Costus Root Research Articles

(E)‐9‐Isopropyl‐6‐methyl‐5,9‐decadien‐2‐one, a Terpenoid C14‐Ketone with a Novel Skeleton

Abstract(E)‐9‐Isopropyl‐6‐methyl‐5,9‐decadien‐2‐one (1a), a terpenoid C14‐ketone with a novel skeleton, was isolated from costus root oil (Saussurea lappa CLARKE) and its structure established by a two‐step synthesis from thuja ketone (2). The possible role of the new compound as an intermediate in the biosynthesis of the irones is discussed.

(E)-9-isopropyl-6-methyldeca-5,9-dien-2-one, a terpenoid C14-ketone with a novel skeleton

The isolation and synthesis of (E)-9-isopropyl-6-methyldeca-5,9-dien-2-one, a terpenoid C14-ketone with a novel skeleton from costus root oil (Saussurea lappa Clarke) are reported.

Über neue inhaltsstoffe von costuswurzelöl

Apart from the well-known constituents dehydrocostuslactone ( 1), dihydrodehydrocostuslactone, α-ionone, β-elemene, caryophyllene, humulene, costol, β-selinene and aplotaxene, 1-pentadecene, dihydroaplotaxene ( 3) and 3,9,11-guaiatriene-12-acid, which was isolated as the methyl ester ( 5), have been found as new constituents of costus root oil. Costunolide ( 2) and costic acid have not been detected. The mass spectra of characteristic constituents are given.

Composition of Punjab costus root oil

Composition of Punjab costus root oil

Terpenoids—CIV : Costol fraction of costus root oil

The ‘costol’ fraction of costus root oil is an intimate mixture of several alcohols. The presence of “true” costol (I) has been proved by conversion to crystalline costic acid (IB), the methyl ester of which on reduction with LAH-AlCl 3 gives pure costol of high rotation. The tertiary alcohol, elemol (VI) has been identified as another constituent of the mixture.

Toxicological tests on flavouring matters

Short-term feeding studies in rats have been carried out on the following 23 flavouring matters: Methyl N-methylanthranilate; methyl β-naphthyl ketone; methyl octanoate; α-amylcinnamaldehyde; tolualdehydes; α-ionone; β-ionone; α-irone; α-isomethylionone; β-naphthyl ethyl ether; musk ambrette; γ-nonalactone; γ-undecalactone; γ-valerolactone; 1-( p-methoxyphenyl)-1-penten-3-one; m-dimethoxybenzene; patchouly, oil; davana, oil; guaiac wood, oil; costus root, oil; walnut hull, extract; yerba santa, fluid extract; mountain maple, solid extract. These compounds appear in the ‘GRAS’ (“generally recognized as safe”) list compiled by the Expert Panel of the Flavouring Extract Manufacturers' Association of the United States (FEMA). Administration of any one of these flavouring matters for 90 days at a level in excess of at least 100 times the maximum estimated daily dietary intake in man evoked no adverse effect on growth, food consumption, haematology, blood chemistry, liver and kidney weights or on gross and microscopic appearance of major organs at autopsy.

Terpenoids—LXVIII : Structure and absolute configuration of costic acid—a new sesquiterpenic acid from costus root oil

The acidic fraction of costus root oil is composed of several acids, one of which, costic acid, has been obtained in the pure crystalline form via its amine salts. By systematic chemical degradation, spectral studies and subsequent conversion to dihydroeudesmol (XIII), the structure and absolute configuration of costic acid have been determined as I. It is the acid corresponding to costol (II), the selinenic allylic alcohol previously isolated by Sorm. Costol fraction of costus root oil has also been shown to be composed of several components, one of which can be converted to costic acid.

Terpenoids-XXIV : Isolation of 12-methoxydihydrocostunolide from costus root oil

The methoxylactone isolated from costus root oil is shown to be 12-methoxydihydrocostunolide.

Terpenoids—XXI : The structure of costunolide, a new sesquiterpene lactone from costus root oil

Costunolide, the new sesquiterpene lactone isolated from costus root oil ( Saussurea lappa Clarke) is shown to have the structure I on the basis of dehydrogenation, ozonolyses and the formation of santanolide 'C' under mild conditions.