Functional Crosstalk between Discrete Indole Terpenoid Gene Clusters in .

Indole terpenoids make up a large group of secondary metabolites that display an enticing array of bioactivities. While indole diterpene (IDT) and rarely indole sesquiterpene (IST) pathways have been found individually in filamentous fungi, here we show that both cluster types are encoded within the genome of . Through heterologous reconstruction, we demonstrate the cluster encodes for IST biosynthesis and can tailor IDT substrates produced by the cluster.

Generation of Alternate Indole Diterpene Architectures in Two Species of .

The significant structural diversity and potent bioactivity of the fungal indole diterpenes (IDTs) has attracted considerable interest in their biosynthesis. Although substantial skeletal diversity is generated by the action of noncanonical terpene cyclases, comparatively little is known about these enzymes, particularly those involved in the generation of the subgroup containing emindole SA and DA, which show alternate terpenoid skeletons. Here, we describe the IDT biosynthetic machinery generating these unusual IDT architectures from and .

Biosynthesis of Nodulisporic Acids: A Multifunctional Monooxygenase Delivers a Complex and Highly Branched Array.

Nodulisporic acids (NAs) are structurally complex potent antiinsectan indole diterpenes. We previously reported the biosynthetic gene cluster for these metabolites in Hypoxylon pulicicidum and functionally characterised the first five steps of the biosynthetic pathway. Here we reveal a highly complex biosynthetic array, furnishing multiple end products through expression of cluster components in Penicillium paxilli.

2-O-β-d-Glucopyranosyl l-Ascorbic Acid, a Stable Form of Vitamin C, Is Widespread in Crop Plants.

2-O-β-d-Glucopyranosyl l-ascorbic acid (AA-2βG) is a stable, bioavailable vitamin C (AA) derivative. We report the distribution and seasonal variation of AA-2βG in apples and its occurrence in other domesticated crops and in wild harvested Ma̅ori foods. Liquid chromatography-mass spectrometry analyses showed high AA-2βG concentrations in crab apples () but low concentrations in domesticated apples.

Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris).

Non-targeted LC-MS metabolomics on fruit of three wild and domesticated apple species (Malus sylvestris, M. sieversii and M. domestica) showed that two crab apple (M.

Phenylanthraquinones and flavone-C-glucosides from the disjunct Bulbinella in New Zealand.

The genera Bulbine, Bulbinella and Kniphofia produce phenylanthraquinones and are mostly found in southern Africa, although a disjunct group of Bulbinella species endemic to New Zealand also contain phenylanthraquinones as reported herein. The sub-Antarctic megaherb B. rossii yielded sulphated phenylanthraquinones, including a phenylanthraquinone found to carry a sulphated glycoside substituent, 4'-O-demethylknipholone-4'-β-D-xylopyranosyl-3″-sulphate.

Cytotoxic Amides from Fruits of Kawakawa, Macropiper excelsum.

Cytotoxic amides have been isolated from the fruits of the endemic New Zealand medicinal plant kawakawa, Macropiper excelsum (Piperaceae). The main amide was piperchabamide A and this is the first report of this rare compound outside the genus Piper. Eleven other amides were purified including two new compounds with the unusual 3,4-dihydro-1(2H)-pyridinyl group.