4
Antifungal Properties of
Bioactive Compounds from Plants
F. Castillo1, D. Hernández1, G. Gallegos1, R. Rodríguez2 and C. N. Aguilar2
1Universidad
Autónoma Agraria Antonio Narro
Autónoma de Coahuila
México
2Universidad
1. Introduction
Currently, the consequences derived from application of fungicides in traditional
agricultural production systems for control of crop diseases have impacted negatively this
activity. Fungicides application, where the indiscriminate use and application frequency
high has led to problems and constraints in the control of these diseases by loss in efficiency,
increased resistance to active ingredients, ecological damage and a serious negative impact
on the human health. For this reason, it is had carryed out research to develop new
products, methods and strategies for diseases control. The investigation and development of
bio-based products is of great interest to subtract the negative effects generated by
traditional agricultural production systems. The use and application of bioactive
phytochemicals with antifungal properties represent an attractive and efficient alternative to
inhibit the growth of several fungal pathogens.
These bioactive compounds are naturally produced in the plants how secondary
metabolites, the principal groups with antifungal activity were terpenes, tannins, flavonoids,
essential oil, alkaloids, lecithin and polypeptides. These groups of compounds are important
for the physiology of plants contributing properties confer resistance against
microorganisms, other organisms and help preserve the integrity of the plant with
continuous exposure to environmental stressors, such as ultraviolet radiation, high
temperatures or dehydration.
2. Bioactive antifungal activity groups
2.1 General
Plants have developed natural defense mechanisms to protect themselves long before the
man played an active role in protecting them. It is known that plants synthesize a variety of
groups of bioactive compounds in plant tissues as secondary metabolites that have
antifungal activity to stop or inhibit the development of mycelia growth, inhibition of
germination or reduce sporulation of fungal pathogens, each these groups presented
variable mechanisms of action, for example, the toxicity of polyphenols in microorganisms
is attributed to enzyme inhibition by oxidation of compounds. For essential oils is
82
Fungicides for Plant and Animal Diseases
postulated that cause disruption of the membrane by the action of lipophilic compounds,
the use or employment as formulations of these compounds is in the form of extracts. The
process of extraction of secondary metabolites from plant extracts is variable, can be
obtained as aqueous extracts or powders using different solvents used for many different
compounds, depending on their polarity. It is considered that these compounds obtained
from plants are biodegradable and safe for use as an alternative for disease control in a
traditional production system (Sepulveda et al., 2003; Hernandez et al., 2007; Wilson et al.,
1997; Bautista et al., 2002; Abou-Jawdah et al., 2002; Cowan, 1999).
These substances known as secondary metabolites, secondary products, or natural products,
have no generally recognized, direct roles in the processes of photosynthesis, respiration,
solute transport, translocation, protein synthesis, nutrient assimilation, differentiation or
metabolism processes as the formation of carbohydrates, proteins and lipids. That is,
particular secondary metabolites are often found in only one plant species or related group
of species, whereas primary metabolites are found throughout the plant kingdom. In
function to classify to chemically groups the secondary metabolites can be divided into three
groups: terpenes, phenolics and nitrogen- containing compounds. This classification is due
by the interrelationship with primary metabolism Figure 1.
Fig. 1. A simplified view of the major pathways of secondary metabolites biosynthesis and
their interrelationship with primary metabolism (Taiz & Zeiger, 2002)
2.2 Polyphenols
Plant phenolics are a chemically heterogeneous group of nearly 10,000 individual
compounds: Some are soluble only in organic solvents, some are water-soluble carboxylic
acids and glycosides and others are large, insoluble polymers. Present a structure of various
Antifungal Properties of Bioactive Compounds from Plants
83
groups replaced by hydroxyl functions benzene and its derivatives are simple phenolic
compounds called phenylpropanoids (Figure 2). Allowing them to be highly soluble organic
substances in water and are present in extracts of leaves, bark, wood, fruits and galls of
certain ferns, gymnosperms and angiosperms (Swain, 1979). These polyphenols are
important for the physiology of plants to contribute to resistance to microorganisms, insects
and herbivorous animals that can affect (Haslam, 1996), help to preserve the integrity of the
plant with continuous exposure to environmental stressors, including radiation ultraviolet,
relatively high temperatures and dehydration (Lira et al., 2007). These polyphenol
antioxidants are therefore active in biological systems and probably the capacity or
biological value explains its abundance in plant tissues (Meckes et al., 2004).
Fig. 2. Outline of the biosynthesis of phenols from phenylalanine. The formation of many
plant phenolics, including simple phenylpropanoids, coumarins, benzoic acid derivatives,
lignans, anthocyanins, isoflavones, condensed tannins and other flavonoides, begins with
phenylalanine (Taiz & Zeiger, 2002)
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Fungicides for Plant and Animal Diseases
2.2.1 Hydrolysable tannins (HT)
Are organic compounds, amorphous, taste astringent, weakly acidic, most soluble in
water, only a few in organic solvents are yellow, red, or brown and are located in the
cytoplasm and cell vacuole of plant tissues. Esters of glucose are partially or fully attached
to different polyols such as ellagic acid, say, m-digallic, hexahydroxydiphenic acid or its
derivatives (Figure 3). Obtained by hydrolysis with acids, bases and hydrolytic enzymes
to break the glycosidic bond to liberate the sugar and phenolic compounds in it.
(Gonzalez et al., 2009).
Fig. 3. Hydrolysable tannins and some of its derivatives: A) gallotannins, B) ellagitannins. C)
ellagic acid, D) hydroxyphenolic acid, E) gallic acid
The hydrolysable tannins are divided into the following subgroups: The gallotannins, which
by enzymatic hydrolysis give more sugar and gallic acid of phenolic compounds that
comprise it (Figure 4) and ellagitannins, which give ellagic acid enzymatic hydrolysis more
sugar or a derivative as hexahydrophenic acid (Figure 4).
Fig. 4. Chemical structure of a gallotannins
85
Antifungal Properties of Bioactive Compounds from Plants
2.2.2 Condensed tannins (CT)
Also called proanthocyanidins (PAS), are derived from the oxidation reaction that produces
anthocyanidins (ACS) red in acid-alcohol solution (Figure 5). Are polymers of flavan 3-ol
(catechin) and 3-4 flavan diol (leucoanthocyanidins) and have no sugar residues and their
carbohydrate content is low or negligible. Are polymers of high molecular weight (1000 to
3000 Daltons), which gives them a relative immobility. Its complexity and easy to form
bonds with proteins make them difficult to study. Condensed tannins include flavonoids,
which in turn are subdivided into anthocyanidins and leucoanthocyanidins and catechin
(Makkar et al., 2007; Taiz & Zeiger, 2002).
Fig. 5. Condensed tannins or proanthocyanidins
The substituents in the groups R1, R2 and R3, can have an effect on the reactivity of tannin
(Figure 6). The group R2 is an OH radical can sometimes be esterified gallic acid (known as
Gallo-catechin). For example an increase in the ratio prodelphynidins/procyanidins
enhance the ability of condensed tannins to complex proteins.
R1
OH
OH
H
H
R3
H
OH
H
OH
Class
Proanthocyanidin
Prodelphynidin
Profisetinidin
Prorobinetinidin
Fig. 6. Structure of some condensed tannins
Hydroxyl groups allow the formation of complexes with proteins, metal ions and other
molecules such as polysaccharides. In general, polyphenols identified and grouped
according to their basic result is a chain of six carbons (Table 1).
86
Fungicides for Plant and Animal Diseases
Atoms number
Basic carbon skeleton
6
C6
7
C6 - C1
Phenolic acids
8
C6 - C2
Acetofenons and fenilacetonics acids
9
C6 - C3
hidroxicinamics Acids, fenilpropanoids
10
C6 - C4
Naftoquinones
13
C6 - C1- C6
Xantones
14
C6 - C2- C6
Estilbens and anthraquinones
15
C6 - C3- C6
Flavonoids and isoflavonoids
18
(C6 - C3)2
Lignans and neolingnans
30
N
Compounds
Simple Phenols and Benzoquinones
Biflavonoids
(C6 - C3)n
Lignins, Catecol Melanins and flavolans
(C6)6 (C6-C3 - C6)n
Table 1. Classification of phenolics compounds in carbons atoms to base number (Garcia,
2004)
2.3 Terpenes
The terpenoids, constitute the largest class of secondary products, the diverse substances of
this class are generally insoluble in water. The terpenes are biosynthesized from primary
metabolites by at least two different routes, a route mevalonic acid, where three molecules
of acetyl CoA is condensed step by step to form mevalonic acid. This six-carbon molecule is
pirofosforilada and dehydrated to form isopentyl diphosphate and this is the basic unit of
the terpenes active, the other route is called route metileritritol phosphate that functions in
chloroplasts and other plastids. All terpenes are derived from the union of five-carbon
elements that have the branched carbon skeleton of isopentane:
The basic structural elements of terpenes are sometimes called isoprene units because
terpenes can decompose at high temperatures to give isoprene:
The terpenes or isoprenoids are classified by the number of five-carbon units they contain,
example: Ten-carbon terpenes, which contain two C5 units, are called monoterpenes; 15carbon terpenes (three C5 units) are sesquiterpenes; and 20-carbon terpenes (four C5 units)
are diterpenes. Larger terpenes include triterpenes (30 carbons), tetraterpenes (40 carbons) and
polyterpenoids ([C5] n carbons, where n > 8) (Taiz and Zeiger, 2002).
87
Antifungal Properties of Bioactive Compounds from Plants
2.4 Nitrogenous compounds
A large variety of plant secondary metabolites have nitrogen in their structure. Included in
this category are such well-known anti-defenses as alkaloids, amines, cyanogenic
glycosides, non-protein amino acids, glucosinolates, alkamides and peptides (Wink &
Schimmer, 2010). Most nitrogenous secondary metabolites are biosynthesized from
common amino acids.
2.5 Plants with antifungal properties
It´s has studied the secondary metabolites present in various plant species, one to identify
its presence, chemical structure and effect on the plant and on other organisms, so that the
number of Identified Substances exceed to 100 000 at present (Wink and Schimmer, 2010) in
table 2 shows a relationship of phenolic compounds in other organisms different to the
plants with presence of these compounds.
Phylum
Bacteria
Fungi
Algae
Lichens
Bryophytes
Ferns, conifers and
flowering plants
Structural patrons
Phenols from polyketides and quinones (occasionally
present)
Simple phenols, phenylpropanoids, quinones (usually
present)
Oidados and brominated phenols, phloroglucinol
derivatives from cell wall
Anthraquinones, xanthones and depsidones
Phenols in the cell wall, phenylpropanoids, stilbenes and
some flavonoids
Lignin in the cell wall and wide range of phenols of all
kinds
Table 2. Distribution of polyphenols compounds on different phylum’s in comparative to
Plant phylum (Garcia, 2004, as cited in Harborne, 1990)
The number of plant species containing one or more of the major groups of compounds with
anti-fungal activity is very diverse (Glasby, 1991), in Table 3 lists some of the studied plant
with antifungal effect.
Specie
Simmondsia chinensis
Thymus zygis subsp.
sylvestris,
A. gypsicola and A.
biebersteinii
Larrea tridentata
Compounds Identifying
Glucosides
Reference
Abbassy et al., 2007
Carvacrol
Gonçalves et al., 2010
Camphor , 1,8-cineole, piperitone ,
borneol and -terpineol, n-eicosane ,
n-heneicosane , n-tricosane, linoleic
acid
lignans, methyl-nordihydroguaiaretic
acid and nordihydroguaiaretic acid
Kordali et al., 2009
Vargas-Arispuro et al.,
2005
88
Fungicides for Plant and Animal Diseases
Specie
Compounds Identifying
Chenopodium quinoa
triterpenoid saponins
Aloe vera
Crude extracts
Drimys winteri
Pimenta dioica
essential oil
Essential oils
Catharanthus roseus
5-hydroxy flavones
Reference
Stuardo & Sn Martin,
2008
Jasso de Rodríguez et
al., 2005
Monsálvez et al., 2010,
Zabka et al., 2009.
Roy & Chatterjee,
2010
Larrea tridentata,
Flourensia cernua, Agave
lechuguilla, Opuntia sp.
and Yucca sp.
Flourensia microphylla,
Flourensia cernua
and Flourensia
retinophylla
Salvia officinalis
Carya illinoensis shells
and Punica granatum
Bulnesia sarmientoi
Condensed and hidrolizables
Tannins
Castillo et al., 2010,
Crude extracts
Jasso de Rodríguez et
al., 2007
essential oil
Pinto et al., 2007
polyphenolic extracts
Osorio et al., 2010
bulnesol, hanamyol
Caesalpinia cacalaco
gallic and tannic acids
Clausena anisata
essential oils
2-undecanone, 2-decanone and 2dodecanone
Rodilla et al., 2011
Veloz-García et al.,
2010
Osei-Safo et al., 2010
Ruta chalepensis
Bucida buceras,
Breonadia salicina,
Harpephyllum caffrum,
Olinia ventosa,
Vangueria infausta
and
Xylotheca kraussiana
Agapanthus africanus
Reynoutria sachalinensis
Laurus nobilis
Asarum heterotropoides
var. mandshuricum
Rumex crispus
Mejri et al., 2010
crude plant
Mahlo et al., 2010
Crude extracts
Tegegne et al., 2008
Pasini et al., 1997
1.8-cineole, linalool, terpineol acetate,
methyl eugenol, linalyl acetate,
eugenol, sabinene, -pinene, terpineol.
methyleugenol, eucarvone, 5-allyl1,2,3-trimethoxybenzene and 3,7,7trimethylbicyclo(4.1.0)hept-3-ene
chrysophanol, parietin and nepodin
Corato et al., 2010
Dan et al., 2010
Choi et al., 2004;
Gyung et al., 2004
89
Antifungal Properties of Bioactive Compounds from Plants
Specie
Astronium fraxinifolium,
Inga marginata, Malva
sylvestris, Matayba
elaeagnoides, Miconia
argyrophylla, Myrcia
fallax, Ocimum
gratissimum, Origanum
vulgare, Rollinia
emarginata, Siparuna
arianeae, Styrax pohlii,
Tabebuia serratifolia and
Trichilia pallid
Piper longum
Datura metel
Calotropis procera,
Nerium oleander,
Eugenia jambolana,
Citrullus colocynthis,
Ambrosia maritima,
Acacia nilotica and
Ocimum basilicum and
fruit extracts of C.
colocynthis, C. procera
and E. jambolana
Robinia pseudoacacia
Cassia sp
Reynoutria sachalinensis
Compounds Identifying
Crude extracts
Eugenol, piperine, piperlongumine
and piperettine)
Enzymes, peroxidase, ǃ-1,3-glucanase
and chitinase
Crude extracts
Crude extracts
cassia oil
Crude extracts
Aegle marmelos
Allium sativum
-pinene, allo-aromadendrene,
germacrene-D, n-octane, -selinene
and -selinene.
Menthone, n-octane, caryophyllene, -pinene, lauric acid
and -pinene
-pinene, caryophyllene oxide, thujene, bornylene, totarol, caryophyllene, -3-carene, 2- -pinene
and -humulene.
essential oil
essential oil
Bystropogon plumosus
essential oil
Citrus aurantium
Cryptomeria japonica
Cymbopogonflexuosus
Cymbopogon martini
essential oil
essential oil
essential oil
essential oil
Hypericum perfoliatum
and Hypericum
tomentosum
Metasequoia
glyptostroboides
Reference
Andrade et al., 2010
Lee et al., 2001
Devaiah et al., 2009
Abdel-Monaim et al.,
2011
Zhang et al., 2008
Feng et al., 2008
KonstantinidouDoltsinis and Schmit,
1998
Hosni et al., 2008
Bajpai et al., 2007
Pattnaik et al., 1996
Pyun and Shin 2006
Economou &
Nahrstedt, 1991
Pattnaik et al., 1996
Cheng et al., 2005
Pattnaik et al., 1996
Pattnaik et al., 1996
90
Specie
Eucalyptus citriodora
Melaleuca alternifolia
Mentha piperita
Pelargonium graveolens
Pimpinella anisum
Piper angustifolium
Salvia officinalis
Salvia sclarea
Tagetes patula
Thymbra capitata
Thymus pulegioides
Lavandula angustifolia
Dictamnus dasycarpus
Heliotropium bursiferum
Ficus septic
Glycosmis cyanocarpa
Olea europaea
Cochlospermum
tinctorium
Eupatorium riparium
Apium graveolens
Wedelia biflora
Scutellaria spp
Croton sonderianus
Fungicides for Plant and Animal Diseases
Compounds Identifying
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
essential oil
Dictamnine
9-Angeloylretronecine, Heliotrine,
Lasiocarpine, Supinine
Antofine, Ficuseptine
Illukumbin B, Methylillukumbin B,
Methylillukumbin A, NMethylsinharine, Sinharine
Hexanal, E-2-Hexanal, E-2-Heptanal,
Nonanal and E-2-Octenal
Cochloxanthin,
Dihydrocochloxanthin
Methylripariochromene A
Angelicin, Bergapten,
Columbianetin, Xanthotoxin
3´_-Formyl-2´_,4´_,6´_trihydroxydihydrochalcone
Clerodin, Jodrellin A, Jodrellin B
Hardwickic acid, 3,4Secotrachylobanoic acid
Reference
Pattnaik et al., 1996
Nenoff et al., 1996
Pattnaik et al., 1996
Pattnaik et al., (1996
Kosalec et al., (2005
Tirillini et al., 1996
Hili et al., 1997
Pitarokili et al., 2002
Romagnoli et al., 2005
Salgueiro et al., 2004
Pinto et al., 2006
D’Auria et al., 2005
Zhao et al., 1998
Marquina et al., 1989
Baumgartner et al.,
1990
Greger et al., 1992,
1993
Battinelli et al., 2006
Diallo et al., 1991
Bandara et al., 1992
Afek et al., 1995
Miles et al., 1991
Cole et al., 1991
McChesney & Clark,
1991
Gomphrena martiana
and Gomphrena
boliviana
5-Hydoxy-3-methoxy-6,7methylenedioxyflavone
Pomilio et al., (1992
H. nitens
3,5,6,7,8-Pentamethoxyflavone,
3,5,6,7-Tetramethoxyflavone, 5,6,7,8Tetramethoxyflavone,
Dimethylchrysin, Trimethylgalangin
Tomas-Barberan et al.,
1988
H. odoratissimum
3-O-Methylquercetin
Van Puyvelde et al.,
1989
Wedelia biflora
Podophyllum hexandrum
veratrylidenehydrazide,
3,3′-di-O-methylquercetin,
2,7-dihydroxy-3(3t'-methoxy-4′hydroxy)-5-methoxyisoflavone and
3′,7-di-O-methylquercetin
4′-Odemethyldehydropodophyllotoxin
and picropodophyllone
Miles et al., 1993
Rahman et al., 1995
91
Antifungal Properties of Bioactive Compounds from Plants
Specie
Piper angustifolium
Cistus incanus subsp.
creticus
Bystropogon plumosus,
B. origanifolius var.
palmensis, B. wildpretii,
B. maderensis and B.
canariensis var.
smithianus
Zingiber officinale
Coleonema pulchellum
P. argentatum × P.
tomentosa
Bidens cernua
Garcinia mangostana
Thymus pulegioides
Compounds Identifying
Camphene
Reference
Tirillini et al., 1996
Geraniol
Chinou et al., 1994
Pulegone
Economou &
Nahrstedt, 1991;
Gingerenone A
Precolpuchol
8-oxo-Argentone, 8-oxo-15-norArgentone, 15-Hydroxyargentone,
Argentone and 15-nor-Argentone
Cernuol
BR-xanthone A, Garcinone D,
Gartanin, Mangostin, -Mangostin
(E)-3-Chloro-4-stilbenol, (E)-3,5Dimethoxy-4- stilbenol, (E)-3,5Dimethoxystilbene, (E)-3-Methoxy-4stilbenol, (Z)-4-Methoxy-3-stilbenol,
(E)-5-Methoxy-3-stilbenol, (E)-4Stilbenol, (E)-3-Stilbenol, (Z)-3Stilbenol, (E)-3,4-Stilbenediol, (E)-3,5Stilbenediol
Geraniol, Linalool, 1,8-Cineole,
Citral
Isolimonene, Isopulegol, Carvone
5,7-Dihydroxy-4-hydroxyisoflavan,
6,7-Dihydroxy-4_-methoxyisoflavan,
5,7-Dihydroxy-4_-methoxyisoflavan,
Biochanin A
Carvacrol, p-Cymene and Terpinene
8-Acetylheterophyllisine, Panicutin,
Vilmorrianone
Clausenal
Harman, Harmine, Norharman
Calycodendron milnei
Isopsychotridine E, Hodgkinsine A,
Quadrigemine C, Quadrigemine H,
Psychotridine E, Vatine, Vatine A,
Vatamine, Vatamidine,
Endo et al., 1990
Brader et al., 1997
Maatooq et al., 1996
Smirnov et al., 1998
Gopalakrishnan et al.,
1997
Schultz et al., 1992
Pattnaik et al., 1997
Naigre et al., 1996
Weidenborner et al.,
1990
Pinto et al., 2006
Rahman et al., 1997
Chakraborty et al.,
1995
Quetin-Leclercq et al.,
1995
Saad et al., 1995
92
Fungicides for Plant and Animal Diseases
Specie
Compounds Identifying
Dehatrine, Actinodaphnine,
Anhydroushinsunine, Methoiodide,
N-Methylactinodaphnine
Anonaine
Lanuginosine, Lysicamine
Berberine
Alkaloids
3-Methoxysampangine
Steroidal alkaloids
Reference
Tsai et al., 1989
Tsai et al., 1989;
Simeon et al., 1990
Simeon et al., 1990
Okunade et al., 1994
Liu et al., 1990
Fewell & Roddick,
1993
Lee et al., 1999
ǂ-Chaconine, ǂ-Solanine
Polygodial
Table 3. Chemical compounds identified with antifungal properties derived from species
plants
2.6 Effect of compounds in inhibiting mycelia fungi
The most compounds have varied effects on the development of mycelia growth of fungi
and the effect on sporulation rate and inhibition of germination ranging from a fungistatic
effect to complete inhibition. The answer depends on the arrest of compounds derived from
extracts of the species and to inhibit fungus. Table 4 shows the sensitivity of plant pathogen
fungi to bioactive coumponds from plants.
Plant Specie
Achillea gypsicola and
A. biebersteinii
Agapanthus africanus
Aloe vera
Asarum heterotropoides
var. mandshuricum
Plant pathogen
Fusarium equiseti and F.
graminearum
Pythium ultimum,
F. oxysporum,
Alternaria alternata,
Mycosphaerella pinodes
and Ascochyta
Rhizoctonia solani, F.
oxysporum
and Colletotrichum
coccodes
Alternaria humicola,
Colletotrichum
gloeosporioides,
Rhizoctonia solani,
Phytophthora cactorum
and
Fusarium solani
Fungicidal
activity
concentrations
References
Kordali et al., 2009
Tegegne et al., 2008
105 μl L−1
Jasso de Rodríguez
et al., 2005
<0.42 μg mL−1
Dan et al., 2010
93
Antifungal Properties of Bioactive Compounds from Plants
Plant Specie
Plant pathogen
Astronium fraxinifolium,
Inga marginata, Malva
sylvestris, Matayba
elaeagnoides, Miconia
argyrophylla, Myrcia
Colletotrichum
fallax, Ocimum
gratissimum, Origanum lindemuthianum
vulgare, Rollinia
emarginata, Siparuna
arianeae, Styrax pohlii,
Tabebuia serratifolia and
Trichilia pallida
Aspergillus niger,
Bucida buceras,
Aspergillus parasiticus,
Breonadia salicina,
Colletotricum
Harpephyllum caffrum,
gloeosporioides,
Olinia ventosa,
Penicillium janthinellum,
Vangueria infausta and Penicillium expansum,
Trichoderma harzianum
Xylotheca kraussiana
and Fusarium oxysporum
Pythium sp.,
Colletotrichum truncatum,
Colletotrichum coccodes,
Carya illinoensis shells
Alternaria alternata,
and Punica granatum
Fusarium verticillioides,
Fusarium solani,
Fusarium sambucinum
and Rhizoctonia solani
Cassia sp.
Chenopodium quinoa
Drimys winteri
Flourensia microphylla,
Flourensia cernua and
Flourensia retinophylla
Larrea tridentata,
Flourensia cernua,
Agave lechuguilla,
Opuntia sp. and Yucca
sp.,
Fungicidal
activity
concentrations
References
inhibition of
conidial
germination
Andrade et al., 2010
0.02-0.08 mg
mL−1
Mahlo et al., 2010
0.2 mgL−1
Osorio et al., 2010
Alternaria alternate
500 μl L−1
Feng et al., 2008
Botrytis cinerea
5 mg saponins
ml−1, 100% of
conidial
germination
inhibition
Stuardo et al., 2008
Gaeumannomyces
graminis var tritici
Alternaria sp.,
Rhizoctonia solani and
Fusarium oxysporum
Rhizoctonia solani
932- 30.37mg L−1
10 to 1500μl L−1
2000 ppm of
totals
polyphenols
Monsálvez et al.,
2010,
Jasso de
Rodríguez et al.,
2007
Castillo et al., 2010,
94
Fungicides for Plant and Animal Diseases
Plant Specie
Larrea tridentata
Laurus nobilis
Metasequoia
glyptostroboides
Piper longum
Plant pathogen
Aspergillus flavus and
Aspergillus parasiticus
Botrytis cinerea, Monilinia
laxa and Penicillium
digitatum
Fusarium oxysporum,
Fusarium solani,
Sclerotonia sclerotiorum,
Rhizoctonia solani,
Colletotricum capsici,
Botrytis cinerea and
Phytophthora capsici,
Pyricularia oryzae,
Rhizoctonia solani,
Botrytis cineria,
Phytophthora infestans,
Puccinia recondite and
Erysiphe graminis
Fungicidal
activity
concentrations
300-500 μg mL−1
of NDGA
Rumex crispus
Salvia officinalis
Thymus zygis subsp.
sylvestris
Cryptomeria japonica
Melaleuca alternifolia
Pimpinella anisum
Piper angustifolium
Vargas-Arispuro et
al., 2005
1, 2 and 3 mg
mL−1
Corato et al.,, 2010
Inhibition range
of 49–70% and
minimum
inhibitory
concentration
ranging from 500
to 1000 μg mL−1.
Bajpai et al., 2007
1mg mL−1
Lee et al., 2001
Pasini et al., 1997;
KonstantinidouDoltsinis & Schmit,
1998
Sphaerotheca pannosa var.
Reynoutria sachalinensis
rosae
Robinia pseudoacacia
References
Sphaerotheca fuliginea,
80 mg mL−1
Zhang et al., 2008
Blumeria graminis f. sp.
hordei
Penicillium, Aspergillus,
Cladosporium and
Fusarium
30 μg mL−1
Choi et al., 2004
0.63 μl ml−1
Pinto et al., 2007
0.08- 0.16 μL
mL−1
Gonçalves et al.,
2010
MIC(50) values
of 65, 80, 80 and
110 mg mL−1
Cheng et al., 2005
500–6000
Nenoff et al., 1996
MIC to 1.5 and
9.0% (V/V).
Kosalec et al., 2005
10–100
Tirillini et al., 1996
Aspergillus strains
Rhizoctonia solani,
Collectotrichum
gloeosporioides, Fusarium
solani and Ganoderma
australe
Candida albicans and
Candida sp.
Trichophyton rubrum, T.
mentagrophytes,
Microsporum canis and
M. gypseum
Candida albicans,
Cryptococcus neoformans,
Aspergillus flavus,
Aspergillus fumigatus,
95
Antifungal Properties of Bioactive Compounds from Plants
Plant Specie
Plant pathogen
Salvia officinalis
Torulopsis utilis,
Schizosaccharomyces
pombe, Candida albicans
and Saccharomyces
cerevisiae
Salvia sclarea
Soil-borne pathogens
Tagetes patula
Thymbra capitata
Thymus pulegioides
Lavandula angustifolia
3-Methoxysampangine
Fungicidal
activity
concentrations
References
Hili et al., 1997
EC50: 493–584 μL
L−1
Penicillium digitatum and 1.25–10.0 μL
Botrytis cinerea
mL−1
Candida sp., Aspergillus
0.08–0.32 μL
sp
mL−1
Candida, Aspergillus and 0.16–0.64 μL
dermatophyte species
mL−1
Pitarokili et al.,
2002
Romagnoli et al.,
2005
Salgueiro et al.,
2004
Candida albicans
D’Auria et al., 2005
0.69%
Candida albicans,
Aspergillus fumigatus and 0.2–3.1
Cryptococcus neoformans
Pinto et al., 2006
Liu et al., 1990
Steroidal alkaloids
Ascobolus crenulatus,
Alternaria brassicicola,
ǂ-Chaconine
Phoma medicaginis and
Rhizoctonia solani
Ascobolus crenulatus,
Alternaria brassicicola,
ǂ-Solanine
Phoma medicaginis and
Rhizoctonia solani
Cladosporium
Dictamnus dasycarpus
cucumerinum
Tricophyton
mentagrophytes,
Olea europaea
Microsporum canis and
Candida spp
Colletotrichum
Eupatorium riparium
gloeosporioides
Rhizoctonia solani;
Wedelia biflora
Pythium ultimum;
Fusarium oxysporum f.
Scutellaria spp
sp. lycopersici and
Verticillium tricorpus
Rhizoctonia solani;
Wedelia biflora
Pythium ultimum;
Epidermophyton
Podophyllum hexandrum floccosum, Curvularia
lunata, Nigrospora oryzae,
60–100 μM
Fewell & Roddick
1993
80–100 μM
Fewell & Roddick
1993
25
Zhao et al., 1998
1.9 -250
Battinelli et al.,
2006
Bandara et al., 1992
Miles et al., 1991
Cole et al., 1991
Miles et al., 1993
Rahman et al., 1995
96
Fungicides for Plant and Animal Diseases
Plant Specie
Plant pathogen
Fungicidal
activity
concentrations
References
Microsporum canis,
Allescheria boydii and
Pleurotus ostreatus,
Drechslera rostrata
Candida albicans,
Aspergillus flavus,
Aspergillus fumigatus
1.0–5.0 mM;
0.016–0.13% of
oil;
Tirillini et al., 1996
Cistus incanus subsp.
creticus
Candida albicans
125–375
Chinou et al., 1996
Thymus pulegioides
Candida, Aspergillus
1.25–20.0 μL
mL−1
Pinto et al., 2006
Zingiber officinale
Pyricularia oryzae
10.0 ppm
Endo et al., 1990
Coleonema pulchellum
Cladosporium herbarum
Piper angustifolium
Parthenium argentatum
× P. tomentosa
Garcinia mangostana
Brader et al., 1997
mL−1
Aspergillus fumigatus and 0.25 mg
A. niger
1.0 mg mL−1
Fusarium oxysporum
vasinfectum, Alternaria
tenuis and Drechslera
oryzae
Aspergillus repens; A.
amstelodami; A. chevalieri;
A. flavus; A. petrakii;
Coriolus versicolor,
Gloeophyllum trabeum
8-140
and Poria placenta
Aspergillus niger
Maatooq et al., 1996
Gopalakrishnan et
al., 1997
Weidenb¨orner et
al., 1990a, b
Schultz et al., 1992
0.78–100 μL mL−1 Naigre et al., 1996
Candida albicans,
Trichophyton
mentagrophytes, T.
ruburum, Penicillium
0.78–100.0
marneffei, Aspergillus
fumigatus, A. flavus, P.
chrysogenum, C. lipolytica
and C. tropicalis
Lee et al., 1999
Cymbopogonflexuosus
0.16–11.6
Pattnaik et al., 1996
Cymbopogon martini
0.5–8.3
Pattnaik et al., 1996
Eucalyptus citriodora
0.16–10.0
Pattnaik et al., 1996
Bidens cernua
5.0–200
Smirnov et al., 1998
Gomphrena martiana
and G. boliviana
75
Pomilio et al., 1992
97
Antifungal Properties of Bioactive Compounds from Plants
Plant Specie
Plant pathogen
Fungicidal
activity
concentrations
Helichrysum nitens
1- 20 μg
Allium sativum
64
References
Tomas-Barberan et
al., 1988
Pyun and Shin
2006
Psidium acutangulum
Miles et al., 1993
Croton sonderianus
McChesney &
Clark, 1991
Bystropogon plumosus,
B. origanifolius var.
palmensis, B. wildpretii,
B. maderensis and B.
canariensis var.
Smithianus
0.4–85.0% of oil
Economou &
Nahrstedt, 1991;
Kalodera et al.,
1994
Mentha piperita
0.27–10.0
Pattnaik et al., 1996
Pelargonium graveolens
Pattnaik et al., 1996
Table 4. Bioactive compounds from plants on fungal species.
2.7 Commercial use of natural fungicides
Currently, the commercial use of natural fungicides on the market is low, the 5th Annual
Meeting of the biological control industry (Loison, 2010) reports a total of 55 biological
fungicides registered in the U.S. market and in the EU the registered biopesticides are much
fewer: 21 fungicides for be used in Pome fruit, vines and tomato (Table 5).
Commercial name
BC 1000 TM
Active Ingradient
Bioflavonoid of
Seed extracts and
orange pulp
Company
Plant pathogen
Chemie S.A.
Botritys cinérea
Bio save TM
Seed extracts and
orange pulp
Bioland SA
Ascochyta, Pullullaria,
Fusarium, Cercospora,
Botrytis, Septoria,
Alternaria,
Stemphylium,
Rhizoctonia,
Peronospora, Pythium,
Penicilium, Sigatoka,
Aspergillus.
Agrispon TM
Plant and mineral
extacts.
Agric. Sci Dallas
Cercospora beticola
Sincocin TM
Plant extracts
Agric. Sci Dallas
Cercospora beticola
98
Commercial name
Fungicides for Plant and Animal Diseases
Active Ingradient
Timorex Gold
Plant extracts of
Melalueca alternifolia
Evergreen TM
Plant extracts
Gloves Off TM
Thymol, Carvacrol
Garden Fungicide
Rosemary, thyme
and clove oil
Pongamia and Tulsi
oil, Recines
communis
TM
Eco Safe TM
Gloss TM
Natural Alkaloids
Company
Plant pathogen
Stockton Group
Mycosphaerella fijiensis
Aashab bio
industries
Organozoid and
Such
Trichophyton
mentagrophytes
EcoSmart
S. K. Bio Extracts
& Applications
Root rot, Dammping
off, Steam rot, leaf spot
S. K. Bio Extracts
& Applications
fungal diseases in all
field crops,
vegetables and
horticultural crops
Table 5. Some commercial product in the market with active ingredients from plants
3. Conclusions
The plant extracts applied in as crude state or as a fraction affect the development of fungal
colonies to inhibit partially and totally in laboratory tests at low concentrations of bioactive
compounds, besides affecting the incedencia and severity when applied as a treatment to
increase the shelf life of products with excellent results. However, more research is needed
to determine its effect on molecular changes, morphological and biochemical these
compounds cause the pathogen and host.
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