| Identification | Back Directory | [Name]
BETA-BOSWELLIC ACID | [CAS]
631-69-6 | [Synonyms]
B-BOSWELLIC ACID
BOSWELLIC ACID, B-
BETA-BOSWELLIC ACID
BOSWELLIC ACID, a-(P)
3-Hydroxy-12-ursen-24-oic acid
3α-Hydroxyurs-12-en-24-oic acid
(3a,4)-3-Hydroxyurs-12-en-23-oic Acid
(3α,4β)-3-Hydroxyurs-12-en-23-oic Acid
(3A,4B)-3-HYDROXYURS-12-EN-23-OIC ACID
Beta-BoswellicAcidforU.Lingner-HoffmannCHEMOSGmbHsales
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid | [Molecular Formula]
C30H48O3 | [MDL Number]
MFCD04039448 | [MOL File]
631-69-6.mol | [Molecular Weight]
456.7 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
130-135°C | [alpha ]
D +107° (c = 0.75 in CHCl3) | [Boiling point ]
556.0±50.0 °C(Predicted) | [density ]
1.09±0.1 g/cm3(Predicted) | [storage temp. ]
-20?C Freezer | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
4.50±0.70(Predicted) | [color ]
Off-White | [Water Solubility ]
practically insoluble in water | [Major Application]
food and beverages | [InChIKey]
NBGQZFQREPIKMG-AKOQEMLPSA-N | [SMILES]
C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O)[C@@](C)([C@@H]5CC[C@@]34C)C(O)=O)[C@@H]2[C@H]1C | [LogP]
9.105 (est) | [CAS DataBase Reference]
631-69-6 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
The principal constitutents of frankincense (olibanum). A specific, nonredox inhibitor of 5-lipoxygenase used to treat inflammation. | [Description]
β-Boswellic acid is a pentacyclic triterpene originally isolated from Boswellia that has diverse bioactivities.1 It inhibits 5-lipoxygenase (5-LO) with an IC50 value of approximately 5 μM but is less potent than its derivative 3-acetyl-11-keto-β-boswellic acid (Item No. 11672).2 It inhibits cell proliferation in HL-60 cells with IC50 values of 3.7, 7.1, and 6.3 μM for DNA, RNA, and protein synthesis, respectively.3 In human umbilical vein endothelial cells (HUVECs) transiently deprived of oxygen and glucose, β-boswellic acid increases nitric oxide and increases phosphorylation of enzyme nitric oxide synthase (eNOS).4 It also increases calcium mobilization in platelets at concentrations ≥3 μM and induces platelet aggregation (EC50 = 8 μM).5 | [Definition]
ChEBI: Boswellic acid is a triterpenoid. | [Anticancer Research]
It is a natural pentacyclic triterpenediol and occurs in Boswellia serrata plants as anisomeric blend of 3α, 24-dihydroxyolean-12-ene and 3α, 24-dihydroxyurs-12-ene.It induces apoptosis in various cancer cells. The events involved in this process areexcessive reactive oxygen species (ROS), nitric oxide (NO) formation, DNA ladderformation, and increased sub-G0 phase in cell cycle. This ultimately results incleavage of Bcl-2 and translocation of Bax to mitochondria, which lead to the lossof mitochondrial potential and release of cyt-c and other factors into cytosol. All these events are linked with reduced expression of survivin and inhibitor of caspase-activatedDNases (ICAD) that leads to the activation of poly(ADP-ribose) polymerase(PARP). The triterpene upregulates the expression of cell death receptor-4(DR-4) and tumor necrosis factor receptor-1 (TNF-R1), where both lead to activationof caspase-8 (Huang et al. 2000; Desai et al. 2008; Lu et al. 2008). | [References]
[1] H.P.T. AMMON. Mechanism of antiinflammatory actions of curcumine and boswellic acids[J]. Journal of ethnopharmacology, 1993, 38 2: Pages 105-112. DOI: 10.1016/0378-8741(93)90005-p
[2] H SAFAYHI. Boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase.[J]. Journal of Pharmacology and Experimental Therapeutics, 1992, 261 3: 1143-1146.
[3] Y SHAO. Inhibitory activity of boswellic acids from Boswellia serrata against human leukemia HL-60 cells in culture.[J]. Planta medica, 1998, 64 4: 328-331. DOI: 10.1055/s-2006-957444
[4] MINGMING WANG. Pretreatment with β-Boswellic Acid Improves Blood Stasis Induced Endothelial Dysfunction: Role of eNOS Activation.[J]. Scientific Reports, 2015: 15357. DOI: 10.1038/srep15357
[5] ULF SIEMONEIT. Defined Structure-Activity Relationships of Boswellic Acids Determine Modulation of Ca2+ Mobilization and Aggregation of Human Platelets by Boswellia serrata Extracts.[J]. Planta medica, 2017, 83 12-13: 1020-1027. DOI: 10.1055/s-0043-107884 |
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