A pair of new atropisomeric cupressuflavone glucosides isolated from Juniperus communis var. depressa

Inatomi, Yuka; Iida, Naoki; Murata, Hiroko; Inada, Akira; Murata, Jin; Lang, Frank A.; Iinuma, Munekazu; Tanaka, Toŝhiyuki; Nakanishi, Teruyuki

doi:10.1016/j.tetlet.2005.07.091

Cited by 16 publications

(13 citation statements)

References 8 publications

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“…In the current study, we report four new labdane diterpenoidal metabolites (1-4) (Figure 1) together with six known compounds including 7-oxocallitrisic acid (5) (Lee et al, 1994), two triterpenoidal metabolites namely, 2-O-acetyl-11-keto-boswellic acid (6) (Belsner et al, 2003;Csuk et al, 2015) and β-sitosterol-3-O-glucopyranoside (7) (Seo et al, 1978), in addition to phloretic acid (8) (Tanagornmeatar et al, 2014), two methylated bisflavonoids, agathisflavone-4',7,7"-trimethyl ether (9) (Ofman et al, 1995) and cupressuflavone-4',7,7"-trimethyl ether (10) (Inatomi et al, 2005;Ofman et al, 1995). 161.3, 151.4, 148.5 and 127.2 together with two aliphatic quaternary carbons at δ C 40.0 and 38.5 ppm.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii

et al. 2017

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Chemical investigation of a methanolic extract of leaves from Araucaria bidwillii (Araucariaceae) from Egypt afforded four new labdane diterpenoidal metabolites (1-4) together with one known diterpene, 7-oxocallitrisic acid (5), two triterpenoidal metabolites, 2-O-acetyl-11-keto-boswellic acid ( 6) and β-sitosterol-3-O-glucopyranoside (7), phloretic acid (8), and two methylated bisflavonoids, agathisflavone-4',7,7"-trimethyl ether ( 9) and cupressuflavone-4',7,7"-trimethyl ether (10). The new metabolites 1-4 were unambiguously identified by applying extensive 1D and 2D NMR spectroscopic studies as well as HRESIMS. The relative and absolute configurations of 1-4 were determined using ROESY and the modified Mosher's method, respectively. All isolated compounds were assessed for their antimicrobial, antitubercular and cytotoxic activities. Among the tested compounds, the new labdane diterpenes 1-4 revealed significant cytotoxic activity against mouse lymphoma L5178Y cell line with IC 50 values ranging from 1.4 to 12.9 µM, respectively.

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Section: Introductionmentioning

confidence: 99%

Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii

et al. 2017

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“…The active EtOAc soluble fraction (14. [26], cupressuflavone (10) [27], moghatin (11) [27], cupressuflavone 4′-O-β-D-glucoside (12) [28], hinokiflavone (13) [25], and isocryptomerin (14) [25] , (Figure 1). The structures of these 14 compounds were elucidated by 2D-NMR and HR-MS.…”

Section: Resultsmentioning

confidence: 99%

Isolation of tyrosinase and melanogenesis inhibitory flavonoids from Juniperus chinensis fruits

Park

Jegal

Chung

et al. 2018

Bioscience, Biotechnology, and Biochemistry

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A new biflavonoid, amentoflavone-7-O-β-D-glucoside, and thirteen known flavonoids were isolated from the fruits of Juniperus chinensis using a bioactivity-guided method and their tyrosinase inhibitory effects were tested using a mushroom tyrosinase bioassay. Two isolates, hypolaetin-7-O-β-D-glucoside and quercetin-7-O-α-L-rhamnoside, were found to reduce tyrosinase activity at a concentration of 50 μM. Quercetin-7-O-α-L-rhamnoside attenuated cellular tyrosinase activity and melanogenesis in α-MSH plus IBMX-stimulated B16F10 melanoma cells. Molecular docking simulation revealed that quercetin-7-O-α-L-rhamnoside inhibits tyrosinase activity by hydrogen bonding with residues His85, His244, Thr261, and Gly281 of tyrosinase.

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“…Some flavonoid compounds such as quercetin and apigenin derivatives have been isolated from Juniperus chinensis heartwood and bark extracts as also from J. communis var. depressa stem extract (Sato et al, 2000;Nakanishi et al, 2004;Inatomi et al, 2005). Terpenes, lignans and coumarins have been shown to be active against a wide variety of microorganisms, including gram-positive and gram-negative bacteria and fungi (Andrews et al, 1980;Uribe et al, 1985;Cowan, 1999;Kawaguchi et al, 2009;Nakato et al, 2009;Widelski et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

In vitroeffect of branch extracts ofJuniperusspecies from Turkey onStaphylococcus aureusbiofilm

Marino

Bellinghieri

Nostro

et al. 2010

FEMS Immunol Med Microbiol

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Methanol and aqueous branch extracts of five Juniperus species were examined for their effects on Staphylococcus aureus ATCC 6538P and S. aureus 810 biofilm. The Turkish plant material was Juniperus communis L. var. communis, J. communis L. var. saxatilis Pall., Juniperus drupacea Labill., Juniperus oxycedrus L. ssp. oxycedrus, J. oxycedrus L. ssp. macrocarpa (Sibth. & Sm.) Ball. The Juniperus extracts were subjected to preliminary phytochemical analysis by thin-layer chromatography. The antimicrobial activity was evaluated using the minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC). The effects of the extracts on biofilm formation and preformed biofilm were quantified by both biomass OD and the CFU counting method. The phytochemical screening revealed the presence of polyphenols, coumarins, lignans, steroids, alkaloids and terpenes. For both strains, the MICs of all extracts were in the range of 4.88-78.12 mg mL À1 . On S. aureus ATCC 6538P, the effects of subinhibitory concentration (0.5 MIC) of the extracts were minimal on planktonic growth and on adhering cells, whereas they were greater on biofilm formation. Differently, on S. aureus 810, they showed only a rather low efficacy on biofilm formation. The extracts at 2 MIC demonstrated a good activity on a preformed biofilm of S. aureus ATCC 6538P.

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A pair of new atropisomeric cupressuflavone glucosides isolated from Juniperus communis var. depressa

Cited by 16 publications

References 8 publications

Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii

Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii

Isolation of tyrosinase and melanogenesis inhibitory flavonoids from Juniperus chinensis fruits

In vitroeffect of branch extracts ofJuniperusspecies from Turkey onStaphylococcus aureusbiofilm

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