Three new 5,10-epoxygermacranolides from Liatris chapmanii and Liatris gracilis

Examination of Liatris chapmanii (T + G) Kuntze led to the isolation of two new germacranolides, chapliatrin (1a) and isochapliatrin (1b). Liatris gracilis Pursh gave chapliatrin and acetylchapliatrin 1c). The stereochemistry assigned to C-3, C-4 and C-10 is tentative. All three compounds possess the hitherto-unreported 5,10-oxygen linkage. L. gracilis also gave the benzofuran euparin (2) and the flavones hispidulin (dinatin, 3a and 3′,6-dimethoxy-4′,5,7-trihydroxyflavone (3b). L. chapimanii also gave 5-hydroxy-3′,4′,6,7-tetramethoxyflavone (3c).     

Deltoidin A and B,two new germacrolides from Eupatorium deltoideum

Investigation of E. deltoideum provided two new germacrolide-type sesquiterpene lactones, deltoidin A and B, besides the known guaianolide ligustrin, and diterpenes and triterpenes.     

3-Germacren-612-olides,from an undescribed liatris taxon

A previously undescribed variant of Liatris gracilis whose taxonomic status is still uncertain furnished a series of 3-germacren-6,12-olides different from the chapliatrin analogues found in authentic L. gracilis. The stereochemistry of one of the new sesquiterpene lactones was established by X-ray diffraction. A eudesmanolide previously isolated from L. gracilis was also found in the variant.     

New types of sesquiterpene lactones and other constituents from Trichogonia species

The investigation of five Trichogonia species afforded seven new furanoheliangolides, three dilactones of a new type, four pairs of epimeric rearra     

Two sesquiterpene lactones from Trichogonia gardneri

The structures and stereochemistries of two sesquiterpene lactones from Trichogonia gardneri were established as (6R,7S,8S,9S,IOR)-4E-9,10-dihydroxy-8-tigloxygermacr-4-en-6,12-olide) and (5R*,6R*,7S*,8S*,9R*)-14-acetoxy-3-chloro-9-hydroxy-2-oxo-8-tigloxyguia-1(10),3-dien-6,12-of olide by a combination of NMR spectrometry and X-ray diffraction. The results show that the structures of several sesquiterpene lactones which were isolated previously from related species require revision.     

Four guaianolides and other constituents from three kaunia species*

The investigation of three species of the new genus Kaunia afforded four new guaianolides and four thymol derivatives. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

Guaianolides from Liatris squarrosa

The isolation of three new guaianolides related to spicatin from Liatris squarrosa is reported.     

Further glaucolides from south african Vernonia species

The investigation of three South African Vernonia species afforded minute amounts of five new glaucolides, two monoepoxides and three diepoxides. The structures were elucidated by ¹H NMR spectroscopy. The roots of Vernonia sutherlandii contain, in addition to vernonataloide, bergamotene and santalene, minute amounts of the corresponding acetoxy derivatives.     

Sesquiterpene lactones and diterpenes from Mikania periplocifolia

The aerial parts of two collections of Mikania periplocifolia gave, in addition to mikanolide, miscandenin and several other known sesquiterpene dilactones related to them, the new dilactones 3β-hydroxy-11βH,13-dihydroisabelin, 11βH,13-dihydrodeoxymikanolide and mikaperiplocolide and three new geranylnerol derivatives.     

Sesquiterpene lactones of Eupatorium scabridum

Eupatorium scabridum, a hybrid biotype presumed to arise by hybridization of E. rotundifolium and E. semiserratum furnished anti-tumor sesquiterpene lactones characteristic of the putative parents.     

Guaianolides from Tricholepis glaberrima

Cynaropicrin and 11,13-dihydrodesacylcynaropicrin were isolated from Tricholepis glaberrima.     

Three eudesmanolides from Pluchea rosea

Three eudesmanolides of Pluchea rosea were found to be structurally related to the eudesmane, cuauthemone, earlier reported from plants of the same genus.     

Germacra-1(10),4-dien-cis-6,12-olides and elemanolides from Montanoa atriplicifolia

The investigation of the aerial parts of Montanoa atriplicifolia afforded, in addition to known compounds, two pairs of isomeric cis-6,12-germa     

Pseudoguaianolides related to confertin from Stevia isomeca

The aerial parts of Stevia isomeca afforded, in addition to known compounds, four new sesquiterpene lactones, three pseudoguaianolides related to stevin and a xanthanolide. The structures were elucidated by spectroscopic methods and a few chemical transformations.     

A heliangolide from Schkuhria pinnata

Re-investigation of the aerial parts of Schkuhria pinnata afforded in addition to the heliangolides isolated previously a new one, the structure of