Analysis of the polar fraction of Haitian vetiver oil

Abstract

The polar part of commercial Haitian vetiver oil was converted to the methyl ethers, and this product separated by distillation and repeated flash chromatography (FC). The following new (nor‐) sesquiterpene alcohols were isolated as their methyl ethers and identified by their 1H‐ and 13C‐NMR spectra: 12‐nor‐ziza‐6(13)‐en‐2β‐ (2) and ‐2α‐ol (3), eudesma‐4(15),7‐dien‐3β‐ (7) and ‐2β‐ol (18), eudesma‐3,5‐dien‐1α‐ol (26), eremophila‐1(10),4(15)‐dien‐2α‐ol (31), eremophila‐1(10),11‐dien‐2α‐ol (nootkatol, 38), guaia‐1(5),11‐dien‐3‐ol (11), spirovetiva‐3,7(11)‐dien‐12‐ol (42), preziza‐7(15)‐en‐3α‐ol (14) and helifol‐1‐en‐14‐ol (syn. khusien‐14‐ol, 12). Furthermore, the hemi‐acetal 7,10‐epoxy‐salvialan‐10‐ol (8) was identified. The structure of some artefacts formed by alkylation of β‐vetivone 52 (→M 39, M 43) and of 11,12,13‐tri‐nor‐eudesmenone (→16, 17) was also elucidated. Copyright © 2000 John Wiley & Sons, Ltd.

Eremophilane-type sesquiterpenes from Alpinia oxyphylla with inhibitory activity against nitric oxide production

“…Semipreparative reverse-phase (RP) HPLC was performed on TABLE 1. NMR Data of 1 (400 MHz for 1 H, 100 MHz for 13 an Agilent 1100 liquid chromatograph with a Zorbax SB-C 18 column. Solvents were of industrial purity and distilled prior to use.…”

“…Furthermore, we recently reported a series of new sesquiterpenes, including seven new eudesmane sesquiterpenes, against NO production from A. oxyphylla [6][7][8]. In continuation of our search for bioactive metabolites from the fruits of A. oxyphylla, we have further isolated 12 eremophilane-type sesquiterpenes, including a new compound, (4R*,5R*)-7-acetyl-4,5-dimethyl-4,5,8,9-tetrahydronaphthalen-2(3H)-one (oxyphyllanone A, 1), along with eleven known sesquiterpenes, (4R*,5S*,7R*)-7-acetyl-4,5-dimethyl-4,5,6,7,8,9-hexahydronaphthalen-2(3H)-one (2) [9], (11R)-nootkatone-11,12-diol (3) [9], (11S)-nootkatone-11,12-diol (4) [9], 11-hydroxyvalenc-1(10)-en-2-one (5) [10], 9E-hydroxynootkatone (6) [9], oxyphyllol B (7) [2], oxyphyllol C (8) [2], epinootkatol (9) [11, 12], nootkatol (10) [12,13], 12-hydroxynootkatone (11) [9,14], and nootkatone (12) [11]. Among them, compounds 2-6, 9, and 11 were isolated from this genus for the first time.…”

Highly Volatile Constituents of Vetiveria zizanioides Roots Grown under Different Cultivation Conditions

“…Apart from the mass spectral comparison with the mass spectral library software, the volatile components were identified by comparing their Kovát indices with reported data [6][7][8][9][10][11].…”

“…This tonality indicates the presence of some volatile compounds that have been reported to be mainly sesquiterpenes and their derivatives. Among these, the major active constituents identified are khusimol, vetivone, eudesmol, khusimone, zizaene, and prezizaene, which are considered to be the fingerprint of the oil [6][7][8][9][10][11].…”

Volatile constituents of vetiver: a review

“…Indeed, even when powerful techniques are involved, it may happen that the ‘spectroscopically compliant’ chemical structure is not confirmed by univocal synthesis. The epimeric structure proposed initially was then renamed as 3‐ epi ‐zizanol, and was proved later to be an actual constituent of VEO, like its corresponding diastereoisomer 80 (Figure ).…”