New sesquiterpenes and phenolic compound from Ficus foveolata

Somwong, Pathom; Suttisri, Rutt; Buakeaw, Anumart

doi:10.1016/j.fitote.2012.12.026

Cited by 22 publications

(7 citation statements)

References 20 publications

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“…Oleanolic acid has been identified in Ficus microcarpa ( Ao et al, 2008 ), Ficus hispida Linn ( Joseph and Raj, 2011 ), and Ficus nervosa ( Chen et al, 2010 ). Betulin was identified in Ficus foveolata ( Somwong et al, 2013 ), Ficus racemosa ( Bopage, 2016 ), and Ficus carica L. ( Oliveira et al, 2012 ). Lupenone was identified in Ficus pseudopalma ( Ragasa et al, 2009 ), Ficus microcarpa ( Kuo and Lin, 2004 ), and Ficus sycomorus ( Ahmadu et al, 2007 ).…”

Section: Discussionmentioning

confidence: 99%

In Vitro Pro-apoptotic and Anti-migratory Effects of Ficus deltoidea L. Plant Extracts on the Human Prostate Cancer Cell Lines PC3

Hanafi¹,

Afzan

Yaakob

et al. 2017

Front. Pharmacol.

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This study aims to evaluate the in vitro cytotoxic and anti-migratory effects of Ficus deltoidea L. on prostate cancer cells, identify the active compound/s and characterize their mechanism of actions. Two farmed varieties were studied, var. angustifolia (FD1) and var. deltoidea (FD2). Their crude methanolic extracts were partitioned into n-hexane (FD1h, FD2h) chloroform (FD1c, FD2c) and aqueous extracts (FD1a, FD2a). Antiproliferative fractions (IC50 < 30 μg/mL, SRB staining of PC3 cells) were further fractionated. Active compound/s were dereplicated using spectroscopic methods. In vitro mechanistic studies on PC3 and/or LNCaP cells included: annexin V-FITC staining, MMP depolarization measurements, activity of caspases 3 and 7, nuclear DNA fragmentation and cell cycle analysis, modulation of Bax, Bcl-2, Smac/Diablo, and Alox-5 mRNA gene expression by RT-PCR. Effects of cytotoxic fractions on 2D migration and 3D invasion were tested by exclusion assays and modified Boyden chamber, respectively. Their mechanisms of action on these tests were further studied by measuring the expression VEGF-A, CXCR4, and CXCL12 in PC3 cells by RT-PCR. FD1c and FD2c extracts induced cell death (P < 0.05) via apoptosis as evidenced by nuclear DNA fragmentation. This was accompanied by an increase in MMP depolarization (P < 0.05), activation of caspases 3 and 7 (P < 0.05) in both PC3 and LNCaP cell lines. All active plant extracts up-regulated Bax and Smac/DIABLO, down-regulated Bcl-2 (P < 0.05). Both FD1c and FD2c were not cytotoxic against normal human fibroblast cells (HDFa) at the tested concentrations. Both plant extracts inhibited both migration and invasion of PC3 cells (P < 0.05). These effects were accompanied by down-regulation of both VEGF-A and CXCL-12 gene expressions (P < 0.001). LC–MS dereplication using taxonomy filters and molecular networking databases identified isovitexin in FD1c; and oleanolic acid, moretenol, betulin, lupenone, and lupeol in FD2c. In conclusion, FD1c and FD2c were able to overcome three main hallmarks of cancer in PC3 cells: (1) apoptosis by activating of the intrinsic pathway, (2) inhibition of both migration and invasion by modulating the CXCL12-CXCR4 axis, and (3) inhibiting angiogenesis by modulating VEGF-A expression. Moreover, isovitexin is here reported for the first time as an antiproliferative principle (IC50 = 43 μg/mL, SRB staining of PC3 cells).

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Section: Discussionmentioning

confidence: 99%

In Vitro Pro-apoptotic and Anti-migratory Effects of Ficus deltoidea L. Plant Extracts on the Human Prostate Cancer Cell Lines PC3

Hanafi¹,

Afzan

Yaakob

et al. 2017

Front. Pharmacol.

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show abstract

“…The discovery of compounds 1 and 3 showed the relevance between this species and other Ficus species such as F. platypoda and F. pumila . Compound 6 is a derivative of plant hormone abscisic acid that can be classified as carotenoid sesquiterpenoid, which is different from other sesquiterpenoids isolated from the genus Ficus [ 32 , 33 ]. Compound 7 is a norsesquiterpenoids with 11C skeleton with different linkage with other 11C skeleton norsesquiterpenoids previously isolated from Ficus microcarpa [ 34 , 35 ].…”

Section: Discussionmentioning

confidence: 99%

Chemical Constituents and Antifungal Activity of Ficus hirta Vahl. Fruits

Wan

Chen

et al. 2017

Plants

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Phytochemical investigation of Ficus hirta Vahl. (Moraceae) fruits led to isolate two carboline alkaloids (1 and 2), five sesquiterpenoids/norsesquiterpenoids (3–7), three flavonoids (8–10), and one phenylpropane-1,2-diol (11). Their structures were elucidated by the analysis of their 1D and 2D NMR, and HR-ESI-MS data. All of the isolates were isolated from this species for the first time, while compounds 2, 4–6, and 8–11 were firstly reported from the genus Ficus. Antifungal assay revealed that compound 8 (namely pinocembrin-7-O-β-d-glucoside), a major flavonoid compound present in the ethanol extract of F. hirta fruits, showed good antifungal activity against Penicillium italicum, the phytopathogen of citrus blue mold caused the majority rotten of citrus fruits.

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“…However, the ethyl acetate extract of F. foveolata exhibited the highest antibacterial activity against S. pyogenes, S. mitis, and S. mutans with MICs of 19.5, 19.5, and 39.0 mg/mL, and MBCs of 39.0, 78.1, and 156.2 mg/mL, respectively, followed by the methanol extract of C. sappan that had MICs of 39.0, 39.0, and 78.1 mg/mL, and MBCs of 78.1, 78.1, and 156.2 mg/ mL. Recently, there have also been two reports of potent and selective butyrylcholinesterase inhibitors (Sermboonpaisarn & Sawasdee, 2012), and cytotoxic compounds against cancer cell lines (Somwong et al, 2013) obtained from F. foveolata stems. This is the first report of the antibacterial activity of a F. foveolata stem extract.…”

Section: Bioassay-guided Isolationmentioning

confidence: 99%

Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds fromFicus foveolata

Meerungrueang

Panichayupakaranant

2014

Pharmaceutical Biology

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The ethyl acetate extract of F. foveolata showed the strongest antibacterial activity with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 19.5-39.0 and 39.0-156.2 µg/mL, respectively. On the basis of an antibacterial assay-guided isolation, seven antibacterial compounds, including 2,6-dimethoxy-1,4-benzoquinone (1), syringaldehyde (2), sinapaldehyde (3), coniferaldehyde (4), 3β-hydroxystigmast-5-en-7-one (5), umbelliferone (6), and scopoletin (7), were purified. Among these isolated compounds, 2,6-dimethoxy-1,4-benzoquinone (1) exhibited the strongest antibacterial activities against S. pyogenes, S. mitis, and S. mutans with MIC values of 7.8, 7.8, and 15.6 µg/mL, and MBC values of 7.8, 7.8, and 31.2 µg/mL, respectively. In addition, this is the first report of these antibacterial compounds in the stems of F. foveolata.

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New sesquiterpenes and phenolic compound from Ficus foveolata

Cited by 22 publications

References 20 publications

In Vitro Pro-apoptotic and Anti-migratory Effects of Ficus deltoidea L. Plant Extracts on the Human Prostate Cancer Cell Lines PC3

In Vitro Pro-apoptotic and Anti-migratory Effects of Ficus deltoidea L. Plant Extracts on the Human Prostate Cancer Cell Lines PC3

Chemical Constituents and Antifungal Activity of Ficus hirta Vahl. Fruits

Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds fromFicus foveolata

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