Arthrinone, a Novel Fungal Metabolite from Arthrinium sp. FA 1744

Abstract

A novel fungal metabolite, arthrinone [1], was isolated from the culture broth oí Arthrinium sp. FA 1744 by chromatographic methods. The structure and relative stereochemistry of arthrinone were determined by spectral and single-crystal X-ray analyses.

Synthesis of propellane-containing natural products

“…FA 1744 in 1994. 105 Its only total synthesis was reported in 2000 by Uchiyama and co-workers (Scheme 22). 106 The key ring-forming steps in the synthesis include a Diels-Aldercycloreversion reaction of a diene and an acetylene to form a highly substituted aromatic ring, as well as a Dieckmann condensation.…”

Chemoselective Synthesis of Novel Heterocyclic [3.3.3]Propellane Derivatives via a One‐pot Three‐component Reaction

“…[2] They are present in many different classes of natural products, such as Marasmic acid, Sterepolide and Merrilactone A (Figure 1). [3] Moreover, heterocyclic propellanes possess a wide range of medicinal properties such as anticancer, [4] antibacterial, [5] selective T-cell cytotoxicity, [6] antibiotic, [7] antifungal, [8] antiamnesic [9] and platelet-activating factor antagonistic activities. [10][11] By far, most methods for synthesis of propellane system are using the Diels-Alder reaction.…”

Arthrinins A–D: Novel diterpenoids and further constituents from the sponge derived fungus Arthrinium sp.

“…Previous chemical investigations of fungal strains of the genus, Arthrinium, a dematiaceous anamorph of the teleomorph genus Apiospora, revealed a plethora of structurally interesting secondary metabolites such as arthrinone, 29 arthrichitin, 30 terpestacin, 31 CAF-603, 32 norlichexanthone, 33 apiosporamide, 34 the cyclopeptides TMC-95A-D, 35 and the pimarane-type diterpene myrocin A. 36 We now report the isolation and structural elucidation of five new diterpenoids (1)(2)(3)(4)(5) as well as five known natural products (6)(7)(8)(9)(10), and on their antiproliferative activities against a panel of human and murine cell lines (Chart 1).…”