Unique Diketopiperazine Dimers from the Insect Pathogenic Fungus <i>Verticillium hemipterigenum</i> BCC 1449

Isaka, Masahiko; Palasarn, Somporn; Rachtawee, Pranee; Vimuttipong, Saovaluk; Kongsaeree, Palangpon

doi:10.1021/ol0507266

Cited by 50 publications

(44 citation statements)

References 13 publications

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“…The presence of the diketopiperazine 127 as a co-metabolite in BCC 1449 indicated that replacement of the a-H-atoms with S-atoms (i.e., 127 to 128) should take place with retention of configuration. Also other possible mechanisms for the formation of 126 have been considered, for example, a) a radical pathway, instead of the ionic dimerization shown, and b) dimerization of bis-thioradical intermediates, generated by the cleavage of SÀS bond in 128 or directly from 127 [96]. Notoamide E (129) was a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus Aspergillus sp., which was produced by the fungus in the early phase of growth and was presumably rapidly converted to notoamide E4 (130) [97].…”

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confidence: 99%

Diketopiperazines from Marine Organisms

Huang

Zhou

Tian

et al. 2010

Chemistry & Biodiversity

145

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Diketopiperazines (DKPs), which are cyclic dipeptides, have been detected in a variety of natural resources. Recently, the interest in these compounds increased significantly because of their remarkable bioactivity. This review deals with the chemical structures, biosynthetic pathways, and biological activities of DKPs from marine microorganisms, sponges, sea stars, tunicates (ascidians), and red algae. The literature has been covered up to December 2008, and a total 124 DKPs from 104 publications have been discussed and reviewed. Some of these compounds have been found to possess various bioactivities including cytotoxicity, and antibacterial, antifungal, antifouling, plant-growth regulatory, and other activities.

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confidence: 99%

Diketopiperazines from Marine Organisms

Huang

Zhou

Tian

et al. 2010

Chemistry & Biodiversity

145

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“…This observation was supported by the fact that the aliphatic CH 2 and CH groups at d(C) 29.4 (C(8)) and 54.5 (C(9)) in 4 were replaced by the olefinic CH group and the quaternary C-atom at d(C) 112.2 (C(8)) and 124.4 (C(9)) in 2, respectively. The placement of the C¼C bond at C(8) and C(9) was further 3 ). From the above deductions, the structure of 2 was assigned to be (6S)-3-{[2-(1,1-dimethylprop-2-en-1-yl)-5,7-bis(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methylidene}-6-methylpiperazine-2,5-dione, which was named dehydroechinulin.…”

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confidence: 99%

Dioxopiperazine Alkaloids Produced by the Marine Mangrove Derived Endophytic Fungus Eurotium rubrum

et al. 2008

Helvetica Chimica Acta

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Cultivation of the fungal strain Eurotium rubrum, an endophytic fungus that was isolated from the inner tissue of stems of the mangrove plant Hibiscus tiliaceus, resulted in the isolation of two new dioxopiperazine derivatives, namely, dehydrovariecolorin L (1) and dehydroechinulin (2), together with eight known dioxopiperazine compounds including variecolorin L (3), echinulin (4), isoechinulin A (5), dihydroxyisoechinulin A (6), preechinulin (7), neoechinulin A (8), neoechinulin E (9), and cryptoechinuline D (10). The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data as well as by comparison with literature. Compounds 1, 2, 9, and 10 were investigated for their a,a-diphenyl-b-picrylhydrazyl (DPPH) radical-scavenging activity. In addition, the new compounds, 1 and 2, were evaluated for their cytotoxic activity against the P-388, HL-60, and A549 cell lines.Introduction. -A number of tryptophan-derived alkaloids, characterized by a reversed isoprenic chain in the C(2) position of the indole and a 2,5-dioxopiperazine moiety, have been isolated from the genus Aspergillus [1 -5]. These metabolites are of interest because of their activity in various pharmacological assay systems [6]. The genus Eurotium is the teleomorphs of Aspergillus, and is also a common source of tryptophan-derived alkaloids, i.e., echinulins and neoechinulins [7].This article describes the isolation, structure elucidation, and biological activity of two new dioxopiperazine derivatives (1 and 2) from the endophytic fungal strain Eurotium rubrum which was isolated from the inner tissue of stems of the marine mangrove plant Hibiscus tiliaceus. In addition, eight known dioxopiperazine derivatives, including variecolorin L (3) [8], echinulin (4) [9], isoechinulin A (5) [10], dihydroxyisoechinulin A (6) [4], preechinulin (7) [11], neoechinulin A (8) [12], neoechinulin E (9) [12], and cryptoechinuline D (10) [13], were also isolated and identified. It deserves to be mentioned that just at the time when we started to prepare this manuscript, compound 3 was reported as a new metabolite of Aspergillus variecolor B-17, a halotolerant fungal strain isolated from a sediment collection of a salt field in inner Mongolia, China [8].

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“…Vertihemiptellides A (281) and B (282), unique diketopiperazine dimers, were isolated from the insect pathogenic fungus Verticillium hemipterigenum [204]. Both compounds exhibited growth inhibitory activity against Mycobacterium tuberculosis but also showed moderate cytotoxic activities, see Table 8.…”

Section: Epipolythiodioxopiperazinesmentioning

confidence: 99%

“…The epicorazines A(203), B(204), C(205), and 3822-A(206) were isolated from fermentations of Stereum hirsutum[158] and from the saprophyte Epicoccum nigrum (epicorazine A and B), E. purpurascens (epicorazine B)…”

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confidence: 99%

Pharmacologically Active Sulfur-Containing Compounds

Řezanka¹,

Sobotka²,

Spížek³

et al. 2006

AIAMC

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In addition to sulfur-containing compounds that form essential and indispensable constituents of all living cells, there is a plethora of less wide-spread sulfur-containing compounds with much less common and often unexpected properties, chemical structures and biological activities. Some of these compounds have long been known as efficient antibiotics. This review surveys these less known compounds with two and more sulfur atoms in their molecule. In particular, it deals with natural heterocyclic compounds isolated, e.g., from bacteria, fungi, lichens, plants, and animals but also from unusual and exotic sources such as sea invertebrates (coelenterates, sponges, tunicates, sea worms), etc. Compounds such as calicheamicins, thiazole-related compounds and epipolythiodioxopiperazines may serve as examples. Because of their vast variety, individual compounds are grouped according to their chemical structure (only compounds whose chemical structure has been identified are included). These compounds affect a huge array of organisms from microorganisms to man, and the pharmacological activities they exert range from antiviral, antibacterial, antifungal, insecticidal or antiprotozoan effects to regulation of gene expression, cytoskeleton disruption, immunomodulation, plant growth stimulation or inhibition, pro-or antioxidant action, effects on selected enzymes, receptors and signal transduction pathways, etc. The activities are however often known only sketchily, and this paucity of data, and the fact that the activities were tested on a diverse spectrum of test organisms, cell lines, etc., is of necessity reflected in our survey. Two seemingly trivial but important points deserve attention: (a) compounds with widely different structures and from widely different sources have often very similar pharmacological effects; (b) a slight modification in the molecule may bring vast changes in the biological effects of the compound, in terms of quality, quantity and targeting. The purpose of the review was to show both the unique and common features of these compounds and to point out their potential usefulness for mankind.

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Unique Diketopiperazine Dimers from the Insect Pathogenic Fungus Verticillium hemipterigenum BCC 1449

Cited by 50 publications

References 13 publications

Diketopiperazines from Marine Organisms

Diketopiperazines from Marine Organisms

Dioxopiperazine Alkaloids Produced by the Marine Mangrove Derived Endophytic Fungus Eurotium rubrum

Pharmacologically Active Sulfur-Containing Compounds

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