Lasiodiplodiapyrones A and B, Pyrone–Preussomerin Adducts with Highly Strained Polycyclic Ring Systems from Lasiodiplodia pseudotheobromae

Abstract

Lasiodiplodiapyrones A and B (1 and 2), two new preussomerin derivatives, possessing an unexpected 6-methyl-4H-furo[3,2-c]pyran-4-one moiety and a highly functionalized conjoint and complicated polycyclic ring system, along with two known congeners (3 and 4), were isolated from the fungus Lasiodiplodia pseudotheobromae. Their structures including absolute configurations were determined by spectroscopic analyses, Mosher’s method, and ECD calculations. A biosynthetic pathway was proposed to explain the origin of lasiodiplodiapyrones A and B as well as their relationship with preussomerins. Compounds 1–4 showed suppressive effects on the production of NO with IC50 values of 4.8 ± 0.3, 8.5 ± 1.1, 5.9 ± 0.8, and 12.8 ± 1.3 μM, respectively.

Highly Functionalized Spirobisnaphthalenes from Roussoella sp. KT4147

“…Although the specific electronic excitation causing this effect could not be pinpointed, this structural alignment was considered to have caused the negative Cotton effect in this wavelength region. All fungal bicyclic diacetal spirobisnaphthalenes, preussomerin derivatives, ,,, and lasiodiplodiapyrones, have been reported to exhibit characteristic negative Cotton effects within 200–235 nm.…”

Total Synthesis and Biological Activity of (±)-Guignardin A, (±)-Palmarumycin B9, and Their Derivatives

“…Spirobisnaphthalene natural products, which were divided into five types based on the different linkages of the two naphthalenes, have a broad biological activities, such as antifungal, antimicrobial, antitumor, anticancer, antiparasitic, anti-inflammatory, and cytotoxic activity. − Many reports related to the total synthesis, structure revision, and modification, and biological activity evaluation of the spirobisnaphthalene natural products have appeared in recent years, − in which spiromamakone A and its monobenzo analogue (Figure B) showed excellent cytotoxicity against cervical carcinoma HeLa cells with IC 50 value of 0.77 and 0.56 μM, respectively. − Some of works have also been carried out in the total synthesis and biological activities of this family of natural products in our group. − …”

Hot off the Press

“…Lasiodiplodiapyrone A 14 is a metabolite of Lasiodiplodia pseudotheobromae with a novel strained polycyclic skeleton. 14 The authors propose that lasiodiplodiapyrone A 14 is formed from three polyketide precursors.…”