Cordybislactone, a stereoisomer of the 14-membered bislactone clonostachydiol, from the hopper pathogenic fungus Cordyceps sp. BCC 49294: revision of the absolute configuration of clonostachydiol

Ojima, Ken Ichi; Yangchum, Arunrat; Laksanacharoen, Pattiyaa; Tasanathai, Kanoksri; Thanakitpipattana, Donnaya; Tokuyama, Hidetoshi; Isaka, Masahiko

doi:10.1038/s41429-017-0008-9

Cited by 12 publications

(16 citation statements)

References 12 publications

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“…This macrolide 29 is a bisacetylated, diastereomeric derivative of the anthelmintic 14-membered macrolide clonostachydiol (30), which was originally isolated from the fungus Clonostachys cylindrospora [48], but found in a Xylaria sp. [49] recently. E1011 (29) exhibited moderate cytotoxicity against diverse human cell lines like HL-60 or A-549 with IC 50 values of 4.9 and 25.6 µM, respectively [47].…”

Section: Non-ribosomal Peptides From Xylariaceae (Fig 5)mentioning

confidence: 99%

“…8) Co-cultivation is a regularly applied approach to induce activation of so-far silent gene clusters. One recent positive example of a novel backbone discovered is the meroterpenoid wheldone (49), which was produced (presumably) by X. flabelliformis when co-cultured with two different Aspergillus spp., respectively [68]. A moderate cytotoxicity was measured for 49 with lowest IC 50 values of 2.4 µM against MDA-MB-435 (human melanoma cancer cell line).…”

Section: Benzenoids and Lactones From Xylariaceae (Fig 7)mentioning

confidence: 99%

“…E1011 ( 29 ) exhibited moderate cytotoxicity against diverse human cell lines like HL-60 or A-549 with IC 50 values of 4.9 and 25.6 µM, respectively [ 47 ]. Clonostachydiol ( 30 ), was also found to be weakly cytotoxic (KB: IC 50 39 µg/mL, NCI-H187: 17 µg/mL) [ 49 ].

Fig.…”

Section: Novel Secondary Metabolites From the Xylariaceae Smentioning

confidence: 99%

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Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Becker

Stadler

2020

J Antibiot

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The families Xylariaceae and Hypoxylaceae (Xylariales, Ascomycota) represent one of the most prolific lineages of secondary metabolite producers. Like many other fungal taxa, they exhibit their highest diversity in the tropics. The stromata as well as the mycelial cultures of these fungi (the latter of which are frequently being isolated as endophytes of seed plants) have given rise to the discovery of many unprecedented secondary metabolites. Some of those served as lead compounds for development of pharmaceuticals and agrochemicals. Recently, the endophytic Xylariales have also come in the focus of biological control, since some of their species show strong antagonistic effects against fungal and other pathogens. New compounds, including volatiles as well as nonvolatiles, are steadily being discovered from these ascomycetes, and polythetic taxonomy now allows for elucidation of the life cycle of the endophytes for the first time. Moreover, recently high-quality genome sequences of some strains have become available, which facilitates phylogenomic studies as well as the elucidation of the biosynthetic gene clusters (BGC) as a starting point for synthetic biotechnology approaches. In this review, we summarize recent findings, focusing on the publications of the past 3 years.

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Section: Non-ribosomal Peptides From Xylariaceae (Fig 5)mentioning

confidence: 99%

Section: Benzenoids and Lactones From Xylariaceae (Fig 7)mentioning

confidence: 99%

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Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Becker

Stadler

2020

J Antibiot

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“…It exhibited anthelimintic activity against abomasum nematode Haemonchus cortorus in artificially infected lambs [ 59 ]. Four stereocenters in clonostachydiol were revised later [ 71 ].…”

Section: Polyketides and Their Biological Activitiesmentioning

confidence: 99%

Metabolites from Clonostachys Fungi and Their Biological Activities

Han

Zhang

et al. 2020

JoF

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Clonostachys (teleomorph: Bionectria) fungi are well known to produce a variety of secondary metabolites with various biological activities to show their pharmaceutical and agrochemical applications. Up to now, at least 229 secondary metabolites, mainly including 84 nitrogen-containing metabolites, 85 polyketides, 40 terpenoids, and 20 other metabolites, have been reported. Many of these compounds exhibit biological activities, such as cytotoxic, antimicrobial, antileishmanial, antimalarial activities. This mini-review aims to summarize the diversity of the secondary metabolites as well as their occurrences in Clonostachys fungi and biological activities.

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“…[12] and Xylaria sp. [13,14]; 4-keto-clonostachydiol from Gliocladium sp. [12,15]; cordybislactone from Cordyceps sp.…”

Section: Introductionmentioning

confidence: 99%

Halosmysin A, a Novel 14-Membered Macrodiolide Isolated from the Marine-Algae-Derived Fungus Halosphaeriaceae sp.

et al. 2020

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Halosmysin A, a new 14-membered macrodiolide with an unprecedented skeleton, was isolated from the fungus Halosphaeriaceae sp. OUPS-135D-4, which, in turn, was obtained from the marine algae Sargassum thunbergii. The chemical structure of the macrodiolide was elucidated using 1D and 2D NMR, as well as high resolution fast atom bombardment mass (HRFABMS) spectral analysis. The absolute stereochemistry was determined via chemical derivatization and comparison with a known compound, (6R,11R,12R,14R)-colletodiol. Additionally, halosmysin A was shown to be very potent against murine P388 leukemia, human HL-60 leukemia, and murine L1210 leukemia cell lines, with IC50 values ranging from 2.2 ± 3.1 to 11.7 ± 2.8 μM.

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Cordybislactone, a stereoisomer of the 14-membered bislactone clonostachydiol, from the hopper pathogenic fungus Cordyceps sp. BCC 49294: revision of the absolute configuration of clonostachydiol

Cited by 12 publications

References 12 publications

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Metabolites from Clonostachys Fungi and Their Biological Activities

Halosmysin A, a Novel 14-Membered Macrodiolide Isolated from the Marine-Algae-Derived Fungus Halosphaeriaceae sp.

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