Semi-preparative liquid-chromatographic separation of all four stereoisomers of ?-bisabolol on tribenzoylcellulose

Günther, Kurt; Carle, Reinhold; Fleischhauer, Ilona; Merget, Stefan

doi:10.1007/bf00323012

Cited by 14 publications

(4 citation statements)

References 24 publications

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“…None of the reported HPLC methods for (−)-α-bisabolol determination were validated. Günther et al (1993) determined the (−)-α-bisabolol content in chamomile essential oil using a chiral stationary phase. The time of analysis was relatively long, providing a retention time of 120 min for the sesquiterpene.…”

Section: Methods Validationmentioning

confidence: 99%

Validation of a high‐performance liquid chromatography method for the determination of (−)‐α‐bisabolol from particulate systems

Pedro

Detoni

Ferreira

et al. 2009

Biomedical Chromatography

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A reversed-phase high performance liquid chromatography method has been developed and validated for determination and quantitation of the natural sesquiterpene (-)-alpha-bisabolol. Furthermore the application of the method was done by characterization of chitosan milispheres and liposomes entrapping Zanthoxylum tingoassuiba essential oil, which contains appreciable amount of (-)-alpha-bisabolol. A reversed-phase C(18) column and gradient elution was used with the mobile phase composed of (A) acetonitrile-water-phosphoric acid (19:80:1) and (B) acetonitrile. The eluent was pumped at a flow rate of 0.8 mL/min with UV detection at 200 nm. In the range 0.02-0.64 mg/mL the assay showed good linearity (R(2 )= 0.9999) and specificity for successful identification and quantitation of (-)-alpha-bisabolol in the essential oil without interfering peaks. The method also showed good reproducibility, demonstrating inter-day and intra-day precision based on relative standard deviation values (up to 3.03%), accuracy (mean recovery of 100.69% +/- 1.05%) and low values of detection and quantitation limits (0.0005 and 0.0016 mg/mL, respectively). The method was also robust for showing a recovery of 98.81% under a change of solvent in standard solutions. The suitability of the method was demonstrated by the successful determination of association efficiency of the (-)-alpha-bisabolol in chitosan milispheres and liposomes.

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Section: Methods Validationmentioning

confidence: 99%

Validation of a high‐performance liquid chromatography method for the determination of (−)‐α‐bisabolol from particulate systems

Pedro

Detoni

Ferreira

et al. 2009

Biomedical Chromatography

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“…The odor-active compound 4a showed a signal at 0.91 ppm, pointing to a (6S*,7S*) configuration. To determine the absolute configuration of 4a, one could envisage several methods, e.g., enantioselective synthesis starting from (E)-12 and using enantioselective epoxidation or separation of the racemic mixture of 4a by chiral HPLC [23], followed by derivatization and X-ray diffractometry. However, all attempts were, so far, unsuccessful.…”

Section: B Vs 2 C)mentioning

confidence: 99%

Enantioselectivity in Odor Perception: Synthesis and Olfactory Properties of Iso‐β‐Bisabolol, a New Natural Product

Braun

Meier

Schmaus

et al. 2003

Helvetica Chimica Acta

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The odorous trace constituent iso-b-bisabolol (4) was isolated from East Indian and Western Australian sandalwood oil and synthesized by using the (E/Z)-triene 12 (iso-g-bisabolene) as a key intermediate. Only one of four stereoisomeric forms of 4, (6R,7R)-4a, is odor active, having a strong floral, muguet-like, very pleasant scent.Introduction. ± Odor perception is initiated by an interaction of a volatile stimulant with a proteinaceous receptor [1]. Different diastereoisomers and enantiomers of the same molecular structure can elicit different odor impressions, both qualitative and quantitative [2]. In our continuous search for new natural trace constituents with high odor impact, we analyzed sandalwood oils of East Indian as well as Western Australian origin [3]. The oils are obtained from wood, trunk butt, or roots of Santalum album L. and Santalum spicatum (R. Br.) A. DC. by different extraction and/or distillation techniques [4].Among a broad range of compounds, the odorless sesquiterpene alcohols abisabolol (1) and b-bisabolol (2) were detected by GC-MS analysis in both Santalum species [3a] [3b]. The corresponding iso-a-bisabolol (3) 2 ) and iso-b-bisabolol (4), however, have, to the best of our knowledge, neither been found in nature nor synthesized so far.

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“…Compound 5 ( Table S3 , Figures S40 and S41 ) was (3 R ,6 E )-nerolidol ([α] 20 D −16 ( c 0.1, CHCl 3 )), and its specific rotation was consistent with [α] 23 D −12.5 ( c 0.022, CHCl 3 ) ( Cane et al., 1990a ). Compound 6 ( Table S3 , Figures S42 and S43 ) was (+)- α -bisabolol ([α] 20 D +51.7 ( c 0.06, CHCl 3 )), and the NMR data of which were different from those of epi - α -bisabolol ( Chen et al., 2002 ) and its specific rotation was sufficiently close to the reported [α] 22 D +51.3 ( c 0.06, CHCl 3 ) ( Bian et al., 2018 ; Gnther et al., 1993 ). Thus, TVY81921.1 as the second (+)- α-trans -bergamotene synthase was named as LsBERS, and XP_001546971.2 was designated as BcBOS which is the first identified fungal (+)- α -bisabolol synthase.…”

Section: Resultsmentioning

confidence: 57%

Unusual (2R,6R)-bicyclo[3.1.1]heptane ring construction in fungal α-trans-bergamotene biosynthesis

et al. 2022

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Semi-preparative liquid-chromatographic separation of all four stereoisomers of ?-bisabolol on tribenzoylcellulose

Cited by 14 publications

References 24 publications

Validation of a high‐performance liquid chromatography method for the determination of (−)‐α‐bisabolol from particulate systems

Validation of a high‐performance liquid chromatography method for the determination of (−)‐α‐bisabolol from particulate systems

Enantioselectivity in Odor Perception: Synthesis and Olfactory Properties of Iso‐β‐Bisabolol, a New Natural Product

Unusual (2R,6R)-bicyclo[3.1.1]heptane ring construction in fungal α-trans-bergamotene biosynthesis

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