![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-Oglucoside, K-rut = kaempferol-3-O-rutinoside. nd = not detected, it = in trace. identified in methanolic extract of fresh leaves (apigenin-8-Cglucoside 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].](https://www.researchgate.net/profile/Ivana-Sola/publication/320992025/figure/fig1/AS:677983345987585@1538655234313/Composition-of-flavonoid-glycosides-in-water-and-methanolic-extracts-of-Ailanthus_Q320.jpg)
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Volume 12. Issue 10. Pages 1529-1672. 2017
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G.B. Elyakov Pacific Institute of Bioorganic Chemistry,
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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.
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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
