Armochaetoglobins A–J: Cytochalasan Alkaloids from <i>Chaetomium globosum</i> TW1-1, a Fungus Derived from the Terrestrial Arthropod <i>Armadillidium vulgare</i>

Chen, Chunmei; Wang, Jianping; Liu, Junjun; Zhu, Hucheng; Sun, Bin; Wang, Jing; Zhang, Jinwen; Luo, Zengwei; Yao, Guangmin; Xue, Yongbo

doi:10.1021/np500626x

Cited by 62 publications

(46 citation statements)

References 29 publications

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“…The structures of compounds 3 – 9 were established by comparison with the published data as chaetoglobosin G [26], chaetoglobosin F [6,27], chaetoglobosin C [6], chaetoglobosin A [6], chaetoglobosin E [6], armochaetoglobosin I [28], and cytoglobosin C [29]. …”

Section: Resultsmentioning

confidence: 99%

“…This deduction could also be concluded by comparison of the cytotoxic activities between compounds 3 and 7 . In previous investigations, the known chaetoglobosins covered in the study had shown cytotoxicity against many different human cancer cell lines [15,16,27,28,29,32,33]. To our best knowledge, there were no previous reports on the cytotoxicity of these chaetoglobosins to MDA-MB-435, A549 and SGC-7901 cell lines, except compounds 8 and 9 , which were tested on the A549 cell line [28,29] with IC 50 values almost identical to our current results.…”

Section: Resultsmentioning

confidence: 99%

“…V11) harbored inside the normal vein attracted our interests due to its antifungal activity exhibited by the methanol extract in vitro. In this study, the chemical investigation of the fungal Penicillium chrysogenum V11 was carried out, and resulted in a novel chaetoglobosin termed Penochalasin I ( 1 ) bearing an unprecedented 6/5/6/5/6/13 six polycyclic system, and a new chaetoglobosin named Penochalasin J ( 2 ), along with seven known chaetoglobosins, chaetoglobosin G ( 3 ) [26], chaetoglobosin F ( 4 ) [6,27], chaetoglobosin C ( 5 ) [6], chaetoglobosin A ( 6 ) [6], chaetoglobosin E ( 7 ) [6], armochaetoglobosin I ( 8 ) [28], and cytoglobosin C ( 9 ) [29] (Figure 1). Details of the isolation, structure characterization, and bioactivity evaluation are reported herein.…”

Section: Introductionmentioning

confidence: 99%

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Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

Huang

Chen

et al. 2016

Marine Drugs

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A novel chaetoglobosin named penochalasin I (1) with a unprecedented six-cyclic 6/5/6/5/6/13 fused ring system, and another new chaetoglobosin named penochalasin J (2), along with chaetoglobosins G, F, C, A, E, armochaetoglobosin I, and cytoglobosin C (3–9) were isolated from the culture of Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound 1 was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2′ of the chaetoglobosin class. Compounds 5–8 remarkably inhibited the plant pathogenic fungus R. solani (minimum inhibitory concentrations (MICs) = 11.79–23.66 μM), and compounds 2, 6, and 7 greatly inhibited C. gloeosporioides (MICs = 23.58–47.35 μM), showing an antifungal activity higher than that of carbendazim. Compound 1 exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC50 < 10 μM), and compounds 6 and 9 showed potent cytotoxicity against SGC-7901 and A549 cells (IC50 < 10 μM).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

Huang

Chen

et al. 2016

Marine Drugs

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“…Taken together, the complete structure of 1 was established and accordingly assigned as 6-O-methyl-chaetoglobosin Q, which was probably obtained as an artifact from acidic solvolisis of the epoxide of chaetoglobosin A (2). Additionally, the structures of these known compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were mainly elucidated by spectral data analysis as well as comparison with those reported in the literature. They were identified as chaetoglobosins A-G (2-8) [16][17][18], aureochaeglobosin B (9) [6], isochaetoglobosin D (10) [18], chaetoglobosin Fex (11) [16], penochalasin G (12) [19], armochaetoglobin G (13) [7], prochaetoglobosin I (14) [8], chaetoglobosins V b (15) [8] and Y (16) [18], respectively ( Figure 1).…”

Section: Structural Elucidationmentioning

confidence: 99%

“…Recently, a variety of cycloaddition heterodimers of cytochalasans with novel complicated architectures have been reported, exemplified by asperflavipine A [5], aureochaeglobosins A−C [6]. Chaetoglobosins, 10-(indol-3-yl)- [13]cytochalasans were recently reported to have cytotoxicity [6,7] and antibacterial activity [8], and have attracted great interest from both chemists and pharmacologists [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

HPLC-DAD-Guided Isolation of Diversified Chaetoglobosins from the Coral-Associated Fungus Chaetomium globosum C2F17

Luo

Gao

et al. 2020

Molecules

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Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium globosum C2F17. Their structures were accomplished by extensive spectroscopic analysis combined with single-crystal X-ray crystallography and ECD calculations. Meanwhile, the structures and absolute configurations of the previously reported compounds 6, 12, and 13 were confirmed by single-crystal X-ray analysis for the first time. Chaetoglobosins E (6) and Fex (11) showed significant cytotoxicity against a panel of cancer cell lines, K562, A549, Huh7, H1975, MCF-7, U937, BGC823, HL60, Hela, and MOLT-4, with the IC50 values ranging from 1.4 μM to 9.2 μM.

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Epicochalasines A and B: Two Bioactive Merocytochalasans Bearing Caged Epicoccine Dimer Units from Aspergillus flavipes

et al. 2016

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Tw ob ioactive merocytochalasans,e picochalasines A( 1)a nd B( 2), an ew class of cytochalasans bearing unexpected scaffolds consisting of fused aspochalasin and epicoccine dimer moieties,were isolated from the liquid culture broth of Aspergillus flavipes.B oth 1 and 2 possess ah endecacyclic 5/6/11/5/6/5/6/5/6/6/5 ring system containing an adamantyl cage and as many as 19 stereogenic centers;h owever, the fusion patterns of 1 and 2 differ greatly,t hus resulting in different carbon skeletons.T he absolute configurations of 1 and 2 were determined by X-ray diffraction and calculated ECD,r espectively.T he biogenetic pathwayso f1 and 2 are proposed to involve Diels-Alder and nucleophilic addition reactions.B oth 1 and 2 induced significant G2/M-phase cellcycle arrest. Furthermore,w ef ound that merocytochalasans induce apoptosis in leukemia cells through the activation of caspase-3 and the degradation of PARP.Cytochalasans have received considerable attention from both chemists and pharmacologists over the past 50 years because of their intriguing structures and potent biological activity, [1] which is exemplified by immunomodulatory, [2] cytotoxic, [3] and nematicidal activity.[4] To date,m ore than 200 cytochalasans have been reported, from various fungi origins,s uch as Chaetomium, Aspergillus,a nd Penicillium species.[1b] Epicoccine derivatives,especially their dimers,are ac lass of aromatic polyketides with diverse structures that exhibit numerous forms of bioactivity,f or example,a ntimicrobial, [5] antiviral, [6] and enzyme-inhibition activity. [5,7] Because of their considerable activity and intricate polycyclic structures,t he total synthesis of epicoccine dimers (e.g., dibefurin and epicolactone) has attracted considerable attention from the synthesis community.[8]During our continuous search for structurally intriguing and biologically valuable natural products from fungi, several fungi of different origins have been phytochemically investigated.[9] In our previous study on Aspergillus flavipes cultured on rice,w ed iscovered ac ytochalasan dimer (asperchalasine A, Scheme 1). [10] Considering that the fermentation of fungi under different conditions may lead to different secondary metabolites,w ef urther investigated the metabolites of A. flavipes cultured in al iquid culture broth. In this study,t wo novel merocytochalasans,e picochalasines A( 1) and B( 2;S cheme 1), with high degrees of functionalization and intricate polycyclics tructures,w ere isolated from the liquid culture broth of A. flavipes.Compounds 1 and 2 appear to belong to the same structural family.However,because of the 1808 8 rotation of the oxidized epicoccine moiety c (Scheme 2) in 2,t heir fusion patterns differ substantially, thus resulting in different carbon skeletons.M ost notably, compounds 1 and 2 are the first examples of cytochalasan adducts characterized by an adamantyl cage in ah endecacyclic 5/6/11/5/6/5/6/5/6/6/5 ring system formed by the polymerization of an epicoccine dimer with acytochalasan moiety.Herein, t...

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Armochaetoglobins A–J: Cytochalasan Alkaloids from Chaetomium globosum TW1-1, a Fungus Derived from the Terrestrial Arthropod Armadillidium vulgare

Cited by 62 publications

References 29 publications

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

HPLC-DAD-Guided Isolation of Diversified Chaetoglobosins from the Coral-Associated Fungus Chaetomium globosum C2F17

Epicochalasines A and B: Two Bioactive Merocytochalasans Bearing Caged Epicoccine Dimer Units from Aspergillus flavipes

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