Abstract The fragmentation mechanisms leading to the formation of several pronounced fragment ions formed during EI mass spectrometry diterpene hydrocarbons polytrichastrene A and wanju‐2,5‐diene were investigated by isotopic labelling experiments. All twenty singly 13 C‐labelled isotopomers these diterpenes enzymatically synthesised from ( C)geranylgeranyl diphosphate using synthase Chryseobac...

Vascular plants invariably contain a class II diterpene cyclase (EC 5.5.1.x), as an entcopalyl diphosphate synthase is required for gibberellin phytohormone biosynthesis. This has provided the basis for evolution of a functionally diverse enzymatic family. A bifunctional diterpene synthase was characterized from the lycophyte Selaginella moellendorffii. The structure of its product, labda-7,13E...

A phytochemical investigation of the CHCl (3)-soluble extract of the entire plant of Egletes viscosa (Asteraceae), collected in Peru, afforded two new labdane glycosides, 13-hydroxy-7-oxolabda-8,14-diene 13( R)- O-alpha- L-arabinopyranoside and 13-hydroxylabda-7,14-diene 13( R)- O-alpha- L-arabinopyranoside, along with four known compounds. The structures of the new compounds were elucidated by...

The evolution of natural product biosynthetic pathways can be envisioned to occur via a number of mechanisms. In the present study we provide evidence that latent plasticity plays a role in such metabolic evolution. In particular, rice (Oryza sativa) produces both ent- and syn-CPP (copalyl diphosphate), which are substrates for downstream diterpene synthases. In the present paper we report that...

W e present a novel application of Inductive Logic Programming (ILP) to the problem of diterpene structure elucidation from 1 3 C NMR spectra. Diterpenes are organic compounds of low molecular weight with a skeleton of 20 carbon atoms. T hey are of signicant chemical and commercial interest because of their use as lead compounds in the search for new pharmaceutical e ectors. T he interpretation...

Diterpene esters of the phorbol and ingenol types are known to be highly active tumor promoting agents that typically occur in members of the Euphorbiaceae. In the present work, Euphorbia leuconeura, a rare indoor plant, is analyzed for its tumor promoting potential. Latex as well as total leaf extracts exhibited Epstein-Barr-virus (EBV) inducing activity comparable to 12-O-tetradecanoyl-phorbo...

Isoprenoid precursors readily undergo (poly)cyclization in electrophilic reaction cascades, presumably as internal addition of the carbon-carbon double-bonds from neighboring isoprenyl repeats readily forms relatively stable cyclohexyl tertiary carbocation intermediates. This hypothesis is agnostic regarding alkene configuration (i.e., Z or E). Consistent with this, here it is shown that certai...

From the flowers of Baccharis medullosa DC (Asteraceae) two new ent-labdane-type diterpene glycosides were isolated. Structures were established by application of various spectroscopic techniques. The sugar residues were identified after acid hydrolysis of the isolated products.

Three novel diterpene glycosides were isolated for the first time from the commercial extract of the leaves of Stevia rebaudiana, along with several known steviol glycosides, namely stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-15-en-19-oic acid, 13-[(2-O-β-D-glu...