Oleanonic acid from Lippia lupulina (Verbenaceae) shows strong in vitro antileishmanial and antitrypanosomal activity

Funari, Cristiano Soleo; Almeida, Letícia de; Passalacqua, Thaís Gaban; Martínez, Isabel; Ambrósio, Daniela Luz; Cicarelli, Regina Maria Barretto; Silva, Dulce Helena Siqueira; Graminha, Márcia Aparecida Silva

doi:10.1590/1809-4392201600204

Cited by 18 publications

(10 citation statements)

References 33 publications

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“…iowensis DSM 45197 as biocatalysts of the OA (approximately 0.3 g/L) transformation process for 13 days resulted in the formation of methyl OA ( 91 ) as the main bioconversion product (more than 60.0%), small amounts (≤5.0%) of methyl 3-oxo-olean-12-en-28-oat ( 92 ), and metabolite 93 unidentified by the authors [ 16 ]. 3-oxo-OA ( 92 ) was shown to have pronounced antimelanoma [ 124 ], antileishmanial, and antitrypanosomal effects [ 125 ]. Despite numerous successful examples to increase the efficiency of the biotransformation process by immobilizing microbial cells [ 126 ], the use of fixed Nocardia cells in alginate carriers led to a decrease in their catalytic activity, as confirmed by a 10-fold decrease in the formation of compound 91 and only a short-term occurrence of compound 93 in the culture medium [ 16 ].…”

Section: Biological Transformationmentioning

confidence: 99%

Biotransformation of Oleanane and Ursane Triterpenic Acids

2020

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Oleanane and ursane pentacyclic triterpenoids are secondary metabolites of plants found in various climatic zones and regions. This group of compounds is highly attractive due to their diverse biological properties and possible use as intermediates in the synthesis of new pharmacologically promising substances. By now, their antiviral, anti-inflammatory, antimicrobial, antitumor, and other activities have been confirmed. In the last decade, methods of microbial synthesis of these compounds and their further biotransformation using microorganisms are gaining much popularity. The present review provides clear evidence that industrial microbiology can be a promising way to obtain valuable pharmacologically active compounds in environmentally friendly conditions without processing huge amounts of plant biomass and using hazardous and expensive chemicals. This review summarizes data on distribution, microbial synthesis, and biological activities of native oleanane and ursane triterpenoids. Much emphasis is put on the processes of microbial transformation of selected oleanane and ursane pentacyclic triterpenoids and on the bioactivity assessment of the obtained derivatives.

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Section: Biological Transformationmentioning

confidence: 99%

Biotransformation of Oleanane and Ursane Triterpenic Acids

2020

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“…The isolated compounds (Holaphylline, Saracodine) were evaluated for anti-leishmanial activity. From the viable promastigotes, bulk culture (3.7×10 7 /mL), 1×10 5 promastigotes/well in 200 µL fresh M-199 medium were seeded in 96-well plate. Four concentrations of the compounds were prepared and the control was placed in one row of 12 wells having only the growth medium.…”

Section: Anti-promastigote Potential For Isolated Compoundsmentioning

confidence: 99%

“…Plant based medicines are being claimed as one of the important source for the development of drug in treating leishmaniasis diseases. 5 Many research studies showed that many plants extract and thire derived possess anti-leishamanial activity against different species of Leishmania. 5 In the same way one of the plant belongs to Sarcococca species of Buxaceae family have rich source of steroidal alkaloids that possess different biological activities in endemic region of Pakistan.…”

Section: Introductionmentioning

confidence: 99%

“…5 Many research studies showed that many plants extract and thire derived possess anti-leishamanial activity against different species of Leishmania. 5 In the same way one of the plant belongs to Sarcococca species of Buxaceae family have rich source of steroidal alkaloids that possess different biological activities in endemic region of Pakistan. 6 Sarcococca saligna (D.Don) Muel belongs to family of Buxaceae, that exist in the northern areas of Pakistan.…”

Section: Introductionmentioning

confidence: 99%

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Potential Effect of Steroidal Alkaloids from Sarcococca saligna against Leishmania tropica

Jan¹,

Ahmad²,

Kifayatullah³

et al. 2019

IJPER

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Background and Objectives: Sarcococca species have a rich source of steroidal alkaloids that possess different biological and pharmacological activities. Hence, present research was design to isolate the steroidal alkaloid from Sarcococca saligna and to evaluate it for in-vitro antileishmanial activity. Materials and Methods: Compound Holaphylline and Saracodine were isolated through column chromatography followed by spectroscopic techniques for elucidation and were assayed against promastigotes of Leishmania tropica. Results: Saracodine compound eliminates 71.12%, 63.9%, 54.18% and 38.88% of the promastigotes at concentration 100 µM; 75 µM, 50 µM and (25 µM). While, the elimination of promastigotes with compound holaphylline were 82.5%, 76.68%, 65%, 47.22% respectively as compared to untreated group. Conclusion: In present study, compound Holaphylline and Saracodine exhibited inhibition against the promastigotes and justified the claimed medicinal importance of Sarcococca saligna as a remedy for leishmaniasis especially against Leishmania tropica.

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“…The mass spectrum of the obtained compound corresponded to the mass spectrum of the methyl ester of 3-oxo-olean-12-en-28-oic acid. It is known that 3-oxo-olean-12-en-28-oic acid has a pronounced in vivo antimelanoma [7] and in vitro antileishmanial and antitripanosomal effects [8]. The literature describes the formation of 3-oxoolean-12-en-28-oic acid using actinobacteria Nocardia iowensis DSM 45197 as a biocatalyst.…”

mentioning

confidence: 99%

Actinobacterial Transformation of Oleanane Triterpenoids

Luchnikova¹,

Ivanova²,

Tarasova³

et al. 2021

Фундаментальные И Прикладные Аспекты Биоинформатики, Биотехнологии И Недропользования

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Drugs derived from secondary plant metabolites make up about 25% of the global pharmaceutical market [1]. Oleanane pentacyclic triterpenoids, in particular oleanolic (OA) and glycyrrhetinic (GA) acids, are the most of interest for researchers in medical chemistry and used to obtain derivatives with pronounced antiviral, antimicrobial, anti-inflammatory, antitumor, and hepatoprotective activities. Along with chemical synthesis, biological methods of OA and GA transformations have been actively developing, which allow to obtain valuable derivatives without the use of aggressive reagents and can be carried out under normal temperature, pressure and pH values. Furthermore, microbial conversion ensures selective modifications of triterpenic molecule sites that are either not modified or poorly modified by chemical transformations [2]. Among the known microbial biocatalysts, members of mycelial fungi are the most studied, but their use on a preparative scale is technologically impossible and dangerous due to the mycelial type of their growth and the ability to produce mycotoxins with pronounced mutagenic and carcinogenic effects. Whereas bacterial catalysts are only represented by a few species of Bacillus, Nocardia and Streptomyces genera, including pathogens, exhibiting catalytic activity at a concentration of OA and GA no more than 0.3 g/L [3]. In this context, it is essential to search for new non-pathogenic bacterial strains able to carry out site-directed transformations of OA and GA. One of the intensively studied groups of microorganisms in terms of biotechnological application is non-pathogenic actinobacteria. Nonmycelial growth, synthesis of biosurfactants, the ability to grow on minimal media, a flexible metabolic system and high oxygenase activity determine the prospects for actinobacteria to be used as perspective biocatalysts for biotransformation of OA and GA [4]. Moreover, the ability of actinobacteria of genus Rhodococcus to transform pentacyclic triterpenoid betulin with formation of betulone was previously shown [5]. In this work, 76 strains of actinobacteria from the Regional Specialized Collection of Alkanotrophic Microorganisms (official acronym IEGM; the World Federation of Culture Collections number 285; the Unique Research Facility number 73559; www.iegmcol.ru) belonging to the species Corynebacterium ammoniagenes (1), C. glutamicum (1), Gordonia terrae (4), R. aetherivorans (1), R. cercidiphylli (1), R. erythropolis (14), R. fascians (2), R. jostii (3), R. opacus (15), R. qingshengii (2), R. rhodochrous (6) and R. ruber (26) were used. OA (≥98%, Acros Organics, USA) and GA (≥98%, Shanghai Yuanye Bio-Technology Co, China), dissolved in dimethyl sulfoxide (1:10 mg/μL), were used at a concentration of 1.0 g/L.Bacterial cells were visualized and their morphometric parameters were measured using an Axio Imager M2 microscope (Zeiss, Germany) equipped with an Axiocam 506 Color camera (Zeiss, Germany) in phase contrast mode with a magnification of x1000. To determine the localization of enzymes, crude...

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Oleanonic acid from Lippia lupulina (Verbenaceae) shows strong in vitro antileishmanial and antitrypanosomal activity

Cited by 18 publications

References 33 publications

Biotransformation of Oleanane and Ursane Triterpenic Acids

Biotransformation of Oleanane and Ursane Triterpenic Acids

Potential Effect of Steroidal Alkaloids from Sarcococca saligna against Leishmania tropica

Actinobacterial Transformation of Oleanane Triterpenoids

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