Friedolanostanes and Lanostanes from the Leaves of <i>Garcinia hombroniana</i>

Rukachaisirikul, Vatcharin; Saelim, Somsak; Karnsomchoke, Pueksa; Phongpaichit, Souwalak

doi:10.1021/np050131j

Cited by 34 publications

(15 citation statements)

References 7 publications

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“…Methyl-3α,23-dihydroxy-17,14-friedolanstan-8,14,24-trien-26-oat (labelled as GC3) was isolated from F4 (11.1 mg) and F5 (32.1 mg). The spectroscopy analysis of the third compound (methyl-3α,23-dihydroxy-17,14-friedolanstan-8,14,24-trien-26-oat) confirmed the identity of the compound, based on data from the previous study (see Supplementary Materials) [22].…”

Section: Extraction Isolation and Bioassaysupporting

confidence: 72%

“…Viera et al (2004) reported on the isolation of 11 friedolanostane-related compounds from Garcinia speciosa leaves [26]. Five other friedolanostanes were isolated by Rukachaisirikul et al (2005) from Garcinia hombroniana leaves [22], whilst two friedolanostane compounds were reported by Klaiklay et al (2013) from the twigs of Garcinia hombroniana [24]. Nguyen et al (2011), on the other hand, reported on the isolation of eight friedolanostane compounds from Garcinia benthami bark and leaves [27].…”

Section: Binding Interaction Of the Isolated Compound From Garcinia Cmentioning

confidence: 99%

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Anti-Neuraminidase Bioactives from Manggis Hutan (Garcinia celebica L.) Leaves: Partial Purification and Molecular Characterization

et al. 2020

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The neuraminidase enzyme (NA) from the influenza virus is responsible for the proliferation and infections of the virus progeny, prompting several efforts to discover and optimize effective neuraminidase inhibitors. The main aim of this study is to discover a new potential neuraminidase inhibitor that comes from Garcinia celebica leaves (GCL). The bioassay-guided isolation method was performed to obtain lead compounds. The binding interaction of the isolated compounds was predicted by using molecular docking studies. Friedeline (GC1, logP > 5.0), two lanastone derivatives (methyl-3α,23-dihydroxy-17,14-friedolanstan-8,14,24-trien-26-oat (GC2) and 24E-3a,9,23-trihydroxy-17,14-friedolanostan-14,24-dien-26-oate (GC3) with LogP > 5.0) and catechin (GC4, LogP = 1.4) were identified. The inhibitory potency of these four compounds on NA from C. perfringens and H1N1 was found to be as follows: GC4 > GC2 > GC3 > GC1. All compounds exhibited higher inhibitory activity towards C. perfringens NA compared to H1N1 NA. From the molecular docking results, GC4 favorably docked and interacted with Arg118, Arg371, Arg292, Glu276 and Trp178 residues, whilst GC2 interacted with Arg118, Arg371, Arg292, Ile222, Arg224 and Ser246. GC3 interacted with Tyr406 only. GC4 had potent NA inhibition with free energy of binding of −12 kcal/mol. In the enzyme inhibition study, GC4 showed the highest activity with an IC50 of 60.3 µM and 91.0 µM for C. perfringens NA and H1N1 NA—respectively.

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Section: Extraction Isolation and Bioassaysupporting

confidence: 72%

Section: Binding Interaction Of the Isolated Compound From Garcinia Cmentioning

confidence: 99%

Anti-Neuraminidase Bioactives from Manggis Hutan (Garcinia celebica L.) Leaves: Partial Purification and Molecular Characterization

et al. 2020

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“…[1] This genus is found to be a rich source of bioactive secondary metabolites, including oxygenated prenylated xanthones and benzophenones, flavonoids, biflavonoids and triterpenes. [2][3][4][5] These chemical constituents are well known for their pharmacological potential including antimicrobial, anti-HIV, anticancer, anti-inflammatory and hepatoprotective activities. [6][7][8] Garcinia hombroniana, a seashore mangosteen in Malaysia, is used as a protective medicine after child birth and to cure skin allergies.…”

Section: Introductionmentioning

confidence: 99%

“…Garcinia , the largest genus of the family Clusiaceae, is native to the regions of Asia, northeast Australia, southern Africa and tropical America . This genus is found to be a rich source of bioactive secondary metabolites, including oxygenated prenylated xanthones and benzophenones, flavonoids, biflavonoids and triterpenes . These chemical constituents are well known for their pharmacological potential including antimicrobial, anti‐HIV, anticancer, anti‐inflammatory and hepatoprotective activities .…”

Section: Introductionmentioning

confidence: 99%

Complete NMR assignments of bioactive rotameric (3 → 8) biflavonoids from the bark of Garcinia hombroniana

Jamila

Khairuddean

Khan

et al. 2014

Magnetic Reson in Chemistry

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The genus Garcinia is reported to possess antimicrobial, anti-inflammatory, anticancer, hepatoprotective and anti-HIV activities. Garcinia hombroniana in Malaysia is used to treat itching and as a protective medicine after child birth. This study was aimed to isolate the chemical constituents from the bark of G. hombroniana and explore their possible pharmacological potential. Ethyl acetate extract afforded one new (1) and six (2-7) known 3 → 8 rotameric biflavonoids. Their structures were elucidated by UV, IR and NMR (1D and 2D) spectroscopy together with electron ionization/ESI mass spectrometric techniques and were identified as (2R, 3S) volkensiflavone-7-O-rhamnopyranoside (1), volkensiflavone (2), 4″-O-methyl-volkensiflavone (3), volkensiflavone-7-O-glucopyranoside (4), morelloflavone (5), 3″-O-methyl-morelloflavone (6) and morelloflavone-7-O-glucopyranoside (7). The absolute configuration of compound 1 was assigned by circular dichroism spectroscopy as 2R, 3S. The coexistence of conformers of isolated biflavonoids in solution at 25 °C in different solvents was confirmed by variable temperature NMR studies. At room temperature (25 °C), compounds 1-7 exhibited duplicate NMR signals, while at elevated temperature (90 °C), a single set of signals was obtained. Compound 5 showed significant in vitro antioxidant activities against 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azino-bis-3-ethyl benzthiazoline-6-sulfonic acid radicals. The antibacterial studies showed that compounds 5 and 6 are the most active against Staphylococcus aureus, Bacillus subtilis and Escherichia coli. Compounds 3 and 6 also showed moderate antituberculosis activity against H38 Rv. Based on the research findings, G. hombroniana could be concluded as a rich source of flavanone-flavone (3 → 8) biflavonoids that exhibit rotameric behaviour at room temperature and display significant antioxidant and antibacterial activities.

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“…Xanthones, 2-5 benzophenones, 4,6,7 depsidones, [8][9][10] flavonoids, 11,12 biflavonoids, 13 and triterpenes 14 have been reported from Garcinia species. Previous phytochemical investigations on G. bracteata resulted in the isolation of caged-prenylxanthones and benzophenones.…”

mentioning

confidence: 99%

New Xanthones from Garcinia bracteata and Their Cytotoxicities

Hu¹,

Niu²,

Li³

et al. 2013

HETEROCYCLES

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Two new xanthones, bracthones A (1) and B (2), together with four known xanthones (3-6) were isolated from the stems of Garcinia bracteata. Their structures were elucidated by spectroscopic methods, including extensive 1D-and 2D-NMR techniques. Compounds 1-6 were tested for their cytotoxicities against five human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7).Compounds 1 and 2 showed high cytotoxicities against PC3 cell with IC 50 values of 3.24 and 2.15 μM, respectively.

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Friedolanostanes and Lanostanes from the Leaves of Garcinia hombroniana

Cited by 34 publications

References 7 publications

Anti-Neuraminidase Bioactives from Manggis Hutan (Garcinia celebica L.) Leaves: Partial Purification and Molecular Characterization

Anti-Neuraminidase Bioactives from Manggis Hutan (Garcinia celebica L.) Leaves: Partial Purification and Molecular Characterization

Complete NMR assignments of bioactive rotameric (3 → 8) biflavonoids from the bark of Garcinia hombroniana

New Xanthones from Garcinia bracteata and Their Cytotoxicities

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