Diterpenes from eupatorium turbinatum

The aerial parts of Eupatorium turbinatum afforded three diterpenes, a known clerodane derivative, an unusual abietane derivative and a friedolabdane, liliolide, β-farnesene and the flavonol pachypodol. The structures were elucidated by highfield NMR spectroscopy. The chemotaxonomy is discussed briefly.     

Diterpenes from sideritis infernalis

Five new ent-kaurene diterpenes, episinfernal, sinfernal, sinfernol, epoxysinfernol and canditriol, and the known one, candol B, candicandiol and candidiol, have been isolated from the aerial parts of Sideritis infernalis.     

Diterpenes from Stevia monardaefolia

An investigation of Stevia monardaefolia resulted in the isolation of two new labdane type diterpenes, 6α-angeloyloxy nidorellol and 6α-angeloy     

Diterpenes from Salvia breviflora

In addition to compounds which are ubiquitous in Salvia species, like ursolic and oleanolic acids, we have isolated two heterobicyclic diterpenes, brevifloralactone and brevifloralactone acetate.     

Diterpenes from Ballota species

Hispanolone was isolated from Ballota andreuzziana; B. pseudodictamnus contains ballonigrin, 18-hydroxyballonigrin, marrubenol, and the flavone 7, 4′-di-O-methylapigenin.     

Diterpenes from Araucaria bidwilli

Eight diterpent acids of the labdane or clerodane type were obtained from the oleoresin of Araucaria bidwilli and characterized as their methyl esters.     

Diterpenes from Baccharis species

The aerial parts of Baccharis minutiflora afforded in addition to known compounds eight new ent-kaurane derivatives, one being a homo kaurane, while the aerial parts of B. alatemoides gave two pairs of epimeric clerodane derivatives, which, however, had to be modified chemically before they could be separated. The stereochemistry of these diterpenes could not be elucidated with certainty.     

Diterpenes from Laennecia sophiifolia

From the aerial parts of Laennecia sophiifolia (Kunth) G.L. Nesom, a neo-clerodane and an acyclic furano diterpene were isolated, along with four known compounds, 2beta-hydroxyhardwickiic acid, hawtriwaic acid, apigenin, and beta-sitosterol. Their structures were established as 12-epi-bacchotricuneatin A and (2E,6E)-9-(3-furyl)-6-methyl-2-(4-methylpent-3-enyl)-nona-2,6-dienoic acid, by analysis of spectral evidence. The absolute structure of 12-epi-bacchotricuneatin A was determined by a circular dichroism spectral comparison with that of bacchotricuneatin A.     

Diterpenes from Koanophyllon species

The investigation of two Koanophyllon species afforded, in addition to known compounds, several new diterpenes, two new geranylgeraniol derivatives and four diterpenes, most probably closely related to clerodanes; their structures, however, could not be deduced with certainty. The chemotaxonomic situation of this genus is discussed briefly.     

Diterpenes from sideritis nutans

Four new ent-labdane oxide diterpenes, sidnutol, gomerol, 13-epi-gomerol and 3α-hydroxy-gomeric acid, and the previously known gomeraldehyde, 13-epi-gomeraldehyde, ent-norambreinolide, ent-2α-hydroxy-13-epi-manoyloxide, gomeric acid and 13-epi-gomeric acid, have been isolated from the aerial parts of Siderius nutans.     

Diterpenes from Palafoxia texana

The investigation of Palafoxia texana afforded in addition to the known compound jesromotetrol two new rosene derivatives: 3β-acetoxy-jesromotetrol and 3β,19-diacetoxy-jesromotetrol. The structures were determined by spectroscopic methods and chemical transformations.     

Diterpenes from Mikania species

The investigation of four further Mikania species afforded several diterpenes, four geranylgeraniol derivatives and three kaurane epoxides. The structures were elucidated by spectroscopic methods and a few chemical transformations.     

Diterpenes from Baccharis species

The investigation of ten Baccharis species afforded in addition to known compounds eight new diterpenes, four ent-labdanes, three kaurenes and a clerodane derivative. Furthermore, two new p-hydroxyacetophenones, a flavone, 3′-methoxyxanthomicrol and two matricaria ester derivatives were isolated. The structures were elucidated by spectroscopic methods and a few chemical transformations. The chemotaxonomic situation of the large genus is discussed briefly.     

Diterpenes from Dysoxylum lukii Merr

Six new diterpenes and two known compounds were isolated from the stems of Dysoxylum lukii Merr and characterized on the basis of spectral data. Dysokusone F(1), 2-Oxoneoclerod-3, 13Z-dien-15-ol (2), 3α-(4-Hydroxy-3,5-dimethoxy-benzoyloxyl)-clerod-14-ene-4β,13-diol (3), 3α-(4-Hydroxybenzoyloxyl)-clerod-14-ene-4β,13-diol (4), and 3α-(4-Hydroxy-3-methoxybenzoyloxyl)-clerod-14-ene-4β,13-diol (5) exhibited inhibitory effects against PTP-1B with IC₅₀ values of 51.62±6.55, 56.74±7.96, 17.04±3.43, 28.96±4.59, and 19.70±2.57 μM, respectively.     

Abietane Diterpenes from Hyptis suaveolens

Investigation of the constituents of the whole plant of Hyptis suaveolens led to the isolation of three new abietane diterpenes, isosuaveolic acid ( 1 ), 8α,9α‐epoxysuaveolic acid ( 2 ), and 14‐O‐methylsuaveolic acid ( 3 ), together with eleven known compounds. The structures of 1 – 3 were established by spectroscopic methods and chemical correlations. Some isolates were tested for their antimycobacterial and cytotoxic activities.     

Diterpenes derived from clerodanes from Pulicaria angustifolia

The investigation of Pulicaria angustifolia afforded, in addition to known triterpenes and caryophyllene epoxide, four methyl esters of diterpenes, all derived from clerodane. Three of them are derivatives of seco-nidoresedic acid. The structures were elucidated by spectroscopic methods.