**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

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)

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

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.,*

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

Fig. 1. A simplified view of the major pathways of secondary metabolites biosynthesis and

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

their interrelationship with primary metabolism (Taiz & Zeiger, 2002)

**2.2 Polyphenols** 

1997; Bautista *et al.,* 2002; Abou-Jawdah *et al.,* 2002; Cowan, 1999).

by the interrelationship with primary metabolism Figure 1.

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)

Antifungal Properties of Bioactive Compounds from Plants 85

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

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

> **R1**  OH OH H H

Hydroxyl groups allow the formation of complexes with proteins, metal ions and other molecules such as polysaccharides. In general, polyphenols identified and grouped

**R3**  H OH H OH **Class** 

Proanthocyanidin Prodelphynidin Profisetinidin Prorobinetinidin

**2.2.2 Condensed tannins (CT)** 

(Makkar *et al.,* 2007; Taiz & Zeiger, 2002).

Fig. 5. Condensed tannins or proanthocyanidins

Fig. 6. Structure of some condensed tannins

enhance the ability of condensed tannins to complex proteins.

according to their basic result is a chain of six carbons (Table 1).

#### **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

#### **2.2.2 Condensed tannins (CT)**

84 Fungicides for Plant and Animal Diseases

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.

Fig. 3. Hydrolysable tannins and some of its derivatives: A) gallotannins, B) ellagitannins. C)

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

ellagic acid, D) hydroxyphenolic acid, E) gallic acid

Fig. 4. Chemical structure of a gallotannins

sugar or a derivative as hexahydrophenic acid (Figure 4).

**2.2.1 Hydrolysable tannins (HT)** 

(Gonzalez *et al.,* 2009).

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.

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).

Antifungal Properties of Bioactive Compounds from Plants 87

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

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

**Phylum Structural patrons** 

present)

present)

kinds

Plant phylum (Garcia, 2004, as cited in Harborne, 1990)

acid

*Larrea tridentata* lignans, methyl-nordihydroguaiaretic

Bacteria Phenols from polyketides and quinones (occasionally

Fungi Simple phenols, phenylpropanoids, quinones (usually

Bryophytes Phenols in the cell wall, phenylpropanoids, stilbenes and

Table 2. Distribution of polyphenols compounds on different phylum's in comparative to

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

**Specie Compounds Identifying Reference**  *Simmondsia chinensis* Glucosides Abbassy *et al.,* 2007

*sylvestris*, Carvacrol Gonçalves *et al.,*<sup>2010</sup>

Camphor , 1,8-cineole, piperitone , borneol and α-terpineol, *n*-eicosane , *n*-heneicosane , *n*-tricosane, linoleic

acid and nordihydroguaiaretic acid

Lignin in the cell wall and wide range of phenols of all

Kordali *et al.,* 2009

2005

Vargas-Arispuro *et al.,*

Algae Oidados and brominated phenols, phloroglucinol derivatives from cell wall

Lichens Anthraquinones, xanthones and depsidones

some flavonoids

**2.4 Nitrogenous compounds** 

**2.5 Plants with antifungal properties** 

plants with presence of these compounds.

common amino acids.

Ferns, conifers and flowering plants

with antifungal effect.

*Thymus zygis* subsp.

*A. gypsicola* and *A. biebersteinii* 


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:

$$\mathcal{C}^{\mathsf{H}^{\mathsf{C}}}\_{\mathsf{H}^{\mathsf{C}}} \gtrsim \mathsf{H}^{-\mathsf{CH}^{\mathsf{H}}} \mathsf{C}^{\mathsf{H}}$$

The basic structural elements of terpenes are sometimes called **isoprene units** because terpenes can decompose at high temperatures to give isoprene:

$$\mathbf{p} = \mathbf{p} - \mathbf{w} \bigvee\_{\mathbf{x}\mathbf{f}}^{\mathcal{H}}$$

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*; 15 carbon 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).

### **2.4 Nitrogenous compounds**

86 Fungicides for Plant and Animal Diseases

6 C6 Simple Phenols and Benzoquinones

8 C6 - C2 Acetofenons and fenilacetonics acids 9 C6 - C3 hidroxicinamics Acids, fenilpropanoids

N (C6 - C3)n Lignins, Catecol Melanins and flavolans

Table 1. Classification of phenolics compounds in carbons atoms to base number (Garcia,

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

The basic structural elements of terpenes are sometimes called **isoprene units** because

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*; 15 carbon 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

14 C6 - C2- C6 Estilbens and anthraquinones 15 C6 - C3- C6 Flavonoids and isoflavonoids 18 (C6 - C3)2 Lignans and neolingnans

**Atoms number Basic carbon skeleton Compounds** 

7 C6 - C1 Phenolic acids

10 C6 - C4 Naftoquinones

13 C6 - C1- C6 Xantones

30 Biflavonoids

(C6)6 (C6-C3 - C6)n

elements that have the branched carbon skeleton of isopentane:

terpenes can decompose at high temperatures to give isoprene:

*polyterpenoids* ([C5] *n* carbons, where *n* > 8) (Taiz and Zeiger, 2002).

2004)

**2.3 Terpenes** 

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.


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.


Antifungal Properties of Bioactive Compounds from Plants 89

**Specie Compounds Identifying Reference** 

*Piper longum* Eugenol, piperine, piperlongumine

*Datura metel* Enzymes, peroxidase, *β*-1,3-glucanase

*Robinia pseudoacacia* Crude extracts Zhang *et al.,* 2008 *Cassia* sp cassia oil Feng *et al.,* 2008

> α-pinene, *allo*-aromadendrene, germacrene-D, *n*-octane, α-selinene

caryophyllene, α-pinene, lauric acid

caryophyllene, δ-3-carene, 2-β-pinene

α-pinene, caryophyllene oxide, αthujene, bornylene, totarol, β-

*Aegle marmelos* essential oil Pattnaik *et al.,* 1996 *Allium sativum* essential oil Pyun and Shin 2006

*Citrus aurantium* essential oil Pattnaik *et al.,* 1996 *Cryptomeria japonica* essential oil Cheng *et al.,* 2005 *Cymbopogonflexuosus* essential oil Pattnaik *et al.,* 1996 *Cymbopogon martini* essential oil Pattnaik *et al.,* 1996

*Bystropogon plumosus* essential oil Economou &

and β-selinene. Menthone, *n*-octane, β-

and β-pinene

and α-humulene.

Crude extracts Andrade *et al.,* 2010

and piperettine) Lee *et al.,*<sup>2001</sup>

and chitinase Devaiah *et al.,*<sup>2009</sup>

Crude extracts Abdel-Monaim *et al.,*

2011

1998

Konstantinidou-Doltsinis and Schmit,

Hosni *et al.,* 2008

Bajpai *et al.,* 2007

Nahrstedt, 1991

*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* 

*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*

*Hypericum perfoliatum* and *Hypericum tomentosum* 

*Metasequoia glyptostroboides* 

*Reynoutria sachalinensis* Crude extracts


**Specie Compounds Identifying Reference**  *Chenopodium quinoa* triterpenoid saponins Stuardo & Sn Martin*,*

*Aloe vera* Crude extracts Jasso de Rodríguez *et* 

*Drimys winteri* essential oil Monsálvez *et al.,* 2010, *Pimenta dioica* Essential oils Zabka *et al.,* 2009. *Catharanthus roseus* 5-hydroxy flavones Roy & Chatterjee,

Condensed and hidrolizables

*Salvia officinalis* essential oil Pinto *et al.,* 2007

and *Punica granatum* polyphenolic extracts Osorio *et al.,*<sup>2010</sup> *Bulnesia sarmientoi* bulnesol, hanamyol Rodilla *et al.,* 2011 *Caesalpinia cacalaco* gallic and tannic acids Veloz-García *et al.,*

*Clausena anisata* essential oils Osei-Safo *et al.,* 2010

*Agapanthus africanus* Crude extracts Tegegne *et al.,* 2008 *Reynoutria sachalinensis* Pasini *et al.,* 1997

> 1.8-cineole, linalool, terpineol acetate, methyl eugenol, linalyl acetate, eugenol, sabinene, β-pinene, α-

methyleugenol, eucarvone, 5-allyl-1,2,3-trimethoxybenzene and 3,7,7 trimethylbicyclo(4.1.0)hept-3-ene

*Rumex crispus* chrysophanol, parietin and nepodin Choi *et al.,* 2004;

*Ruta chalepensis* 2-undecanone, 2-decanone and 2-

terpineol.

*Larrea tridentata*, *Flourensia cernua*, *Agave lechuguilla*, *Opuntia* sp.

and *Yucca* sp.

*Flourensia microphylla*, *Flourensia cernua* and *Flourensia retinophylla* 

*Carya illinoensis* shells

*Bucida buceras*, *Breonadia salicina*, *Harpephyllum caffrum*,

*Olinia ventosa*, *Vangueria infausta*

*Laurus nobilis* 

*Xylotheca kraussiana* 

*Asarum heterotropoides* var. *mandshuricum* 

and

2008

2010

*al.,* 2007

2010

Corato *et al.,* 2010

Dan *et al.,* 2010

Gyung *et al.,* 2004

Tannins Castillo *et al.,* 2010,

Crude extracts Jasso de Rodríguez *et* 

dodecanone Mejri *et al.,*<sup>2010</sup>

crude plant Mahlo *et al.,* 2010

*al.,* 2005


Antifungal Properties of Bioactive Compounds from Plants 91

**Specie Compounds Identifying Reference**  *Piper angustifolium* Camphene Tirillini *et al.,* 1996

Pulegone Economou &

Nahrstedt, 1991;

Maatooq *et al.,* 1996

Gopalakrishnan *et al.,* 

Schultz *et al.,* 1992

Weidenborner *et al.,* 

1990

1995

1995

Saad *et al.,* 1995

1997

*creticus* Geraniol Chinou *et al.,* <sup>1994</sup>

*Zingiber officinale* Gingerenone A Endo *et al.,* 1990 *Coleonema pulchellum* Precolpuchol Brader *et al.,* 1997

> 8-oxo-Argentone, 8-oxo-15-nor-Argentone, 15-Hydroxyargentone, Argentone and 15-nor-Argentone

*Bidens cernua* Cernuol Smirnov *et al.,* 1998

Gartanin, Mangostin, γ -Mangostin

(*E*)-3-Chloro-4-stilbenol, (*E*)-3,5- Dimethoxy-4- stilbenol, (*E*)-3,5- Dimethoxystilbene, (*E*)-3-Methoxy-4 stilbenol, (*Z*)-4-Methoxy-3-stilbenol, (*E*)-5-Methoxy-3-stilbenol, (*E*)-4- Stilbenol, (*E*)-3-Stilbenol, (*Z*)-3- Stilbenol, (*E*)-3,4-Stilbenediol, (*E*)-3,5-

Geraniol, Linalool, 1,8-Cineole,

5,7-Dihydroxy-4-hydroxyisoflavan, 6,7-Dihydroxy-4\_-methoxyisoflavan, 5,7-Dihydroxy-4\_-methoxyisoflavan,

8-Acetylheterophyllisine, Panicutin,

 Isopsychotridine E, Hodgkinsine A, Quadrigemine C, Quadrigemine H, Psychotridine E, Vatine, Vatine A,

Vatamine, Vatamidine,

Citral Pattnaik *et al.,* <sup>1997</sup> Isolimonene, Isopulegol, Carvone Naigre *et al.,* 1996

Terpinene Pinto *et al.,* <sup>2006</sup>

Vilmorrianone Rahman *et al.,* <sup>1997</sup> Clausenal Chakraborty *et al.,* 

Harman, Harmine, Norharman Quetin-Leclercq *et al.,* 

*Garcinia mangostana* BR-xanthone A, Garcinone D,

Stilbenediol

Biochanin A

*Thymus pulegioides* Carvacrol, p-Cymene and γ -

*Cistus incanus* subsp*.* 

*Bystropogon plumosus, B. origanifolius* var*. palmensis, B. wildpretii, B. maderensis* and *B. canariensis* var*. smithianus* 

*P. argentatum × P.* 

*Calycodendron milnei* 

*tomentosa* 


**Specie Compounds Identifying Reference**  *Eucalyptus citriodora* essential oil Pattnaik *et al.,* 1996 *Melaleuca alternifolia* essential oil Nenoff *et al.,* 1996 *Mentha piperita* essential oil Pattnaik *et al.,* 1996 *Pelargonium graveolens* essential oil Pattnaik *et al.,* (1996 *Pimpinella anisum* essential oil Kosalec *et al.,* (2005 *Piper angustifolium* essential oil Tirillini *et al.,* 1996 *Salvia officinalis* essential oil Hili *et al.,* 1997 *Salvia sclarea* essential oil Pitarokili *et al.,* 2002 *Tagetes patula* essential oil Romagnoli *et al.,* 2005 *Thymbra capitata* essential oil Salgueiro *et al.,* 2004 *Thymus pulegioides* essential oil Pinto *et al.,* 2006 *Lavandula angustifolia* essential oil D'Auria *et al.,* 2005 *Dictamnus dasycarpus* Dictamnine Zhao *et al.,* 1998

*Ficus septic* Antofine, Ficuseptine Baumgartner *et al.,*

*Eupatorium riparium* Methylripariochromene A Bandara *et al.,* 1992

Columbianetin, Xanthotoxin

*Scutellaria* spp Clerodin, Jodrellin A, Jodrellin B Cole *et al.,* 1991

3,5,6,7,8-Pentamethoxyflavone, 3,5,6,7-Tetramethoxyflavone, 5,6,7,8-

Dimethylchrysin, Trimethylgalangin

*H. odoratissimum* 3-*O*-Methylquercetin Van Puyvelde *et al.,*

demethyldehydropodophyllotoxin

Secotrachylobanoic acid

Tetramethoxyflavone,

veratrylidenehydrazide, 3,3′-di-*O*-methylquercetin, 2,7-dihydroxy-3(3t'-methoxy-4′ hydroxy)-5-methoxyisoflavone and

3′,7-di-*O*-methylquercetin

and picropodophyllone

4′-*O*-

5-Hydoxy-3-methoxy-6,7-

Methylillukumbin A, *N*-Methylsinharine, Sinharine

Illukumbin B, Methylillukumbin B,

Lasiocarpine, Supinine Marquina *et al.,* <sup>1989</sup>

Nonanal and E-2-Octenal Battinelli *et al.,* <sup>2006</sup>

Dihydrocochloxanthin Diallo *et al.,* <sup>1991</sup>

trihydroxydihydrochalcone Miles *et al.,* <sup>1991</sup>

methylenedioxyflavone Pomilio *et al.,* (1992

1990

1993

1991

1988

1989

Greger *et al.,* 1992,

Afek *et al.,* 1995

McChesney & Clark,

Tomas-Barberan *et al.,*

Miles *et al.,* 1993

Rahman *et al.,* 1995

*Heliotropium bursiferum* 9-Angeloylretronecine, Heliotrine,

*Olea europaea* Hexanal, E-2-Hexanal, E-2-Heptanal,

*Apium graveolens* Angelicin, Bergapten,

*Wedelia biflora* 3´\_-Formyl-2´\_,4´\_,6´\_-

*Croton sonderianus* Hardwickic acid, 3,4-

Cochloxanthin,

*Glycosmis cyanocarpa*

*Cochlospermum tinctorium* 

*Gomphrena martiana* and *Gomphrena boliviana* 

*H. nitens* 

*Wedelia biflora* 

*Podophyllum hexandrum* 


Antifungal Properties of Bioactive Compounds from Plants 93

**Fungicidal activity concentrations** 

inhibition of conidial germination

0.02-0.08 mg

5 mg saponins ml−1, 100% of conidial germination inhibition

*graminis* var *tritici* 932- 30.37mg L−1 Monsálvez *et al.,*

10 to 1500μl L−<sup>1</sup>

2000 ppm of totals polyphenols

mL−1 Mahlo *et al.,*<sup>2010</sup>

0.2 mgL−1 Osorio *et al.,* 2010

Stuardo *et al.,* 2008

Castillo *et al.,* 2010,

2010,

2007

 Jasso de Rodríguez *et al.,*

**References** 

Andrade *et al.,* 2010

**Plant Specie Plant pathogen** 

*Colletotrichum lindemuthianum* 

*Aspergillus niger*, *Aspergillus parasiticus*,

*Penicillium janthinellum*, *Penicillium expansum, Trichoderma harzianum* and *Fusarium oxysporum* 

*Colletotrichum truncatum*, *Colletotrichum coccodes*, *Alternaria alternata*, *Fusarium verticillioides*, *Fusarium solani*, *Fusarium sambucinum* and *Rhizoctonia solani* 

*Cassia* sp. *Alternaria alternate* 500 μl L−1 Feng *et al.,* 2008

*Colletotricum gloeosporioides*,

*Pythium* sp*.*,

*Alternaria* sp.,

*Rhizoctonia solani* and *Fusarium oxysporum* 

*Rhizoctonia solani* 

*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 pallida* 

*Bucida buceras*, *Breonadia salicina*, *Harpephyllum caffrum*, *Olinia ventosa*,

*Vangueria infausta* and *Xylotheca kraussiana* 

*Carya illinoensis* shells and *Punica granatum* 

*Flourensia microphylla*, *Flourensia cernua* and *Flourensia retinophylla* 

*Larrea tridentata*, *Flourensia cernua*, *Agave lechuguilla*, *Opuntia* sp. and *Yucca*

sp.,

*Chenopodium quinoa Botrytis cinerea* 

*Drimys winteri Gaeumannomyces*


Table 3. Chemical compounds identified with antifungal properties derived from species plants
