Hydrogenation of vermistatin

Proksa, B.; Uhrínová, Stanislava; Adamcová, Jana; Fuska, J.

doi:10.1007/bf00810473

Cited by 8 publications

(2 citation statements)

References 4 publications

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“…Finally, further pharmaceutical perspectives of vermistatin can be considered in view of the anxiolytic effects shown by other compounds with a benzalphthalide skeleton [ 41 ]. Actually, the phthalide moiety seems to be quite important for biological activity, as some derivatives obtained by artificial hydrogenation proved to be inactive when modifications were introduced in this part of the molecule [ 42 ]. However, the inactivity observed in the case of dihydrovermistatin [ 11 ] suggests that the propenyl tail is also quite relevant to this regard.…”

Section: Biological Activities Of Funicone-related Compoundsmentioning

confidence: 99%

Occurence and Bioactivities of Funicone-Related Compounds

Nicoletti¹,

Manzo

Ciavatta

2009

IJMS

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Studies on production of secondary metabolites by fungi have received a substantial boost lately, particularly with reference to applications of their biological properties in human medicine. Funicones represent a series of related compounds for which there is accumulating evidence supporting their possible use as pharmaceuticals. This paper provides a review on the current status of knowledge on these fungal extrolites, with special reference to aspects concerning their molecular structures and biological activities.

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Section: Biological Activities Of Funicone-related Compoundsmentioning

confidence: 99%

Occurence and Bioactivities of Funicone-Related Compounds

Nicoletti¹,

Manzo

Ciavatta

2009

IJMS

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“…It was reported to inhibit the RNA synthesis in EAC and P-388 leukemia cells [3], as an elastase inhibitor [7], and as a phytotoxin on various banana cultivars [7] [8]. Vermistatin (1) was reported to have no antifungal activity [9], except towards Candida albicans [10].…”

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confidence: 99%

ChemInform Abstract: Structural and Biological Properties of Vermistatin and Two New Vermistatin Derivatives Isolated from the Marine‐Mangrove Endophytic Fungus Guignardia sp. No. 4382.

et al. 2008

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Vermistatin (¼ (3R)-4,6-dimethoxy-3-{4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-yl}-2-benzofuran-1(3H)-one; 1) and two new vermistatin derivatives, compounds 2 and 3, were isolated from the fungal strain Guignardia sp. No. 4382 obtained from the South-China Sea. Their structures were elucidated by various methods, including circular dichroism (CD), 1D-and 2D-NMR, and HR-EI-MS. The structures of 1 and 2 were unequivocally corroborated by X-ray crystallography, and their absolute configurations were derived by CD spectroscopy based on a literature comparison. The in vitro cytotoxic and antifungal activities of 1 and 2 were tested.Introduction. -Endophytic fungi are a well-established source for structurally diverse and biologically active secondary metabolites [1]. In continuation of our ongoing search for potential antitumor and antifugal natural products from marinemangrove fungi [2], the metabolites of the Guignardia fungal strain No. 4382, a marine endophytic fungus collected from the South-China Sea, were studied. Together with the known vermistatin (1), two new compounds were isolated: methoxyvermistatin (2) and hydroxyvermistatin (3). Their structures and absolute configurations were elucidated by circular-dichroism (CD) and 1D-and 2D-NMR experiments, as well as by HR-EI-MS and X-ray diffraction analyses. The cytotoxic activities of 1 and 2 in vitro and their antifugal activities were tested.

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Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides

Sicignano

Schettini

Sica

et al. 2019

Chemistry A European J

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The first highly enantioselective arylogous Michael reaction (AMR) of 3‐unsubstituted phthalides has been described. This phase‐transfer methodology, which uses catalytic amounts of KOH/18‐crown‐6 catalyst in mesitylene in the presence of N,O‐bis(trimethylsilyl)acetamide (BSA), gives access to a broad range of 3‐monosubstituted phthalides with high levels of syn diastereoselectivity and good yields, starting from 3‐unsubstituted derivatives and diverse α,β‐unsaturated carbonyl compounds. The reaction also applies to unactivated 3‐alkyl phthalides to afford 3,3‐dialkyl derivatives. A plausible mechanism has been suggested. DFT analysis of possible transition states gives a rationale of the high syn diastereoselectivity observed and its correlation with the solvent's dielectric constant.

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Hydrogenation of vermistatin

Cited by 8 publications

References 4 publications

Occurence and Bioactivities of Funicone-Related Compounds

Occurence and Bioactivities of Funicone-Related Compounds

ChemInform Abstract: Structural and Biological Properties of Vermistatin and Two New Vermistatin Derivatives Isolated from the Marine‐Mangrove Endophytic Fungus Guignardia sp. No. 4382.

Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides

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