Stereospecific syntheses of the diastereomeric (.+-.)-.alpha.-bisabolols. A caveat on the assignment of stereochemistry to natural .alpha.-bisabolol

Schwartz, Martin A.; Swanson, Gerald C.

doi:10.1021/jo01320a013

Cited by 51 publications

(13 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This alcohol is structurally similar to α-bisabolol for which all four stereoisomers are known from Nature (Scheme 7B). The stereoisomer (6S,7S)-35 occurs in chamomile oil, [22,23] (6S,7R)-35 ("anymol") is known from Myoporum crassifolium, [24] (6R,7R)-35 occurs in Populus balsamifera [24] and (6R,7S)-35 in Rosa rugosa. [25] Assignment of the relative and absolute configurations of the obtained compounds 27-29, 33 and 34 proved to be a particular problem, because in all five compounds the neighbouring stereogenic centres at C6 and C7 are connected by a single bond around which free rotation is possible, which hampers NOE based assignments.…”

Section: Resultsmentioning

confidence: 99%

“…This alcohol is structurally similar to α‐bisabolol for which all four stereoisomers are known from Nature (Scheme 7B). The stereoisomer (6 S ,7 S )‐ 35 occurs in chamomile oil, [22,23] (6 S ,7 R )‐ 35 (“anymol”) is known from Myoporum crassifolium , [24] (6 R ,7 R )‐ 35 occurs in Populus balsamifera [24] and (6 R ,7 S )‐ 35 in Rosa rugosa [25] …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Rerouting and Improving Dauc‐8‐en‐11‐ol Synthase from Streptomyces venezuelae to a High Yielding Biocatalyst

Lauterbach

Hou

Dickschat

2021

Chemistry A European J

View full text Add to dashboard Cite

The dauc-8-en-11-ol synthase from Streptomyces venezuelae was investigated for its catalytic activity towards alternative terpene precursors, specifically designed to enable new cyclisation pathways. Exchange of aromatic amino acid residues at the enzyme surface by site-directed mutagenesis led to a 4-fold increase of the yield in preparative scale incubations, which likely results from an increased enzyme stability instead of improved enzyme kinetics.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Rerouting and Improving Dauc‐8‐en‐11‐ol Synthase from Streptomyces venezuelae to a High Yielding Biocatalyst

Lauterbach

Hou

Dickschat

2021

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Obwohl die Identität und die chemische Konstitution des (-)-a-Bisabolols schon früh bestimmt werden konnten, brachten es die teilweise nur geringfügigen Substituentenunterschiede an den chiralen Zentren des Moleküls mit sich, daß die genaue stereochemische Zuordnung dieses Kamillenwirkstoffes zu einer der vier theoretisch ableitbaren stereoisomeren Strukturen des a-Bisabolols erst in jüngster Zeit getroffen werden konnte [13,14]. Heute kann die absolute Konfiguration jedes optisch einheitlichen a-Bisabolols mit Hilfe NMR-spektrometrischer Verfahren bestimmt werden [15].…”

unclassified

Zur Stereochemie der Bisaboloide aus Matricaria chamomilla L/On the Stereochemistry of the Bisaboloids from Matricaria chamomilla L.

Flaskamp¹,

Nonnenmacher²,

Zimmermann

et al. 1981

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

Abstract The stereochemistry of the bisaboloids in chamomile-with the exception of bisabolol-oxide C-has been elucidated. The in-vitro-examination of the mutual convertibilities of some bisaboloids gave evidence for the stereochemical accordance of the common chiral centres of all the bisaboloids. The absolute configurations of the remaining third asymmetric carbon atoms in bisabololoxide A and B have been determined by NMR spectrometric studies in comparison with their unnatural semisynthetic epimers. All the stereogenic centres of the bisabololoxides A and B, of (-)-α-bisabolol and of bisabolonoxide A turn out to be S-configurated.

show abstract

“…The most bio-active form of bisabolol is the (–)-α-Bisabolol, with the (4S, 8S)-configuration. Chemical synthesis of bisabolol results in racemic mixtures, which have a lower bio-activity compared to the Candeia oil ingredient ( Schwartz and Swanson, 1979 ). Candeia wood essential oil was reported to be dominated by (–)-α-bisabolol, up to a level of 66 to 91%.…”

Section: Introductionmentioning

confidence: 99%

Identification of the Bisabolol Synthase in the Endangered Candeia Tree (Eremanthus erythropappus (DC) McLeisch)

et al. 2018

View full text Add to dashboard Cite

Candeia (Eremanthus erythropappus (DC) McLeisch, Asteraceae) is a Brazilian tree, mainly occurring in the cerrado areas. From ethnobotanical information its essential oil is known to have wound healing and nociceptive properties. These properties are ascribed to result from a sesquiterpene alcohol, (–)-α-bisabolol, which is present at high concentrations in this oil. Bisabolol is highly valued by the cosmetic industry because of its antibacterial, anti-inflammatory, skin-smoothing and wound healing properties. Over the past decades, Candeia timber has been collected at large scale for bisabolol extraction from wild reserves and the species is thereby at risk of extinction. To support the development of breeding and nursing practices that would facilitate sustainable cultivation of Candeia, we identified a terpene synthase gene, EeBOS1, that appears to control biosynthesis (–)-α-bisabolol in the plant. Expression of this gene in E. coli showed that EeBOS1 protein is capable of producing (–)-α-bisabolol from farnesyl pyrophosphate in vitro. Analysis of gene expression in different tissues from Candeia plants in different life stages showed a high correlation of EeBOS1 expression and accumulation of (–)-α-bisabolol. This work is the first step to unravel the pathway toward (–)-α-bisabolol in Candeia, and in the further study of the control of (–)-α-bisabolol production.

show abstract

Stereospecific syntheses of the diastereomeric (.+-.)-.alpha.-bisabolols. A caveat on the assignment of stereochemistry to natural .alpha.-bisabolol

Cited by 51 publications

References 7 publications

Rerouting and Improving Dauc‐8‐en‐11‐ol Synthase from Streptomyces venezuelae to a High Yielding Biocatalyst

Rerouting and Improving Dauc‐8‐en‐11‐ol Synthase from Streptomyces venezuelae to a High Yielding Biocatalyst

Zur Stereochemie der Bisaboloide aus Matricaria chamomilla L/On the Stereochemistry of the Bisaboloids from Matricaria chamomilla L.

Identification of the Bisabolol Synthase in the Endangered Candeia Tree (Eremanthus erythropappus (DC) McLeisch)

Contact Info

Product

Resources

About