Secondary metabolites by chemical screening. 21. Clonostachydiol, a novel anthelmintic macrodiolide from the fungus Clonostachys cylindrospora (strain FH-A 6607).

Abstract

Application of our chemical screening methodology2) to different new fungal isolates gave rise to the detection, isolation, structure elucidation, and widespread biological testing of a new fungal metabolite named clonostachydiol (1), which is related to the macrodiolides of the colletodiol family3 '4).The producing organism, strain FH-A 6607, was isolated from a soil sample collected near Rantepao, Sulawesi Island (Indonesia) and exhibited a characteristic brown to yellow colored mycelium. The typical conidiophores were found to be in close morphological analogy to gliocladium and are arranged in self-contained long rows (Fig.

Nematicidal Substances from Fungi

“…This compound has also been isolated from other fungal species such as Monosporium bonorden, Pencicillium luteoaurantium [86] and Chaetomium chiversii [87]. Its two dialkoxy derivatives radicicol B (96) and radicicol C (97) also possessed nematicidal activities against an unidentified soil nematode with an LD 50 value at 200 μg mL -1 [88]. A 9-lactide decane compound lethaloxin (98) isolated from Mycosphaerella lethalis [89] was also proven capable of killing C. elegans with an LD 50 at 25 g mL -1 [88].…”

“…This compound is related to the macrodiolides of the colletodiol family and its synthesis in vitro has been achieved [97]. A dose of 2.5 mg kg -1 subcutaneously administered to sheep artificially infected with the nematode Haemunchus cortortus caused 80 to 90% reduction of abomasum nematodes [96]. Four macrolides including a new compound dehydrocurvularin (101) and three known ones -dehydrocurvularin (102), 8--hydroxy-7-oxocurvularin (103) and 7-oxocurvularin (104) were obtained from Aspergillus spp.…”

“…A 14-membered macrodiolide clonostachydiol (100) was isolated from the ascomycete Clonostachys cylindrospora [96]. This compound is related to the macrodiolides of the colletodiol family and its synthesis in vitro has been achieved [97].…”

In Vitro Lethal Activity of the Nematophagous Fungus Clonostachys rosea (Ascomycota: Hypocreales) against Nematodes of Five Different Taxa

“…Such compound was called “Clonostachydiol” and it was classified into the macrodiolids group. In addition, such biocompound possesses an important nematicidal activity against H. contortus when is subcutaneously administered at 2.5 mg/kg BW producing 80 to 90% parasitic burden reduction [40]. In the present research, no chemical study was performed; however, the C. rosea strain could be a good candidate to search for metabolites with nematicidal activity against H. contortus and other ruminant parasitic nematodes of importance for livestock industry.…”

5-Substituted [1]pyrindine derivatives with antiproliferative activity

“…1). Molecules bearing the [1]pyrindine moiety have also been described such as streptazolin [3,4], a tricyclic compound displaying antibiotic and antifungal properties and its by-product, the 5-O-(b-D-xylopyranosyl)-streptazolin [5] which shows in vitro cytotoxic activity against several human cancer cell lines (Fig. 1).…”