment and repetition, and the results are expressed
as mean values ± standard error (SE). Antioxidant capacity (AC) of
extracts was determined using DPPH, ABTS and FRAP assays. All
procedures are described in details by Poljuha et al. [24]. The
results of DPPH and ABTS assays were expressed in mmol of
Trolox equivalents (TE) per 100 g of dw while results of FRAP
assay were expressed as reducing ability equivalent to 1 mmol
FeSO4+ per 100 g of dw. All AC measurements were performed in
triplicates per treatment and repetition, and the results are presented
as mean values ± SE.
RP-HPLC analysis of phenolics: RP-HPLC analyses were
performed using the Agilent 1100 Series system equipped with C-
18 column as described in Poljuha et al. [24]. Gradient profile was
1612 Natural Product Communications Vol. 12 (10) 2017 Poljuha et al.
(A/B): 0-30 % B for the first 20 min, then to 100 % B over the next
1 min, maintained at 100 % B for 5 min, and returned to the initial
conditions. Injection volume was 5 µl. Phenolic compounds were
characterized and quantified as in Poljuha et al. [24]. The
calibration curves were made by plotting the mean peak area versus
the concentration of standards, and are together with their R2 values
shown in Supplementary Table 1. For the purpose of phenolic
aglycones analysis, acid hydrolysis of each extract was conducted
as follows: 250 µL of each phenolic extract was mixed with 28.3 µl
of concentrated HCl, and incubated for 2 h at 80 °C and 300 rpm.
The solutions were centrifuged three times (13000 rpm, 5 min) and
the supernatants stored at -20 °C until analysis.
Antimicrobial testing: The dried extracts were made up to a
concentration of 10 mg/mL in acetone because acetone is not toxic
to microorganisms, dissolves non-polar and polar compounds and is
miscible with the microbial growth medium [23]. The minimum
inhibitory concentration (MIC) was determined in a serial dilution
microplate method using p-nitrotetrazolium violet as a growth
indicator for bacteria [25] and a slightly modified method of
Masoko et al. [26], for fungi.
Statistical analysis: On the obtained herbicidal effect data ANOVA
+ Tukey test, p ≤ 0.05 were performed to determine if there was any
significant difference in different treatments on tested species. TP,
TNF, TF contents and AC data were analyzed by ANOVA + Tukey
test, p 0.05 and p ≤ 0.01 to determine the significant difference
between the contents and antioxidant capacities of each extract.
Supplementary data: Calibration curves and R2 values of the
selected phenolic standards.
Acknowledgments - This research was financially supported by
Croatian Ministry of Science, Education and Sports and by National
Research Foundation of South Africa.
References
[1] DAISIE (2014) Delivering alien invasive species inventories for Europe (DAISIE). http://www.europe-aliens.org/default.do. Accessed 20 February
2017
[2] Heisey RM, Heisey TK. (2003) Herbicidal effects under field conditions of Ailanthus altissima bark extract, which contains ailanthone. Plant Soil,
256, 85-99.
[3] Kožuharova E, Lebanova H, Getov I, Benbassat N, Kochmarov V. (2014) Ailanthus altissima (Mill.) Swingle - a terrible invasive pest in Bulgaria
or potential useful medicinal plant? Bothalia, 44, 213–230.
[4] Luís A, Gil N, Amaral ME, Domingues F, Duarte AP. (2012) Ailanthus altissima (Miller) Swingle: A source of bioactive compounds with
antioxidant activity. BioResources, 7, 2105-2120.
[5] Pedersini C, Bergamin M, Aroulmoji V, Baldini S, Picchio R, Gutierrez Pesce P, Ballarin L, Murano E. (2011) Herbicide activity of extracts from
Ailanthus altissima (Simaroubaceae). Natural Product Communications, 6, 593-596.
[6] Tsao R, Romanchuk F, Peterson CJ, Coats JR. (2002) Plant growth regulatory effect and insecticidal activity of the extracts of the tree of heaven (A.
altissima). BMC Ecology, 2, DOI: 10.1186/1472-6785-2-1.
[7] Albouchi F, Hassen I, Casabianca H, Hosni K. (2013) Phytochemicals, antioxidant, antimicrobial and phytotoxic activities of Ailanthus altissima
(Mill.) Swingle leaves. South African Journal of Botany, 87, 164–174.
[8] Loizzo MR, Said A, Tundis R, Rashed K, Statti GA, Hufner A, Menichini F. (2007) Inhibition of angiotensin converting enzyme (ACE) by
flavonoids isolated from Ailanthus excelsa (Roxb) (Simaroubaceae). Phytotherapy Research, 21, 32–36.
[9] Said A, Hawas UW, El-Shenawy S, Nofal SM, Rashed K. (2010) Flavonoids and some biological activities of Ailanthus excelsa leaves. IUFS
Journal of Biology 69, 41-55.
[10] Cheynier V, Comte G, Davies KM, Lattanzio V, Martens S. (2013) Plant phenolics: Recent advances on their biosynthesis, genetics, and
ecophysiology. Plant Physiology and Biochemistry, 72, 1-20.
[11] Torres-Contreras AM, Nair V, Cisneros-Zevallos L, Jacobo-Velázquez DA. (2014) Plants as biofactories: Stress-induced production of chlorogenic
acid isomers in potato tubers as affected by wounding intensity and storage time. Industrial Crops and Products, 62, 61-66.
[12] Sánchez-Rangel JC, Benavides J, Jacobo-Velázquez DA. (2014) Abiotic stress based bioprocesses for the production of high value antioxidant
phenolic compound in plants: an overview. Revista Mexicana de Ingenieria Química, 13, 49-61.
[13] Tomás-Barberán FA, Loaiza-Velarde J, Bonfanti A, Saltveit ME. (1997) Early wound- and ethylene-induced changes in phenylpropanoid
metabolism in harvested lettuce. Journal of the American Society for Horticultural Science, 122, 399–404.
[14] Pauw E, Eloff JN. (2014) Which tree orders in southern Africa have the highest antimicrobial activity and selectivity against bacterial and fungal
pathogens of animals? BMC Complementary and Alternative Medicine, 14, 317.
[15] Balkan B, Balkan S, Aydoğdu H, Özcan Ö. (2014) Antifungal activities of Ailanthus altissima Swingle and Juglans regia L. leaves against some
cereal fungi. Journal of Applied Environmental and Biological Sciences, 8, 76-79.
[16] Eloff JN, McGaw LJ. (2014) Using African plant biodiversity to combat microbial infections. In Novel plant bioresources: Applications in Food,
Medicine and Cosmetics. Gurib-Fakim A (Ed). Wiley, Chichester, 163-173.
[17] Rahman A, Kim EL, Kang SC. (2009) Antibacterial and antioxidant properties of Ailanthus altissima Swingle leave extract to reduce foodborne
pathogens and spoiling bacteria. Journal of Food Safety, 29, 499–510.
[18] Lawrence JG, Colwell A, Sexton OJ. (1991) The ecological impact of allelopathy in Ailanthus altissima (Simaroubaceae). American Journal of
Botany, 78, 948–958.
[19] Eloff JN. (1998) Which extractant should be used for the screening and isolation of antimicrobial components from plants? Journal of
ethnopharmacology, 60, 1-8.
[20] Kotze M, Eloff JN. (2002) Extraction of antibacterial compounds from Combretum microphyllum (Combretaceae). South African Journal of
Botany, 68, 62-67.
[21] Singleton VL, Rossi JA. (1965) Colorimetry of total phenolics with phosphotungstic acid reagents. American Journal of Enology and Viticulture,
16, 144-158.
[22] Ough CS, Amerine MA. (1988) Methods for Analysis of Musts and Wine. Wiley, New York, 1-377.
[23] Martins D, Barros L, Carvalho AM, Ferreira ICFR. (2011) Nutritional and in vitro antioxidant properties of edible wild greens in Iberian Peninsula
traditional diet. Food Chemistry, 125, 488–494.
[24] Poljuha D, Šola I, Bilić J, Dudaš S, Bilušić T, Markić J, Rusak G. (2015) Phenolic composition, antioxidant capacity, energy content and
gastrointestinal stability of Croatian wild edible plants. European Food Research and Technology, 241, 573–585.
[25] Eloff JN. (1998) A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta
Medica, 64, 711-714.
[26] Masoko P, Picard J, Eloff JN. (2005) Antifungal activities of six South African Terminalia species (Combretaceae). Journal of Ethnopharmacology,
99, 301-308.
Natural Product Communications Vol. 12 (10) 2017
Published online (www.naturalproduct.us)
Pseudoalteromone C: a Novel Ubichromenol Derivative from Bacterium Pseudoalteromonas sp. CGH2XX Isolated from the
Cultured-type Octocoral Lobophytum crassum
Yu-Hsin Chen, Wu-Fu Chen, Juan-Cheng Yang, Mei-Chin Lu, Jimmy Kuo, Jui-Hsin Su, Ching-Feng Weng, Yang-Chang Wu
and Ping-Jyun Sung 1615
Non-alkaloid Constituents from Mahonia bealei
Bui Van Thanh, Nguyen Thi Van Anh, Do Hoang Giang, Nguyen Hai Dang, Luu Dam Ngoc Anh, Bui Van Huong,
Ngo Duc Phuong and Nguyen Tien Dat 1619
Zingerone Suppresses the Shedding of Endothelial Protein C Receptor
In-Chul Lee, Dae Yong Kim and Jong-Sup Bae 1623
Suppressive Effects of Sulforaphane on TGFBIp-mediated Sepsis
In-Chul Lee and Jong-Sup Bae 1627
Enzyme-treated Asparagus Extract (ETAS) Enhances Memory in Normal Rats and Induces Neurite-outgrowth in PC12 Cells
Tomoko Koda, Jun Takanari, Kentaro Kitadate and Hideki Imai 1631
In Vivo and In Vitro Evidence for the Antihyperuricemic, Anti-inflammatory and Antioxidant Effects of a Traditional
Ayurvedic Medicine, Triphala
Vilasinee Hirunpanich Sato, Bunleu Sungthong, Narawat Nuamnaichati, Prasob-orn Rinthong, Supachoke Mangmool and Hitoshi Sato 1635
Comparison of Volatiles of Sideritis caesarea Specimens Collected from Different Localities in Turkey
Tuğba Günbatan, Betül Demirci, İlhan Gürbüz, Fatih Demirci and Ayşe Mine Gençler Özkan 1639
Chemical Composition of Essential Oil among Seven Populations of Zanthoxylum armatum from Himachal Pradesh:
Chemotypic and Seasonal Variation
Vinod Bhatt, Sushila Sharma, Neeraj Kumar, Upendra Sharma and Bikram Singh 1643
Composition, in vitro Antibacterial and Anti-mildew Fungal Activities of Essential Oils from Twig and Fruit Parts of
Eucalyptus citriodora
Yu-Chang Su, Kuang-Ping Hsu and Chen-Lung Ho 1647
Antibacterial, Antiviral, Antioxidant and Antiproliferative Activities of Thymus guyonii Essential Oil
Assia Zeghib, Ahmed Kabouche, Souheila Laggoune, Claude-Alain Calliste, Alain Simon, Philippe Bressolier, Mahjoub Aouni,
Jean-Luc Duroux and Zahia Kabouche 1651
Chemoinformatic Investigation of Antibiotic Antagonism: The Interference of Thymus glabrescens Essential Oil Components
with the Action of Streptomycin
Budimir S. Ilić, Dragoljub L. Miladinović, Branislava D. Kocić, Boban R. Spalović, Marija S. Marković, Hristina Čolović and
Dejan M. Nikolić 1655
Insecticidal Effect of Essential Oils Against Fall Webworm (Hypantria cunea Drury (Lepidoptera: Arctiidae))
Temel Gokturk, Saban Kordali and Ayse Usanmaz Bozhuyuk 1659
Natural Product Communications
2017
Volume 12, Number 10
Contents
Original Paper Page
Fungal Biotransformation of Cyclademol and Antimicrobial Activities of Its Metabolites
Ismail Kiran, Özge Özşen, K. Hüsnü Can Başer and Fatih Demirci 1529
Quantitative Analysis and Pharmacological Effects of Artemisia ludoviciana Aqueous Extract and Compounds
Isabel Rivero-Cruz, Gerardo Anaya-Eugenio, Araceli Pérez-Vásquez, Ana Laura Martínez and Rachel Mata 1531
Guaiane Sesquiterpenes from the Rhizome of Curcuma xanthorrhiza and Their Inhibitory Effects on UVB-induced MMP-1
Expression in Human Keratinocytes
Ji-Hae Park, Mohamed Antar Aziz Mohamed, Nhan Nguyen Thi, Kyeong-Hwa Seo, Ye-Jin Jung, Sabina Shrestha, Tae Hoon Lee,
Jiyoung Kim and Nam-In Baek 1535
Further Guaianolides from Chrysophthalmum montanum
Perihan Gürbüz and Şengül D. Doğan 1539
Anti-allergic and Cytotoxic Effects of Sesquiterpenoids and Phenylpropanoids Isolated from Magnolia biondii
Thi Tuyet Mai Nguyen, Thi Thu Nguyen, Hyun-Su Lee, Bomi Lee, Byung Sun Min and Jeong Ah Kim 1543
Metabolomic and Proteomic Analysis of the Response of Angelica acutiloba after Herbivore Attack
Risa Kato, Yusuke Morita, Atsutoshi Ina, Yoshiaki Tatsuo, Takayuki Tamura, Yasuhiro Tezuka and Ken Tanaka 1547
Two New Abietane-type Diterpenes from the Bark of Cryptomeria japonica
Chi-I Chang, Chien-Chih Chen, Che-Yi Chao, Horng-Huey Ko, Hsun-Shuo Chang, Sheng-Yang Wang, Jih-Jung Chen,
Cheng-Chi Chen and Yueh-Hsiung Kuo 1553
Complete Structure Elucidation of New Steviol Glycosides Possessing 9 Glucose Units Isolated from Stevia rebaudiana
Indra Prakash, Sangphyo Hong, Gil Ma, Cynthia Bunders, Krishna P. Devkota, Romila D. Charan, Catherine Ramirez and
Tara M. Snyder 1557
Cytotoxic Activities of Different Iranian Solanaceae and Lamiaceae Plants and Bioassay-Guided Study of an Active Extract
from Salvia lachnocalyx
Hossein H. Mirzaei, Omidreza Firuzi, Ian T. Baldwin and Amir Reza Jassbi 1563
Synthesis and Cytotoxic Evaluation of Betulin–Triazole–AZT Hybrids
Dang Thi Tuyet Anh, Le Nhat Thuy Giang, Nguyen Thi Hien, Dinh Thi Cuc, Nguyen Ha Thanh, Nguyen Thi Thu Ha,
Pham The Chinh, Nguyen Van Tuyen and Phan Van Kiem 1567
A Novel Cycloartane Triterpenoid Bisdesmoside from Actaea vaginata
Qiongyu Zou, Meichun Wu, Yindi Zhu, Jinping Shen, Guoxu Ma, Xudong Xu, Gui Chen, Li Zhang, Zijian Zhao, Dizhao Chen and
Haifeng Wu 1571
Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”
Anne-Sophie Champy, Anne-Claire Mitaine-Offer, Thomas Paululat, Anna-Maria Papini and Marie-Aleth Lacaille-Dubois 1573
Magnumosides B3, B4 and C3, Mono- and Disulfated Triterpene Tetraosides from the Vietnamese Sea Cucumber
Neothyonidium (= Massinium) magnum
Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Vladimir I Kalinin, Pelageya V. Andrijaschenko,
Pavel S. Dmitrenok, Ekaterina A. Chingizova, Svetlana P. Ermakova, Olesya S. Malyarenko and Tatyana N. Dautova 1577
Chemical Analysis of the Edible Mushroom Tricholoma populinum: Steroids and Sulfinyladenosine Compounds
Bernadett Kovács, Zoltán Béni, Miklós Dékány, Orsolya Orbán-Gyapai, Izabella Sinka, István Zupkó, Judit Hohmann and
Attila Ványolós 1583
A New Steroidal Glycoside Granulatoside C from the Starfish Choriaster granulatus, Unexpectedly Combining Structural
Features of Polar Steroids from Several Different Marine Invertebrate Phyla
Natalia V. Ivanchina, Timofey V. Malyarenko, Alla A. Kicha, Anatoly I. Kalinovsky, Pavel S. Dmitrenok and Valentin A. Stonik 1585
A Novel Cytotoxic Physalin from Physalis angulata
Jia-Jia Fan, Xia Liu, Xi-Long Zheng, Hai Yu Zhao, Huan Xia and Yi Sun 1589
Efficient Bioproduction of Mycosporine-2-glycine, Which Functions as Potential Osmoprotectant, using Escherichia coli Cells
Tanutcha Patipong, Takashi Hibino, Rungaroon Waditee-Sirisattha and Hakuto Kageyama 1593
Anti-inflammatory Effect of Discretamine, a Protoberberine Alkaloid Isolated from Duguetia moricandiana
Danilo Eduardo Costa Vieira Lemos, Luiz Henrique Agra Cavalcante-Silva, Éssia de Almeida Lima, Adriano Francisco Alves,
Ana Silvia Suassuna Carneiro Lúcio, José Maria Barbosa-Filho and Sandra Rodrigues Mascarenhas 1595
Asymmetric Synthesis of Tetrahydroisoquinoline Alkaloids Using Ellman's Chiral Auxiliary
Y. Vikram Reddy, Dhanraj. O. Biradar, B. Jagan Mohan Reddy, Aravinda Rathod, M. Himabindu and B. V. Subba Reddy 1599
Chemical Constituents of the Aerial Parts of Santolina chamaecyparissus and Evaluation of Their Antioxidant Activity
Fatiha Labed, Milena Masullo, Antonietta Cerulli, Fadila Benayache, Samir Benayache and Sonia Piacente 1605
Phenolic Composition of Leaf extracts of Ailanthus altissima (Simaroubaceae) with Antibacterial and Antifungal Activity
Equivalent to Standard Antibiotics
Danijela Poljuha, Barbara Sladonja, Ivana Šola, Slavica Dudaš, Josipa Bilić, Gordana Rusak, Katlego E Motlhatlego and Jacobus N Eloff 1609
Synthesis of an Antileukemic Pyrone from Alternaria phragmospora
Yang Qu and George A. Kraus 1613
Continued inside backcover
... On the other side, some invasive species have compounds potentially useful to humans and could provide valuable ecosystem services [7]. Many plant species possess antifungal and antibacterial activity [8][9][10]. Antimicrobial agents produced by plants' specialised metabolism serve as their natural protective mechanism, increasing their competitiveness. ...
... Up to date, there have been very little literature data on the phytochemical potential of IAPS or their exploration in Croatia [9,[12][13][14]. For our study, we selected six IAPS, all included in the list of the most relevant invasive plant species of Croatia [15] and widely present in the Istria region (the peninsula in west Croatia). ...
... The extracts of selected plant species are used in traditional medicine in China and India, and their antimicrobial properties have been reported [22][23][24][25][26][27]. Our previous research [9] showed that A. altissima from Croatia could be a valuable resource for antimicrobial activity since its leaf extracts were as effective against Escherichia coli and Candida albicans as standard antibiotics. ...
Article
Full-text available
Invasive plants’ phytochemicals are important for their invasiveness, enabling them to spread in new environments. However, these chemicals could offer many pharmaceutical compounds or active ingredients for herbal preparations. This study provides the first LC–MS phytochemical screening of six invasive alien plant species (IAPS) in the Istria region (Croatia): Ailanthus altissima, Ambrosia artemisiifolia, Conyza canadensis, Dittrichia viscosa, Erigeron annuus, and Xanthium strumarium. The study aims to identify and quantify the phenolic content of their leaf extracts and assess their antimicrobial and cytotoxic potential. A total of 32 species-specific compounds were recorded. Neochlorogenic, chlorogenic, and 5-p-coumaroylquinic acids, quercetin-3-glucoside, and kaempferol hexoside were detected in all the tested IAPS. Hydroxycinnamic acid derivatives were the main components in all the tested IAPS, except in E. annuus, where flavanones dominated with a share of 70%. X. strumarium extract had the best activity against the tested bacteria, with an average MIC value of 0.11 mg/mL, while A. altissima and X. strumarium extracts had the best activity against the tested fungi, with an average MIC value of 0.21 mg/mL in both cases. All the plant extracts studied, except X. strumarium, were less cytotoxic than the positive control. The results provided additional information on the phytochemical properties of IAPS and their potential for use as antimicrobial agents.
... 206 TANASKOVIĆ, S., GVOZDENAC, S., KOLAROV, R. et al. Various factors affect the content of phenolic compounds and antioxidant activity in A. altissima extracts: selected tissue or organ (Luis, Gil, Amaral, Domingues & Duarte, 2012;Aissani et al, 2018), growing conditions (Vidović, Morina, Milić & Veljović Jovanović, 2015), extraction solvent (Luis et al, 2012;Poljuha et al, 2017;Aissani et al, 2018), and processing conditions (Poljuha et al, 2017). According to several authors (Luis et al, 2012;Albouchi et al, 2013;Poljuha et al, 2017;Aissani et al, 2018) leaves and bark of A. altissima are rich sources of polyphenolic compounds and possess very strong antioxidant activity. ...
... 206 TANASKOVIĆ, S., GVOZDENAC, S., KOLAROV, R. et al. Various factors affect the content of phenolic compounds and antioxidant activity in A. altissima extracts: selected tissue or organ (Luis, Gil, Amaral, Domingues & Duarte, 2012;Aissani et al, 2018), growing conditions (Vidović, Morina, Milić & Veljović Jovanović, 2015), extraction solvent (Luis et al, 2012;Poljuha et al, 2017;Aissani et al, 2018), and processing conditions (Poljuha et al, 2017). According to several authors (Luis et al, 2012;Albouchi et al, 2013;Poljuha et al, 2017;Aissani et al, 2018) leaves and bark of A. altissima are rich sources of polyphenolic compounds and possess very strong antioxidant activity. ...
... Various factors affect the content of phenolic compounds and antioxidant activity in A. altissima extracts: selected tissue or organ (Luis, Gil, Amaral, Domingues & Duarte, 2012;Aissani et al, 2018), growing conditions (Vidović, Morina, Milić & Veljović Jovanović, 2015), extraction solvent (Luis et al, 2012;Poljuha et al, 2017;Aissani et al, 2018), and processing conditions (Poljuha et al, 2017). According to several authors (Luis et al, 2012;Albouchi et al, 2013;Poljuha et al, 2017;Aissani et al, 2018) leaves and bark of A. altissima are rich sources of polyphenolic compounds and possess very strong antioxidant activity. Presented work is in agreement with the results obtained in our study that reveal that the bark extract possessed ten times higher content of total phenolics and total tannins compared to leaf extracts. ...
Article
Full-text available
Gypsy moth (Lymantria dispar (L.) is one of most important defoliating pests of deciduous trees. Due to increased environmental demands, the use of plant-based preparations is gaining in importance as a control option for this pest in forestry, agriculture and horticulture. The aim of this study was to evaluate antifeeding and insecticidal activity of 0.5, 1 and 2% extracts of Ailanthus altissima bark and leaves, and Morus alba leaves, against L. dispar larvae under laboratory conditions. Antioxidant capacity of plant extracts was determined, as well as the content of phenolic compounds by spectrophotometric and HPLC-DAD methods. Antifeeding and insecticidal effects were tested in a "no-choice" test. The highest content of all bioactive phenolic compounds was in A. altissima bark and M. alba leaf extracts. The lowest leaf consumption after 24 and 48 h was in A. аltissima bark (5.03, 9.30%, respectively) and M. alba leaf (1.44, 3.22%, respectively) extracts. A. altissima bark and M. alba leaf extracts expressed strong antifeeding activity. After 24 h, all extracts expressed slight insecticidal effect (2.25-17.50% of mortality). The mortality increased after 48 h in treatments with A. altissima bark extract, at all applied concentrations (40.0-57.50%) and M. alba leaves at 1 and 2% concentrations (30.0-62.50%). Our results indicate that extracts of A. altissima bark and M. alba leaves may act as effective low-cost natural protectants able to control the presence of gypsy moth in ecosystems. Extracts of A. altissima bark and M. alba leaves expressed strong antifeeding activity and significant insecticidal effect on gypsy moth larvae, at all applied concentrations.
... Swingle (Simabouracea)) and black locust (Robinia pseudoacacia L., (Fabaceae)] (Sanz Elorza et al. 2004;Swan et al. 2008;DAISIE 2015). Both species have been found to exert allelopathic and antibiotic effects on terrestrial organisms (Heisey 1996;Nasir et al. 2005;Small et al. 2010;Huo et al. 2012;Albouchi et al. 2013;Catalán et al. 2013;Marinas et al. 2014;Cioch et al. 2017;Poljuha et al 2017). However, their potential to have toxicological effects to aquatic animals have been largely ignored. ...
... The aims of our study are: (1) to assess the direct toxicity of aqueous extracts of leaf litter from trees native and exotic to Europe on two ecotoxicological model organisms: the freshwater cladoceran Daphnia magna Straus, 1820 and the aquatic snail Potamopyrgus antipodarum Gray, 1843, and (2) to estimate and compare the ecotoxicological risk of the native and exotic leaf litter in simulated lacustrine scenarios. We expect the extracts of the two exotic trees to be more toxic to the aquatic invertebrates, given the allelopathic and antibiotic effects already reported on other groups of terrestrial organisms (Heisey 1996;Nasir et al. 2005;Small et al. 2010;Huo et al. 2012;Albouchi et al. 2013;Catalán et al. 2013;Marinas et al. 2014;Cioch et al. 2017;Poljuha et al 2017). The results would contribute to understand the ecological risk associated with the replacement of native by exotic trees in floodplains of Europe. ...
Article
Full-text available
Upper reaches of temperate streams and oligotrophic lakes depend trophically on the organic matter coming from the surrounding watershed. These aquatic ecosystems accumulate particulate and dissolved organic matter, and chemical compounds liberated from decomposing leaves or from the leachates of leaf litter. These materials supply a wide range of chemical compounds, which may serve as food, but also cause ecotoxicological effects on aquatic organisms. However, this ecotoxicological risk has been amply ignored, especially for freshwater invertebrates. The aims of our study are: (1) to assess the direct toxicity of aqueous extracts of leaf litter from two native (Populus alba, Fraxinus angustifolia) and two tree species exotic to Europe (Robinia pseudoacacia, Ailanthus altissima) on a pelagic and a benthic species of model aquatic invertebrates: Daphnia magna (Cladocera) and Potamopyrgus antipodarum (Mollusca) and (2) to estimate the ecotoxicological risk of the leaf litter extracts to lacustrine ecosystems using different simulated scenarios of shallow lakes. For both invertebrate species, we assessed the effective concentration of leaf extract causing an effect on 50% of the population (EC50) by means of laboratory bioassays. Our results show that the extracts of leaf litter from all the tested trees have a potential ecotoxicological risk in some scenarios, which is independent from the geographic origin of the tree species.
... Similarly, other members of the Simaroubaceae family have been reported to possess antibacterial activity, whereby Ailanthus altissima extracts display antibacterial activity against different bacteria and fungi (Poljuha et al. 2017;Rahman et al. 2009). Other plants of the family showing antibacterial activity in different extracts include Simaba ferruginea (Gazoni et al. 2018) and Samadera indica (Viswanad et al. 2012). ...
Article
Full-text available
Picrasma javanica Blume is a plant belonging to Simaroubaceae. It is known for its secondary metabolites, namely quassinoids, offering various pharmacological properties including antitumor, antimalarial, and antiviral. The plant is traditionally used as a source medicine for different diseases in Myanmar, Thailand, and Indonesia. Despite the extensive studies on P. javanica, there is no concise and conclusive information regarding the phytochemical and phytochemistry of the plant has been reported. Thus, we aimed to discern the phytochemical constituents and pharmacological activities of P. javanica. The phytochemical constituents and pharmacological benefits of P. javanica were reviewed and supported from previous in vivo and in vitro studies. The literature used in this review were retrieved from electronic database such as Scopus, Semanticscholar, Sciendirect, Google scholar, Researchgate, Pubmed, and websites. P. javanica possesses several phytochemical constituents, such as quassinoids, alkaloids, and triterpenoids. The compounds of the plant have been isolated and studied for their pharmacological activities, encompassing antimalarial, antiproliferative, antiviral, antimicrobial, and membrane-stabilizing activities. It was found that the pharmacological activities in the plant were attributable to the key ingredients of quassinoids and alkaloids present. However, further extensive studies must be carried out to explore more potential benefits that the plant could offer.
... The evaluation of the phenolic compounds' content, flavonoids, and non-flavonoids was also performed by Poljuha et al. [79], using a new HPLC procedure equipped with a C 18 column using wavelengths of 360 nm and 310 nm to identify flavonoids and phenolic acids, respectively, which was faster (26 min) and used fewer solvents than other works. The extractions in deionised water were performed after maceration and respective extraction for 48 h, followed by filtration. ...
Article
Full-text available
Many species of the so-called exotic plants coexist with native species in a balanced way, but others thrive very quickly and escape human control, becoming harmful—these are called invasive alien species. In addition to overcoming geographic barriers, these species can defeat biotic and abiotic barriers, maintaining stable populations. Ailanthus altissima is no exception; it is disseminated worldwide and is considered high risk due to its easy propagation and resistance to external environmental factors. Currently, it has no particular use other than ornamental, even though it is used to treat epilepsy, diarrhea, asthma, ophthalmic diseases, and seborrhoea in Chinese medicine. Considering its rich composition in alkaloids, terpenoids, sterols, and flavonoids, doubtlessly, its use in medicine or other fields can be maximised. This review will focus on the knowledge of the chemical composition and the discovery of the biological properties of A. altissima to understand this plant better and maximise its possible use for purposes such as medicine, pharmacy, or the food industry. Methods for the extraction and detection to know the chemical composition will also be discussed in detail.
... Moreover, different parts of the plants have also been reported to have antifungal, antiviral and insecticidal effects additional to phytotoxic effect on neighboring plants [30,31]. For example, Poljuha et al. [32] reported that glycosides (quercetin-3-O-glucoside) and caffeic acid were predominant flavonid and phenolic acid, respectively, in the extracts of fresh and dry leaves of A. altissima and the leaf extracts were active against Escherichia coli. Previous studies also suggested that the leaf extracts of A. altissima had herbicidal activity. ...
Article
This study was conducted to test the possibility of using leaf extracts of invasive weed tree-of-heaven (Ailanthus altissima (Mill.) Swingle) for the postharvest quality preservation of apricot (cv. ‘Şalak’) fruits. Two different doses of A. altissima leaf extracts (0.5% and 2.5%) with and without supplements (0.1% g Arabic gum, 0.05% citric acid, 0.05% potassium sorbate and 0.05% ascorbic acid) were tested. Results showed that the extracts of A. altissima leaves have strong ability to prevent weight loss, reduce decay incidence, protect visual quality, delay the occurrence of chilling injury, keep fruit firmness and delay the reduction in ascorbic acid content.
... H. klaineana has antimicrobial activity. According to Danijela et al. [15], methanol and acetone extract of the leaf extracts of Ailanthus altissima (Simaroubaceae) has antibacterial and antifungal activity equivalent to standard antibiotics. The MIC of positive control gentamicin for antibacterial activity was 0.0 mg/mL in all cases, and positive control Bamphotericin for antifungal was 0.1 mg/mL. ...
Article
Quercetin as a valuable natural flavonoid has shown extensive biological activities, including anticancer, antioxidant, antibacterial, antiinflammatory, anti-Alzheimer, antifungal, antiviral, antithalassemia, iron chelation, antiobesity, antidiabetic, antihypertension, and antiphospholipase A2 (PLA2) activities, by the modulation of various targets and signaling pathways that have attracted much attention. However, the low solubility and poor bioavailability of quercetin have limited its applications; therefore, the researchers have tried to design and synthesize many new derivatives of quercetin through different strategies to modify quercetin restrictions and improve its biological activities. This review categorized the O-glycoside derivatives of Quercetin into two main classes, 3-O-glycoside and other O-glycoside derivatives. Also, it studied biological activities, structure–activity relationship (SAR), and the action mechanism of O-glycoside quercetin derivatives. Overall, we summarized past and present research for discovering new potent lead compounds. Highlights • Quercetin is a natural flavonoid with a valuable scaffold. • O-Glycoside quercetin derivatives represents broad-spectrum biological activities. • The structure–activity relationship investigation is discussed after modifying the scaffold of quercetin. • This review can help researchers to rationally design/develop various drugs.
Article
Full-text available
A new triterpene, named milemaronol (1), was isolated from Homalolepis suffruticosa Engl., Simaroubaceae, along with 10 known metabolites, chaparrinone (2), scopoletin (3), 5-methoxycanthin-6-one (4), eurylene (5), hispidol A (6), hispidol B (7), nilocitine (8), α-dihydronylocytine (9), β-dihydronylocytine (10), and teurilene (11). These compounds were characterized based on their spectral data, mainly 1D ( ¹ H, ¹³ C-APT) and 2D ( ¹ H- ¹ H-COSY, NOESY, HSQC, HMBC) NMR and their mass spectra (HR-ESI-MS), in comparison with data from the literature. Compounds 1 to 6, 8, and 9 were evaluated for their antimycobacterial activity against 2 strains (H37Rv and M299).
Article
Full-text available
Spectrophotometric and chromatographic analysis of phenolics in water and ethanolic extracts of wild asparagus, butcher’s broom and black bryony from Croatia was conducted. Their antioxidant capacity (ABTS, DPPH and FRAP assay) and energy content were determined. The gastrointestinal stability of detected phenolics was determined using a two-phase in vitro digestion method with human enzymes. The highest phenolics yield, radical scavenging activity and ferric reducing antioxidant potential were recorded in 40 % ethanolic extract of black bryony, with glycosylated forms of kaempferol as dominant components. Quercetin-3-O-rutinoside and isorhamnetin-3-Orutinoside were dominant phenolics in all wild asparagus extracts, and salicylic acid was predominant in butcher’s broom 40 % ethanolic extract. Phenolic acids of the three species were not stable during gastric and duodenal phases of simulated digestion. Two main black bryony kaempferol glycosides were best preserved after digestion (50 % of each). Black bryony contains more energy than wild asparagus and butcher’s broom. Accordingly, we propose black bryony as a valuable source of antioxidant kaempferol glycosides with relevant gastrointestinal stability and higher energy content than so far more conventional vegetable wild asparagus.
Article
Full-text available
The phenolic composition of whole heads and excised midrib sections of iceberg, butter leaf, and romaine lettuce (Lactuca sativa L.) was followed at 5 and 10 °C during the first 3 days after wounding or during continuous exposure to 10 μL·L-1 ethylene in air. After 3 days of storage at 5 and 10 °C, only 5-caffeoylquinic acid (chlorogenic acid), 3,5-dicaffeoylquinic acid (isochlorogenic acid), caffeoyltartaric acid, and dicaffeoyltartaric acid were detected in wounded lettuce midribs. Of these four compounds, chlorogenic acid accumulated to the highest level in all three lettuce types. The content of caffeic acid derivatives increased 3- and 6-fold after 72 hours of storage at 5 and 10 °C, respectively. The synthesis of caffeoyltartaric acid was not induced by wounding in iceberg lettuce, while chlorogenic acid increased 5-fold at 5 °C and 10-fold at 10 °C. Similar relative phenolic compositions were detected in the three lettuce types studied, although at different concentrations. Changes observed in the content of individual phenolic compounds during the first 3 days of ethylene exposure seemed to follow the same pattern observed during wound induction of the synthesis of phenolic compounds. Chlorogenic acid increased 5-fold and isochlorogenic acid increased 10-fold, while the content of caffeoyltartaric derivatives were not significantly altered by ethylene treatment. Isochlorogenic acid, which was only present in low amounts in the control, was synthesized in the later steps of wound and ethylene induction. Similar kinetics for the induction of phenolic compounds were observed in the three lettuce types studied, suggesting that the mechanisms by which wounding induces phenylpropanoid synthesis are common for the different lettuce types.
Article
Full-text available
Phenolic compounds (PC) are secondary metabolites produced by plants that have diverse applications in the pharmaceutical, cosmetics, nutraceutical and food industries. Therefore, the design of bioprocesses for their production, extraction and purification is of major relevance. The application of postharvest abiotic stresses (i.e., wounding, modified atmospheres, UV radiation) can be used as an approach to increase the concentration of PC during postharvest of diverse plant tissues. Herein, we propose an abiotic stress based bioprocess for the production of high commercial value antioxidant PC. The strategy proposed was exemplified with experimental data showing how abiotic stresses can be applied to produce resveratrol and quercetin-3-O-glucoside in grapes, and chlorogenic acid in carrots. Finally, different procedures to extract and purify PC produced in the stressed plant tissue are discussed.
Article
Full-text available
A comprehensive study on the volatile oil and phenolic constituents of Ailanthus altissima Swingle (Simaroubaceae) leaves was performed. Methanolic extracts of leaves and their hydrodistilled residues were screened for their antioxidant, antimicrobial and phytotoxic properties. The results showed that the leaf volatile oils were a complex mixture of more than a hundred components, mainly composed by non-terpenic compounds (tetradecanol, heneicosane, tricosane and docosane) and sesquiterpene hydrocarbons (α-curcumene and α-gurjunene). Methanolic extracts from leaves contain the highest level of total phenolic content, while those from the hydrodistilled residues showed the highest total flavonoid content. The most frequent phenolic compounds identified by HPLC-DAD–MS were gallic acid, chlorogenic acid, HHDP-galloylglucose, epicatechin, rutin, hyperoside and quercetin-3-galloyl hexoside. Evaluation of the antioxidant activities by using four complementary tests (DPPH, ABTS, 2-deoxyribose and FRAP) showed that both extracts exhibited strong concentration-dependent antioxidant activities. These extracts were efficient against Gram-positive bacteria, but not active against Gram-negative bacterial strains and the yeast Candida albicans. They also exhibited strong inhibitory effects on the germination and the radicle growth of the wild Daucus carota. This work provides scientific supports for the high antioxidant and phytotoxic activities of this species and thus, it may find potential applications in the development of natural herbicides and antioxidants for agro-food and pharmaceutical industries.
Article
Full-text available
Background The study randomly screened leaf extracts of several hundred southern African tree species against important microbial pathogens to determine which taxa have the highest activity and may yield useful products to treat infections in the animal health market. Methods We determined the antibacterial and antifungal activity of 714 acetone leaf extracts of 537 different tree species against Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans and Cryptococcus neoformans. A sensitive serial dilution microplate method was used. Results Several extracts had MICs as low as 0.02 mg/ml. We analysed 14 out of the 38 tree orders where we determined the activity of more than 8 different tree species representing 89% of all species examined. There were statistically significant differences in some cases. Celastrales, Rosales and Myrtales had the highest activity against Gram-positive bacteria, the Myrtales and Fabales against the Gram-negative bacteria and the Malvales and Proteales against the fungi. Species present in the Asterales followed by the Gentiales and Lamiales had the lowest activities against all the microorganisms tested. Fabales species had the highest activities against all the microorganisms tested. There was substantial selectivity in some orders. Proteales species had very high activity against the fungi but very low activity against the bacteria. The species in the Celastrales and Rosales had very low antifungal activity, low activity against Gram-negative bacteria and very high activity against Gram-positive bacteria. Conclusion Against all classes of microorganisms, the four orders containing species with the highest average antimicrobial activities also contained several species with low activities against different pathogens and vice versa. These results therefore should be used with circumspection in selecting tree orders that would yield the highest probability of finding species with promising activities. Nevertheless there was a twofold increase in probability of finding extracts with interesting antifungal activity from orders with high mean activity than from orders with low mean activity. The probability increased to threefold and fivefold for Gram-positive and Gram-negative bacteria respectively.
Article
Compounds inhibitory to the growth of neighboring plant species were found in significant concentrations in the leaves and stems of young Ailanthus altissima ramets. The surrounding soil also contained appreciable concentrations of similarly acting toxins. Individuals of neighboring plant species have either incorporated active portions of inhibitory compounds or responded to Ailanthus by producing growth-inhibiting substances. Under greenhouse conditions, individuals of neighboring plant species previously unexposed to Ailanthus in the field were found to be more susceptible to the Ailanthus toxins than individuals previously exposed. Moreover, seeds produced by unexposed populations were also more susceptible to Ailanthus toxins than seeds produced by previously exposed populations. These differences demonstrated that the allelochemicals of Ailanthus altissima exhibited a measurable impact upon neighboring plant species. Since the progeny of these populations displayed a differential response to Ailanthus toxin, this phenotypic difference between the two populations may have a heritable basis.
Article
The aim of this investigation was to simplify extracts to facilitate the isolation of antibacterial compounds from the complex mixture of chemicals in the plant by using different extractants. Intact dried leaves were extracted with acetone and 1% aqueous sodium bicarbonate and ground leaves were extracted by hexane, carbon tetrachloride, di-isopropylether, ethyl ether, methylene dichloride, tetrahydrofuran, acetone, ethanol, ethyl acetate, methanol and water. TLC was used to determine chemical composition and antibacterial activity of extracts was determined by a microplate serial dilution method. The different solvents extracted from 2.6 to 17.4% of the dry weight. Methanol, methylene dichloride and tetrahydrofuran extracted the most components. The chemical composition of the non-polar components of the different extracts were remarkably similar. The minimum inhibitory concentration for the different extractants varied from 0.01 to 1.25mg/ml with the four test organisms used (Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and Enterococcus faecalis). The extracts had similar activity towards Gram-negative and Gram-positive bacteria. Diisopropyl ether, ethanol, ethyl ether, acetone and ethyl acetate extracted high antibacterial activity with a lower quantity of other non-active compounds and could be useful for isolating bioactive compounds.
Article
The aim of this investigation was to simplify extracts to facilitate the isolation of antibacterial compounds from the complex mixture of chemicals in the plant by using different extractants. Intact dried leaves were extracted with acetone and 1% aqueous sodium bicarbonate and ground leaves were extracted by hexane, carbon tetrachloride, di-isopropylether, ethyl ether, methylene dichloride, tetrahydrofuran, acetone, ethanol, ethyl acetate, methanol and water. TLC was used to determine chemical composition and antibacterial activity of extracts was determined by a microplate serial dilution method. The different solvents extracted from 2.6 to 17.4% of the dry weight. Methanol, methylene dichloride and tetrahydrofuran extracted the most components. The chemical composition of the non-polar components of the different extracts were remarkably similar. The minimum inhibitory concentration for the different extractants varied from 0.01 to 1.25mg/ml with the four test organisms used (Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and Enterococcus faecalis). The extracts had similar activity towards Gram-negative and Gram-positive bacteria. Di-isopropyl ether, ethanol, ethyl ether, acetone and ethyl acetate extracted high antibacterial activity with a lower quantity of other non-active compounds and could be useful for isolating bioactive compounds.
Chapter
Despite many thousands of publications investigating the antibiotic activity of plant extracts and the widespread use of African medicinal plants to treat animal and human microbial infections, no single-entity commercial antimicrobial product has yet been developed from plants. This is in contrast to many commercial medicinal products that have been developed from plants for other diseases. After an extensive survey of the literature, it appears that plants combat infections by using synergistic interactions between different compounds and not single highly active compounds. The random screening of acetone leaf extracts of more than 700 tree species yielded many extracts with high activities. Although the chance of developing single-entity antibiotics seems elusive, there are examples where plant extracts can be used to deliver highly effective products that can compete with current commercially used antimicrobial agents. By manipulating extracts the biological activity can be enhanced and patentable products can be developed.