Aranorosinol A and aranorosinol B, two new metabolities from Pseudoarachniotus roseus: Production, isolation, structure elucidation and biological properties.

Abstract

Two new secondary metabolites, aranorosinol A (1) and aranorosinol B (2), were isolated from a strain of Pseudoarachniotus roseus. Their structures were elucidated on the basis of their spectral properties and chemical transformations and were found to be similar to aranorosin (3) isolated from the samestrain.We have recently isolated two new metabolites, aranorosinol A (1) and aranorosinol B (2), from the fungal strain Y-30499 identified as Pseudoarachniotus roseus. Herein we report the isolation, structure elucidation and biological properties of these two metabolites. Compounds1 and 2 are structurally related to aranorosin (3) which was isolated earlier from the same fungal strain1~3). FermentationFermentation was carried out in shake flasks as well as in laboratory fermenters using the methods and conditions reported earlierX). The progress of the fermentation was monitored by the agar diffusion assay using Bacillus subtilis as the test strain. The antibiotics were present in both the culture filtrate and the mycelial cake. IsolationThe culture filtrate (40 liters) was extracted with ethyl acetate (2 x 15 liters). The mycelial cake (3.7 kg) Dedicated to Prof. Ch. Bheemasankara Rao of Andhra University on the occasion of his 60th birthday.

Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus

“…This class of fungal derived natural products contains a 4,6-dimethyl-dodecadien-2E,4E-oic acid unit connected to a tyrosine unit through an amide linkage. The tyrosine unit can have various degrees of oxygenation, halogenation, cyclisation and esterification, as found in aranorosin (4), 5 aranorosinol A (2), aranorosinol B, 4 aranochlor A and aranochlor B from Pseudoarachniotus roseus, 6 gymnastatin A (5) to E, 7 F to H (6) 8 and I (7) to M 9 from Gymnastella dankaliensis (Fig. 1).…”

“…Bioassay guided fractionation led to the isolation of the new natural product, gymnastatin N (1) and the known compound aranorosinol A (2) (Fig. 1), 4 with IC 50 values of 13 and 118 mM, respectively. A 12 0 -hydroxy analog of gymnastatin N, 3, was also isolated as a minor component (Fig.…”

Cytotoxic acyl amides from the soil fungus Gymnascella dankaliensis

“…The best of our knowledge, 4 represents a new natural product, which was reported before only as semisynthetic derivative of 7 in a structure relationship study. 32 The remaining compounds (5 -10) were elucidated on the basis of their NMR and mass spectrometric data and by comparison with the literature as 12`-hydroxygymnastatin N (5), 28 farinosone C (6), 29 aranorosin (7), 33,34 aranorosinol A (8) and B (9) 34 and gymnamide (10). 30 The biosynthesis of the tyrosine derived amides obtained from G. dankaliensis is suggested to start with an intact tyrosine moiety like in 2, 5 and in the known gymnastatin N (Scheme 1).…”

Bacterial protein kinase inhibitors

“…Aranorosinol B (24), isolated from Pseudoaracniotus roseus [Roy et al, 1992], inhibited autophosphorylation of YycG from B. subtilis and S. aureus with IC 50 values of 232 and 211 mM, respectively. Aranorosinol B also showed antibacterial activity against B. subtilis and S. aureus with MICs of 31.25 and 15.62 mg/ml, respectively [Okada et al, 2007].…”