Professional Documents
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DOI 10.1007/s11101-013-9295-3
Introduction
A great variety of chemical compounds with antimicrobial activity, traditionally known as secondary
metabolites, are produced by higher plants. Thousands
of diverse natural products, often involved in plant
defense against pest and pathogens, have been identified including terpenoids, saponins, phenolics and
phenylpropanoids, pterocarpans, stilbens, alkaloids,
glucosinolates, tiosulfinates and indoles among many
others (Dixon 2001). The phytochemical diversity of
plant antimicrobial compounds has been previously
reviewed by examining their involvement in constitutive (Wittstock and Gershenzon 2002) and inducible
chemical defenses (Hammerschmidt 1999), mechanisms of plant resistance (Morrisey and Osbourn
123
Phytochem Rev
Fig. 1 Schematic
representation of major
chemical classes of natural
compounds from Allium
species with antimicrobial
activity. These natural
compounds have been
isolated from the different
plant tissues (roots, bulbs,
leaves and flowers) and
seeds
123
Thiosulfinates
(allicin)
Flavonoids (quercetin)
Phytochem Rev
NH2
HS
NH
L-Glu
CO2H
HS
L-Cys
Glu
CO2H
S
CO2H
NH
Glu
NH
Ox
CO2H
Glu
CO2H
L-Glu L-Cys
O
NH
- CO2
Glu
CO2H
double bond
Isomerization
O
NH2
S
Alliin ( 1a)
O
Alliinase
CO2H
Sulfenic acid
Intermediate
H2O
condensation
Allicin (1b)
123
Phytochem Rev
Fig. 3 Sulfoxide and
sulfide compounds from
Allium
123
Phytochem Rev
Table 1 List of organic sulfur compounds from the genus Allium with related antibacterial, antifungal, antiparasitic and antiviral
activities
Species name
Antimicrobial compounds
Activity
References
A. sativum
Allicin (1b)
Antifungal
A. ursinum
Aspergillus flavus
Aspergillus fumigatus
Aspergillus niger
Aspergillus terreus
Candida albicans
Candida krusei
Candida neoformans
Candida tropicalis
Cryptococcus sp.
Epidermophyton foccosum
Microsporum gypseum
S. cerevisiae
Torulopsis glabrata
Trichophyton ferrugineum
Trichophyton mentagrophytes
Trichophyton rubrum
Antibacterial
Acinetobacter baumanii
Bacillus dysenteriae
Bacillus enteriditis
Bacillus morgani
Bacillus paratyphosus
Bacillus subtilis
Bacillus typhosus
Enterococcus durans
Enterococcus faecalis
Enterococcus faecium
E. coli
H. pylori
Klebsiella pneumonia
Mycobacterium tubercolosis
Proteus mirabilis
P. aeruginosa
S. typhimurium
Shigella flexneri
Shigella dysenteriae
S. aureus
Streptococcus hemolyticus
Streptococcus pyogenes
Streptococcus viridans
V. cholera
123
Phytochem Rev
Table 1 continued
Species name
Antimicrobial compounds
Activity
References
Antiparasitic
Crithidia fasciculate
Entamoebe histolytica
Giardia lamblia
Leishmania major
Leptomonas colosoma
Spironucleus vortens
Antiviral
Antifungal
Alternaria solani
Alternaria tenuissima
Alternaria triticina
A. niger
C. albicans
Candida valida
Colletotrichum sp.
Curvularia sp.
Fusarium lini
F. oxysporum
Fusarium semitectum
Fusarium udum
Hanseniaspora valbyensis
Kluyveromyces lactis
Paracoccidioides brasiliensis
Pichia anomala
S. cerevisiae
Schizosaccharomyces pombe
Tinea corporis
Tinea cruris
Tinea pedis
Antibacterial
B. cereus
B. subtilis
E. coli
K. pneumoniae
Lactobacillus plantarum
M. luteus
Mycobacterium phlei
123
Phytochem Rev
Table 1 continued
Species name
Antimicrobial compounds
Activity
References
P. aeruginosa
S. aureus
Streptomyces griseus
Xanthomonas maltophilia
Antiparasitic
Plasmodium berghei
S. vortens
Trypanosoma cruzi
Antiviral
Antifungal
A. flavus
A. fumigatus
A. niger
C. albicans
Candida glabrata
C. krusei
Antibacterial
Camplobacter jejuni
K. pneumoniae
L. monocytogenes
S. typhimurium
S. aureus
A. sativum
Antifungal
Allium odorum
A. flavus
A. cepa
A. fumigatus
A. niger
C. albicans
C. glabrata
C. krusei
Candida utilis
Antibacterial
B. cereus
Camplobacter jejuni
H. pylori
K. pneumoniae
L. monocytogenes
S. typhimurium
S. aureus
123
Phytochem Rev
Table 1 continued
Species name
Antimicrobial compounds
Activity
References
A. sativum
Antifungal
Allium odorum
A. flavus
A. cepa
A. fumigatus
A. niger
C. albicans
C. glabrata
C. krusei
C. utilis
Penicillium expansum
Antibacterial
Cryptococcus neoformans
H. pylori
S. aureus
Antiparasitic
E. histolytica
G. lamblia
Trichomonas vaginalis
Trypanosoma brucei
Trypanosoma congolese
Trypanosoma equiperdum
Trypanosoma evansi
A. sativum
Antifungal
Allium odorum
A. flavus
A. cepa
A. fumigatus
A. niger
C. albicans
C. glabrata
C. krusei
C. utilis
Antibacterial
H. pylori
S. aureus
A. sativum
A. cepa
123
Antifungal
C. utilis
Antibacterial
S. aureus
Phytochem Rev
Table 1 continued
Species name
Antimicrobial compounds
Activity
References
A. sativum
Antifungal
C. valida
H. valbyensis
K. lactis
P. anomala
S. cerevisiae
S. pombe
Antibacterial
B. cereus
B. subtilis
E. coli
K. pneumoniae
M. luteus
M. phlei
P. aeruginosa
S. aureus
X. maltophilia
A. sativum
Antiviral
Antiviral
Antifungal
S. cerevisiae
S. pombe
Antibacterial
B. cereus
B. subtilis
E. coli
K. pneumoniae
M. luteus
P. aeruginosa
S. aureus
X. maltophilia
123
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123
Phytochem Rev
Table 2 List of saponins from the genus Allium and related biological activities
Species name
Compounds
Activity
References
Allium
ampeloprasum
Antifungal
A. cepa
Mortierella ramanniana
Cytotoxic
Antifungal
Alternaria alternata
A. niger
B. cinerea
F. oxysporum
Mucor sp.
Phomopsis sp.
R. solani
Sclerotium cepivorum
Trichoderma atroviride
T. harzianum
A. leucanthum
Antifungal
A. minutiflorum
Antifungal
A. alternata
Alternaria porri
B. cinerea
F. oxysporum
F. oxysporum f.sp. lycopersici
Fusarium solani
P. ultimum
R. solani
T. harzianum
A. porrum
Antifungal
F. culmorum
A. sativum
Antifungal
B. cinerea
T. harzianum
A. sativum
Antifungal
C. albicans
A. ursinum
Antifungal
C. glabrata
Candida parapsilosis
Microsporum canis
Trichophyton mentagrophytes
Cytotoxic
Allium vineale
Antifungal
P. expansum
Molluscicidal
Biomphalaria pfeifferei
Allium fistulosum
Antihypoxic
Allium
macrostemon
Antiplatelet
Ou et al. (2012)
A. sativum
Antiplatelet
A. cepa
Antispasmodic
123
Phytochem Rev
Table 2 continued
Species name
Compounds
Activity
References
Barile et al. (2005)
Allium hirtifolium
Antispasmodic
A. chinense
Antitumor; Cytotoxic
Allium macleanii
Antitumor
A. porrum
Four sapogenins
Antitumor
Allium senescens
Antitumor
A. chinense
ATPase inhibition
Allium giganteum
A. macrostemon
Allium aflatunense
Cytotoxic
Allium
karataviense
Cytotoxic
A. leucanthum
Cytotoxic
A. nigrum
Cytotoxic
A. porrum
Cytotoxic
A. tuberosum
Cytotoxic
A. macrostemon
Cytotoxic, antitumour
A. macrostemon
Cytotoxic; antitumour
A. ampeloprasum
Haemolytic, anti-inflammatory,
gastroprotective
A. aflatunense
Not assessed
Allium albanum
Five saponins
Not assessed
Allium albiflorus
One saponin
Not assessed
Allium
albopilosum
Not assessed
A. ascalonicum
Not assessed
Allium
atroviolaceum
Not assessed
A. cepa var.
tropeana
Not assessed
A. chinense
Not assessed
Allium cyrillii
Not assessed
Allium elburzense
Not assessed
Allium erubescens
Not assessed
A. fistulosum
Not assessed
Do et al. (1992)
A. fistulosum
Seven sapogenins
Not assessed
A. giganteum
Not assessed
A. giganteum
One sapogenin
Not assessed
Allium jesdianum
Not assessed
A. karataviense
Not assessed
A. karataviense
Not assessed
Allium
narcissiflorum
Not assessed
Allium nutans
Not assessed
Allium
ostrowskianum
Not assessed
Allium rotundum
Not assessed
Allium rubellum
Four saponins
Not assessed
Allium schubertii
Not assessed
123
Phytochem Rev
Table 2 continued
Species name
Compounds
Activity
References
Allium
sphaerosephalon
Not assessed
Allium triquetrum
Not assessed
A. tuberosum
Not assessed
A. tuberosum
Not assessed
A. tuberosum
Not assessed
A. tuberosum
Not assessed
Allium
turcomanicum
Not assessed
Allium waldsteinii
Not assessed
Note that only in few cases (9 out of 62) antifungal activity was assessed
Fig. 5 Aglycon
biosynthesis in Allium
saponins
123
Phytochem Rev
123
Phytochem Rev
more recently, to saponins, other antimicrobial compounds that belong to different chemical classes have
been discovered (Fig. 1; Table 3).
Several proteins and peptides with antimicrobial
activity have been found. For instance, the 10 kD
AceAMP1 protein from A. cepa inhibited twelve
fungal and two bacterial species (Phillippe et al. 1995).
Wang and Ng (2002, 2004) discovered ascalin and
allicepin, two peptides with antifungal activity from A.
ascalonicum and A. cepa, respectively. In addition, it
has been found in garlic and leek roots and bulbs the
presence of high amounts of two N-feruloyl amides,
N-feruloytyrosine (32) and N-feruloyltyramine (33)
(Fig. 9) (Fattorusso et al. 1999). Because the infusion
of garlic roots is used in traditional medicine as
antielminthic, the possible antimicrobial activity of
these two compounds was evaluated. Both compounds
were active against the pathogen Fusarium culmorum
with ED50 of 20 and 22 lg/ml, respectively. Recently,
ODonnell et al. (2009) discovered from A. stipitatum
Fig. 8 Key pharmacophoric elements for the antifungal activity of Allium saponins
123
Phytochem Rev
Table 3 List of other organic compounds with antimicrobial activity extracted from the genus Allium
Species name
Compounds
Activity
References
A. ascalonicum
Ascalin (peptide)
Antifungal
B. cinerea
A. cepa
Allicepin (peptide)
Antifungal
B. cinerea
F. oxysporum
Mycosphaerella arachidicola
Physalospora piricola
A. cepa
Antibacterial
B. cereus
E. coli
L. monocytogenes
M. luteus
P. aeruginosa
S. aureus
A. cepa
Antibacterial
M. luteus
S. aureus
A. cepa
Antifungal
Alternaria brassicola
Ascochyta pisi
B. cinerea
Colletotrichum
lindemuthianum
F. culmorum
F. oxysporum f.sp. pisi
F. oxysporum f.sp. lycopersici
Nectria haematococca
Phoma betae
Pyrenophora tritici-repentis
Pyricularia oryzae
Verticillium dahliae
Antibacterial
Bacillus megaterium
Sarcina lutea
Allium
fistolosum
Fistulosin (octadecyl
3-hydroxyindole)
Antifungal
F. oxysporum
F. solani
Fusarium moniliforme
Verticillium dahliae
Penicillium roqueforti
Aspergillus oryzae
Magnaporthe grisea
Rhizopus oryzae
123
Phytochem Rev
Table 3 continued
Species name
Compounds
Activity
References
A. porrum
Antifungal
Cercospora musae
C. lindemuthianum
Trichoderma viride
Trochoderma hamatum
A. sativum
Antifungal
B. cinerea
M. arachidicola
Physalospora piricola
A. sativum
N-amides (3233)
A. porrum
Allium
stipitatum
Antifungal
F. culmorum
Pyridine-N-oxide alkaloids (3436)
Antibacterial
S. aureus
M. phlei
M. smegmatis
Mycobacterium fortuitum
A. tuberosum
Antifungal
B. cinerea
Coprinus comatus
F. oxysporum
M. arachidicola
R. solani
Conclusions
From the ancient Egyptian period to the discovery of
antibiotics, garlic has been used as an antimicrobial
remedy in folk medicine. Scientific investigations
have demonstrated that besides the well-studied
sulphur compounds there are other classes of compounds, e.g. saponins, flavonoids, nitrogen compounds and peptides, that make garlic and Allium
species effective against pathogenic microbes. Despite
the great number of antimicrobial compounds isolated,
Allium species may still be an important source of such
molecules. Isolation and identification of other antimicrobial compounds should be pursued to meet the
urgent need for new classes of drugs. However, the
development of more effective antimicrobial agents
or a group of agents can also be achieved through
123
Phytochem Rev
Fig. 9 Aromatic N-amides
and N-oxides from Allium
Fig. 10 Flavonoids in
onion and garlic and their
contents
Compound
Substituents
structural modifications of the already known compounds. Existing structureactivity data suggest that it
might be possible, for example, to prepare potent
antibacterial saponins by obtaining compounds with a
spirostanol skeleton and oxygenation at C-3 and C-6.
Further studies are also required to completely understand the mechanism of action of the known compounds. This is an important step to be able to use
these antimicrobial compounds to the maximum of
their potential. For instance, it has been shown that
these compounds may synergistically increase their
activity when they work together. Future studies can
address this issue by testing combinations of antimicrobial compounds (e.g. organosulfur compounds and
saponins) that co-occur in plant tissues. In addition,
characterization of the interaction between the antimicrobial compounds and their target sites could
reduce resistance mechanisms thus allowing the
123
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