Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines

Baratto, Leopoldo Clemente; Porsani, Mariana Vieira; Pimentel, Ida Chapaval; Netto, Adaucto B. Pereira; Paschke, Ralf; Oliveira, Brás Heleno de

doi:10.1016/j.ejmech.2013.07.012

Cited by 48 publications

(33 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…in the acetylation of the C‐3 hydroxyl of BA, giving 28 . Other derivatives ( 29–32 ) bearing a hydrazone, ketone, oxime, and oxime ether at C‐3 have been reported …”

Section: Chemistry Of Betulinic Acid and Its Derivativesmentioning

confidence: 99%

Betulinic Acid and its Derivatives as Potential Antitumor Agents

Zhang

Wang

et al. 2015

Medicinal Research Reviews

163

View full text Add to dashboard Cite

Betulinic acid (BA) is a lupane-type pentacyclic triterpene, distributed ubiquitously throughout the plant kingdom. BA and its derivatives demonstrate multiple bioactivities, particularly an antitumor effect. This review critically describes the recent research on isolation, synthesis, and derivatization of BA and its natural analogs betulin and 23-hydroxybetulinic acid. The subsequent part of the review focuses on the current knowledge of antitumor properties, combination treatments, and pharmacological mechanisms of these compounds. A 3D-QSAR analysis of 62 BA derivatives against human ovarian cancer A2780 is also included to provide information concerning the structure-cytotoxicity relationships of these compounds.

show abstract

“…in the acetylation of the C‐3 hydroxyl of BA, giving 28 . Other derivatives ( 29–32 ) bearing a hydrazone, ketone, oxime, and oxime ether at C‐3 have been reported …”

Section: Chemistry Of Betulinic Acid and Its Derivativesmentioning

confidence: 99%

Betulinic Acid and its Derivatives as Potential Antitumor Agents

Zhang

Wang

et al. 2015

Medicinal Research Reviews

163

View full text Add to dashboard Cite

show abstract

“…biotransformed 154 to 156 and methyl 3-oxolup-20(29)-en-28-oate ( 157 ), and P. citreonigrum transformed 156 to methyl 3-hydroxylup-20(29)-en-28-oate ( 158 ). Biotranformation of 156 with carrot cell yielded 3-hydroxy-(20 R )-29-oxolupan-28-oic acid ( 159 ) in 14 days [57]. These biotransformations are shown in Figure 44.…”

Section: Microbial Transformation Of Natural and Semi-synthetic Pementioning

confidence: 99%

Microbial-Catalyzed Biotransformation of Multifunctional Triterpenoids Derived from Phytonutrients

Shah

Tan

Sultan

et al. 2014

IJMS

View full text Add to dashboard Cite

Microbial-catalyzed biotransformations have considerable potential for the generation of an enormous variety of structurally diversified organic compounds, especially natural products with complex structures like triterpenoids. They offer efficient and economical ways to produce semi-synthetic analogues and novel lead molecules. Microorganisms such as bacteria and fungi could catalyze chemo-, regio- and stereospecific hydroxylations of diverse triterpenoid substrates that are extremely difficult to produce by chemical routes. During recent years, considerable research has been performed on the microbial transformation of bioactive triterpenoids, in order to obtain biologically active molecules with diverse structures features. This article reviews the microbial modifications of tetranortriterpenoids, tetracyclic triterpenoids and pentacyclic triterpenoids.

show abstract

“…As mentioned in Figure 1: betulin has three most prominent positions where chemical modifications can be easily accomplished, namely primary hydroxyl group at position C-28, secondary hydroxyl group at position C-3, and alkene moiety at position C-20.The bio-chemical modifications at positions C-28 of the parent structure of betulin produces betulinic acid [12,27,[38][39][40][41]. The chief source of Betulin is bark of Birch trees, belonging to family Betulaceae the family of flowering plants.…”

Section: Occurrence Of Betulin In Naturementioning

confidence: 99%

Betulin, a Pentacyclic Tri-Terpenoid: An Hour to Rethink the Compound

Singh¹

2017

OAJTMR

View full text Add to dashboard Cite

Betulin, a pentacyclic triterpenoid member of lupane family occurs widely in numerous plants. Betulin, unlike most other constituents is easily isolated that it can be utilized for various pharmacological actions. It is interesting to know that betulin can be easily extracted from bark, stem, leaves, flower, roots etc. of the plant. This review summarizes plethora of reliable pharmacological activities like antiinflammatory, anti-ulcer, anti-diabetic, anti-bacterial, anti-microbial, anti-malarial, anti-viral, anti hyperlipidaemic, anti-cancer and anti HIV exhibited by betulin and its derivatives. For this it can be utilized in herbal as well as synthetic pharmaceutical industries because of its promising efficacy and low levels of toxicity. Although betulin possess a wide range of pharmacological activities, there is still lack of awareness of its proper utilization in the field of medicine. So, need of the hour is to refocus on naturally occurring betulin and its derivatives to avoid side effects caused by synthetic compounds utilized in treating various ailments. Therefore, the aim of the present review is to re-explore the potential of betulin, as an alternative to the compounds possessing higher side effects. Keywords: Table1:Represents the physical properties of betulin [1,30,31] Occurrence of Betulin in NatureBetulin has long been explored by research scientist because of the fact that it has anticancer properties [35,36] and its derivative Betulinic acid is favored due to its anti-HIV activity [12,6,37]. As mentioned in Figure 1: betulin has three most prominent positions where chemical modifications can be easily accomplished, namely primary hydroxyl group at position C-28, secondary hydroxyl group at position C-3, and alkene moiety at position C-20.The bio-chemical modifications at positions C-28 of the parent structure of betulin produces betulinic acid [12,27,[38][39][40][41]. The chief source of Betulin is bark of Birch trees, belonging to family Betulaceae the family of flowering plants. Mostly placed in order Fagales, it can also be placed in order Betulales. The subfamilies include Betuloideae genera Betula (birch), Alnus (alder) and Coryloideaegenera Carpinus (hornbeam), Corylus (hazel), Ostrya and Ostryopsis [42][43][44]. Betulin, a pentacyclictriterpenoid is derived from linear hydrocarbon squalene [31]. Triterpenes have three main classes oleane, ursane and lupane triterpenes. Lupane class comprises betulin, betulinic acid, lupeol [6,45]. Triterpenes are used as traditional herbal medicine and the esters of betulin and fatty acids are used in the production of cosmetics and as plasticizers for PVC [31,46] (Table 2). Pharmacological StudiesBetulin, as we all known till now possess vast pharmacological properties including choleritic, antihelmintic, powerful prophylactic, anti-HIV, antimutagene agent, antiviral, antifungal, anti-leukemia, anti-leishmanial, anti-inflammatory, immunomodulator activities. The latest research suggests some of the major pharmacological properties as discu...

show abstract

Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines

Cited by 48 publications

References 38 publications

Betulinic Acid and its Derivatives as Potential Antitumor Agents

Betulinic Acid and its Derivatives as Potential Antitumor Agents

Microbial-Catalyzed Biotransformation of Multifunctional Triterpenoids Derived from Phytonutrients

Betulin, a Pentacyclic Tri-Terpenoid: An Hour to Rethink the Compound

Contact Info

Product

Resources

About