Bioactive caffeic acid derivatives from Wedelia trilobata

Ren, Hai; Xu, Qiao-Lin; Zhang, Mei; Dong, Lu; Zhang, Qiang; Luo, Bi; Luo, Qin-Wen; Tan, Jian‐Wen

doi:10.1016/j.phytol.2016.11.001

Cited by 11 publications

(3 citation statements)

References 21 publications

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“…Our recent study on this plant also revealed a group of rare C-9 hydroxylated ent -kaurene diterpene glucosides [ 13 ]. During our ongoing phytochemical research on invasive plants in China [ 14 , 15 , 16 , 17 , 18 , 19 ], two new ( 1 and 2 ) and twelve known ( 3 – 14 ) phenolic compounds ( Figure 1 ), were further isolated from the aerial parts of M. micrantha . Herein, we report the isolation and structure elucidation of these compounds, as well as their antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

Phenolics from Mikania micrantha and Their Antioxidant Activity

et al. 2017

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A phytochemical study on the aerial parts of Mikania micrantha led to the isolation of two new phenolic compounds, benzyl 5-O-β-d-glucopyranosyl-2,5-dihydroxybenzoate (1) and (7S,8R)-threo-dihydroxydehydrodiconiferyl alcohol 9-acetate (2), together with twelve known compounds, benzyl 2-O-β-d-glucopyranosyl-2,6-dihydroxybenzoate (3), 4-allyl-2,6-dimethoxyphenol glucoside (4), (+)-isolariciresinol (5), icariol A2 (6), 9,10-dihydroxythymol (7), 8,9,10-trihydroxythymol (8), caffeic acid (9), p-coumaric acid (10), ethyl protocatechuate (11), procatechuic aldehyde (12), 4-hydroxybenzoic acid (13), and hydroquinone (14). Their structures were elucidated on the basis of extensive spectroscopic analysis. Except 8 and 9, all the other compounds were isolated from this plant species for the first time. The antioxidant activity of those isolated compounds were evaluated using three different assays. Compounds 1, 2, 3, 9, 10, 13, and 14 demonstrated significant 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) free radical cation scavenging activity ranging from SC50 0.31 to 4.86 µM, which were more potent than l-ascorbic acid (SC50 = 10.48 µM). Compounds 5, 9, 11, and 12 exhibited more potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (SC50 = 16.24–21.67 µM) than l-ascorbic acid (39.48 µM). Moreover, the ferric reducing antioxidant power (FRAP) of compounds 2, 5, 9, and 11 were discovered to be also comparable to or even more potent than l-ascorbic acid.

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Section: Introductionmentioning

confidence: 99%

Phenolics from Mikania micrantha and Their Antioxidant Activity

et al. 2017

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“…Compounds 1 and 2 have antioxidant [ 60 ], anti-diabetic [ 61 ], and anti-inflammatory effects [ 62 ]. Kwon et al [ 49 ] revealed that compounds 3 and 5 have a strong inhibitory effect on diabetics and diabetic complications and can scavenge free radicals.…”

Section: Discussionmentioning

confidence: 99%

An Arylbenzofuran, Stilbene Dimers, and Prenylated Diels–Alder Adducts as Potent Diabetic Inhibitors from Morus bombycis Leaves

Ali

et al. 2023

Antioxidants

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Morus bombycis has a long history of usage as a treatment for metabolic diseases, especially, diabetes mellitus (DM). Thus, we aimed to isolate and evaluate bioactive constituents derived from M. bombycis leaves for the treatment of DM. According to bioassay-guided isolation by column chromatography, eight compounds were obtained from M. bombycis leaves: two phenolic compounds, p-coumaric acid (1) and chlorogenic acid methyl ester (2), one stilbene, oxyresveratrol (3), two stilbene dimers, macrourin B (4) and austrafuran C (6), one 2-arylbenzofuran, moracin M (5), and two Diels–Alder type adducts, mulberrofuran F (7) and chalcomoracin (8). Among the eight isolated compounds, the anti-DM activity of 3–8 (which possess chemotaxonomic significance in Morus species) was evaluated by inhibition of α-glucosidase, protein tyrosine phosphatase 1B (PTP1B), human recombinant aldose reductase (HRAR), and advanced glycation end-product (AGE) formation as well as by scavenging peroxynitrite (ONOO−), which are crucial therapeutic targets of DM and its complications. Compounds 4 and 6–8 significantly inhibited α-glucosidase, PTP1B, and HRAR enzymes with mixed-type and non-competitive-type inhibition modes. Furthermore, the four compounds had low negative binding energies in both enzymes according to molecular docking simulation, and compounds 3–8 exhibited strong antioxidant capacity by inhibiting AGE formation and ONOO− scavenging. Overall results suggested that the most active stilbene-dimer-type compounds (4 and 6) along with Diels–Alder type adducts (7 and 8) could be promising therapeutic and preventive resources against DM and have the potential to be used as antioxidants, anti-diabetic agents, and anti-diabetic complication agents.

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“…Several other pharmacological activities of W. trilobata have been reported, including antioxidant, analgesic, anti-inflammatory, antimicrobial, wound healing, uterine contraction, antitumor, antidiabetic and menstrual pain relief (Balekar et al, 2014). In addition, phytochemical studies have identified some diverse chemicals from this plant, including terpenoids, steroids, flavonoids and phenolics (Balekar et al, 2014;Ren et al, 2017) . Many reports did not separate the flower, leaf and stem parts and instead just used the above-ground part or did not use the flower part (Balekar et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Biological activities supporting development of cosmeceutical skin products from Wedelia trilobata (L.) Hitch. flower extract

2023

ANRES

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Importance of the work: This is the first report to demonstrate the potential of Wedelia trilobata (L.) Hitch. as an ingredient in cosmeceutical products. Objectives: To examine the biological activities associated with cosmeceutical products of W. trilobata extract. Materials & Methods:The flowers (WTF), leaves (WTL) and stems (WTS) of W. trilobata were separately extracted using 50% ethanol and freeze-drying to obtain WTF, WTL and WTS extracts, respectively. Then, the antioxidant, anti-tyrosinase, antimicrobial, cytoprotective and anti-inflammatory activities of the extracts were investigated. Results: Screening tests, using the three extracts of the plant showed different positive effects, with WTF having the highest antioxidant, tyrosinase and nitric oxide inhibitory activities. Therefore, WTF was further studied to find the mechanisms involved in anti-inflammatory, antimicrobial and cytoprotective effects. WTF at concentrations of 50-200 µg/mL down-regulated the expression of cyclooxygenase-2 (COX-2), interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) genes in macrophages using a semi-quantitative reverse-transcriptase polymerase chain reaction technique and the production of tumor necrosis factor-α in keratinocytes. The antimicrobial activity of WTF was demonstrated on many bacteria and Candida albicans. WTF prevented H 2 O 2 -induced cell death of human keratinocyte via down-regulation on the expression of matrix metalloproteinase-1 (MMP-1) and MMP-2 genes and up-regulation on the expression of procollagen type 1 genes. The gel formulations containing WTF were developed with good stability and inhibited the growth of Propionibacterium acnes at statistically significant levels. Main finding: W. trilobata flowers demonstrated a potential source of an active ingredient in skin product development. The plant may have more value-added components for application in cosmeceuticals as well as being useful as a ground cover weed.

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Bioactive caffeic acid derivatives from Wedelia trilobata

Cited by 11 publications

References 21 publications

Phenolics from Mikania micrantha and Their Antioxidant Activity

Phenolics from Mikania micrantha and Their Antioxidant Activity

An Arylbenzofuran, Stilbene Dimers, and Prenylated Diels–Alder Adducts as Potent Diabetic Inhibitors from Morus bombycis Leaves

Biological activities supporting development of cosmeceutical skin products from Wedelia trilobata (L.) Hitch. flower extract

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