Neue diterpene und sesquiterpene aus südafrikanischen Helichrysum-arten

The investigation of several South African Helichrysum species afforded in addition to known compounds two new kaurenic acid derivatives, three new labdane derivatives, three aromadendrene derivatives and geranylterpinene. The structures are elucidated mainly by extensive ¹H NMR-studies. The chemotaxonomic importance of these findings is discussed briefly.     

Neue labdan-derivate aus Carterothamnus anomalochaeta

The investigation of a Carterothamnus species afforded in addition to known euparine derivatives four new diterpenes, all being labdane derivatives. The structures are elucidated by ¹H-NMR-studies and by some chemical transformations. The chemotaxonomic situation is briefly discussed. The constituents of the Carterothamnus species show a distinct differentiation to those of the neighbouring groups; however, in addition they also indicate some relationships.     

Labdane derivatives and a himachalanolide from Acritopappus longifolius

The investigation of Acritopappus longifolius afforded, in addition to known compounds, further labdane derivatives and a new type of himachalanolide sesquiterpene lactone. The results support the chemotaxonomy of the genus and its relationship to Radlkoferotoma placed in the same group.     

New labdane derivatives from Madia sativa

The aerial parts of Madia sativa afforded, in addition to known compounds, two labdane derivatives whose structures were elucidated by spectroscopic methods. The absolute configuration was determined by chemical transformations. From the roots a new tremetone derivative was isolated. The constituents indicated close relationships of Madia to Hemizonia.     

Neue α-santalen- und labdan-derivate aus Ayapana amygdalina

While the roots of Ayapana amygdalina contain typical euparine derivatives, the aerial parts afforded in addition to known compounds two new α-santalene derivatives as well as twelve new labdane derivatives with a partly unusual oxidation pattern, two being norditerpenes. Furthermore, a new bisabolene isomer is present. The structures were elucidated by spectroscopic methods and a few chemical transformations. The chemotaxonomy is discussed briefly.     

Neue ent-atisiren- und ent-kaurensäure-derivate aus Helianthus-arten

The investigation of four Helianthus species afforded, in addition to known compounds, four new atisirenic acid derivatives, a new ent-kaurenic acid derivative, three new labdane derivatives and an unknown C₁₅-acetylenic compound. The structures of the diterpenes were elucidated by intensive NMR studies and some chemical transformations. An unusual fragmentation in the mass spectra of the atisirenes is discussed briefly.     

Neue labdan- und pimaren-derivate aus Palafoxia rosea

The investigation ofPalafoxia rosea afforded in addition to known compounds five new labdane derivatives and five pimarene derivatives. The structures are elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomic situation of the genus is discussed briefly.     

Clerodane and labdane diterpenoids from Baccharis species

The investigation of eight Baccharis species afforded, in addition to known compounds, five new clerodanes, three labdane derivatives and a nor-diterpene as well as one hydroperoxide derived from 4α-hydroxygermacra-1(10), 5-diene. The structures were elucidated by spectroscopic methods. The structures of esters isolated previously from B. cassinaefolia have to be revised. Chemotaxonomic aspects are discussed briefly.     

Neue labdan-derivate und andere inhaltsstoffe aus Relhania acerosa

The investigation of Relhania acerosa afforded, in addition to known compounds, three new labdane derivatives, two of which are esterified with succinic acid and one which has an anomalous carbon skeleton. Furthermore, several new aromatic compounds are isolated, which are most probably degradated thymol derivatives. The structures are elucidated by spectroscopic methods and by some chemical transformations. The stereochemistry of one of the new labdanes has been established by a partial synthesis. The chemotaxonomic situation is briefly discussed.     

Labdane and dehydronerolidol derivatives from Brickellia diffusa

An investigation of Brickellia diffusa afforded three new dehydronerolidol derivatives and five new labdane derivatives, all highly oxygenated. The structures were elucidated by spectroscopic methods and a few chemical transformations. The compounds isolated showed close relationships to those isolated from Brickellia sp.     

Sesquiterpenes,guaianolides and diterpenes from Stevia myriadenia

The investigation of Stevia myriadenia afforded in addition to known compounds a new clerodane and a labdane derivative, two guaianolides, a bisabolene and a germacrene derivative. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

2-Oxo-labda-8(17),13-dien-15-OL from Ophryosporus chilca

The aerial parts of Ophryosporus chilca afforded several prenylated p-hydroxyacetophenones, two labdane derivatives and a cinnamyl ester. Ophryosporus peruvianus also contains prenylated p-hydroxyacetophenones. Three compounds were isolated for the first time; their structures were established by ¹H NMR spectroscopy.     

Labdane derivatives and flavones from Gutierrezia dracunculoides

An investigation of the aerial parts of Gutierrezia dracunculoides afforded, in addition to known compounds, three new labdane derivatives, all related to lambertianic acid, 17-hydroxy- and 17-acetoxylambertianic acid and 7α- hydroxylambertianic acid, two esterified and three highly oxygenated flavones, 5,7,4′-trihydroxy-3,3′-dimethoxy- flavone-4′-O- [2-methylbutyrate] and isovalerate, 3′,5′-dihydroxy-3,5,6,7,8,4′-hexamethoxyflavone, 5,3′,5′-trihydroxy- 3,6,7,8,4′-pentamethoxyflavone and 5,7,3′,5′-tetrahydroxy-3,6,8,4′-tetramethoxyflavone. The structures were elucidated by spectroscopic methods and a few chemical transformations.     

New germacranolides and other constituents from Trichogoniopsis morii

Trichogoniopsis morii afforded, in addition to known compounds, a new toxol derivative, two diterpenes, a labdane and an ent-kaurane derivative, an eudesmanolide and five germacranolides, a furanoheliangolide and four 1-oxo-germacranolides. The structures were elucidated by spectroscopic methods and a few chemical transformations. The chemotaxonomy of the genus Trichogoniopsis is discussed briefly.     

New labdane diterpenoids from Sideritis chamaedryfolia

From the aerial parts of Sideritis chamaedryfolia six previously known ent-kaurene diterpenoids have been isolated. In addition, seven new labdane derivatives have also been obtained from the same source. The structures of these new natural diterpenoids have been established by chemical spectroscopic means and by correlation with known products.     

Four oplopanone and bisabolone derivatives from Rugelia nudicaulis

Rugelia nudicaulis afforded, in addition to known compounds, three new highly oxygenated oplopanone derivatives and a bisabolone derivative. The structures were elucidated by high field ¹H NMR spectroscopy. The chemotaxonomic situation is discussed briefly.     

Neue diterpene aus Schkuhria-arten

The investigation of two further Schkuhria species afforded, in addition to several known compounds, three new diterpenes from the labdane series of the manoyl oxide type. The structures were elucidated by spectroscopic methods and by some chemical transformations, although the absolute configuration and that at C-13 could not be established with certainty. Furthermore a new thymol derivative was obtained. The chemotaxomonic situation is discussed briefly.     

Germacrene derivatives and other sesquiterpenes from Senecio species and Lordhowea insularis

From Senecio galpinii six new highly oxygenated germacrene derivatives were isolated, while S. coronatus afforded in addition to known cacalol derivatives two new ones. This species also contained a rare tricyclic sesquiterpene angelate, so far only isolated from one species. From the aerial parts of S. pleistocephalus an angelate derived from cadinene was isolated, while Lordhowea insularis (Benth.) B. Nord. afforded farnesyl angelate, which was reported previously. The structures were elucidicated mainly by high field ¹H NMR spectroscopy.     

Labdane derivatives from Planaltoa lychnophoroides

The investigation of a representative of the small Brazilian genus Planaltoa afforded, in addition to known compounds, a new toxol derivative and two ent-labdane derivatives, closely related to austrofolin. The structures were elucidated by high field ¹H NMR spectroscopy. The chemotaxonomic situation is discussed briefly.     

Caryophyllene derivatives and a hydroxyisocomene from Pulicaria dysenterica

The investigation of the aerial parts of Pulicaria dysenterica afforded, in addition to known compounds, nine new caryophyllene derivatives with oxygen functions at C-7, C-13 and either C-14 or C-5. One of the keto diols was also present as an ester of a caryophyllenic acid. The roots afforded a new derivative of isocomene together with its precursor. The structures were elucidated by highfield ¹H NMR spectroscopy and by some chemical transformations.