Wickerols A and B: novel anti-influenza virus diterpenes produced by Trichoderma atroviride FKI-3849

Assigning the Origin of Microbial Natural Products by Chemical Space Map and Machine Learning

“…Another striking insight is provided by inspecting the TMAP colored by the fraction of sp3 carbons (fsp3C, Figure 1 B), which allows the identification of areas rich in aromatic polyphenols with very low fsp3C, such as nocatrione A (NPA014210, bacterial) [ 50 ] and sydowiol E (NPA001030, fungal) [ 51 ], as well as areas populated by terpenoids with very high fsp3C such as neoverrucosane diterpenoids (e.g., neoverrucosan-5β,9β,18β-triol, NPA001820, bacterial) [ 52 ] and the anti-influenza virus diterpene wickerol B (NPA008911, fungal) [ 53 ]. The structures of these compounds are shown in Figure 2 .…”

Development of anti‐influenza agents from natural products

“…Thus, the modification at C-8 may be an important determinant of the antiviral properties and spectra. 60 The inhibition percentages of four diterpenes (33)(34)(35)(36) from the brown alga Dictyota plectens on HA-mediated viral entry of influenza virus strain A/Viet Nam/1203/2004 (H5N1) were 50% to 62% at 30.0 μM (CC 50 > 60 µM). 61 respectively) were about 100-fold more potent than 37 against IAV, and the benzyl ester 40 was 10-fold more potent than 37 (EC 50 = 1.59 μM).…”

Herquline A, produced by Penicillium herquei FKI-7215, exhibits anti-influenza virus properties

“…2,3) As a result of our continuous screening for new antiviral antibiotics from microbial metabolites, we have recently identified new anti-influenza virus diterpene compounds with a novel fused 6/5/6/6 ring skeleton, wickerols A and B, isolated from the culture broth of a fungus, Trichoderma atroviride FKI-3849. 4) We have subsequently isolated herquline A from a culture broth of Penicillium herquei FKI-7215, which also possesses potent anti-influenza virus properties in our screening system. 4) In this paper, we report the taxonomy of the producing strain, fermentation, isolation, and initial assessment of some bioactive characteristics of herquline A.…”

“…4) We have subsequently isolated herquline A from a culture broth of Penicillium herquei FKI-7215, which also possesses potent anti-influenza virus properties in our screening system. 4) In this paper, we report the taxonomy of the producing strain, fermentation, isolation, and initial assessment of some bioactive characteristics of herquline A.…”

“…Anti-influenza virus activity and cell cytotoxicity of the compounds were evaluated by the crystal violet staining method. 4) The absorbance (A 595 ) of each well was measured by a microplate reader SH-9000 Lab (Corona Electric Co., Ltd. Ibaraki, Japan.). Ribavirin (viral RNA synthesis inhibitor), amantadine (influenza A virus M2 proton channel blocker), zanamivir (neuraminidase inhibitor), and oseltamivir (neuraminidase inhibitor) were purchased from Sigma-Aldrich (St. Louis, MO, USA).…”