Chemical modifications of natural triterpenes—glycyrrhetinic and boswellic acids: evaluation of their biological activity

Rao, G. Sasibhushana; Kondaiah, Paturu; Singh, Sanjay K.; Ravanan, Palaniyandi; Sporn, Michael B.

doi:10.1016/j.tet.2008.10.035

Cited by 59 publications

(41 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Many data from the literature link GAinduced cytotoxic effects in cancer cells to proapoptotic stimuli [22,25]. Some GA derivatives display higher proapoptotic effects than GA itself [27][28][29][30], some of which are attributable to activation of the non-steroidal antiinflammatory drug-activated gene-(NAG-1) related proapoptotic protein [31]. The induction of apoptosis by GA relies, at least partly, on modifications of mitochondrial membrane permeability that result in cytochrome c release and caspase-3 activation [32,33].…”

Section: Historical Overview Of the Anticancer Potential Of Glycyrrhementioning

confidence: 99%

“…It appears that the most effective compound in terms of in vitro anticancer activity are compounds containing a cyano C-2, oxidated C-3 and an esterified C-30 carboxyl group ( Table 1; entry 6) [27,42]. Additional SAR analyses underscored the importance of the alcohol functional group at C-3 and its oxidized form ( Table 1; entries 6-8) [30,43].…”

Section: Sar Analyses Of Glycyrrhetinic Acid and Its Derivatives As Amentioning

confidence: 99%

See 1 more Smart Citation

Structure-Activity Relationship Analyses of Glycyrrhetinic Acid Derivatives as Anticancer Agents

Lallemand¹,

Gelbcke²,

Dubois³

et al. 2011

MRMC

View full text Add to dashboard Cite

Cancer cell resistance to kinase inhibitors and targeted agents, acquisition of a multidrug-resistant (MDR) phenotype and/or intrinsic resistance to apoptosis prevent effective treatment in about 50% of solid cancers in adults, and the percentage is even higher in children. Glycyrrhetinic acid (GA) and some of its derivatives may offer hope in combating cancer types associated with poor prognoses. Some GA derivatives are indeed able to target both the proteasome and peroxisome proliferator-activated receptors (PPARs), two proteins that play major roles in cancer cell biology but are not related to MDR and/or apoptosis-related resistance phenotypes.

show abstract

Section: Historical Overview Of the Anticancer Potential Of Glycyrrhementioning

confidence: 99%

Section: Sar Analyses Of Glycyrrhetinic Acid and Its Derivatives As Amentioning

confidence: 99%

Structure-Activity Relationship Analyses of Glycyrrhetinic Acid Derivatives as Anticancer Agents

Lallemand¹,

Gelbcke²,

Dubois³

et al. 2011

MRMC

View full text Add to dashboard Cite

show abstract

“…Recrystallization from methanol yielded 3 (29.09 g, 91.1%) as a colourless crystalline solid; mp 254-2588C (lit. 254-2588C [12], 254-2568C [17], 248-2508C [18,19] Methyl 3b-hydroxy-oleana-9(11),12-dien-30-oate (4) To a solution of 3 (240 mg, 0.49 mmol) in dry THF (10 mL), borane (1 M in THF, 7 mL, 7 mmol) was slowly added. After 20 h of stirring at 258C, ethyl acetate (25 mL) was added and the organic layer was washed with a solution of citric acid (10%), a saturated solution of sodium hydrogen carbonate and water.…”

Section: Methyl 3b-hydroxy-11-oxo-olean-12-en-30-oate (3)mentioning

confidence: 99%

Does One Keto Group Matter? Structure‐Activity Relationships of Glycyrrhetinic Acid Derivatives Modified at Position C‐11

Csuk¹,

Schwarz²,

Kluge³

et al. 2011

Archiv der Pharmazie

View full text Add to dashboard Cite

Several triterpenoic acids display a remarkable cytotoxicity on tumor cells. Glycyrrhetinic acid - the main content of the licorice root - possesses an apoptotic effect on tumor cells. Previous studies pointed out the presence of a keto group at position C-11 in glycyrrhetinic acid derivatives as the main reason for its apoptotic activity. Several pairs of derivatives were synthesized differing only at position C-11. These compounds were tested in a sulforhodamine B colorimetric assay for cytotoxicity screening on 12 tumor cell lines and mouse embryonic fibroblasts (NIH3T3). Our results show that there is no direct relation between the existence of the C-11 keto group and the apoptotic activity of the compounds.

show abstract

“…Glycyrrhetinic acid and their derivatives have been used for along time in traditional medicines for the treatment of hepatic ailments, pulmonary and allergies [1,2]. The broad spectrum comprises antioxidative, antiproliferative, antiulcer, cytotoxic, antiinflammatory and endocrine activities [3,4]. The asymmetric unit of the title crystal structure consists of one 7b,15a-dihydroxy-18b-glycyrrhetinic acid (3b,7b,15a-trihydroxy-11-oxo-18b,20b-olean-12-en-30-oic acid) molecule, one waterm olecule and one chloroform molecule.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3β,7β,15α-trihydroxy-11-oxo-18β,20β-olean-12-en-30- oic acid – chloroform – water (1:1:1), C30H46O6 · CHCl3 · H2O

He¹,

Hua²,

Li³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Source of materialStock cultures of Absidia coerulea AC307 was stored on potato dextrose agar slants (PDA) at 4°C. The spores of A. coerulea AC307 were gained by washing the slant agar using sterilized water. Then the suspension of certain spore concentration was transferred into the sterilized liquid medium. The composition of the medium was as follows (g/L): glucose 10.5, yeast extract 2.5, corn porridge 12.0, (NH 4 ) 2 SO 4 5.0. The experiment was conducted in 250 mL shake flasks containing 30 mL culture media inoculated with A. coerulea AC307. The flasks were shaken at 28°Cand 150 rpm for 19 h. Then the rotation speed was changed to 170 rpm for the rest of time. Glycyrrhetinic acid was dissolved in ethanol (100 g/L) and distributed among the flasks (0.2 g/L) and the reaction was allowed to proceed for 24 h. The mycelium was then removed by filtration, and the biomass was extracted with EtOAc (100 mL) for 5min in an ultrasonic bath and filtered again. The broth was extracted with the same solvent (3 × 100 mL) and all extracts were combined and dried anhydrous Na 2SO4.A fter filtration, the solvents were evaporated under reduced pressure. Controls were carried out in order to verify the action of the medium (without fungi) on the substrates and the presence of similar metabolites on the fungi cultures (without substrates). The crude extracts were purified by Si gel column using petroleum ether/acetone (9:2, v/v). The white powder was diffused with petroleum ether/chloroform (2:1, v/v)a tr oom temperature. Colourless prismatic crystals suitable for X-ray analysis were obtained. Experimental detailsHatoms of water molecule were located from difference Fourier maps and refined freely. All Hatoms bound to Catoms and on hydroxy Oa toms were generated geometrically and refined as riding with. The Flack paremeter of 0.06 (13) is in agreement with the absolute configuration of the known absolute configuration. DiscussionGlycyrrhetinic acid is apentacyclic triterpenoid derivative of the b-amyrin type. Glycyrrhetinic acid and their derivatives have been used for along time in traditional medicines for the treatment of hepatic ailments, pulmonary and allergies [1,2]. The broad spectrum comprises antioxidative, antiproliferative, antiulcer, cytotoxic, antiinflammatory and endocrine activities [3,4]. The asymmetric unit of the title crystal structure consists of one 7b,15a-dihydroxy-18b-glycyrrhetinic acid (3b,7b,15a-trihydroxy-11-oxo-18b,20b-olean-12-en-30-oic acid) molecule, one waterm olecule and one chloroform molecule. The 7b,15a-dihydroxy-18b-glycyrrhetinic acid has five fused six-membered rings (A/B/C/D/E). The cyclohexane rings A, B and E are in chair conformation, cyclohexene ring C is in an envelope conformation. The D and E rings are cis-fused. The other ring junctions are trans-fused. The torsion angle of C5-C6-C7-O2 (-176.3(2)°)indicates that the 7-hydroxy is b configuration. The 15-hydroxy is b configuration with the torsion angle C13-C14-C15-O3 of -158.6(2)°.The orientation of the carboxylic acid group with ...

show abstract

Chemical modifications of natural triterpenes—glycyrrhetinic and boswellic acids: evaluation of their biological activity

Cited by 59 publications

References 19 publications

Structure-Activity Relationship Analyses of Glycyrrhetinic Acid Derivatives as Anticancer Agents

Structure-Activity Relationship Analyses of Glycyrrhetinic Acid Derivatives as Anticancer Agents

Does One Keto Group Matter? Structure‐Activity Relationships of Glycyrrhetinic Acid Derivatives Modified at Position C‐11

Crystal structure of 3β,7β,15α-trihydroxy-11-oxo-18β,20β-olean-12-en-30- oic acid – chloroform – water (1:1:1), C30H46O6 · CHCl3 · H2O

Contact Info

Product

Resources

About