Betulinic acid in the dilleniaceae and a review of its natural distribution

Pavanasasivam, Gowsala; Sultanbawa, M. Uvais S.

doi:10.1016/0031-9422(74)85143-5

Cited by 12 publications

(8 citation statements)

References 24 publications

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“…Koetjapic acid ( 1 ) together with betulinic acid ( 3 ) are suggested as the chemical markers of D. serrata . Betulinic acid has been reported from several genera of the Dilleniaceae family, including Dillenia , Wormia , and Acrotrema [ 16 ]. The presence of a considerable amount of betulinic acid in these genera suggests that this compound may be a chemotaxonomic marker of the family.…”

Section: Resultsmentioning

confidence: 99%

“…To the best of our knowledge, the phytochemistry and pharmacology of D. serrata have yet to be established and remain to be explored. Meanwhile, other Dillenia species such as D. indica , D. papuana , D. pentagyna , D. philippinensis , D. parviflora , and D. retusa have already been reported to contain several types of triterpenoids [ 15 , 16 , 17 , 18 , 19 ], flavonoids, and flavonoid glycosides [ 20 , 21 , 22 ], as well as phenolic compounds [ 21 , 23 ]. Bioactivities such as antimicrobial [ 18 , 24 , 25 , 26 ], anti-inflammatory [ 27 ], antinociceptive and antioxidant [ 26 , 28 ], antidiabetic and hypolipidemic [ 29 ], anti-leukemic [ 30 ], anti-tumor [ 23 , 31 ], anti-hypertension [ 32 ], and anti-protozoal [ 33 ] have been attributed to these species.…”

Section: Introductionmentioning

confidence: 99%

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Inhibitory Effect of Triterpenoids from Dillenia serrata (Dilleniaceae) on Prostaglandin E2 Production and Quantitative HPLC Analysis of Its Koetjapic Acid and Betulinic Acid Contents

et al. 2015

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The crude methanol extracts and fractions of the root and stem barks of Dillenia serrata Thunb. showed 64% to 73% inhibition on the production of prostaglandin E2 (PGE2) in lipopolysaccharide-induced human whole blood using a radioimmunoassay technique. Three triterpenoids isolated from the root bark of the plant, koetjapic (1), 3-oxoolean-12-en-30-oic (2), and betulinic (3) acids, exhibited significant concentration-dependent inhibitory effects on PGE2 production with IC50 values of 1.05, 1.54, and 2.59 μM, respectively, as compared with the positive control, indomethacin (IC50 = 0.45 μM). Quantification of compounds 1 and 3 in the methanol extracts and fractions were carried out by using a validated reversed-phase high performance liquid chromatography (RP-HPLC) method. The ethyl acetate fraction of the stem bark showed the highest content of both compound 1 (15.1%) and compound 3 (52.8%). The strong inhibition of the extracts and fractions on cyclooxygenase-2 (COX-2) enzymatic activity was due to the presence of their major constituents, especially koetjapic and betulinic acids.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inhibitory Effect of Triterpenoids from Dillenia serrata (Dilleniaceae) on Prostaglandin E2 Production and Quantitative HPLC Analysis of Its Koetjapic Acid and Betulinic Acid Contents

et al. 2015

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“…of /S-sitosterol-|3-d-glucoside (7).-Fraction 8 (2.3 g), when chromatographed on a column of silica gel (60 g, 70-230 mesh) eluted with chloroform, chloroform-methanol (97:3) and chloroform-methanol (19:1), afforded 3 fractions. The last fraction (1.6 g) on crystallization from chloroform yielded /3-sitosterol-d-D-glucoside (7) as a white powder (0.045 g, 0.003%), mp 292°d ec, [ ] -42°( c 0.4, pyridine) [Lit.…”

Section: Isolation and Identificationmentioning

confidence: 99%

3β-Hydroxy-28-P-Coumaroyloxy-lup-20(29)-en-27-oic Acid From Caraipa Densifolia

Gunasekera¹,

Cordell²,

Farnsworth³

1983

J. Nat. Prod.

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“…(Loranthaceae), Tectona grandis L. f. (Verbenaceae), Davilla rugosa and other species of Dilleniaceae family ( Dillenia , Wormia and Acrotrema ). Thus, BA may be considered as a chemotaxonomic marker for these families/genera [ 9 , 10 , 11 ]. This compound seems to be biosynthesized from lupeol (LU, Figure 1 ) by the cytochrome CYP716A12, which has been characterized as a multifunctional enzyme showing lupeol 28-oxidase activities.…”

Section: Introductionmentioning

confidence: 99%

Chemical Strategies towards the Synthesis of Betulinic Acid and Its More Potent Antiprotozoal Analogues

et al. 2021

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Betulinic acid (BA, 3β-hydroxy-lup-20(29)-en-28-oic acid) is a pentacyclic triterpene acid present predominantly in Betula ssp. (Betulaceae) and is also widely spread in many species belonging to different plant families. BA presents a wide spectrum of remarkable pharmacological properties, such as cytotoxic, anti-HIV, anti-inflammatory, antidiabetic and antimicrobial activities, including antiprotozoal effects. The present review first describes the sources of BA and discusses the chemical strategies to produce this molecule starting from betulin, its natural precursor. Next, the antiprotozoal properties of BA are briefly discussed and the chemical strategies for the synthesis of analogues displaying antiplasmodial, antileishmanial and antitrypanosomal activities are systematically presented. The antiplasmodial activity described for BA was moderate, nevertheless, some C-3 position acylated analogues showed an improvement of this activity and the hybrid models—with artesunic acid—showed the most interesting properties. Some analogues also presented more intense antileishmanial activities compared with BA, and, in addition to these, heterocycles fused to C-2/C-3 positions and amide derivatives were the most promising analogues. Regarding the antitrypanosomal activity, some interesting antitrypanosomal derivatives were prepared by amide formation at the C-28 carboxylic group of the lupane skeleton. Considering that BA can be produced either by isolation of different plant extracts or by chemical transformation of betulin, easily obtained from Betula ssp., it could be said that BA is a molecule of great interest as a starting material for the synthesis of novel antiprotozoal agents.

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Betulinic acid in the dilleniaceae and a review of its natural distribution

Cited by 12 publications

References 24 publications

Inhibitory Effect of Triterpenoids from Dillenia serrata (Dilleniaceae) on Prostaglandin E2 Production and Quantitative HPLC Analysis of Its Koetjapic Acid and Betulinic Acid Contents

Inhibitory Effect of Triterpenoids from Dillenia serrata (Dilleniaceae) on Prostaglandin E2 Production and Quantitative HPLC Analysis of Its Koetjapic Acid and Betulinic Acid Contents

3β-Hydroxy-28-P-Coumaroyloxy-lup-20(29)-en-27-oic Acid From Caraipa Densifolia

Chemical Strategies towards the Synthesis of Betulinic Acid and Its More Potent Antiprotozoal Analogues

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