Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives

Csuk, René; Niesen-Barthel, Anja; Schäfer, Renate; Barthel, Alexander; Al‐Harrasi, Ahmed

doi:10.1016/j.ejmech.2015.01.039

Cited by 31 publications

(26 citation statements)

References 68 publications

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“…Frankincense was bought from different commercial suppliers in bulk quantities. The SRB assays were performed as previously reported 6,8,34 . NMR assignments were in full agreement with data previously published.…”

Section: Methodsmentioning

confidence: 99%

“…Analyses of commercial samples reported for -boswellic acid (-derivatives) up to 10.1% of BA (1, -boswellic acid), 6.8% of ABA (2, 3-O-acetyl--boswellic acid), 5.1% of -KBA (3, 11-keto--boswellic acid) and 3.8% of AKBA (4, 3-O-acetyl-11-keto--boswellic acid) in frankincense 4 . These values vary highly in practice, and they strongly depend on the quality of the resin, its origin, the time of harvesting and from the species of boswellia ( Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Because of these limitations, the number of publications dealing with synthetic transformations 2, 6-8 of boswellic acids remained low compared to the number of publications on frankincense; even less is known about the cytotoxicity of BA and derivatives 6,[8][9][10][11][12][13] . Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and cytotoxic screening of beta-boswellic acid derivatives

et al. 2017

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Beta-boswellic acids are triterpenoids being generic to the plants of genus boswellia. Although they were shown to exhibit different biological activities, the cytotoxic potential of b-boswellic acid derivatives remained by and large unexploited. To expand the potential of these compounds we developed simple procedures for the interconversion of the most important b-boswellic acids 1-4 and prepared several other derivatives 5-48. These compounds were screened for their cytotoxic activity in sulforhodamine B assays employing several human tumor cell lines and nonmalignant mouse fibroblasts. One of these compounds, a difluoromethylester of 3-O-acetyl-11-keto-beta-boswellic acid 23, was cytotoxic for human breast adenocarcinoma cells MCF-7 (EC50 = 6.5 mM) while being significantly less cytotoxic for the mouse fibroblasts.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and cytotoxic screening of beta-boswellic acid derivatives

et al. 2017

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“…20 Frankincense was bought from different commercial suppliers in bulk quantities, and the SRB assays were performed as previously reported 15,16 . 3-O-Acetyl-11-keto--boswellic acid (1, AKBA) was isolated following a modified Jauch's procedure 21 , and (3, 4) 3-hydroxy-11-oxo-urs-12-en-24-oic acid (= 11-keto-boswellic acid, 2, KBA) was prepared as reported.…”

Section: Methodsmentioning

confidence: 99%

“…Several studies revealed these pentacyclic triterpenoids to have antitumor activity [10][11][12] . While the cytotoxicity of 1 or 2 is low, derivatives of AKBA or KBA showed significant higher activity 5,11,[13][14][15][16][17][18][19][20] .…”

Section: Introductionmentioning

confidence: 99%

β-11-Keto-boswellic acid derived amides: synthesis and cytotoxicity

et al. 2017

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The aim of this study was to prepare 11-keto-β-boswellic acid derivatives modified at C-24 and to evaluate their in vitro cytotoxicity. Acetyl-11-keto-β-boswellic acid (AKBA) was isolated from frankincense and transformed into 11-keto-β-boswellic acid (KBA). Both compounds served as starting materials for the synthesis of several amides or hydrazides. The derivatives were fully characterized, and their cytotoxicity was evaluated in vitro using sulforhodamine B (SRB) assays employing two human tumor cell lines (A2780 and MCF7) as well as nonmalignant mouse fibroblasts (NIH 3T3). Nearly all of the compounds were more cytotoxic than their parent compounds. The highest cytotoxicity was observed for (3 α, 4 β) 3-acetyloxy-N-(3- aminopropyl)-11-oxo-urs-12-en-24-amide (15) and (3 α, 4 β) 3-acetyloxy-N-[4-(3-aminopropyl)piperazin-1-yl]- propyl-11-oxo-urs-12-en-24-amide (16) and the ovarian carcinoma cell line A2780. These compounds showed EC50 = 1.0-1.7 µM while being significantly less toxic for the mouse fibroblasts NIH 3T3 (EC50 = 9.3-16.3µM). Thus, compounds 15 and 16 have good antitumor effects and may serve as starting points for developing potential and selective antitumor agents

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Synthesis of Novel Acetyl‐11‐keto‐β‐boswellic Acid Derivatives as Potential Anti‐GBM Agents

Sun,

Zhang,

Wang

et al. 2024

Chemistry & Biodiversity

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Acetyl‐11‐keto‐β‐boswellic acid (AKBA) is known to inhibit the growth of glioblastoma (GBM) cells and subcutaneous GBM. A series of acetyl‐11‐keto‐β‐boswellic acid (AKBA) derivatives containing the oxime‐ester functionality or amide side chains were synthesized, and their anti‐GBM activities were evaluated. Some of these compounds exhibited significant inhibitory activity against cell proliferation in U87 and U251 GBM cell lines, with IC50 values in the micromolar concentration range. Cellular thermal shift analysis showed that A‐01 and A‐10 improved the thermal stability of FOXM1, indicating that these highly active compounds may directly bind to FOXM1 in cells. Docking studies of the two most active compounds, A‐01 and A‐10, revealed key interactions between these compounds and the active site of FOXM1, in which the amide moiety at the C‐24 position was essential for improving the activity. These results suggested that A‐10 is a suitable lead molecule for the development of FOXM1 inhibitors. Thus, the rational design of AKBA derivatives with amide side chains holds significant potential for discovering of a new class of triterpenoids capable of inhibiting GBM cell proliferation.

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Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives

Cited by 31 publications

References 68 publications

Synthesis and cytotoxic screening of beta-boswellic acid derivatives

Synthesis and cytotoxic screening of beta-boswellic acid derivatives

β-11-Keto-boswellic acid derived amides: synthesis and cytotoxicity

Synthesis of Novel Acetyl‐11‐keto‐β‐boswellic Acid Derivatives as Potential Anti‐GBM Agents

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