Phenylpropanoid and flavonoid glycosides from the leaves of Clerodendrum infortunatum (Lamiaceae)

Uddin, Md. Josim; Çiçek, Serhat Sezai; Willer, Johanna; Shulha, Oleksandr; Abdalla, Muna Ali; Sönnichsen, Frank D.; Girreser, Ulrich; Zidorn, Christian

doi:10.1016/j.bse.2020.104131

Cited by 11 publications

(9 citation statements)

References 40 publications

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“…In another study, both leaf and root extracts were found safe in the in vivo experimental model ( Nandi et al, 2017 ). Several compounds have been identified from C. infortunatum with important medicinal values ( Nandi and Mawkhlieng Lyndem, 2016 ), the major being 3-deoxy-d-mannoic lactone, glycerin, and xylitol as analyzed using the gas chromatography coupled with mass spectroscopy (GC-MS) technique ( Ghosh et al, 2015 ) along with viscosene and several flavonoid glycosides ( Uddin et al, 2020 ). Anti-inflammatory moieties reported from this plant include apigenin ( 5 ) ( Sinha et al, 1981 ), quercetin ( 6 ) ( Gupta and Gupta, 2012 ), oleanolic acid ( 7 ) ( Sannigrahi et al, 2012 ), β-sitosterol ( 8 ) ( Gupta and Singh, 2012 ; Paniagua-Pérez et al, 2017 ), and squalene ( 9 ) ( Figure 4 ) ( Choudhury et al, 2009 ).…”

Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Medicinal Plants of Bangladesh—A Pharmacological Evaluation

Akhtar

2022

Front. Pharmacol.

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Inflammatory diseases are considered major threats to human health worldwide. In Bangladesh, a number of medicinal plants have been used in traditional medicine from time immemorial in the treatment of diverse diseases, including inflammatory disorders. This assignment aims at providing the status of the medicinal plants of Bangladesh which are traditionally used in the management of inflammatory disorders and are investigated for their anti-inflammatory prospects using different preclinical studies and future research directions. The information of medicinal plants assembled in this review was obtained from a literature search of electronic databases such as Google Scholar, PubMed, Scopus, Web of Science and ScienceDirect up to December, 2020 from publications on plants investigated for their anti-inflammatory activities, in which the place of plant sample collection was identified as Bangladesh. Keywords for primary searches were “anti-inflammatory,” “Bangladeshi,” and “medicinal plants.” Criteria followed to include plant species were plants that showed significant anti-inflammatory activities in 1) two or more sets of experiments in a single report, 2) same or different sets of experiments in two or more reports, and, 3) plants which are traditionally used in the treatment of inflammation and inflammatory disorders. In this study, 48 species of medicinal plants have been reviewed which have been used in traditional healing practices to manage inflammatory disorders in Bangladesh. The mechanistic pathways of the in vivo and in vitro study models used for the evaluation of anti-inflammatory properties of plant samples have been discussed. Selected plants were described in further detail for their habitat, anti-inflammatory studies conducted in countries other than Bangladesh, and anti-inflammatory active constituents isolated from these plants if any. Medicinal plants of Bangladesh have immense significance for anti-inflammatory activity and have potential to contribute toward the discovery and development of novel therapeutic approaches to combat diseases associated with inflammation. However, the plants reviewed in this article had chiefly undergone preliminary screening and require substantial investigations including identification of active molecules, understanding the mechanism of action, and evaluation for safety and efficacy to be followed by the formulation of safe and effective drug products.

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Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Medicinal Plants of Bangladesh—A Pharmacological Evaluation

Akhtar

2022

Front. Pharmacol.

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“…Furthermore, phenylpropanoids represented by isoacteoside, acteoside martynoside, leucosceptoside A, incanoside C, jionoside C, and jionoside D were αpreviously identified from C. infortunatum in addition to the presence of acetylated phenylpropanoids such as 2″-O-acetyl-martyonside and 3″-O-acetyl-martyonside which further confirms our results. Regarding flavonoids, apigenin 7-O-glucuronide and acacetin 7-O-glucuronide were also present in C. infortunatum [ 45 ].…”

Section: Resultsmentioning

confidence: 99%

Metabolomics-Based Profiling of Clerodendrum speciosum (Lamiaceae) Leaves Using LC/ESI/MS-MS and In Vivo Evaluation of Its Antioxidant Activity Using Caenorhabditis elegans Model

et al. 2022

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We investigated the antioxidant activity of the total methanol extract of C. speciosum leaves (CST), the ethyl acetate (CSE), and the remaining aqueous (CSR) fractions in vitro, in vivo using Caenorhabditis elegans model, and in silico. LC-ESI-MS/MS analysis was employed for metabolic profiling of CST. ADME/TOPAKT prediction was performed to determine the potential pharmacokinetic, pharmacodynamic, and toxicity properties of the major identified phytoconstituents. All examined samples showed considerable antioxidant activity where CST, CSE, and CSR displayed EC50 values of 27.1, 16.2, and 21.3 µg/mL, respectively, in 2,2-diphenyl-1-picrylhydrazyl (DPPH•) assay, whereas they showed 11.44, 16.27, and 12.16 Fe2+ equivalents/mg of sample, respectively, in ferric reducing antioxidant power (FRAP) assay. CST, CSE, and CSR displayed total phenolic content of 262, 326, and 289 mg GAE/g sample, respectively. In vivo antioxidant study revealed that CST at 150 μg/mL increased the survival rate of C. elegans by 71.88% compared to untreated group. Regarding intracellular reactive oxygen species (ROS), worms treated with 150 μg/mL of CSE exhibited 60.42% reduction of ROS compared to the untreated group. Quantitation of hsp-16.2/GFP expression in Caenorhabditis elegans showed that worms treated with 150 μg/mL of CSR exerted 40.43% reduction in fluorescence with respect to the untreated group. LC-ESI-MS/MS of CST revealed the presence of sixteen secondary metabolites belonging mainly to polyphenolics with phenyl propanoids constituting the major detected class. The in silico study showed that rosmarinic acid displayed the best fitting within the active sites of Daf-2 protein with considerable safety profile and limited pharmacokinetic and pharmacodynamic that could be slightly enhanced by certain treatment.

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“…A butanol fraction of acetone extract of C. infortunatum leaves was subjected to open column chromatography using a silica gel and subsequent semi-preparative HPLC with reversed phase column, and the abietanes ( 1 and 2 ) were obtained as amorphous solids, together with the previously reported C 13 nor-isoprenoid glycoside ( 3 ) ( Figure 1 ). In our previous study, five phenylpropanoid glycosides: 6′- O -caffeoyl-12-glucopyranosyloxyjasmonic acid ( 4 ), jionoside C ( 5 ), jionoside D ( 6 ), brachynoside ( 7 ) , and incanoside C ( 8 ) were reported from the same source ( Figure 1 ) [ 12 ].…”

Section: Resultsmentioning

confidence: 99%

“…Some experimental evidence has proven the traditional claims, showing various biological effects, such as anti-snake venom activity [ 6 ], analgesic and anticonvulsant activities [ 7 ], nootropic activity [ 8 ], antimicrobial activity [ 9 ], antioxidative potential [ 10 ], and hepatoprotective activity [ 11 ]. Earlier, phytochemical studies of C. infortunatum leaves revealed the presence of flavonoids, phenolic compounds, terpenoids, steroids, and phenylpropanoids [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae)

et al. 2021

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In this study, two previously undescribed diterpenoids, (5R,10S,16R)-11,16,19-trihydroxy-12-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-3,8,11,13-abietatetraene-7-one (1) and (5R,10S,16R)-11,16-dihydroxy-12-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-4-carboxy-3,8,11,13-abietatetraene-7-one (2), and one known compound, the C13-nor-isoprenoid glycoside byzantionoside B (3), were isolated from the leaves of Clerodendrum infortunatum L. (Lamiaceae). Structures were established based on spectroscopic and spectrometric data and by comparison with literature data. The three terpenoids, along with five phenylpropanoids: 6′-O-caffeoyl-12-glucopyranosyloxyjasmonic acid (4), jionoside C (5), jionoside D (6), brachynoside (7), and incanoside C (8), previously isolated from the same source, were tested for their in vitro antidiabetic (α-amylase and α-glucosidase), anticancer (Hs578T and MDA-MB-231), and anticholinesterase activities. In an in vitro test against carbohydrate digestion enzymes, compound 6 showed the most potent effect against mammalian α-amylase (IC50 3.4 ± 0.2 μM) compared to the reference standard acarbose (IC50 5.9 ± 0.1 μM). As yeast α-glucosidase inhibitors, compounds 1, 2, 5, and 6 displayed moderate inhibitory activities, ranging from 24.6 to 96.0 μM, compared to acarbose (IC50 665 ± 42 μM). All of the tested compounds demonstrated negligible anticholinesterase effects. In an anticancer test, compounds 3 and 5 exhibited moderate antiproliferative properties with IC50 of 94.7 ± 1.3 and 85.3 ± 2.4 μM, respectively, against Hs578T cell, while the rest of the compounds did not show significant activity (IC50 > 100 μM).

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Phenylpropanoid and flavonoid glycosides from the leaves of Clerodendrum infortunatum (Lamiaceae)

Cited by 11 publications

References 40 publications

Anti-Inflammatory Medicinal Plants of Bangladesh—A Pharmacological Evaluation

Anti-Inflammatory Medicinal Plants of Bangladesh—A Pharmacological Evaluation

Metabolomics-Based Profiling of Clerodendrum speciosum (Lamiaceae) Leaves Using LC/ESI/MS-MS and In Vivo Evaluation of Its Antioxidant Activity Using Caenorhabditis elegans Model

Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae)

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