Two new meroterpenoids produced by the endophytic fungus Penicillium sp. SXH-65

Abstract

Two new meroterpenoids, arisugacins I (1) and J (2), together with five known meroterpenoids including arisugacin B (3), arisugacin F (4), arisugacin G (5), territrem B (6) and territrem C (7) were isolated from an endophytic fungus Penicillium sp. SXH-65. Their structures were determined by extensive spectroscopic experiments and comparison with literature data. Their cytotoxicities were evaluated against Hela, HL-60 and K562 cell lines, and only 3 and 4 exhibited weak cytotoxicities against Hela, HL-60 and K562 cell lines with IC50 values ranging from 24 to 60 μM.

Meroterpenes from an algicolous strain of Penicillium echinulatum

“…The structures and relative configurations of four known meroterpenes, including arisugacin J ( 2 ), arisugacin G ( 3 ), arisugacin C ( 4 ), and territrem C ( 5 ), were characterized by NMR data comparison with literature values. Because most of the chiral centers (C‐4a, C‐6a, C‐12a, and C‐12b) in arisugacin and territrem meroterpenes were conservative, the absolute configurations of them could be deduced by the identical ECD spectra and specific optical rotations with their analogs.…”

“…During our continuing investigations toward the bioactive compounds from algicolous fungi, a fungal strain Penicillium echinulatum pt‐4 obtained from the inner tissue of the marine red alga Chondrus ocellatus was chemically examined. As a result, one new meroterpene, arisugacin K ( 1 ), and four known ones, arisugacin J ( 2 ), arisugacin G ( 3 ), arisugacin C ( 4 ), and territrem C ( 5 ), were isolated and identified (Fig. ).…”

Endophytic Fungi—Alternative Sources of Cytotoxic Compounds: A Review

“…The isolated compounds were evaluated against a panel of cancer cell lines. Arisugacin B and Arisugacin F exhibited weak cytotoxicity against HeLa, HL-60, and K562 cell lines with IC 50 values ranging from 24 to 60 μM (Sun et al, 2014 ). A new sesquiterpenoid, Perenniporin A (64) , from the endophytic fungus Perenniporia tephropora Z41 from T. chinensis var.…”

Endophytism of Penicillium Species in Woody Plants

“…Insecticidal properties have been also pointed out for the brasiliamides by an endophytic strain of P. brasilianum, which were found to induce convulsive effects in silkworms (Bombyx mori) [50] similar to those referable to penitrems [51] and other tremorgenic meroterpenoids of Penicillium. The latter class of compounds also includes the arisugacins and the territrems recently reported by a strain from Tamarix chinensis [52]. Alanditrypinone and related spiroquinazoline alkaloids, well known for their insecticidal activity [53], have been found as secondary metabolites of a strain (Eupenicillium sp.)…”