Helmanticine,a phenylpropanoid from Thapsia villosa

Helmanticine, a new phenylpropanoid esterified by angelic and 2,3-dihydroxy-2-methylbutyric acids, was isolated from Thapsia villosa and its full structure established by spectroscopic methods and chemical transformations. Hydrocarbons, 12-nonacosanone, sitosterol and latifolone were also isolated.     

Tovarol and other germacrane derivatives from Thapsia villosa

Four tovarol, two epoxytovarol (= shiromodiol) and one diepoxytovarol esters were the new germacrane esters isolated from the roots of Thapsia villosa var. minor. The structures of these substances were assigned on the basis of spectral data and chemical correlations with shiromodiol. The acid catalysed rearrangement of tavarol yielded 1(10),4-bulgaradiene-8-ol.     

(8R,14S)-8-angeloyloxythapsan-14-ol,a sesquiterpene with a novel carbon skeleton,from Thapsia villosa

The roots of Thapsia villosa afforded in addition to other terpenoids, a sesquiterpene, with a new carbon skeleton. The structure, including the relative configuration, was elucidated by spectroscopic methods, a few chemical transformations and by X-ray analysis. The absolute configuration was determined by means of the method of Horeau. The trivial name thapsan is suggested for the parent structure [2aR,2bR,6aS,7aS]-2b,3,3,6a-tetramethylperhydroindeno[2,3-c]-furan.     

Pseudoguaianolides carabrone derivatives from Loxothysanus sinuatus

The aerial parts of Loxothysanus sinuatus afforded in addition to known compounds nine new pseudoguaianolides, three guaianolides and five carabrone derivatives. The structures were elucidated by spectroscopic methods. The chemotaxonomy is discussed briefly. The configurations of two guaianolides were corrected.     

Dimeric guaianolides from Artemisia sieversiana

The aerial parts of Artemisia sieversiana afforded in addition to known compounds five new guaianolides and four dimeric guaianolides, three of them closely related to absinthin and one derived from estafiatin as a monomer. The structures were elucidated by extensive NMR studies, which allowed the assignment of the 14 chiral centres. Artemisia frigida afforded several known compounds and one new guaianolide, 8-desoxy-cumambrin B, the most likely precursor of many guaianolides.     

Guaianolides from Saussurea affinis

Cynaropicrin, 11βH-11,13-dihydrodesacylcynaropicrin, aguerins A and B, isoamberboin and the new guaianolides saussureolide and 11βH-11,13-dihydrodesacylcynaropicrin 8-β-d-glucoside were isolated from Saussurea affinis.     

Guaianolides from Calea subcordata

Chemical analysis of Calea subcordata yielded three new guaianolides, 8-epi-isobutyrylrupicolin A, 8-epi-isobutyrylrupicolin B and subcordatolide A, which represent the first guaianolide-type sesquiterpene lactones reported in the genus Calea. The structures of the new compounds were established by chemical and spectroscopic methods.     

Daucane esters from Ferula communis subsp. communis

Fourteen daucane esters together with a known propiophenone 3,4-methylenedioxy-5-hydroxy-propiophenone, were isolated from Ferula communis subsp. communis. Except for the 6-(p-anisic acid) ester of jaeschkeanadiol all these esters are new. Structures were elucidated using spectral properties of the esters and their partial hydrolysis products. X-ray diffraction analysis of one of the compounds confirmed its structure including the stereochemical assignments made on the basis of spectral data.     

Guaianolides related to arborescin from Artemisia adamsii

The aerial parts of Artemisia adamsii afforded, among several known compounds, arborescin as the main constituent. Furthermore, 11 new guaianolides, all related to arborescin, were present in minute quantities. The structures were elucidated by spectroscopic methods and the biogenetic relationships are discussed briefly.     

Guaianolides,heliangolides, diterpenes and cycloartenol derivatives from Balsamorhiza sagittata

Investigation of the aerial parts of Balsamorhiza sagittata afforded 12 new sesquiterpene lactones, five guaianolides, three heliangolides, three germacranolides and two geranylnerol derivatives. From the roots eight cycloartane derivatives, a hydroxylanosterone and hexacos-1-ene were isolated. Structures were elucidated mainly by spectroscopic methods, especially high field NMR. The chemotaxonomic situation is discussed briefly.     

Sesquiterpene lactones from Smyrnium cordifolium

In addition to previously obtained furanosesquiterpenes, two new eudesmanolides and a new glechomanolide were isolated from the fruits of Smyrnium cordifolium, while the roots gave two new eudesmanolides. The new compounds from the fruits were 1β-acetoxy-eudesman-4(15), 7(11)-dien-8,12-olide, 1β-acetoxy-8β-hydroxy-eudesman-4(15),7(11)-dien-8,12-olide, 1β,10α;4α,5β-diepoxy-8-hydroxy-glechomanolide, those obtained from the roots were smyrnicordiolide and the corresponding 8β-hydroxy derivative belonging to a new type of oxepine derivative.     

Two phenylpropanoids from Todaroa aurea subsp. Suaveolens

Two new phenylpropanoids, p-methoxytodadiol and suavediol were isolated from the aerial part and roots of Todaroa aurea subsp. suaveolens, together with the acetylenic compound, falcarinol.     

Phenylpropanoids from Thapsia transtagana

Five phenylpropanoids have been isolated from the roots of Thapsia transtagana. Their structures have been elucidated by spectroscopic means.     

Beyerene derivatives and other constituents from Petunia patagonica

Two new diterpenes of the beyerene type, ent-19-hydroxy-1 7-acetoxybeyer-15-ene and ent-beyer-15-en-17-oic acid, and two previously characterized kauranoids, ent-16β-hydroxy-17-acetoxykaurane and ent-16β,1 7-dihydroxy-kaurane, as well as two known flavonoids, luteolin-7,3′,4′-trimethyl ether and luteolin-7,3′-dimethyl ether, and a triterpenoid, oleanoic acid, were obtained from a chloroform extract of Petunia patagonica. The new structures were elucidated by spectral data and chemical transformations.     

Guaianolides from the leaves of Centaurea incana

Six guaianolides have been isolated from the aerial parts of Centaurea incana from Algeria. They were identified as desoxyrepin, repin or subluteolide, repin monochlorhydrin, acroptilin, janerin and repdiolide triol.     

Sesquiterpene lactone glycosides from Crepis capillaris

Four new sesquiterpene lactone glucosides, in addition to known compounds, have been isolated from the roots of Crepis capillaris and their structures elucidated on the basis of spectral analysis and hydrolytic studies.     

Sesquiterpene lactones from Sonchus macrocarpus

Eight sesquiterpene lactones were isolated from the roots of Sonchus macrocarpus. The eudesmanolides 15-hydroxy-4β, 15-dihydroreynosin and 15-hydroxy-4β, 15, 11β, 13-tetrahydroreynosin were isolated for the first time.     

Isocedrene derivatives and other sesquiterpenes from moscharia pinnatifida

From the aerial parts of Moscharia pinnatifida nine further α-isocedrene, two guaiane, three cyperene and two nerolidol derivatives were isolated. The structures were elucidated by high field NMR studies. Chemotaxonomic aspects are discussed.     

Sesquiterpene lactones from Centaurea solstitialis

Eight sesquiterpene lactones were isolated from Centaurea solstitialis (yellow starthistle). They are solstitialin A, repin, subluteolide, acroptilin, janerin, cynaropicrin, and the new lactones solstitiolide and episolstitiolide.