An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported. Key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized norcaradiene intermediate.

lation of five neo-clerodane diterpenoid alkaloids from the aerial parts of Scutellaria barbata. As part of our continuing work to discover more novel neo-clerodane diterpenoids, we have re-investigated the aerial parts of this species and isolated the previously isolated scutebarbatine B (6), scutebarbatine D (7) and scutebarbatine F (8), together with five new neo-clerodane diterpenoid alkalo...

Five new diterpenoid alkaloids, ajacisines A–E (1–5), were isolated from Delphinium ajacis, along with seven known alkaloids (6–12). On the basis of their spectral data (IR, UV, HR‐ESI‐MS, 1D and 2D NMR) and chemical properties, the structures of compounds 1–12 were identified. All isolated compounds were evaluated for their in vitro antiviral activities against respiratory syncytial virus, and...

Miltiradiene (1) is the precursor of phenolic diterpenoids such as ferruginol (2), requiring aromatization and hydroxylation. While this has been attributed to a single cytochrome P450 (CYP76AH1), characterization of the rosemary ortholog CYP76AH4 led to the discovery that these CYPs simply hydroxylate the facilely oxidized aromatic intermediate abietatriene (3).

This work describes the configurational and conformational analyses of 1,6,7-triacetoxy-8,13-epoxy-14-labden11-one, a labdane diterpenoid isolated from Plectranthus ornatus. Its relative stereochemistry was previously proposed by comparison with H and C NMR data of forskolin (2); however, the configurations of C-8 and C-13 have not been confirmed. Correlations between C NMR experimental data an...

Diterpenoid natural products cover a vast chemical diversity and include many medicinally and industrially relevant compounds. All diterpenoids derive from a common substrate, (E,E,E)-geranylgeranyl diphosphate, which is cyclized into one of many scaffolds by a diterpene synthase (DTS). While diterpene biosynthesis has been extensively studied in plants and fungi, bacteria are now recognized fo...

A rapid and effective method was developed for separation and identification of diester-diterpenoid alkaloids (DDA) in the roots of Aconitum carmichaeli by ultra-high-pressure liquid chromatography coupled with high resolution LTQ-Orbitrap tandem mass spectrometry (UHPLC-LTQ-Orbitrap-MS(n)). According to accurate mass measurement and the characteristic neutral loss filtering strategy, a total o...

Ginkgo biloba L. has attracted much attention due to its medicinal properties, particularly those of terpenoid and flavonoid contents. However, the content utilization efficiency terpenoids remain low. The enzyme 3-hydroxy-3-methylglutaryl CoA synthase (HMGS) is a major rate-limiting factor, RNA-seq revealed that mRNA expression this differentially expressed during biosynthesis. Here, we invest...

THE TITLE COMPOUND [SYSTEMATIC NAME: 6β,10-dihy-droxy-1α,14α,16β-trimeth-oxy-4-methyl-7β,8-(methyl-enedi-oxy)-20-ethyl-aconitan-6-yl acetate], C(27)H(41)NO(8), is a C(19)-diterpenoid alkaloid and a major diterpenoid alkaloid component of the roots of Delphinium delavayi Franch. var. pogonanthum (Hand.-Mazz.) W. T. Wang. The mol-ecule has a lycoctonine carbon-atom skeleton with four six-membered...

While terpenoid production is generally associated with plants, a variety of fungi contain operons predicted to lead to such biosynthesis. Notably, fungi contain a number of cyclases characteristic of labdane-related diterpenoid metabolism, which have not been much explored. These also are often found near cytochrome P450 (CYP) mono-oxygenases that presumably further decorate the ensuing diterp...