Three New Phenolic Glycosides and a New Triterpenoid from the Stems of<i>Scolopia chinensis</i>

Lu, Ya‐Nan; Chai, Xingyun; Xu, Zhengren; Bi, Dan; Ren, Hong-Yan; Zhao, Min; Tu, Pengfei

doi:10.1055/s-0029-1186157

Cited by 10 publications

(6 citation statements)

References 10 publications

(15 reference statements)

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“…Phenolic glycosides have been studied extensively for their fundamental role in the interaction of plant species of the Salicaceae family with their natural herbivore enemies . In addition, phenolic glycosides are known for their anti-inflammatory activity by inhibiting COX-2, inhibitory activity on snake venom phosphodiesterase I, − antimalarial activity, and inhibitory activity on HIV-1 RNase H …”

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confidence: 99%

Flacourtosides A–F, Phenolic Glycosides Isolated from Flacourtia ramontchi

et al. 2012

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In an effort to identify novel inhibitors of chikungunya (CHIKV) and dengue (DENV) virus replication, a systematic study with 820 ethyl acetate extracts of madagascan plants was performed in a virus-cell-based assay for CHIKV, and a DENV NS5 RNA-dependent RNA polymerase (RdRp) assay. The extract obtained from the stem bark of Flacourtia ramontchi was selected for its significant activity in both assays. Six new phenolic glycosides, named flacourtosides A-F (1-6), phenolic glycosides itoside H, xylosmin, scolochinenoside D, and poliothrysoside, and betulinic acid 3β-caffeate were obtained using the bioassay-guided isolation process. Their structures were elucidated by comprehensive analyses of NMR spectroscopic and mass spectrometric data. Even though several extracts and fractions showed significant selective antiviral activity in the CHIKV virus-cell-based assay, none of the purified compounds did. However, in the DENV RNA polymerase assay, significant inhibition was observed with betulinic acid 3β-caffeate (IC(50) = 0.85 ± 0.1 μM) and to a lesser extent for the flacourtosides A and E (1 and 5, respectively), and scolochinenoside D (IC(50) values ~10 μM).

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confidence: 99%

Flacourtosides A–F, Phenolic Glycosides Isolated from Flacourtia ramontchi

et al. 2012

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“…Within this group, the subclasses of flavonoids ( 117 – 120 ), hydroxycinnamic acids and derivatives ( 103 , 121 – 125 ); hydroxybenzoic acids ( 81 , 126 – 130 ), tannins ( 109 – 133 ), coumarins ( 103 , 134 ), among others. The second majority group of substances with antivenom activity are terpenes ( 97 , 105 , 106 , 112 , 135 – 139 ), which are followed by alkaloids ( 140 – 146 ), modified glycosides ( 110 , 111 , 147 ), saponins ( 100 , 101 , 103 , 148 ) and polyketides ( 86 , 149 , 150 ). In addition, proteins and peptides are reported as inhibitors of snake venom ( 61 , 107 , 151 – 153 ).…”

Section: Ethnopharmacology For Snakebite Treatmentmentioning

confidence: 99%

“…Some papers have already reported flavan-3-ols as potential antivenom substances. Flavan-3-ol catechin ( 50 ), isolated from the stem of Scolopia chinensis (Salicaceae) from China, also showed inhibitory activity (16%) against snake venom phosphodiesterase I (PDE I) ( 110 ). This substance also showed PLA 2 s inhibitory activity of C. atrox venom, and is of synthetic origin ( 164 ).…”

Section: Plant Products As Antivenom Agentsmentioning

confidence: 99%

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Plant-Derived Toxin Inhibitors as Potential Candidates to Complement Antivenom Treatment in Snakebite Envenomations

et al. 2022

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Snakebite envenomations (SBEs) are a neglected medical condition of global importance that mainly affect the tropical and subtropical regions. Clinical manifestations include pain, edema, hemorrhage, tissue necrosis, and neurotoxic signs, and may evolve to functional loss of the affected limb, acute renal and/or respiratory failure, and even death. The standard treatment for snake envenomations is antivenom, which is produced from the hyperimmunization of animals with snake toxins. The inhibition of the effects of SBEs using natural or synthetic compounds has been suggested as a complementary treatment particularly before admission to hospital for antivenom treatment, since these alternative molecules are also able to inhibit toxins. Biodiversity-derived molecules, namely those extracted from medicinal plants, are promising sources of toxin inhibitors that can minimize the deleterious consequences of SBEs. In this review, we systematically synthesize the literature on plant metabolites that can be used as toxin-inhibiting agents, as well as present the potential mechanisms of action of molecules derived from natural sources. These findings aim to further our understanding of the potential of natural products and provide new lead compounds as auxiliary therapies for SBEs.

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“…The location of glucose at C-3, rhamnose at C-2′, and fatty acid at C-6′ was determined by HMBC correlations between H-1′/C-3, H-1″/C-2′, and H-6′/C-1‴, respectively. Comparative analysis of 13 C NMR data of 1 with that of progenin III ( 3 ) [7, 8] also supported the position of a fatty acid moiety at C-6′ due to the downfield shift of C-6′ and the upfield shift of C-5′ resonances in 1 [9–12]. Acid hydrolysis of 1 with HCl-MeOH yielded methyl palmitate, which was identified by GCMS analysis as having the same retention time ( t R for methyl palmitate: 28.6 min) as that of the standard (Sigma-Aldrich).…”

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confidence: 91%

Two Spirostan Steroid Glycoside Fatty Esters from Dioscorea cayenensis

Ali

Smillie

Khan

2013

Natural Product Communications

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Two new fatty acid-spirostan steroid glycoside esters, progenin III palmitate (1) and progenin III linoleate (2), were isolated from the MeOH extract of Dioscorea cayenensis rhizomes. The extract also yielded seven previously known spirostan and furostan steroid glycosides (3–9). The structures of the new compounds were established as (25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-palmitoyl]-O-β-D-glucopyranoside (1) and (25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-linoleoyl]-O-β-D-glucopyranoside (2) by chemical and spectroscopic methods, including 1D and 2D NMR. The known compounds were identified as progenin III (3), dioscin (4), deltonin (5), asperin (6), gracillin (7), protodioscin (8)], and methyl protodioscin (9).

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Three New Phenolic Glycosides and a New Triterpenoid from the Stems ofScolopia chinensis

Cited by 10 publications

References 10 publications

Flacourtosides A–F, Phenolic Glycosides Isolated from Flacourtia ramontchi

Flacourtosides A–F, Phenolic Glycosides Isolated from Flacourtia ramontchi

Plant-Derived Toxin Inhibitors as Potential Candidates to Complement Antivenom Treatment in Snakebite Envenomations

Two Spirostan Steroid Glycoside Fatty Esters from Dioscorea cayenensis

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