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 2014
NPC Natural Product Communications Vol. 9
No. 7
Essential Oils from Schinus Species of Northwest Argentina: 1019 - 1022
Composition and Antifungal Activity
Diego A. Sampietroa,*, María Melina E. Belizana, Zareath P. Terán Baptistaa,
Marta A. Vattuonea and Cesar A. N. Catalánb
a
LABIFITO, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471,
4000, San Miguel de Tucumán, Argentina
b
INQUINOA-CONICET, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán,
Ayacucho 471, 4000, San Miguel de Tucumán, Argentina

Dasampietro2006@yahoo.com.ar

Received: April 11th, 2014; Accepted: May 3rd, 2014

The composition of the essential oils from leaves (Sal) and fruits of S. areira (Saf), and fruits of S. fasciculatus (Sff) and S. gracilipes (Sgf) were analyzed by
GC/MS. The major compounds identified were sabinene (26.0±0.5%), bicyclogermacrene (14.5±0.4%), and E-citral (6.7±0.2%) in Sal oil, limonene
(27.7±0.7%), sabinene (16.0±0.5%), β-phellandrene (14.6±0.8%) and bicyclogermacrene (8.1±0.2%) in Saf oil, sabinene (22.7±0.6%), α-phellandrene
(18.7±0.3%), β-phellandrene (15.7±0.4%), and bicyclogermacrene (8.1±0.2%) in Sff oil and β-pinene (25.4±0.8%), α-pinene (24.7±0.7%), and sabinene
(13.6±0.4%) in Sgf oil.The antifungal activity of the four oils was evaluated on strains of Fusarium verticillioides and F. graminearum, and the results
compared with the effect of epoxyconazole, pyraclostrobin and thyme oil. The Sff oil had the highest antifungal activity among the Schinus oils tested, with
MIC100 (F. graminearum) = 6 ‰ and MIC100 (F. verticillioides) = 12 ‰. A principal component analysis suggests that 9 constituents (α-thujene, α-terpinene, p-
cymene, γ-terpinene, terpinolene, 1-terpineol, α-calacorene, α-phellandrene, and terpinen-4-ol) explain the higher antifungal effect of Sff. The MIC100s of
Schinus oils were on average 30-60 and 8.5-17 fold lower than those obtained for thyme oil on F. verticillioides and F. graminearum, respectively. In the case
of commercial fungicides, their MIC100s were three orders of magnitude lower than those of Schinus oils. The last ones showed an additive interaction when
assayed in mixtures with the commecial fungicides and thyme oil. The results suggest that the doses of fungicides required for control of the Fusarium species
can be reduced when they are assayed in mixtures with the Schinus oils.

Keywords: Schinus fasciculatus, Schinus gracilipes, Schinus areira, Essential oils, Fusarium, Antifungal activity.

The genus Schinus (Anacardiaceae) comprises 30 species native to
South America, including S. areira L., S. fasciculatus (Griseb.) I.M.
Johnst and S. gracilipes I.M.Johnst. endemic for northwest
Argentina [1]. These plants are known as false peppers because
their berries have been used to spice food in South American
countries for centuries. The fruits are used in the preparation of a
beverage named “Chicha de molle”. In the case of S. areira, the
stems and leaves are used in folk medicine as an antiseptic,
antimicrobial and as insect repellents [2]. The fruit oil showed
antimutagenic activity and is used as a substitute for black pepper in
formulation of spices [3]. The essential oil of leaves and fruits of S.
areira displayed several biological activities including inhibition of
acetylcholinesterase, and insecticidal, allelopathic, antibacterial and
antioxidant activities in laboratory tests [4a-4c].
Fusarium graminearum (teleomorph Gibberella zeae) and F.
verticillioides (teleomorph G. moniliformis) cause ear rot diseases
in cereals from the subtropical and temperate regions of Argentina
[5]. They not only reduce cereal yields but also contaminate
infected grains with mycotoxins noxious for human and animal
health. Exposure to fumonisins produced by F. verticillioides has
been associated with several diseases in animals including
leucoencephalomalacia in equines, pulmonary edema in swine, liver
cancer in rats, and immunosuppression in poultry. Epidemiological
studies suggest that fumonisins increase the incidence of human
esophageal cancer in Africa, Brazil, China, and Italy [6].
Application of fungicides at cereal flowering is a strategy
performed to reduce the mycotoxigenic risk. However, the intensive
use of these biocides has also increased the resistance to xenobiotics
of the Fusarium species [7]. New fungicides, or additives to
commercial ones, able to control fungal progress are needed in
order to solve this problem. Essential oils might be used to either
replace or reduce the doses of fungicides applied for control of the
toxigenic Fusarium species. As part of a systematic study of the
chemical composition of essential oils and the antifungal potential
of aromatic plants that occur in the northwest of Argentina, the aim
of the present study was to describe the chemical composition of the
essential oils obtained from fruits and leaves of S. areira, S.
fasciculatus, and S. gracilipes and their antifungal activity on F.
verticillioides and F. graminearum.
The hydrodistillation of leaves from S. areira (Sal) and fruits from
S. areira (Saf), S. fasciculatus (Sff) and S. gracilipes (Sgf) yielded
pale yellow oils with markedly different aromas. Fruits yielded a
high percentage (w/w) of essential oils (Saf = 4.5%±0.2%, Sff =
3.4±0.1%, and Sgf 3.4±0.1%), while Sal had the lowest yield
(1.7±0.1%) and no essential oil was extracted from leaves of the
remaining Schinus species. GC-MS analysis of the oils revealed a
total of 38, 41, 29 and 30 constituents for Sal, Saf, Sff, and Sgf,
respectively (Table 1). These analyses accounted for more than 89%
of the chemical composition of the oils. Hydrocarbon monoterpenes
(Saf = 63.4±0.2, Sff = 74.2±0.2, and Sgf = 81.0±0.4) dominate the
terpene composition of the fruit oils, a feature also observed in fruit
oils of S. molle and S. terebinthifolius [8a-8b]. In contrast,
hydrocarbon monoterpenes and sesquiterpenes were found in
similar levels in Sal. Regarding the major constituents, Sal
contained sabinene (26.0±0.5%), bicyclogermacrene (14.5±0.4%),
and E-citral (6.7±0.2%), while Saf contained limonene
(27.7±0.7%), sabinene (16.0±0.5%), β-phellandrene (14.6±0.8%)
and bicyclogermacrene (8.1±0.2%). Sff had high contents of
1020 Natural Product Communications Vol. 9 (7) 2014 Sampietro et al.

Table 1: Constituents of the essential oils obtained from leaves of S. areira and from Table 2: Concentrations of the Schinus oils needed to inhibit 100% (MIC100) of the
fruits of S. areira, S. fasciculatus and S. gracilipes. growth of F. verticillioides (strains LABI6 and LABI28) and F. graminearum sensu
stricto (LABI25 and LABI26) in microdilution assays. Fungi grew in YES semiliquid
Compounds KI1 Area %2
Sal Saf Sff Sgf
medium. Commercial fungicides and thyme oil (from leaves of Thymus vulgaris) were
assayed as positive controls.
α-Thujene 930 0.4±0.1 0.2±0.0 0.9±0.1 0.4±0.1 MIC100 (‰)
α-Pinene 939 0.7±0.1 1.3±0.2 5.5±0.2 24.7±0.7 Strains Sal Saf Sff Sgf
Camphene 953 0.5±0.0 0.2±0.0 - 0.5±0.1 LABI6 24 24 12 24
Sabinene 975 26.9±0.5 16.0±0.5 22.7±0.6 13.6±0.4 LABI25 12 12 6 12
β–Pinene 979 0.3±0.1 0.1±0.0 0.8±0.1 25.4±0.8 LABI26 12 12 6 12
β-Myrcene 990 0.4±0.1 1.1±0.2 2.1±0.1 6.3±0.3 LABI28 24 24 12 24
α-Phellandrene 1002 tr 0.8±0.3 18.7±0.3 tr
α-Terpinene 1017 - - 1.0±0.1 -
p-Cymene 1026 1.9±0.2 1.0±0.1- 4.4±0.2 0.6±0.1 MIC100 (ppm) MIC100 (‰)
Limonene 1029 1.2±0.1 27.7±0.7 tr 6.9±0.4 Epoxyconazole Pyraclostrobin Ketoconazole Thymus vulgaris
β-Phellandrene 1031 3.7±0.3 14.6±0.8 15.7±0.4 2.6±0.3 LABI6 2 50 16 0.4
γ-Terpinene 1059 0.7±0.1 0.2±0.0 1.7±0.2 - LABI25 8 25 32 0.7
cis-Sabinene 1070 0.2±0.1 0.2±0.0 0.1±0.0 - LABI26 8 25 32 0.7
Hydrated LABI28 2 50 16 0.4
Terpinolene 1088 0.4±0.1 0.2±0.1 0.7±0.1 -
1-Terpineol 1120 - 0.1±0.0 0.2±0.0 -
Menth-2-en-1-ol 1140 0.2±0.1 0.2±0.1 0.3±0.1 -
Essential oils from the same plant source and organ often show
Terpinen-4-ol 1177 2.8±0.2 1.2±0.3 5.2±0.1 0.3±0.0 qualitative and quantitative variations in chemical composition
Isopinocarveol 1180 - - - 0.3±0.0 related to their geographical origin. In Buenos Aires province, leaf
4-Isopropyl-2- 1188 - 1.6±0.2 - 0.3±0.3
Cyclohexen-1-one oils of S. areira contained α-phellandrene (28.5%), 3-carene
E-citral 1271 6.7±0.2 - - - (20.8%), and camphene (10.9%) as major constituents while fruit
Bornyl acetate 1283 1.0±0.1 - - 0.6±0.2
α –Copaene 1337 0.3±0.0 0.1±0.0 0.4±0.1 -
oils contained α-phellandrene (24.8%), 3-carene (21.3%) and β-
Linalyl propionate 1338 - - 0,5±0.2 - myrcene (19.7%) [4a]. In Jujuy province (north end of northwest
β –Cubebene 1387 - 0.3±0.0 - - Argentina), α- and β-phellandrene were found as the major
β-Elemene 1391 1.1±0.2 0.4±0.1 0.2±0.0 0.4±0.1
Junipene 1408 - 0.9±0.1 - - constituents of the fruit oils [9]. To the best of our knowledge this
α-Gurjunene 1410 2.0±0.1 0.6±0.2 0.3±0.0 0.5±0.3 work reports for the first time the composition of fruit oils from S.
β-Caryophyllene 1418 1.7±0.1 0.4±0.1 1.2±0.2 0.9±0.2 fasciculatus and S. gracilipes.
Aromadendrene 1447 0.6±0.2 0.4±0.2 0.2±0.1 -
α-Humulene 1455 1.7±0.1 0.7±0.1 0.3±0.2 0.4±0.0
(Z,E)-α-Farnesene 1480 - - - 1.1±0.2 The essential oils of Schinus spp. inhibited the growth of F.
Germacrene 1480 0.5±0.1 0.1±0.0 - 3.2±0.1
β-Selinene 1489 - - - 0.3±0.2
graminearum more than that of F. verticillioides (Table 2).
Valencene 1496 - 0.2±0.0 - - However, the MIC100s of Schinus oils were on average 30-60 and
Bicyclogermacrene 1499 14.5±0.4 8.1±0.2 - - 8.5-17 fold lower than those obtained for thyme oil on F.
α –Muurolene 1500 1.3±0.2 0.5±0.1 0.9±0.2 0.3±0.2
α-Amorphene 1506 0.4±0.1 0.5±0.1 0.4±0.1 0.3±0.0 verticillioides and F. graminearum, respectively. Thyme oil also
-Cadinene 1522 5.1±0.2 1.3±0.2 2.9±0.3 0.7±0.1 had biocidal activity at the MIC100 while Schinus oils were only
1S,cis-Calamenene 1526 0.3±0.1 - - - fungistatic in the range of concentrations assayed. In the case of
α–Cadinene 1537 0.3±0.1 - - -
α-Calacorene 1544 - - 0.2±0.0 - commercial fungicides, their MIC100s were three orders of
Elemol 1548 0.3±0.1 0.3±0.0 - 1.5±0.4 magnitude lower than those of Schinus oils. The complex
Ledol 1565 - 0.2±0.1 - -
Palustrol 1567 0.4±0.1 0.2±0.0 - -
composition of the tested essential oils makes it difficult to
Spathulenol 1577 5.5±0.2 3.8±0.2 0.9±0.2 1.0±0.2 elucidate which constituents contribute to the antifungal activity.
Caryophyllene 1582 - - 0.5±0.0 0.3±0.0 The expected order of contribution of the constituents, in order of
oxide
Viridiflorol 1597 1.0±0.2 0.5±0.2 0.2±0.1 - more to less antifungal activity, is phenols > alcohols > aldehydes >
Guaiol 1600 2.0±0.1 1.8±0.3 - - ketones > ethers > hydrocarbon compounds [10]. In agreement with
10-epi-γ-Eudesmol 1622 - - - 0.4±0.1
Isospathulenol 1639 0.2±0.1 0.2±0.0 - -
this explanation, thyme oil was the only one containing phenolic
T-Muurolol 1640 1.1±0.2 1.0±0.2 - - compounds and showed the highest antifungal activity. The fruit oil
α-Eudesmol 1652 - - - 0.9±0.2 of S. fasciculatus showed the highest contents of alcohols and was
α-Cadinol 1660 0.8±0.1 0.3±0.1 - -
Vulgarol 1701 1.9±0.2 1.3±0.3 - 0.9±0.2 the Schinus oil with the highest inhibitory activity on fungal growth.
Patchulane 2095 - - - 0.4±0.0 The biological activity of essential oils is often explained as the
monoterpene joint action of several of their minor and/or major constituents [11].
hydrocarbons 37.1±0.2 63.4±0.2 74.2±0.2 81.0±0.4
oxygenated Principal component analysis (PCA) based on relative participation
sesquiterpenes 4.2±0.1 3.3±0.1 6.3±0.1 1.5±0.1 of constituents and MIC100 of Schinus oils suggests this situation.
monoterpene
hydrocarbons 31.7±0.2 15.8±0.1 7.0±0.1 9.4±0.1
Figure 1 shows the bidimensional graph of components 1 and 2
oxygenated explaining 76.1% of the total variance, with an important
sesquiterpenes 18.0±0.1 11.3±0.1 1.6±0.1 4.1±0.2 divergence of Saf from the other Schinus oils. The contents of 9
TOTAL 91.0±0.2 93.8±0.1 89.1±0.1 96.0±0.2
a
Compounds listed based on elution from a non-polar DB-5 column; 1Kovats Index
constituents (α-thujene, α-terpinene, p-cymene, γ-terpinene,
calculated from retention times in relation to those of a series of n-alkanes on a 30 m terpinolene, 1-terpineol, α-calacorene, α-phellandrene, and terpinen-
DB-5 capillary column; 2percentage of total area. SD = Standard deviation; Sal = leaf 4-ol) were directly correlated (r2>0.8, p = 0.05) to component 1 and
oil of Schinus areira; Saf = fruit oil of S. areira; Sff = fruit oil of S. fasciculatus; Sgf = seem to explain the inhibitory effect of Sff on both F. verticillioides
fruit oil of S. gracilipes; tr = traces; - not detected.
and F. graminearum. Most of the 9 constituents were found in the
Sff at contents below 5%, except α-phellandrene (18.7±0.3%) and
sabinene (22.7±0.6%), α-phellandrene (18.7±0.3%), β-phellandrene
terpinen-4-ol (5.2±0.1%). The variation explained by component 2
(15.7±0.4%), and bicyclogermacrene (8.1±0.2%). Sgf contained
and constituents correlated to it were not associated with the
β-pinene (25.4±0.8%), α-pinene (24.7±0.7%), and sabinene
antifungal activity.
(13.6±0.4%). The remaining components were found in the oils at
levels below 6%. Thyme oil, included as a positive control of
Several essential oils with low or no biological activity have
antifungal activity, contained p-cymene (45.1±1.2%) and thymol
synergistic antifungal effects in mixture with biocides [11].
(21.5±1.5%) as main constituents (not shown).
To check this possibility, the Schinus oils were assayed in mixtures
Schinus essential oil Natural Product Communications Vol. 9 (7) 2014 1021

Figure 1: Please Bi-plot of the two first principal components computed from means of the contents of the essential oil constituents, and of the MIC100 for F. verticillioides (MICFv)
and F. graminearum sensu stricto (MICFg). 1: ledol, valencene, m-cresol, jupinene, β-elemene, β-cubenene; 2: T-muurolol, isospathulenol, palustrol, 5-guaiol, spathulenol,
bicyclogermacrene, α-gurjunene, α-humulene; 3: E-citral, α-cadinene, 1-S-cis-calamenene; 4: β-caryophyllene; 5: α-phellandrene, α-calacorene, α-terpinene; 6: isopinocarveol,
patchulane, (Z,E)-α-farnesene, β-selinene, 10-epi-γ-eudesmol; 7: α-eudesmol, germacrene.

Table 3: Fractional inhibitory concentration index (FICI) of combinations of Foundation. Voucher specimens were deposited in the LABIFITO
commercial fungicides and the essential oils from Schinus species, determined by the
checkerboard technique.
(Laboratory of Biology and Bioactive Agents and Phytopathogens,
Fusarium verticillioides FBQF, UNT). Mature fruits and leaves were placed in paper bags
Pyraclostrobin Epoxyconazole Thymol Interpretation of the joint effect and carried to the laboratory for extraction of essential oils. Then,
Sal 2.5-3.1 2.1-3.2 1.9-3.7 Additivism fruits were manually detached from leaves.
Saf 1.5-2.5 2.9-4.0 2.0-3.2 Additivism
Sff 2.5-3.1 0.9-2.5 2.9-4.0 Additivism
Sgf 3.1-3.9 1.0-4.0 2.8-3.9 Additivism Assayed microorganisms: Strains of F. graminearum sensu stricto
Fusarium graminearum (LABI25 and LABI26) and F. verticillioides (LABI6 and LABI28)
Pyraclostrobin Epoxyconazole Thymol Interpretation of the joint effect
Sal 2.1-3.0 1.5-3.0 1.5-2.9 Additivism belong to the collection of the Laboratory of Biology of Bioactive
Saf 1.7-2.6 2.5-4.0 1.8-3.2 Additivism Agents and Phytopathogens (LABIFITO – FBQF - UNT). The
Sff 2.5-4.0 1.5-4.0 2.0-3.0 Additivism microbial strains were preserved in SNA medium (Spezieller
Sgf 1.6-2.8 2.5-3.2 2.0-3.2 Additivism
Nahrstoffarmer agar: 0.1% de K2HPO4, 0.1% NaNO3, 0.05%
MgSO4. 7H2O, 0.05% KCl, 0.02% glucose, 0.2% sucrose and 2%
with epoxyconazole, pyraclostrobin and thymol oil. The selected
agar) at 4ºC.
commercial fungicides are used in the control of the ear rot disease
and their action mechanisms are notably different [12].
Extraction of essential oils: The essential oils were extracted from
Epoxyconazol is a triazol derivative that inhibits ergosterol
the fresh plant materials by hydrodistillation for 2 h in a Clevenger-
biosynthesis, while pyraclostrobin is a strobilurin that inhibits
type apparatus. Three hundred g of fresh ground fruits or leaves
mitochondrial electron transport. In the case of thyme oil, thymol is
were placed in the metal baskets of the apparatus. The oily phase
believed to cause structural and functional damage to the
was collected and dehydrated over anhydrous sodium sulfate, stored
cytoplasmic membrane, while p-cymene is able to modify the
in hermetically sealed glass containers and kept under refrigeration
structure and permeability of cell membranes [13]. The fractional
at + 5ºC until analysis and assay of antifungal activity. Total oil
concentration indexes were higher than 0.5 and lower than 4 in all
yields were expressed as a percentage of the weight of the essential
the mixes assayed. This situation indicates an additive joint action.
oil divided by the weight of fresh plant material.
The fungitoxicity of the Schinus oils was lower than that of Chemical characterization of the essential oils: Analysis of the
synthetic fungicides and thyme oil. However, lower doses of volatile oils was achieved using a Hewlett Packard (6890) GC-MS
fungicides were required for control of the Fusarium species when system coupled to a quadruple mass spectrometer (model HP 5973)
these xenobiotics were assayed in mixtures with the Schinus oils. with a capillary column {HP-5MS (5% phenyl methylsiloxane;
Further in vivo assays are required in order to check the antifungal length = 30 m, inner diameter = 0.25 mm, and film thickness = 0.25
potential of the mixtures. m)}. GC-MS interphase, ion source, and selective mass detector
temperatures were maintained at 280ºC, 230ºC, and 150ºC,
Experimental respectively. Carrier gas used was helium with a flow rate of 1.0
Plant material: Fruits and leaves of Schinus gracilipes were mL min−1. The oven temperature was programmed as follows: 60ºC
collected in Tafi del Valle while those of S. fasciculatus and S. for 1 min then increased from 60 to 220ºC at a rate of 3ºC min−1 and
areira were collected in Ampimpa. These locations are in the then held at 300ºC for10 min.
northwest of Tucuman province (northwest Argentina). Identity of
the plant materials was confirmed by comparison of voucher Identification of components: Most of the components were
specimens with those stored in the Herbarium of the Miguel Lillo identified on the basis of comparison of their retention indices and
1022 Natural Product Communications Vol. 9 (7) 2014 Sampietro et al.

mass spectra with published data [14], and computer matching was
made with the Wiley 275 and National Institute of Standards
Technology libraries provided with computer controlling GC-MS
systems. The retention indices were calculated using a homologous
series of n-alkanes C8–C18 and C8–C22 for essential oils,
respectively, which are reported in Table 1. The normalization
method was used for the chromatographic peaks to calculate the
percentage of oil composition.
Microdilution assays: Mycelial growth was evaluated by the
microdilution method in semiliquid YES medium (20 g/L yeast
extract, 150 g/L sucrose, 20 g/L agar) in 96 flat bottom well
microplates. Protocols were developed according to M38-A and
M38-P documents from the National Committee for Clinical
Laboratory Standards with some modifications [15]. Fungal
colonies were grown in Petri dishes for 7 to 15 days in solid SNA
medium. In the case of F. graminearum, the Petri dishes were
placed under black light with a photoperiod of 12 h light/12 h
darkness to stimulate sporulation. Then, the fungal colonies were
washed with 2 mL of physiological solution (0.9% of NaCl in
distilled water) to obtain either microconidia (F. verticillioides) or
macroconidia (F. graminearum) suspensions. The asexual spores
were counted in a Neubauer chamber, and the growth medium was
diluted to obtain a density of 0.4-5 104 spores/mL. The essential oils
were assayed in 7 serial two fold dilutions comprised between 96
and 1.5 µL/mL, in semiliquid YES medium (20 g/L yeast extract,
150 g/L sucrose, 0.5 g/L magnesium sulfate). The final volume in
each well was 200 µL, which corresponded to 100 µL of spore
suspension and 100 µL of a dilution of the essential oil. Controls of
growth and sterility were also performed. Each treatment (oils or
controls) had 3 repetitions per microplate. Each microplate was
prepared in duplicate. The microplates were incubated for 72 h at
25-26°C. The minimum concentration of the essential oil required
to inhibit 100% of the fungal growth was determined after 72 h of
incubation. Fungal survival at oil concentrations above the MIC100
was checked by transferring 5 µL aliquots from the wells to Petri
dishes containing PDA which were then incubated at 25-26°C for 7
days.
Joint effect of essential oil and xenobiotics on fungal growth: The
joint effect of essential oils was evaluated in microdilution assays
by the chessboard technique. Based on the obtained MIC100, the
inhibitory fractionated concentration (FICI) was calculated as: FICI
= (Concentration of A in MICA+B/Concentration of A in MICA) +
(Concentration of B in MICA+B/Concentration of B). The FICI is
used to interpret the results of the test in the following manner: FICI
≤ 0.5, synergy; FICI 0.5-4.0, no interaction; FICI > 4.0, antagonism
[16].
Statistical analysis: Data obtained were subjected to one way
ANOVA. Differences among means were calculated by the test of
the minimum significant difference (LSD test).
Acknowledgments – This research was supported with grants PIP
850 (CONICET, Argentina) and PICT 0283/12 (ANPCyT,
Argentina)

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 Natural Product Communications Vol. 9 (7) 2014
Published online (www.naturalproduct.us)

A New Cytosporone Derivative from the Endophytic Fungus Cytospora sp.

Tomoya Takano, Takuya Koseki, Hiromasa Koyama, and Yoshihito Shiono 973
Synthesis and Biological Evaluation of Oseltamivir Analogues from Shikimic Acid
Van Hung Nguyen, Van Cuong Pham, Thi Thao Do, Huong Doan Thi Mai, Nguyen Thanh Le, Van Nam Vu, Van Hieu Tran,
Thi Minh Hang Nguyen, Wim Dehaen and Van Minh Chau 977
Quantification and Comparison of Extraction Methods for Alkaloids in Aegle marmelos Leaves by HPLC
Aniket Karmase, Prasanna K, Sruti Rasabattula and Kamlesh K Bhutani 981
Stability of Capsaicinoid Content at Raised Temperatures
Wenhui Si, Sun Wa Man, Zhen-Yu Chen and Hau Yin Chung 985
PPZPMs - a Novel Group of Cyclic Lipodepsipeptides Produced by the Phytophthora alni Associated Strain
Pseudomonas sp. JX090307 - the Missing Link between the Viscosin and Amphisin Group
Hardy Weißhoff, Sarah Hentschel, Irmtraut Zaspel, René Jarling, Eberhard Krause and Thi Lam Huong Pham 989
Chemical Composition of Vernonia albicans Essential Oil from India
Rajesh K. Joshi 997
Identification of Volatiles in Leaves of Alpinia zerumbet ‘Variegata’ Using Headspace Solid-Phase
Microextraction-Gas Chromatography-Mass Spectrometry
Jian Yan Chen, Zheng Mei Ye, Tian Yi Huang, Xiao Dan Chen, Yong Yu Li and Shao Hua Wu 999
Chemical Composition and Biological Activities of the Essential Oil from Anredera cordifolia Grown in Brazil
Lucéia Fátima Souza, Ingrid Bergman Inchausti de Barros, Emilia Mancini, Laura De Martino, Elia Scandolera and Vincenzo De Feo 1003
Profile of Volatile Components of Hydrodistilled and Extracted Leaves of Jacaranda acutifolia and their Antimicrobial Activity
Against Foodborne Pathogens
Abdel Nasser B. Singab, Nada M. Mostafa, Omayma A. Eldahshan, Mohamed L. Ashour and Michael Wink 1007
Chemical Composition, Antioxidant, Antimicrobial and Anti-inflammatory Activities of the Stem and Leaf Essential Oils
from Piper flaviflorum from Xishuangbanna, SW China
Ren Li, Jing-jing Yang, Yuan-fei Wang, Qian Sun and Hua-bin Hu 1011
Essential Oil Composition and Antifungal Activity of Aerial Parts of Ballota nigra ssp foetida Collected at Flowering and
Fruiting Times
Daniele Fraternale and Donata Ricci 1015
Essential Oils from Schinus Species of Northwest Argentina: Composition and Antifungal Activity
Diego A. Sampietro, María Melina E. Belizan, Zareath P. Terán Baptista, Marta A. Vattuone and Cesar A. N. Catalán 1019
Anxiolytic-like Effect of Inhalation of Essential Oil from Lavandula officinalis: Investigation of Changes in 5-HT
Turnover and Involvement of Olfactory Stimulation
Mizuho Takahashi, Ayako Yamanaka, Chihiro Asanuma, Hiroko Asano, Tadaaki Satou and Kazuo Koike 1023

Accounts/Reviews

Biological Properties of 6-Gingerol: A Brief Review 1027

Shaopeng Wang, Caihua Zhang, Guang Yang and Yanzong Yang
Antioxidant Activity of Natural Products Isolated from Red Seaweeds
Caio Cesar Richter Nogueira, Izabel Christina Nunes de Palmer Paixão and Valéria Laneuville Teixeira 1031
Bioactive Secondary Metabolites from Acid Mine Waste Extremophiles
Andrea A. Stierle and Donald B. Stierle 1037
Advances in Herbal Medicine for Treatment of Ischemic Brain Injury
Nilanjan Ghosh, Rituparna Ghosh, Zulfiqar A Bhat, Vivekananda Mandal, Sitesh C. Bachar, Namsa D. Nima,
Otimenyin O. Sunday and Subhash C. Mandal 1045

Additions/Corrections 1056
 Natural Product Communications
2014
Volume 9, Number 7
Contents
Original Paper Page

Three New Monoterpene Glucosides from Senecio solidagineus

Dingxiang Li, Guixin Chou and Zhengtao Wang 889
Two Novel Iridoids from Morinda longifolia
Ninh Khac Ban, Vu Huong Giang, Tran My Linh, Le Quynh Lien, Ninh Thi Ngoc, Le Duc Dat, Nguyen Phuong Thao,
Nguyen Xuan Nhiem, Nguyen Xuan Cuong, Van Cuong Pham, Nguyen Hoai Nam, Jacinto Regalado, Huynh Van Keo,
Phan Van Kiem and Chau Van Minh 891
Antifeedant and Phagostimulant Activity of Extracts and Pure Compounds from Hymenoxys robusta on Spodoptera exigua
(Lepidoptera: Noctuidae) Larvae
Zaida N. Juárez, Antonio M. Fortuna, Eugenio Sánchez-Arreola, Jesús F. López-Olguín, Horacio Bach and Luis R. Hernández 895
Chemical Evidence for the Liverwort Complex, Chiloscyphus concavus and C. horizontalis
Jorge Cuvertino-Santoni, Yoshinori Asakawa, Denilson F. Peralta and Gloria Montenegro 899
Chemical Constituents of Marrubium vulgare as Potential Inhibitors of Nitric Oxide and Respiratory Burst
Farzana Shaheen, Shagufta Rasool, Zafar Ali Shah, Samreen Soomro, Almas Jabeen, M. Ahmed Mesaik and M. Iqbal Choudhary 903
Abietane Diterpenoids from Clerodendrum trichotomum and Correction of NMR Data of Villosin C and B
Linzhen Li, Long Wu, Menghua Wang, Jianbo Sun and Jingyu Liang 907
Theoretical Research into Anticancer Activity of Diterpenes Isolated from the Paraiban Flora
Luciana Scotti, Hamilton Ishiki, Francisco J.B. Mendonça Junior, Paula F.Santos, Josean F. Tavares, Marcelo S. Silva and
Marcus T. Scotti 911
Seed Dormancy Breaking Diterpenoids from the Liverwort Plagiochila sciophila and their Differentiation Inducing Activity
in Human Promyelocytic Leukemia HL-60 Cells
Hiromichi Kenmoku, Hiroyuki Tada, Megumi Oogushi, Tomoyuki Esumi, Hironobu Takahashi, Masaaki Noji, Takeshi Sassa,
Masao Toyota and Yoshinori Asakawa 915
Application of Microalgal Fucoxanthin for the Reduction of Colon Cancer Risk: Inhibitory Activity of Fucoxanthin
Against β-Glucuronidase and DLD-1 Cancer Cells
Arthitaya Kawee-ai and Sang Moo Kim 921
Synthetic and Structure-Activity Relationship of Insecticidal Bufadienolides
Ace Tatang Hidayat, Achmad Zainuddin, Danar Dono, Wawan Hermawan, Hideo Hayashi and Unang Supratman 925
Cytotoxic Alkaloids from Leaves and Twigs of Dasymaschalon sootepense
Sakchai Hongthong, Chutima Kuhakarn, Vichai Reutrakul, Surawat Jariyawat, Pawinee Piyachaturawat, Narong Nuntasaen and
Thaworn Jaipetch 929
The Effect of Zuccagnia punctata, an Argentine Medicinal Plant, on Virulence Factors from Candida Species
Nuño Gabriela, Alberto María Rosa, Zampini Iris Catiana, Cuello Soledad, Ordoñez Roxana Mabel, Sayago Jorge Esteban,
Baroni Veronica, Wunderlin Daniel and Isla María Ines 933
Rare Prenylated Isoflavones from Tephrosia calophylla
Seru Ganapaty, Vimal Nair, Devarakonda Rama Devi, Steve Thomas Pannakal, Hartmut Laatsch and Birger Dittrich 937
Antioxidant Properties of Phenolic Compounds from Baccharis articulata and B. usterii
Simone Quintana de Oliveira, Virgínia Demarchi Kappel, Viviane Silva Pires, Claiton Leoneti Lencina, Pascal Sonnet,
José Cláudio F. Moreira and Grace Gosmann 941
Effect of Silitidil, a Standardized Extract of Milk Thistle, on the Serum Prolactin Levels in Female Rats
Raffaele Capasso 943
Standardization of Solvent Extracts from Onopordum acanthium Fruits by GC-MS, HPLC-UV/DAD, HPLC-TQMS and
1
H-NMR and Evaluation of their Inhibitory Effects on the Expression of IL-8 and E-selectin in Immortalized
Endothelial Cells (HUVECtert)
Armond Daci, Markus Gold-Binder, Davide Garzon, Alessio Patea and Giangiacomo Beretta 945
A New Antimicrobial Anthrone from the Leaf Latex of Aloe trichosantha
Anwar Oumer, Daniel Bisrat, Avijit Mazumder and Kaleab Asres 949
Preparative Production of Spinochrome E, a Pigment of Different Sea Urchin Species
Olga P. Shestak, Victor Ph. Anufriev and Vyacheslav L. Novikov 953
Phenylpropanoids and Furanocoumarins as Antibacterial and Antimalarial Constituents of the Bhutanese Medicinal
Plant Pleurospermum amabile
Phurpa Wangchuk, Stephen G. Pyne, Paul A. Keller, Malai Taweechotipatr and Sumalee Kamchonwongpaisan 957
Spirocyclic Acylphloroglucinol Derivatives from Hypericum pyramidatum
Rebecca Force, Shui Ling Chen, Emily Fortier, Emily Rowlands, Jean Heneks, David Rovnyak and Geneive E. Henry 961
Anti-inflammatory Activity of Constituents Isolated from Terminalia chebula
Min Hye Yang, Zulfiqar Ali, Ikhlas A. Khan and Shabana I. Khan 965
Highly Potent Oligostilbene sbLOX-1 Inhibitor from Gnetum macrostachyum
Serm Surapinit, Piyawit Sri-in and Santi Tip-pyang 969

(Continued inside back cover)