Triterpenes and flavonoids from Combretum leprosum

Facundo, Valdir Alves; Andrade, C. H. S.; Silveira, Edilberto R.; Braz-Filho, Raimundo; Hufford, Charles D.

doi:10.1016/s0031-9422(00)95005-2

Cited by 58 publications

(46 citation statements)

References 7 publications

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“…2 ,3 -dihydroxyurs-12-èn-28-oic acid C. zeyheri [44] 120 6 -hydroxymaslinic acid C. zeyheri [44] 121 terminolic acid C. zeyheri [44] 122 methylsumaresinolate C. zeyheri [44] 123 combretanone A C. quadrangulare [45] 124 combretanone B C. quadrangulare [45] 125 combretanone C C. quadrangulare [45] 126 combretanone D C. quadrangulare [45] ( [34] 162 kinkeloid A2 C. micranthum [34] 163 kinkeloid B1 C. micranthum [34] 164 kinkeloid B2 C. micranthum [34] 165 kinkeloid C1 C. micranthum [34] 166 kinkeloid C2 C. micranthum [34] 167 kinkeloid D1 C. micranthum [34] 168 kinkeloid D2 C. micranthum [34] 169 apigenin C. erythrophyllum [50] 170 genkwanin C. erythrophyllum [50] 171 5-hydroxy-7,4 -dimethoxyflavone C. erythrophyllum [50] 172 Rhamnocitrin C. erythrophyllum C. apiculatum [50,51] 173 kaempferol C. erythrophyllum C .apiculatum [50,51] 174 quercetin-5,3 -dimethylether C. erythrophyllum [50] 175 rhamnazin C. erythrophyllum [50] 176 dillenetin C. lanceolatum [52] 177 isorhamnetin C. lanceolatum [52] 178 quercetin C. leprosum, C. apiculatum [39,40,53] 179 3-0-methylquercetin C. leprosum, C. erythrophyllum [40,50] 180 quercetrin C. leprosum, C. apiculatum [39,51] 181 5,3',4'-trihydroxy-3,7-dimethoxyflavone C. leprosum [40] 182 5,3'-dihydroxy-3,7,4'-trimethoxyflavone C. leprosum [40] 183 cardamonin C. apiculatum [51] 184 pinocembrin C. apiculatum …”

Section: Triterpenoidsmentioning

confidence: 99%

“…Quercetin (178), 3-0-methylquercetin (179), quercetrin (180), 5,3',4'-trihydroxy-3,7-dimethoxyflavone (181) and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (182) was also isolated from C. leprosum [39,40]; cardamonin (183) and pinocembrin (184) from C. apiculatum [51]; dillenetin (176) and isorhamnetin (177) from C. lanceolatum [52] and 2,4,4'-trihydroxychalcon (185) and eriodictyol (186) from C. yannanense [53]. Diarylpropanes [55].…”

Section: Flavonoidsmentioning

confidence: 99%

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Phytochemical Constituents of Combretum Loefl. (Combretaceae)

Dawe¹

2013

TOPHARMCJ

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Abstract:Combretum is the largest and most widespread genus of Combretaceae. The genus comprises approximately 250 species distributed throughout the tropical regions mainly in Africa and Asia. With increasing chemical and pharmacological investigations, Combretum has shown its potential as a source of various secondary metabolites. Combretum extracts or isolates have shown in vitro bioactivitities such as antibacterial, antifungal, antihyperglycemic, cytotoxicity against various human tumor cell lines, anti-inflammatory, anti-snake, antimalarial and antioxidant effects. In vivo studies through various animal models have also shown promising results. However, chemical constituents and bioactivities of most species of this highly diversified genus have not been investigated. The molecular mechanism of bioactivities of Combretum isolates remains elusive. This review focuses on the chemistry of 261 compounds isolated and identified from 31 species of Combretum. The phytochemicals of interest are non-essential oil compounds belonging to the various structural groups such as terpenoids, flavonoids, phenanthrenes and stilbenoids.

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Section: Triterpenoidsmentioning

confidence: 99%

Section: Flavonoidsmentioning

confidence: 99%

Phytochemical Constituents of Combretum Loefl. (Combretaceae)

Dawe¹

2013

TOPHARMCJ

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“…Although the isolation of an active principle was not carried out, it is likely that the molecule presenting the highest antiplasmodial activity is a triterpene, since compounds of this class have several studies reporting its antiplasmodial activities (NOGUEIRA;LOPES, 2011;RAMALHETE et al, 2011;RAMALHETE et al, 2014) and this chemical class seems to be the most abundant in species of the genus Combretum (DAWE et al, 2013) and in the species C. leprosum (FACUNDO et al, 1993;FACUNDO et al, 2008). Triterpenes that were isolated from the genus Combretum also showed activities against another microorganisms, like fungi (BISOLI et al, 2008), bacteria (ANGEH et al, 2007a;ANGEH et al, 2007b;SONGCA, RAMURAFHI;OLUWAFEMI, 2013), viruses (ASRES;BUCAR, 2005) and other species of parasites (TELES et al, 2011;HAAVIKO et al, 2014).…”

Section: Resultsmentioning

confidence: 99%

In Vitro Antiplasmodial Activity of Flower Extracts From Combretum Leprosum Mart (Mofumbo)

Passarini

Medeiros

Meneguetti

et al. 2016

CeN

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Malaria is the cause of hundreds of thousands of deaths per year, besides putting billions of people at risk of developing disease. When it comes to its therapy, the drugs used currently are losing its efficacy due to increase in the frequency of resistant strains of the parasite, highlighting the importance for the search of new classes of molecules presenting antiplasmodial activity. In the present work, the antiplasmodial activities of five extracts (crude, hexane, chloroform, ethyl acetate and methanol) from the flowers of Combretum leprosum are assessed. The method employed for obtaining the extracts was silica gel column chromatography, and the techniques used for the analysis of antiplasmodial activity (IC 50 ) and citotoxicity (MLD 50 ) were ELISA and MTT respectively, where a selectivity index was calculated after the obtaining of these two values. The extract presenting the highest antiplasmodial activity was the chloroform extract (IC 50 = 3.97 µg/mL), however, this extract also presented the higher cytotoxicity (MLD 50 = 18.12 µg/mL), and therefore the extract presenting the best overall activity was the methanolic extract (IS = 18.97 IntrodutionOver 3 billion people are estimated to be at risk of being infected with malaria and therefore developing disease, and according to latest estimates, hundreds of thousands of deaths caused by it occurred in each year of this millennium (WHO, 2014). The world region that suffers the heaviest burden is Africa, where the great majority of cases of malaria occur, mainly in children under the age of five (WHO, 2014). The disease is caused by parasitic protozoa of the genus Plasmodium, of which five species are known to infect humans: P. falciparum, P. vivax, P. malariae, P. ovale, and P. knowlesi (COX, 2010). The parasite life cycle begins when a female mosquito of Anopheles genus bites a human and releases the sporozoites from its salivary glands to the dermis, where they reach the avascular tissue and then a percentage of them migrates and enters the blood vessels, making their way to the liver, where they undergo cellular modifications and perform rounds of asexual replication (ALY; VAUGHAN; KAPPE, 2009).After leaving the liver, the parasite begins other cycles of asexual replication inside red blood cells, using molecules and cellular structures of the host cells to survive, grow and reproduce, generating thousands of merozoites and causing the characteristic symptoms of the disease (TILLEY; DIXON; KIRK, 2011). When it comes to its chemotherapy, most of the cases of uncomplicated malaria are treated currently by the use of ACT's drugs, although is already known that these drugs are losing its efficacy due to the increase in frequency of resistant strains (VISSER; VUGT; GROBUSCH, 2014), which highlights the importance for the search of new molecules bearing antiplasmodial activity.Plants have been used during millennia by humanity, and pharmacological studies of medicinal plants yielded useful molecules in the treatment of various diseases, includ...

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“…4 C. leprosum roots and leaves led to the isolation of arjunolic and mollic acids, 3β,6β,16β-trihydroxylup-20(29)-ene (2), together with the glycosilated flavonoids 3-O-methylquercetin and quercetrin. 5 Arjunolic acid (2α, 3β, 23-trihydroxyolean-12-en-28-oic acid, 1) was first isolated from Terminalia arjuna (Combretaceae), which has been used as a cardiac tonic by native Ayurvedic Indian people for centuries. 6 A patent based on the hormonal, wound healing and bactericide (particularly Mycobacterium tuberculosis and M. leprae) properties of arjunolic acid and its isomer, asiatic acid (2α, 3β, 23-trihydroxyursan-12-en-28-oic acid, 3) was deposited 7 and, since then, a series of other biological activities of arjunolic acid were described.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Arjunolic acid in the ethanolic extract of Combretum leprosum root and its use as a potential multi-functional phytomedicine and drug for neurodegenerative disorders: anti-inflammatory and anticholinesterasic activities

Facundo¹,

Rios²,

Medeiros³

et al. 2005

J. Braz. Chem. Soc.

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Os extratos etanólicos das folhas e raízes de Combretum leprosum Mart. & Eicher (Combretaceae) foram investigados por CGAR-EM, após derivatização com BSTFA/ TMCS. Mono e oligossacarídeos, ácidos graxos e triterpenos foram identificados como componentes majoritários. Análise quantitativa por padronização externa revelou a presença de 65% de ácido arjunólico (1) no extrato etanólico das raízes secas. Foram observadas atividades anti-inflamatória, antinociceptiva e anticolinesterásicas (AChE e BuChE) para o extrato das raízes e para o ácido arjunólico, descortinando uma nova classe de produtos naturais no tratamento da doença de Alzheimer através de drogas multifuncionais.Combretum leprosum Mart. & Eicher (Combretaceae) leaves and roots ethanolic extracts were investigated by HRGC-MS and showed mono-and oligosaccharides, fatty acids and triterpenes as major compounds after derivatization with BSTFA/ TMCS. Arjunolic acid (1) was quantified on dried roots ethanolic extract (65%) by external standard. Anti-inflammatory, antinociceptive and anticholinesterasic (AChE and BuChE) activities were observed for roots ethanolic extract of C. leprosum and arjunolic acid, suggesting both as promising targets for the development of innovative multi-functional medicines for Alzheimer desease treatment.Keywords: Combretum leprosum, Combretaceae, HRGC-MS, arjunolic acid, anti-inflammatory, cholinesterase inhibitor IntroductionCombretum leprosum Mart. & Eicher (Combretaceae), native from Brazil, is a widely distributed shrub in Brazilian Caatinga from Piauí to Bahia states and is commonly known as "mofumbo". 1 It is used by local people on the cicatrisation of wounds, in the treatment of haemorrhages or as a sedative, 2 and the analgesic property of the ethanolic stem barks extract was recently described. 3 Braz-Filho et al. 4 studied two genera of Combretaceae.From Thiloa glaucocarpa they isolated arjunolic acid (1) and from Combretum sp., 3,3',4,5-tetra-Omethylflavellagic acid, ethyl β-D-glucopyranoside and arjunglucoside. 4 C. leprosum roots and leaves led to the isolation of arjunolic and mollic acids, 3β,6β,16β-trihydroxylup-20(29)-ene (2), together with the glycosilated flavonoids 3-O-methylquercetin and quercetrin. 5 Arjunolic acid (2α, 3β, 23-trihydroxyolean-12-en-28-oic acid, 1) was first isolated from Terminalia arjuna (Combretaceae), which has been used as a cardiac tonic by native Ayurvedic Indian people for centuries. 6 A patent based on the hormonal, wound healing and bactericide (particularly Mycobacterium tuberculosis and M. leprae) properties of arjunolic acid and its isomer, asiatic acid (2α, 3β, 23-trihydroxyursan-12-en-28-oic acid, 3) was deposited 7 and, since then, a series of other biological activities of arjunolic acid were described. 8 Continuing our search for anti-inflammatory and anticholinesterasic agents from natural sources, 9 we found Combretum leprosum as an interesting investigation target. It merged from the relatively few reported information about pharmacological profile of C. leprosum and the s...

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Triterpenes and flavonoids from Combretum leprosum

Cited by 58 publications

References 7 publications

Phytochemical Constituents of Combretum Loefl. (Combretaceae)

Phytochemical Constituents of Combretum Loefl. (Combretaceae)

In Vitro Antiplasmodial Activity of Flower Extracts From Combretum Leprosum Mart (Mofumbo)

Arjunolic acid in the ethanolic extract of Combretum leprosum root and its use as a potential multi-functional phytomedicine and drug for neurodegenerative disorders: anti-inflammatory and anticholinesterasic activities

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