Efficient Preparation of Incensole and Incensole Acetate, and Quantification of These Bioactive Diterpenes in Boswellia papyrifera by a RP-DAD-HPLC Method

Abstract

Incensole and incensole acetate, found in incense, are encouraging potent bioactive diterpenic cembrenoids, inhibiting Nuclear Factor-κB activation. Furthermore, incensole acetate elicits psycho-activity in mice by activating the TRPV3 channels in the brain. Starting from crude extracts of the incense species Boswellia papyrifera Hochst., a convenient procedure for the efficient large-scale synthesis of incensole and its acetate is presented. Additionally, a reversed-phase, diode-array-detection, high-performance liquid chromatography (RP-DAD-HPLC) method for the quantification of incensole and incensole acetate is reported, indicating that these two compounds are typical biomarkers for B. papyrifera.

TRPV3: time to decipher a poorly understood family member!

“…Both compounds are potent bioactive diterpenic cembrenoids that activate TRPV3. In addition to TRPV3 activation in the skin with unknown functional effects, IA causes anxiolytic‐like and antidepressive‐like behavioural effects in mice that are absent in Trpv3 knockout animals, also indicating a still unknown role of TRPV3 in the CNS (Moussaieff et al ; Moussaieff & Mechoulam, ; Paul & Jauch, ). TRPV3 is also expressed in a subpopulation of brainstem serotonergic neurons.…”

Quantification of Incensole in Three Boswellia Species by NIR Spectroscopy Coupled with PLSR and Cross‐Validation by HPLC

“…However, no incensole was found in the B. serrata fractions while trace amount was detected in the fractions of B. sacra . Previous study of Paul and Jauch () showed the presence of incensole in different grades of methanolic extract of B. papyrifera in the range 18.8–24.9% using RP‐DAD‐HPLC. Our results are in complete agreement with those published (Paul and Jauch, ).…”

“…Previous study of Paul and Jauch () showed the presence of incensole in different grades of methanolic extract of B. papyrifera in the range 18.8–24.9% using RP‐DAD‐HPLC. Our results are in complete agreement with those published (Paul and Jauch, ). Thus it can be concluded that incensole is genus‐specific.…”

“…A large‐scale preparation of incensole was achieved following the protocol of Paul and Jauch () from the crude extracts of B. papyrifera and purified by silica gel column chromatography and preparative high‐performance liquid chromatography (HPLC). The structure was elucidated through spectroscopic as well as published data (Alemika et al ., ; Avula et al ., ).…”

“…() have analysed the incensole acetate using spectral analysis. A few methods (Paul and Jauch, ; Paul et al ., ) reported the quantification of incensole in the methanol extract of B. papyrifera , but as far as we are aware there is no report on the use of near‐infrared (NIR) spectroscopy. In continuation of our previous work (Rehman et al ., ; Al‐Harrasi et al ., ) we herein report the quantification of incensole through NIR spectroscopy coupled with a partial least squares regression (PLSR) model in the n ‐hexane, ethyl acetate and methanol fractions of B. papyrifera , B. sacra and B. serrata and the results were further cross‐checked by HPLC diode array detector (DAD) method.…”