Genus Pouteria: chemistry and biological activity

Gênero Pouteria: química e atividade biológica

REVISÃO

Genus Pouteria: chemistry and biological activity

Gênero Pouteria: química e atividade biológica

Cíntia A. M. Silva; Luiz A. Simeoni; Dâmaris Silveira^*

Faculdade de Ciências da Saúde, Universidade de Brasília, Campus Universitário Darcy Ribeiro, Asa Norte, 70910-900 Brasília-DF, Brazil

ABSTRACT

The genus Pouteria belongs to the family Sapotaceae and can be widely found around the World. These plants have been used as building material, as food, because the eatable fruits, as well as remedies in folk medicine. Some biological activities have been reported to species of this genus such as antioxidant, anti-inflammatory, antibacterial and antifungal. However, the real potential of this genus as source of new drugs or phytomedicines remains unknown. Therefore, a review of the so far known chemical composition and biological activities of this genus is presented to stimulate new studies about the species already reported moreover that species have no reference about chemistry or biological activities could be found until now.

Keywords: Pouteria, Sapotaceae, triterpene, flavonoid, medicinal plants.

RESUMO

O gênero Pouteria pertence à família Sapotaceae e pode ser encontrado em muitos continentes. As plantas desse gênero têm sido utilizadas na construção civil, na alimentação e também na medicina popular. Algumas atividades biológicas são reportadas às espécies desse gênero, tais como, antioxidante, anti-inflamatória, antibacteriana e antifúngica, mas seu real potencial como fonte de novos fármacos ainda é pouco conhecido. Assim, uma revisão sobre a composição química e as atividades biológicas de Pouteria é apresentada, com o intuito de estimular a continuação dos estudos das espécies aqui citadas, e a investigação de outras espécies para as quais não foram encontrados relatos.

Unitermos: Pouteria, Sapotaceae, triterpenos, flavonoides, plantas medicinais.

INTRODUCTION

The Sapotaceae family is subdivided into five tribes with 53 genera and about 1,250 species, with a worldwide distribution, mainly in the tropical and subtropical regions of Asia and South America (Swenson & Anderberg, 2005). The genus Pouteria Aublet is a pan tropical group consisting in 9 sections and 325 species (Triono et al., 2007). Many of them produce high-quality timber and edible fruit, representing a great economic value. Besides their commercial significance, several species have been used in folk medicine for several purposes. So far, however, few species were studied about chemistry composition or biological properties. Therefore, this report covers the chemical and biological activity studies of the species belonging to this genus until now.

Chemical composition of Pouteria species

Triterpenes and flavonoids are the main constituents of this genus. Some of them have been found in regular basis in all here considered species. Usually, triterpenes has been isolated as long chain or acetate esters. Besides, long chain hydrocarbons, alcohols, acids and esters also are found mainly in species occurring in dry regions, for example, Brazilian savannah (David, 1993; Lopez, 2005; Silva, 2007). In addition, Pouteria species have been evaluated as enzymes sources to be used as synthesis reagent as well as biological activity purposes (Lott & Jackes, 2001; Solis et al., 2004; Hernandez et al., 2006). The mainly compounds isolated from each species are showed at Figure 1 and Table 1.

Pouteria torta (Mart.) Radlk is one of the most studied species. From hexane and dichloromethane extract of flowers and fruits (David, 1993) were isolated α- and β-amyrin (1, 2), also isolated from the leaves (Lopez, 2005), besides lupeol (3), taraxasterol (4), pseudotaraxasterol (5), cycloartenol (6), lanosterol (7), lanosta-7,24-dien (8) and erythrodiol palmitate (9a). Fatty acids, triglycerides and normal and branched hydrocarbons also were isolated from these extracts (David, 1993).

Pouteria torta branches presented a-amyrin acetate (1a), β-amyrin acetate (2a), betulinic acid (10) and ursolic acid (11), isolated from methanol extract (Che et al., 1980). Hexane extract from leaves gave lupeol acetate (3a) (Perfeito et al., 2005) and from ethanol extract was isolated a mixture of α- and β-friedelinol (13, 14) (Lopez, 2005).

Betulinic (10) and ursolic acids (11), as well as α- and β-amyrin acetate (1a, 2a) also were isolated from cortex of Pouteria tomentosa (Roxb.) Baehni (Anjaneyulu, 1965).

The phytochemical study of the benzene extract from Pouteria caimito (Ruiz & Pav.) Radlk. fruits showed the presence of α-amyrin (1), lupeol (3), erythrodiol (9), and dammarenediol (15); and from the barks extract, taraxerol (16) and its acetate (16a), taraxenona (16b) and β-sitosterol (17) (Pellicciari et al., 1972). From hexane extract of the leaves was extracted spinasterol (18) (forthcoming paper), also present in Pouteria venosa (Mart.) Baehni leaves and stem barks and in the Pouteria vitiensis (Gillespie) O.Deg. heartwood (Cambie et al., 1997). Erythrodiol (9) also was isolated from Pouteria mammosa (L.) Cronquist (Bondioli & Folegatti, 1996).

Pouteria venosa leaves and stem bark ethanol extracts gave ursolic acid (11) and taraxerol (16), respectively. From ethanol extract of stems were isolated miriantic acid (19) and 19α,23-dihydroxyursolic acid (19a) (Montenegro et al., 2006).

Hexane extract from Pouteria gardnerii (Mart. & Miq.) Baehni leaves gave α-and β-amyrin (1, 2), α-amyrin acetate (1a), ursolic acid (11) lupeol acetate (3a), and oleanolic acid (10) (Silva, 2007).

The methanol extracts of fruits from Pouteria campechiana (Kunth) Baehni, Pouteria sapota (Jacq.) H. E. Moore & Stern and Pouteria viridis (Pittier) Cronquist gave gallic acid (20), (+)-gallocatechin (21), (+)-catechin (21a), (-)-epicatechin (21b), (+)-catechin-3-O-gallate (21c), dihydromyricetin (22) and myricitrin (23) (Ma et al., 2004). Myricitrin (23) was also isolated from P. torta (forthcoming paper). Pouteria vitiensis gave vanilloyl sucrose (24a) besides myo-inositol (25) and sucrose (Cambie et al., 1997). Pouteria cambodiana (Pierre ex Dubard) Baehni contains protocatechuic acid (24) (Manosroi et al., 2005; 2006), carotenoids (Lanerolle et al., 2008) and stylbenes (Hernandez et al., 2005; Perfeito et al., 2005) 2008).

As several Pouteria species furnish eatable fruits, the composition of the essential oil is valuable information for food sciences, and can be used to develop new flavors and brands. But as far we know, only four species were analyzed about essential oil content: Pouteria (Ducke) Baehni, P. caimito (Maia et al., 2003), P. sapota and Pouteria splendens (A. DC.) Kuntze (Sotes et al., 2006). The mainly component of volatil e oil from fruits of P. pariry is methyl butanoate; and the analysis of oil from P. caimito fruits showed that palmitic acid, hexadecil acetate and α-copaen (26) were the most abundant constituents (Maia et al., 2003). Analysis of oil from fruits of P. sapota revealed the presence, besides others, of benzaldehyde, hexanal, and palmitic acid that were the major ones (Pino et al., 2006). From the almonds of these three species were isolated palmitic, estearic, oleic and linoleic acids (Solis-Fuentes et al., 2001; Solis-Fuentes & Duran-de-Bazua, 2003).

By GC-MS analysis of the essential oil from P. splendens leaves, were identified: cis,trans-α-farnesol (27), trans-nerolidol (28), cis-β-elemene (29), germacrene D (30), β-selinene (31), eremophilene (32), δ-cadinene (33), 10-epi-α-cadinol (34), 10-epi-α-muurolol (35), epi-globulol (36), globulol (37), ledene (38), palustrol (39), isophytol (40), trans-phytol (41). Also were identified: 1-octanol, 2,5-dimethylcyclohexanol, 3,5-dimethylcyclohexanol, dodecanal, tridecanal, tetradecanal, hexadecanal, 2-decyl-oxirane, perhydrofarnesylacetone, tetradecanoic acid, hexadecanoic acid, and 9,12,15-octadecatrienoic acid (α-linolenic acid) (Sotes et al., 2006).

Cyanogenic compounds were detected on leaves, fruits and seeds of the Pouteria subrotata Cronquist and P. torta (Miller et al., 2006), and in leaves of P. amygdalicarpa and P. campechiana (Thomsen & Brimer, 1997). Lucumin (42) was isolated from seeds of P. sapota,P. mammosa and was found in leaves extracts from P. subrotata (Takeda et al., 1997; Miller et al., 2006). Additionally, lucuminic acid (43) and lucuminamide (43a) were isolated from P. sapota (Takeda et al., 1997).

Other interesting compound, pouterin, a protein with lectin-like activity, was isolated from the seeds of P. torta (Boleti et al., 2007).

Biological activities of Pouteria species

Several Pouteria species have been used in folk medicine to treat fever, inflammation, skin eruptions, ulcers, diabetes (Ma et al., 2004; Montenegro et al., 2006) diarrhea (Perfeito et al., 2005), nausea, vomiting, back pain, and to promote lactation on milk feeding mothers (Manosroi et al., 2006). However, there is a lack of scientific evidence for most of these claimed biological activities.

On the other hand, the secondary metabolites present in this genus can explain some of the already proved biological activities as well as the claimed ones. The presence of phenolic compounds in the Pouteria extracts can explain, at least in part, the antioxidant and radical scavenging activities presented by the more polar extracts and fractions (Rice-Evans et al., 1996). In addition, lupeol, ursolic acid and others triterpenes also have demonstrated capacity to intercept free radicals (Bracco et al., 1981; Saleem et al., 2001).

In fact, compounds belonging to both class of substances, phenolics and triterpenes, present several biological activities, since antimicrobial, cytotoxicity to anti-inflamatory and others (Ying et al., 1991; Pelzer et al., 1998; Nijveldt et al., 2001; Hodges et al., 2003; Cushnie & Lamb, 2005; Fontanay et al., 2008).

The biological activity of the species of Pouteria is summarized in Table 2.

Radical scavenging and antioxidant activities

The acetone and hydroethanol extracts from P. campechiana fruits (Suda et al., 2005), aqueous extract from P. caimito fruits (Oliveira et al., 2007) and P. torta leaves and also ethanol extracts from P. caimito, Pouteria ramiflora (Mart.) Radlk and P. torta leaves (Castro et al., 2006) presented 1,1-diphenyl-2- picrylhydrazyl (DPPH) radical-scavenging activity.

This activity was also noted at ethanol extract and some fractions from leaves, stem and stem bark of P. venosa (Montenegro et al., 2006), in the ethyl acetate fraction of methanol extracts from P. sapota and from P. viridis fruits (Ma et al., 2004; Mahattanatawee et al., 2006), and also in the methanol and acetone extracts from P. campechiana fruit and P. sapota juice (Franco, 2006).

The methanol extract of P. campechiana stem bark showed free radical scavenging activity in the DPPH radical assay (IC₅₀ 0.24 mg/mL), but it was less active than ascorbic acid, butylated hydroxytoluene (BHT) and α-tocopherol (IC₅₀ 0.08, 0.10 and 0.11 mg/ mL, respectively). In addition, this extract at doses up to 0.073 mg/mL had no effect on lipid peroxidation (Manosroi et al., 2005).

Chloroform extract from P. campechiana fruits presented antioxidative and antinitrosative activities by employing two cellular experimental systems: phorbol ester-induced O₂^- generation from differentiated HL-60 human promyelocytic leukemia cells; and lipopolysaccharide (LPS)-induced NO generation in RAW264.7 murine macrophages (Murakami et al., 2005). The ethyl acetate extract presented anti-mitotic activity ex vivo (Hernandez et al., 2008).

The fruits of P. viridis also presented antioxidant activity in the deoxyribose degradation and Fenton reaction models (Palomino et al., 2006). Six antioxidant compounds (20, 21, 21a-c, 22) were isolated and identified from the fruits of P. sapota; 20, 21, 21a-b and 23, from P. viridis fruits; and 20 and 21b, from the fruits of P. campechiana (Ma et al., 2004).

Immunomodulatory activity and citoxicity

The methanol extract from Pouteria cambodiana stem bark presented in vitro immunomodulatory activity of mouse immune system for both macrophage phagocytosis (EC₅₀ 0.02mg/mL) and splenocyte proliferation (EC₅₀ 0.01 mg/mL) (Manosroi et al., 2005; 2006).

By the in vitro phagocytic assay on nitroblue tetrazolium (NBT) dye reduction and on cellular lysosomal enzyme activity, different concentrations of aqueous and acetone extracts from P. cambodiana stem bark gave phagocytic modulation without dose response relationship, being acetone the more active extract (Manosroi et al., 2006). On the other hand, using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, the same extracts did not show reduction of proliferation on bone marrow cells and splenocytes (Manosroi et al., 2006). Also, the aqueous extract did not affect male body and testicular weights as well as cauda epididymal sperm counts, after 8 days treatment (Chanda et al., 2008), showing no toxicity at the tested conditions.

Hexane, ethanol and aqueous extracts from P. ramiflora (forthcoming paper) and P. torta leaves (Perfeito et al., 2005) as well as the obtained fractions from these extracts; and methanol extract from P. torta leaves (Alves et al., 2000) were evaluated about toxicity to Artemia salina larvae (Brine Shrimp Toxicity method) (Meyer et al., 1982). The aqueous fraction from ethanol extract of P. ramiflora and the aqueous extract from P. torta were toxic to A. salina (Perfeito et al., 2005). On the other hand, methanol and aqueous extracts from P. caimito bark and P. guianensis roots and wood did not presented toxicity against A. franciscana larvae (Quignard et al., 2003; Libralato et al., 2007).

Hexane and ethanol extracts from P. ramiflora did not inhibit NO production on LPS/IFN-γ-activated J774 macrophages model and did not present cytotoxicity by MTT cell viability test (Napolitano et al., 2005).

Pouterin, from P. torta showed the ability to induce agglutination of human, rabbits and rats erythrocytes (Boleti et al., 2007). Also presented a remarkable activity inducing apoptosis in mammalian cells (Boleti et al., 2008).

Antibacterial and antifungal activities

The hexane and ethanol extracts from P. torta leaves showed antimicrobial activity against Staphylococcus aureus and Pseudomonas aeruginosa. Pseudomonas aeruginosa growth also was inhibited by the aqueous extract. Further, this extract showed activity against Escherichia coli (Lopez, 2005) and the methanol extract was active against Cladosporium sphaerospermum, E. coli, S. aureus, Bacillus cereus and P. aeruginosa (Alves et al., 2000). Pouteria pallida (C.F.Gaertn.) Baehni inhibited multidrug resistant S. aureus (Humason, 2005).

Pouterin, from P. torta seeds, showed antifungal activity against Fusarium oxysporum, Colletotrichum lindemuthianum and Saccharomyces cerevisiae (Boleti et al., 2007).

The pyroligeneous liquor from P. ramiflora wood presented fungicidal activity against Aspergillus niger and Trichoderma sp. (Costa et al., 2003).

The hydroethanol extracts from Pouteria psamophila (Mart.) Radlk. and Pouteria grandiflora (A.DC.) Radlk. leaves were evaluated for antimicrobial and DNA-damaging activities. Pouteria psamophila was active against Cladosporium cladosporioides, but inactive against C. sphaerospermum,E. coli,S. aureus and Candida albicans. On the other hand, P. grandiflora presented a weak activity against C. sphaerospermum, and was inactive against C. cladosporioides, E. coli, S. aureus and C. albicans (Agripino et al., 2004). The dichloromethane extract from Pouteria reticulata (Engler) Eyma barks presented a weak activity against Mycobacterium tuberculosis (Graham et al., 2003)

Allelopathy activity

Aqueous extract from P. torta leaves presented germination and growth inhibition of lettuce in a dose-dependent way (Nascimento et al., 2007) and extract from P. splendens leaves promoted germination inhibition of Triticum spp. (Bustamante et al., 2007).

Trypanocidal and antimalarial activities

The methanol extract from P. sapota stems presented trypanocidal activity in vitro (2 mg/mL) against epimastigote form of Trypanossoma cruzi (Abe et al., 2002). The ethanol extract from P. venosa leaves (250 mg/mL), as well as the hydroethanol fraction (500 mg/mL), presented antimalarial (against Plasmodium berghei) activity in vivo reducing the induced infection in rats (Montenegro et al., 2006).

Insecticidal and antitermite activities

Pouteria venosa also was evaluated about larvicidal activity. The ethanol extract did not presented activity on Aedes aegypti larvae. However, the hexaneethyl acetate (1:1) fraction killed 100% from the larvae after 24h exposure (Montenegro et al., 2006).

Extracts from P. gardnerii,P. ramiflora and P. torta also did not present larvicidal activity against A. aegypti, Rhodnius milesi and Dipetalogaster maxi (Coelho, 2006). On the other hand, pouterin, from P. torta, presented insecticidal activity on Callosobruchus maculatus F. larvae (Boleti et al., 2007).

The hydroethanol extracts from P. guianensis stem and stem bark presented antitermite activity in repelling Nasutitermes sp. (Barbosa et al., 2007).

Others

-Several others biological activities were reported to Pouteria extracts, such as:

-Anti-inflammatory and antinociceptive activities in vivo by the ethanol extract from P. ramiflora leaves(Fontes-Junior, 2004; Nunes, 2004).

-Estrogen antagonist activity by hexane P. torta leaves when tested about agonism and antagonism on estrogen receptor beta (ER_β) (Franzotti, 2004).

-Anti-HIV activity by the methanol extract of P. viridis leaves when tested using MTT and recombinant viruses (RV) assays (Bedoya et al., 2008).

-Subchronic embryotoxicity to the oyster Crassostrea gigas by P. guianensis wood (Libralato et al., 2007).

Although the Pouteria genus has wide ethnobotanical tradition as food, remedies or wood to general uses, most of the available scientific information is limited to few species with economical potential as source of eatable fruits, while several other species remain without information about their pharmacological and economical potential. Indeed, most of them grow in areas suffering accelerated degradation, such as Brazilian savannah and rain forests. Therefore, considering the already isolated compounds, and the potential of Pouteria species as a resource of triterpene-and flavonoid-based material, further investigations should be carried out as part of the effort for a correct exploitation of wild species to be used as cosmetic and pharmaceutical actives.

Received 24 July 2008; Accepted 29 December 2008

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Publication Dates

• Publication in this collection
  01 Sept 2009
• Date of issue
  June 2009

History

• Received
  04 July 2008
• Accepted
  29 Dec 2008