Three New Heptaprenylhydroquinone Derivatives from the Sponge Ircinia fasciculata

Venkateswarlu, Y.; Reddy, M. Venkata Rami

doi:10.1021/np50111a018

Cited by 25 publications

(20 citation statements)

References 4 publications

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“…The methine protons at δ 6.71 (H-7) recorded major HMBC cross-peaks with δ 133.15 (attributed to C-8)/δ 81.75 (C-9) and δ 4.50 (H-9)/δ 154.7 (C-1), which revealed the presence of pyran ring attached to the aromatic group at C-1 and C-6 positions forming a bicylcic 2H-chromenol moiety in 3. The methine carbon appeared at δ 81.75 (assigned to C-9, HSQC with δ 4.50), and the attribution was comparable with the reported -CH carbon of 2-(hexaprenylmethyl)-2-methyl-chromenol isolated from the sponge Ircinia fasciculata (Venkateswarlu and Reddy 1994).…”

Section: Chemistrysupporting

confidence: 66%

Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

Chakraborty

Raola

2018

Med Chem Res

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Previously undescribed oxygenated heterocyclic metabolites were purified from the ethyl acetate fraction of natural mangrove hybrid Rhizophora annamalayana. The purified metabolites were characterized as 11-(tetrahydro-14α-hydroxy-13β-methylfuran-12-yl)-10β-methylbutyl benzoate (1), 13-(tetrahydro-15β,16α-dimethyl-18-oxo-2H-pyran-14-yl)-10β-methylhept-12(E)-enyl benzoate (2), and dihydro-11-((7E)-2-hydroxy-8β-methyl-2H-chromen-9-yl)-13-methylpent-12(E)-enyl)-17β-methylfuran-19(3H)-one (3) by the combined spectroscopic experiments. These metabolites were assessed for their antioxidant and anti-inflammatory activities, and compared with the commercially available standards. The purified compound 3 exhibited greater antioxidant activities as deduced by 2, 2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid and 2, 2-diphenyl-1-picrylhydrazyl quenching properties (IC 50 2.10 and 2.22 mM, respectively) compared to the positive control (α-tocopherol, IC 50 1.46 and 1.69 mM, respectively). Consequently, the anti-inflammatory activity of compound 3 with regard to the inhibitory property towards pro-inflammatory 5-lipoxygenase was greater (IC 50 2.16 mM) than that exhibited by the synthetic anti-inflammatory drug ibuprofen (IC 50 4.51 mM). Electronic and hydrophobic parameters were deduced to find the target bioactivities of the studied compounds. These oxygenated heterocyclic metabolites could be used as potential therapeutic lead compounds in the pharmaceutical applications.

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Section: Chemistrysupporting

confidence: 66%

Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

Chakraborty

Raola

2018

Med Chem Res

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“…According to the EI-MS data, showing molecular-ion peaks at m/z 516 and 584, metabolites 3 and 4 were the previously reported chromene derivatives of 2'-hexaprenyl and 2'-heptaprenyl hydroquinones, respectively [21] [22].…”

mentioning

confidence: 56%

Marine Polyprenylated Hydroquinones, Quinones, and Chromenols with Inhibitory Effects on Leukotriene Formation

Tziveleka

Abatis

Paulus³

et al. 2005

C&B

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A series of polyprenylated hydroquinones, quinones, and chromenols were isolated from the extracts of the marine sponge Ircinia spinosula and the brown alga Taonia atomaria, which gave rise to the constituents 1-4 and 5-8, respectively. Compounds 1, 2, 6, and 7 are new natural products, which were fully characterized. Their anti-inflammatory activities in terms of leukotriene formation were evaluated in an in vitro assay with pork leukocytes. The new hydroxylated compound, 2'-[28-hydroxy]heptaprenyl-1',4'-hydroquinone (= 2-[(2E,6E,10E,14E,18Z,22E)-19-(hydroxymethyl)-3,7,11,15,23,27-hexamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]benzene-1,4-diol; 1), the known tetraprenyl benzoquinone sargaquinone (5), and the known polyprenyl chromenols 3 and 4 exhibited the highest anti-inflammatory activities, with IC50 values of 1.9-9.4 microM (Table 3). Potential structure-activity relationships (SAR) are discussed.

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“…The maximum antiamoebic activity was localized in the n-butanol soluble fraction. It was analyzed by LCMS and xestospongins and araguspongins were identified as major compounds (Venkateshwarlu et al, 1994). Sepaction and purification of the pure compounds is in progress and will be reported separately.…”

Section: Methodsmentioning

confidence: 99%

Antiamoebic Activity of Marine Sponge Spongia officinalis var. ceylonensis Dendy

Lakshmi¹,

Ghosal

2015

Bangla Pharma J

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Human amoebiasis due to infection by Entamoeba histolytica is mainly associated with morbidity thus affecting the quality of life and pace of developmental activities of countries with warm climatic conditions. A consistently high global incidence of this disease has been reported. In an endeavor to identify novel molecules with potent antiamoebic activity and lower side-effect, the present study was designed to investigate antiamoebic activity in Spongia officinalis extracts/fractions followed by isolation and characterization of bioactive molecules. The methanol extract of the S. officinalis showed promising in vitro and in vivo antiamoebic activity. On further fractionation, the activity was localized in the n-butanol soluble fraction from which the major purified fraction was identified as a mixture of alkaloids (xestospongins and araguspongins) by LCMS studies of the n-butanol soluble fraction.

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Three New Heptaprenylhydroquinone Derivatives from the Sponge Ircinia fasciculata

Cited by 25 publications

References 4 publications

Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

Marine Polyprenylated Hydroquinones, Quinones, and Chromenols with Inhibitory Effects on Leukotriene Formation

Antiamoebic Activity of Marine Sponge Spongia officinalis var. ceylonensis Dendy

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