Structure of Colletochlorin D from<i>Colletotrichum nicotianae</i>

Kosuge, Yoshiaki; Suzuki, Akira; Tamura, Saburo

doi:10.1080/00021369.1974.10861376

Cited by 10 publications

(15 citation statements)

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“…To our knowledge, they were mainly isolated from the fermentation broths of the genera Nectria (Aldridge et al, 1972;Bal-Tembe et al, 1999;Guti errez et al, 2005), Fusarium (Ellestad et al, 1969), Cylindrocladium (Hayakawa et al, 1971Kato et al, 1970), Cylindrocarpon (Kawaguchi et al, 2013;Singh et al, 1996), Aspergillus (Takemoto et al, 2005), Ascochyta (Hosono et al, 2009;Tamura et al, 1968;Sasaki et al, 1972Sasaki et al, , 1973Sasaki et al, , 1974Terekhova et al, 1997;Sawada et al, 1973), Verticillium (Takamatsu et al, 1994Seephonkai et al, 2004), Colletotrichum (Kosuge et al, 1973, 1974a, 1974b), and Acremonium (Zhang et al, 2009Wanigesekara et al, 2013) (Ascomycota, Fungi), indicating that these genera might be closely related. In this study, all compounds were isolated from N. sp.…”

Section: Chemotaxonomic Significancementioning

confidence: 95%

Chlorinated phenolic sesquiterpenoids from the Arctic fungus Nectria sp. B-13

Liu

Chen

Qian

et al. 2015

Biochemical Systematics and Ecology

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Section: Chemotaxonomic Significancementioning

confidence: 95%

Chlorinated phenolic sesquiterpenoids from the Arctic fungus Nectria sp. B-13

Liu

Chen

Qian

et al. 2015

Biochemical Systematics and Ecology

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“…The majority of the analogues constitute simple backbone modifications, such as halogenation, dehydrogenation, hydroxylation, as well as acetylation of an alcohol group (2)(3)(4)(5)(6)(7)(8)(9), with alternative sesquiterpene cyclization to form an oxygen-containing heterocycle between 8 OH and C-11 (10)(11) or a linear sesquiterpene chain being the minor analogues (12-17; Figure 1) [5,9,10,12,13]. Furthermore, similar compounds with a single isoprene or monoterpene side chain have also been reported [8,[14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…Interestingly, the biosynthesis of both 1 and 11 starts by farnesylation of orsellinic acid to form the meroterpenoid 12, which upon further modifications result in 13, 14, and 15. The ilicicolin A epoxide (15) is the point of divergence, where 1 is produced through intermediate 5, and 11 through intermediates 16 and 10 (Figure 1). Therefore, by targeted knockout, selective production of either 1 or…”

Section: Introductionmentioning

confidence: 99%

Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria

et al. 2021

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The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19–22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B–D (23–25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2′/C-3′ and C-4′/C-5′ were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4′/C-5′ and C-8′/C-9′ were suggested to be necessary for the observed antibacterial activity.

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“…Compounds 1 and 2 are reported here for the first time. Their 1 H and 13 CNMR data are shown in Table 1.…”

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confidence: 99%

Deleting a Chromatin Remodeling Gene Increases the Diversity of Secondary Metabolites Produced by Colletotrichum higginsianum

et al. 2019

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Colletotrichum higginsianum is the causal agent of crucifer anthracnose disease, responsible for important economic losses in Brassica crops. A mutant lacking the CclA subunit of the COMPASS complex was expected to undergo chromatin decondensation and the activation of cryptic secondary metabolite biosynthetic gene clusters. Liquid-state fermentation of the ΔcclA mutant coupled with in situ solidphase extraction led to the production of three families of compounds, namely, colletorin and colletochlorin derivatives with two new representatives, colletorin D (1) and colletorin D acid (2), the diterpenoid α-pyrone higginsianin family with two new analogues, higginsianin C (3) and 13-epi-higginsianin C (4), and sclerosporide (5) coupling a sclerosporin moiety with dimethoxy inositol.

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Structure of Colletochlorin D fromColletotrichum nicotianae

Cited by 10 publications

References 0 publications

Chlorinated phenolic sesquiterpenoids from the Arctic fungus Nectria sp. B-13

Chlorinated phenolic sesquiterpenoids from the Arctic fungus Nectria sp. B-13

Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria

Deleting a Chromatin Remodeling Gene Increases the Diversity of Secondary Metabolites Produced by Colletotrichum higginsianum

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