Sesquiterpenoids from Costus Root Oil (Saussurea lappa CLARKE)

Abstract

Apart from the well‐known constituents (+)‐β‐selinene (2), (−)‐β‐elemene (4), (+)‐β‐costol (7), (−)‐caryophyllene (17), and (−)‐elemol (19) the following sesquiterpenoids have been isolated for the first time from costus root oil (Saussurea lappa CLARKE): (−)‐α‐selinene (1), (+)‐selina‐4, 11‐diene (3), (−)‐α‐trans‐bergamotene (5), (−)‐α‐costol (6), (+)‐γ‐costol (8), (−)‐elema‐1,3,11 (13)‐trien‐12‐ol (9), (−)‐α‐costal (11), (+)‐γ‐costal (12), (+)‐γ‐costal (13), (−)‐elema‐1,3,11 (13)‐trien‐12‐al (elemenal, 14), (−)‐(E)‐trans‐bergamota‐2, 12‐dien‐14‐al (15), (−)‐ar‐curcumene (16), and (−)‐caryophyllene oxide (18). Compounds 6, 8, 9, and 13 are new sesquiterpenoids. IR. and NMR. spectra of 12 sesquiterpenoids are reproduced.

Preparation and Absolute Configuration of (−)‐(E)‐α‐trans‐Bergamotenone

“…Compound 1 was patented as a flavour (0.005 ppm) in a walnut aroma, as well as in perfumery compositions containing synthetic or natural sandalwood-like alcohols, to reinforce the fatty top notes [la]; its factor of dilution FD is 256. For comparison, the FD of (+) Particularly interested in the absolute configuration of sandalwood-like alcohols [lo], we realized that the absolute configuration indicated for (-)-2, and consequently for (-)-(Z)-3b, (-)-(Z)-4b, and 13) [6], although correct according to the 'Dictionary of Terpenoids and Sesquiterpenoids' [I 11, was in disagreement with previous reports [3] [4a] [5]. Significantly, concerning the determination of the absolute configuration of a-trans-bergamotene (( -)-2), all authors, without exception, referred to the same publication of Kovuts [12].…”

Mast Cell Stabilizing Effect of (−)-Elema-1,3,11(13)-trien-12-ol and Thujopsene from <i>Thujopsis dolabrata</i> Is Mediated by Down-Regulation of Interleukin-4 Secretion in Antigen-Induced RBL-2H3 Cells

“…MeOH), then further purified by reversed-phase HPLC (55% aq. MeCN) to afford 11.6 mg and 14.3 of (−)-elema-1,3,11(13)-trien-12-ol (1) 30) and thujopsene-12-ol (3), 27) respectively. The aliquot (551 mg) of the fraction eluted with 100% nhexane from flash chromatography was separated by silica HPLC (YMC-silica, 100% n-hexane), then further purified by reversed-phase HPLC (YMC ODS-A column, 1 cm×25 cm, 5% aq.…”

Removal of allergens from natural oils by selective binding to polymer supports. II. Application of aminated resins to isoalantolactone and costus oil

“…Complete selectivity of the polymers cannot be claimed since the a$-unsaturated aldehydes and ketones which are reported (18) to be present in small amounts in costus essential oil might also have been retained by the polymer. These compounds are present in such small amounts that they are likely to escape detection by our method.…”