5968-70-7

Usage

Uses

Used in Pharmaceutical Industry:
3-ACETYL-BETA-BOSWELLIC ACID is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate arthritic conditions in mice. Its selective inhibition of 5-LO makes it a promising candidate for the development of new anti-inflammatory drugs.
Used in Anticancer Applications:
In the field of oncology, 3-ACETYL-BETA-BOSWELLIC ACID is used as a chemotherapeutic agent. When studied as a 1:1 mixture with α-acetyl-boswellic acid, it has been shown to inhibit topoisomerase II activity, leading to the arrest of cell cycling or induction of apoptosis in cancer cells. This suggests its potential use in the treatment of various types of cancer.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of 3-ACETYL-BETA-BOSWELLIC ACID, it can be incorporated into novel drug delivery systems. These systems, which may include organic and metallic nanoparticles as carriers, aim to improve the delivery and efficacy of the compound, particularly in the context of cancer treatment.

Biological Activity

β-acetyl-boswellic acid is a specific, nonreducing-type inhibitor of the 5-lo product formation with selectivity over 12-lo and cox [1][2].5-lipoxygenase (5-lo) is a member of the lipoxygenase family of enzymes and transforms efa substrates into leukotrienes.in rat peritoneal neutrophils, boswellic acids concentration dependently decreased the formation of leukotriene b4 from endogenous arachidonic acid. in isolated human platelets, boswellic acids in concentrations up to 400 μm did not impair the cyclooxygenase and 12-lipoxygenase [1]. in calcium/calcium ionophore-stimulated peritoneal neutrophils of rats, boswellic acids significantly decreased production of ltb4 and total 5-lipoxygenase products with ec50 value of about 30 μg/ml [2]. in six human myeloid leukemia cell lines, boswellic acid acetate, a 1:1 mixture of α-boswellic acid acetate and β-boswellic acid acetate induces apoptosis through caspase-mediated pathways [4].boswellic acids are pentacyclic triterpenes with putative anti-inflammatory effects. in a mouse model of osteoarthritis (oa), boswellic acid significantly attenuated articular cartilage erosion and significantly reduced knee synovitis and osteophyte formation. in synovium of mice, boswellic acid directly inhibit il-1β and tlr4 induced inflammatory cytokines production [3].

references

[1]. safayhi h, mack t, sabieraj j, et al. boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase. j pharmacol exp ther. 1992 jun;261(3):1143-6.[2]. ammon hp, safayhi h, mack t, et al. mechanism of antiinflammatory actions of curcumine and boswellic acids. j ethnopharmacol. 1993 mar;38(2-3):113-9.[3]. wang q, pan x, wong hh, et al. oral and topical boswellic acid attenuates mouse osteoarthritis. osteoarthritis cartilage. 2014 jan;22(1):128-32.[4]. xia l, chen d, han r, et al. boswellic acid acetate induces apoptosis through caspase-mediated pathways in myeloid leukemia cells. mol cancer ther. 2005 mar;4(3):381-8.

InChI:InChI=1/C32H50O4/c1-19-11-14-28(4)17-18-30(6)22(26(28)20(19)2)9-10-23-29(5)15-13-25(36-21(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23-,24-,25-,26+,28-,29-,30-,31-,32-/m1/s1

Upstream product

• 631-69-6 beta-boswellic acid 
• 75-36-5 acetyl chloride 
• 8050-07-5 3-O-acetyl-11-keto-β-boswellic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 5798-67-4 3α-acetyl-β-boswellic acid methyl ester 
• 631-69-6 beta-boswellic acid 
• 5986-19-6 10-oxo-1.2.4a.6a.6b.9.12a-heptamethyl-1.2.3.4.4a.5.6.6a.6b.7.8.8a.9.10.11.12.12a.12b.13.14b-eicosahydro-picene 
• 1285527-39-0 butyl 3-α-acetoxyurs-12-en-24-oate 
• 1285527-41-4 butyl 3-α-hydroxyurs-12-en-24-oate 
• 1285527-43-6 butyl 3-oxours-12-en-24-oate 
• 1285527-47-0 C₃₅H₅₃NO₃ 
• 1285527-49-2 butyl 2-cyano-3-oxours-12-en-24-oate 
• 1285527-52-7 butyl 2-cyano-3-oxoursa-1,12-dien-24-oate 
• 1285527-53-8 butyl 2-cyano-3-hydroxyurs-12-en-24-oate 
• 1285527-55-0 2-carbamoyl-3-hydroxyurs-12-en-24-oic acid 
• 1285527-57-2 C₃₁H₄₈N₂O₃ 
• 1285527-59-4 C₃₀H₅₀N₂O₂ 
• 67416-61-9 acetyl-11-keto-beta-boswellic acid 

Relevant academic research and scientific papers

An Efficient Method for the Large-Scale Preparation of 3-O-Acetyl-11-oxo-βboswellic Acid and Other Boswellic Acids

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.

Synthesis of new boswellic acid derivatives as potential antiproliferative agents

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.

Analogues of boswellic acids as inhibitors of pro-inflammatory cytokines TNF-α and IL-6

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.

COMPOSITION FOR PREVENTING HAIR LOSS AND ACCELERATING HAIR GROWTH

Disclosed is a composition for prevention of hair loss and promotion of hair growth. The composition includes a compound represented by Formula 1, wherein A is derived from polycyclic compounds, and R is a hydroxyl group, or a saturated or unsaturated straight or branched alkyloxy or acyloxy group having 1 to 20 carbon atoms.

Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs

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.

A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid

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).