11-KETO-BETA-BOSWELLIC ACID Chemical Properties

Melting point:

190～192℃

Boiling point:

591.8±50.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

4°C, protect from light

solubility 

≤5mg/ml in ethanol;25mg/ml in DMSO;25mg/ml in dimethyl formamide

pka

4.46±0.70(Predicted)

form 

Solid

color 

White

Water Solubility 

insoluble in water

InChIKey

YIMHGPSYDOGBPI-IQQSWPBXSA-N

LogP

7.100 (est)

Safety Information

WGK Germany 

3

HS Code 

29189900

11-KETO-BETA-BOSWELLIC ACID Usage And Synthesis

Uses

A constitutent of frankincense (olibanum) with anti-inflammatory properties. It has been shown to trigger apoptosis via a pathway dependent on caspase-8 activation but independent on Fas/Fas ligand interaction in colon cancer HT-29 cells.

Biological Activity

37.9 μm: blocks a2780 (cis-platin resistant ovarian cancer cells) [1].11-keto-β-boswellic acid, known as kba, is a naturally occurring pentacyclic triterpene isolated from the gum resin of the tree boswellia serrata. kba is non-redox, specific leukotriene synthesis inhibitors through the inhibition of 5-lipoxygenase (5-lox) which has anti-arthritic and anti-inflammatory activities. 5-lox catalyzes essential fatty acids substrates into leukotrienes and a variety of other biologically active products. kba is a novel activator of nuclear factor erythroid-2-related factor 2 (nrf2), which protects against cerebral ischemic injury.

in vitro

kba, concentration dependently, decreased the formation of leukotriene b4 and the synthesis of all 5-lox products from endogenous arachidonic acid in rat peritoneal neutrophils. in contrast, kba exerted no remarkable effects on the 12-lipoxygenase and cyclooxygenase activities. [2].

in vivo

adult male sprague–dawley rats were injected kab intraperitoneally at a dose of 25 mg/kg for 48 hours. kab remarkably decreased infarct volumes as well as apoptotic cells at 1 h, and then increased neurologic scores when applied 48 h. moreover, posttreatment with kba induced the decrease of malondialdehyde levels and the increase of protein nrf2 and heme oxygenase-1 expression in brain tissues, indicating that the nrf2/ho-1 pathway was involved in the neuroprotection of kba against oxidative stress-induced ischemic injury [3].

IC 50

35.8 μm: inhibits mcf-7 (human breast adenocarcinoma) [1].

References

[1]. csuk, r., barthel-niesen, a., barthel, a., schffer, r., & al-harrasi, a. 11-keto-boswellic acid derived amides and monodesmosidic saponins induce apoptosis in breast and cervical cancers cells. european journal of medicinal chemistry. 2015; 100: 98-105.
[2]. safayhi, h., mack, t. h. o. m. a. s., sabieraj, j. o. a. c. h. i. m., anazodo, m. i., subramanian, l. r., & ammon, h. p. boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase. journal of pharmacology and experimental therapeutics. 1992; 261(3):1143-1146.
[3]. ding, y., chen, m., wang, m., li, y., & wen, a. posttreatment with 11-keto-β-boswellic acid ameliorates cerebral ischemia–reperfusion injury: nrf2/ho-1 pathway as a potential mechanism. molecular neurobiology. 2014; 52(3): 1430-1439.

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