Phloroglucinol compounds of natural origin

Singh, Inder Pal; Bharate, Sandip B.

doi:10.1039/b600518g

Cited by 493 publications

(305 citation statements)

References 426 publications

(456 reference statements)

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“…The replacement of a phenol OH by an OCH 3 group is frequent in naturally occurring ACPL [1]. When the replacement occurs at C4 in structures with R 0 = H, the H-bond between the water molecule and the ether O is somewhat stronger than between the water molecule and the phenyl O (by %0.7 for d-r and %0.5 for d-w cases); the length or the energy of the ACPL-water H-bonds with other sites of the ACPL molecule are not affected by the replacement.…”

Section: Adducts With One Water Moleculementioning

confidence: 99%

“…The structures selected are either monomeric structures reported as naturally occurring ACPL [1] or simplified structures that can serve as models for more complex ones, including monomeric units of dimeric or trimeric ACPL. Similar to the calculations in vacuo, the selection takes into account the structural variety of ACPL by considering different R, the possibility of R 0 ¼ H and R 0 = H (mostly mimicked by a methyl) for each R and some cases in which R 00 = H. The selected structures are listed in Table I.…”

Section: Selection Of Structures Conformers and Adductsmentioning

confidence: 99%

“…1) are a broad class of polyphenolic compounds, derived from 1,3,5-trihydroxybenzene (phloroglucinol) and characterized by the presence of at least one COR group (acyl chain), whose sp 2 O can form an intramolecular hydrogen bond (here termed ''first IHB'') with one of the two neighboring phenolic OH. Many ACPL are found in natural sources and exhibit a variety of biological activities [1], which makes them valuable as potential lead structures for drug development [2].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Adducts of acylphloroglucinols with explicit water molecules: Similarities and differences across a sufficiently representative number of structures

Mammino

Kabanda

2010

Int J of Quantum Chemistry

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Acylphloroglucinols constitute a broad class of compounds, derivatives of 1,3,5-trihydroxybenzene, characterized by at least one COR group and exhibiting a variety of biological activities. The presence of several hydrogen bond donor or acceptor sites (the three phenol OH of the phloroglucinol moiety and the sp 2 O of the COR group), and their comparatively close spacing, makes the study of adducts with explicit water molecules particularly interesting, because it is possible to consider adducts in which water molecules surround the entire acylphloroglucinol molecule, or a large part of it, providing expectedly realistic images of possible arrangements of water molecules in the close vicinity of the acylphloroglucinol molecule in the aqueous medium. This work considers a number of different monomeric structures sufficiently representative of the broad structural variety of acylphloroglucinols and considers adducts of all the relevant conformers for each structure. Calculations use the HF/6-31G(d,p) level because of affordability reasons in view of the adducts' size. The results: show that the intramolecular hydrogen bond (IHB) between the sp 2 O of COR and an ortho OH does not break on competition with solute-solvent intermolecular H-bonding; highlight general trends and trends related to specific geometry features of the conformers; enable an interpretation of the additional solvent stabilization of the conformers without IHBs, observed from polarizable continuum model results in water solution; and highlight the significance, for this class of compounds, of considering adducts in which the water molecules directly H-bonded to the central molecule are bridged by other water molecules, to approximate a continuous layer.

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Section: Adducts With One Water Moleculementioning

confidence: 99%

Section: Selection Of Structures Conformers and Adductsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Adducts of acylphloroglucinols with explicit water molecules: Similarities and differences across a sufficiently representative number of structures

Mammino

Kabanda

2010

Int J of Quantum Chemistry

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“…[1][2][3][4][5] The plant Myrtus communis 'Variegata' (Myrtaceae), a colored-leafed evergreen shrub, is native to the Mediterranean region and has been traditionally used as a disinfectant and antiseptic agent. 6 Previous phytochemical investigations on some plants of the genus Myrtus had led to the isolation of terpenoids, avonoids, and meroterpenoid derivatives including triketone-terpene adducts.…”

Section: Introductionmentioning

confidence: 99%

Myrtucomvalones A–C, three unusual triketone–sesquiterpene adducts from the leaves of Myrtus communis ‘Variegata’

Chen

et al. 2017

RSC Adv.

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“…Formyl-phloroglucinol meroterpenoids (FPMs) are an important class of secondary metabolites that are widely available from the genera Eucalyptus and Psidium (14)(15)(16). The past decades have seen increasing reports on structurally diverse FPMs with various bioactivities, such as anti-HIV, antimicrobial, and antitumor effects (17)(18)(19)(20)(21).…”

mentioning

confidence: 99%

In Vitro Antibiofilm Activity of Eucarobustol E against Candida albicans

Liu

Shang

et al. 2017

Antimicrob Agents Chemother

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Formyl-phloroglucinol meroterpenoids (FPMs) are important types of natural products with various bioactivities. Our antifungal susceptibility assay showed that one of the Eucalyptus robusta-derived FPMs, eucarobustol E (EE), exerted a strong inhibitory effect against Candida albicans biofilms at a concentration of 16 g/ml. EE was found to block the yeast-to-hypha transition and reduce the cellular surface hydrophobicity of the biofilm cells. RNA sequencing and real-time reverse transcription-PCR analysis showed that exposure to 16 g/ml of EE resulted in marked reductions in the levels of expressions of genes involved in hyphal growth (EFG1, CPH1, TEC1, EED1, UME6, and HGC1) and cell surface protein genes (ALS3, HWP1, and SAP5). Interestingly, in response to EE, genes involved in ergosterol biosynthesis were downregulated, while the farnesol-encoding gene (DPP3) was upregulated, and these findings were in agreement with those from the quantification of ergosterol and farnesol. Combined with the obvious elevation of negative regulator genes (TUP1, NRG1), we speculated that EE's inhibition of carbon flow to ergosterol triggered the mechanisms of the negative regulation of hyphal growth and eventually led to biofilm inhibition.

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Phloroglucinol compounds of natural origin

Cited by 493 publications

References 426 publications

Adducts of acylphloroglucinols with explicit water molecules: Similarities and differences across a sufficiently representative number of structures

Adducts of acylphloroglucinols with explicit water molecules: Similarities and differences across a sufficiently representative number of structures

Myrtucomvalones A–C, three unusual triketone–sesquiterpene adducts from the leaves of Myrtus communis ‘Variegata’

In Vitro Antibiofilm Activity of Eucarobustol E against Candida albicans

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