- Synthesis of new boswellic acid derivatives as potential antiproliferative agents
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In the current investigation, a series of heterocyclic derivatives of boswellic acids were prepared along with new monomers of 3-O-acetyl-11-keto-β-boswellic acid (AKBA, 1) 11-keto-β-boswellic acid (KBA, 2) and several new bis-AKBA and KBA homodimers and AKBA-KBA heterodimers. The effects of these compounds on the proliferation of different human cancer cell lines, viz., FaDu (pharynx carcinoma), A2780 (ovarian carcinoma), HT29 (colon adenocarcinoma), and A375 (malignant melanoma), have been evaluated. Thus, KBA homodimer 21 effectively inhibited the growth of FaDu, A2780, HT29, and A375 cells with EC50 values below 9 μM. In addition, compounds 7, 8, 11, 12, 15, 16, and 17 also exhibited cytotoxic effects for A2780, HT29, and A375 cancer cells. In particular, the pyrazine analog 8 was highly cytotoxic for A375 cancer cells with an EC50 value of 2.1 μM.
- Shamraiz, Umair,Hussain, Hidayat,Ur Rehman, Najeeb,Al-Shidhani, Sulaiman,Saeed, Aasim,Khan, Husain Yar,Khan, Ajmal,Fischer, Lucie,Csuk, René,Badshah, Amin,Al-Rawahi, Ahmed,Hussain, Javid,Al-Harrasi, Ahmed
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p. 1845 - 1852
(2019/02/05)
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- Analogues of boswellic acids as inhibitors of pro-inflammatory cytokines TNF-α and IL-6
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A library of boswellic acid analogues were synthesized and tested for their anti-inflammatory potential on key inflammatory mediators, TNF-α and IL-6. The study led to the identification of lead compounds showing significant inhibition of the cytokines, TNF-α and IL-6 both in vitro and in vivo.
- Sharma, Simmi,Gupta, Shilpa,Khajuria, Vidushi,Bhagat, Asha,Ahmed, Zabeer,Shah, Bhahwal Ali
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supporting information
p. 695 - 698
(2016/01/09)
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- Oxidative and reductive transformations of 11-keto-β-boswellic acid
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Extraction of frankincense - a fragrant resin obtained from plants of the genus Boswellia - followed by an oxidation furnished high yields of (3β) 3-O-acetyl-11-keto-β-boswellic acid (β-AKBA), a valuable starting material for accessing boswellic acid derivatives. Boswellic acids are fascinating triterpenoic acids that exhibit different biological activities. However, their biological potential, as well as that of their derivatives, remained unexploited due to their limited availability. In this study we were able to prepare derivatives of 11-keto-β-boswellic acid in good to excellent yields by oxidative and reductive transformations mainly in rings A and C of the triterpenoid skeleton. Among other transformations, a highly cytotoxic endoperoxide was obtained in excellent yields.
- Csuk, René,Barthel-Niesen, Anja,Str?hl, Dieter,Kluge, Ralph,Wagner, Christoph,Al-Harrasi, Ahmed
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p. 2025 - 2034
(2015/03/30)
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- Reagent optimization for allylic oxidation of 3-O-acetyl-β-boswellic acid into 3-O-acetyl-11-oxo-β-boswellic acid
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Introduction of the oxo group at the allylic position of 3-acetoxy-urs-12-en-24β-oic acid (ABA) in the presence of the sensitive 3α-acetyl group, thereby converting it into 3-acetoxy-urs-12-en-11-oxo- 24β-oic acid (AKBA), has been tried with various catal
- Shenvi, Suvarna,Reddy, G. Chandrasekara
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p. 1008 - 1012
(2013/04/23)
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- Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs
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Boswellic acid acylates including their epimers were synthesized and screened against a panel of human cancer cell lines. They exhibited a range of cytotoxicity against various human cancer cell lines thereby leading to the development of a possible SAR. One of the identified lead compounds was found to be an inhibitor of the NF-κB and STAT proteins, warranting further investigations to be developed into a potential anticancer lead.
- Kumar, Ajay,Shah, Bhahwal A.,Singh, Samar,Hamid, Abid,Singh, Shashank K.,Sethi, Vijay K.,Saxena, Ajit K.,Singh, Jaswant,Taneja, Subhash C.
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supporting information; experimental part
p. 431 - 435
(2012/03/11)
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- A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid
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Semi-synthetic analogues of β-boswellic acid (BA) and 11-keto-β-boswellic acid (KBA) were comparatively evaluated for in vitro cytotoxicity against human myeloid leukaemia (HL-60) and human cervical carcinoma (HeLa) cells. 2-Cyano analogues of both the triterpenes were observed to have significant cytotoxicity against both the cells, displaying cytotoxicity in HL-60 cells at low concentrations. Further investigations suggested the proapoptotic potential associated with the two molecules to induce cytotoxicity in HL-60 cells, where one of them showed early proapoptotic effect as evidenced by several biological end-points of the apoptosis such as annexinV binding, DNA fragmentation and increase in sub-G0 DNA fraction and apoptotic bodies formation (Hoechst 33258 staining and SEM studies).
- Kaur, Rajbir,Khan, Sheema,Chib, Renu,Kaur, Tandeep,Sharma, Parduman Raj,Singh, Jaswant,Shah, Bhahwal Ali,Taneja, Subhash Chandra
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scheme or table
p. 1356 - 1366
(2011/04/24)
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- An Efficient Method for the Large-Scale Preparation of 3-O-Acetyl-11-oxo-βboswellic Acid and Other Boswellic Acids
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3-O-Acetyl-11-oxo-β-boswellic acid (AKBA), found in incense, is a potent inhibitor of 5-lipoxygenase, p38 and p42 MAP kinase and topoisomerases. Starting from crude extracts from incense, procedures are presented for the efficient large-scale synthesis of AKBA and other boswellic acids. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Jauch, Johann,Bergmann, Jochen
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p. 4752 - 4756
(2007/10/03)
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