Perillanolides A and B, new monoterpene glycosides from the leaves of Perilla frutescens

Yang, Lei; Liu, Xiaohong; San, Zhou; Gao, Hua; Li, Guoliang; Guo, Weijie; Fang, Xinyu; Wang, Wei

doi:10.1016/j.bjp.2017.06.003

Cited by 10 publications

(6 citation statements)

References 17 publications

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“…Scutellarein, a common ingredient identified in many herbal medicines, such as Scutellaria baicalensis (79) and Perilla frutescens (29,80), was reported to exert anti-microbial, anti-viral, anti-tumor, hepatoprotective, anti-neurodegenerative, and anti-oxidant effect (81). As the previous studies showed, scutellarein from different sources, including Indian medicinal plants, Perilla frutescens, Salvia plebeia, and Salvia officinalis L., had a potent inhibitory effect on XDH in vitro (29,73,77,82) and played a significant role in reducing the serum uric acid in vivo (77).…”

Section: Discussionmentioning

confidence: 99%

“…Pharmacological research reveals that PF may have bioactive properties including anti-allergy, anti-inflammatory, anti-oxidation, anti-cancer, anti-bacterial, and anti-depression effects (27). Several laboratory studies indicated that some bioactive constituents of PF showed impressive inhibitory effects on XDH (28)(29)(30). However, the compounds identified from PF are still limited and a more comprehensive and more in-depth study is greatly needed.…”

Section: Introductionmentioning

confidence: 99%

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Identification of inhibitors from a functional food-based plant Perillae Folium against hyperuricemia via metabolomics profiling, network pharmacology and all-atom molecular dynamics simulations

Wu,

Wong,

Chen

et al. 2024

Front. Endocrinol.

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IntroductionHyperuricemia (HUA) is a metabolic disorder caused by purine metabolism dysfunction in which the increasing purine levels can be partially attributed to seafood consumption. Perillae Folium (PF), a widely used plant in functional food, has been historically used to mitigate seafood-induced diseases. However, its efficacy against HUA and the underlying mechanism remain unclear. MethodsA network pharmacology analysis was performed to identify candidate targets and potential mechanisms involved in PF treating HUA. The candidate targets were determined based on TCMSP, SwissTargetPrediction, Open Targets Platform, GeneCards, Comparative Toxicogenomics Database, and DrugBank. The potential mechanisms were predicted via Gene Ontology (GO) and Kyoto Gene and Genome Encyclopedia (KEGG) analyses. Molecular docking in AutoDock Vina and PyRx were performed to predict the binding affinity and pose between herbal compounds and HUA-related targets. A chemical structure analysis of PF compounds was performed using OSIRIS DataWarrior and ClassyFire. We then conducted virtual pharmacokinetic and toxicity screening to filter potential inhibitors. We further performed verifications of these inhibitors’ roles in HUA through molecular dynamics (MD) simulations, text-mining, and untargeted metabolomics analysis. ResultsWe obtained 8200 predicted binding results between 328 herbal compounds and 25 potential targets, and xanthine dehydrogenase (XDH) exhibited the highest average binding affinity. We screened out five promising ligands (scutellarein, benzyl alpha-D-mannopyranoside, elemol, diisobutyl phthalate, and (3R)-hydroxy-beta-ionone) and performed MD simulations up to 50 ns for XDH complexed to them. The scutellarein-XDH complex exhibited the most satisfactory stability. Furthermore, the text-mining study provided laboratory evidence of scutellarein’s function. The metabolomics approach identified 543 compounds and confirmed the presence of scutellarein. Extending MD simulations to 200 ns further indicated the sustained impact of scutellarein on XDH structure. ConclusionOur study provides a computational and biomedical basis for PF treating HUA and fully elucidates scutellarein's great potential as an XDH inhibitor at the molecular level, holding promise for future drug design and development.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Identification of inhibitors from a functional food-based plant Perillae Folium against hyperuricemia via metabolomics profiling, network pharmacology and all-atom molecular dynamics simulations

Wu,

Wong,

Chen

et al. 2024

Front. Endocrinol.

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“…PF, an intervention in our study, is one of the common foods in East Asia and has been traditionally used as a medicinal herb ( Ahmed, 2018 ). PF is composed of approximately 400 different bioactive compounds, including perillaldehyde ( Ahmed and Tavaszi-Sarosi, 2019 ), anthocyanins ( He et al, 2015 ), terpenoids ( Akihisa et al, 2006 ), and coumarins ( Liu et al, 2017 ) etc., and has demonstrated strong anti-inflammatory ( Urushima et al, 2015 ), antioxidant ( Assefa et al, 2018 ), neuroprotective ( Senavong et al, 2016 ), anticancer ( Kwak and Ju, 2015 ), and hepatoprotective effects ( Yang et al, 2013 ) due to these compounds. Previous studies have demonstrated that PF provided anti-arthritic effects by reducing the arthritis score and neutrophil-to-lymphocyte ratio in a Balb/c collagen-induced arthritis model based on its anti-inflammatory and antioxidant effects ( Jin et al, 2019 ).…”

Section: Discussionmentioning

confidence: 99%

Efficacy of Perilla frutescens (L.) Britton var. frutescens extract on mild knee joint pain: A randomized controlled trial

Kim

et al. 2023

Front. Pharmacol.

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Objectives: This study aimed to evaluate the clinical efficacy and safety of PE extracts developed for the purpose of relieving pain and improving knee joint function on semi-healthy people with mild knee joint pain.Methods: A randomized, double-blind, two-arm, single-center, placebo-controlled clinical trial was conducted. Individuals with knee joint pain and a visual analogue scale (VAS) score < 50 mm were included in the study, and participants with radiological arthritis were excluded. Participants were administered either PFE or a placebo capsule (700 mg, twice a day) orally for eight weeks. The comparisons of the changed VAS score and Western Ontario and McMaster Universities Osteoarthritis (WOMAC) scores between the PFE and placebo groups were primary outcomes, while the five inflammation-related laboratory tests including cartilage oligomeric matrix protein, cyclooxygenase-2, neutrophil and lymphocyte ratio, high sensitive C-reactive protein, and erythrocyte sedimentation rate were secondary outcomes. Also, a safety assessment was done.Results: Eighty participants (mean age, 38.4 ± 14.0, male: female, 28:52) were enrolled; 75 completed the trial (PFE 36 and placebo 39). After eight weeks, both VAS and WOMAC scores were reduced in the PFE and placebo groups. The changed scores were significantly higher in the PFE group compared to the placebo group: 19.6 ± 10.9 vs. 6.8 ± 10.5; VAS scores (p < 0.001), and 20.5 ± 14.7 vs. 9.3 ± 16.5; total WOMAC scores (p < 0.01) including the sub-scores for pain, stiffness, and functions. No significant changes were reported in the five inflammation-related laboratory parameters. All adverse events were considered minor and unlikely to result from the intervention.Conclusion: Eight weeks of PFE intake was more effective than placebo in reducing knee joint pain and improving knee joint function in sub-healthy people with mild knee joint pain, and there were no major safety concerns.Clinical Trial Registration:https://cris.nih.go.kr/cris/search/detailSearch.do?search_lang=E&focus=reset_12&search_page=M&pageSize=10&page=undefined&seq=23101&status=5&seq_group=19745, identifier CRIS: KCT0007219

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“…The leaves, stems, fruits, and seeds of P. frutescens constitute different types of flavonoids, including flavones, flavanones, chalcones, and aurones. P. frutescens leaves contain flavones, such as luteolin, apigenin, scutellarein, negletein, vicenin-2, and catechin [ 17 , 28 , 40 ] along with several derivatives of luteolin, apigenin, and scutellarein [ 38 ] which include luteolin-7- O -glucuronide, luteolin-7- O -diglucuronide, luteolin 7-0-glucuronide -6″-methyl ester, luteolin-7- O -glucoside, apigenin-7- O -glucuronide, apigenin-7- O -diglucuronide, apigenin-7- O -glucoside, apigenin 7- O -caffeoylglucoside, scutellarein-7- O -glucuronide, and scutellarein 7- O -diglucuronide. The flavones in P. frutescens fruits include luteolin, apigenin, and chrysoeriol, while those in seeds include luteolin, luteolin-5- O -glucoside, luteolin-7- O -glucoside, apigenin, apigenin-7- O -glucoside, diosmetin, chrysoeriol, and catechin [ 22 ].…”

Section: Phytoconstituents Of P Frutescensmentioning

confidence: 99%

“…An aurone, ((Z)-4,6-dimethoxy-7,4′-dihydroxyaurone), also, presented good XO inhibition. Negletein (5,6-dihydroxy-7-methoxyflavone), scutellarein-7-glucuronide (breviscapin), sericoside (triterpene), loliolide, isololiolide (carotenoids), dehydrovomifoliol, perillanolide A, perillanolide B (monoterpeneglycosides), 4-(3,4-dihydroxybenzoyloxymethyl) phenyl- O -β-d-glucopyranoside, trans-p-hydroxy cinnamic acid, p-hydroxybenzaldehyde, and p-hydroxyacetophenone, also, exerted XO-inhibitory activities, with IC 50 values greater than 200 µM [ 17 ]. Thus, the bioactive compounds of P. frutescens could be used in treating hyperuricemia in patients with gout.…”

Section: Biological Functions Of P Frutescensmentioning

confidence: 99%

Perilla frutescens: A Rich Source of Pharmacological Active Compounds

et al. 2022

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Perilla frutescens (L.) Britton, an important pharmaceutical and nutraceutical crop, is widely cultivated in East Asian countries. In this review, we present the latest research findings on the phytochemistry and pharmacological activities of P. frutescens. Different databases, including PubMed, Scopus, CNKI, Agricola, Scifinder, Embase, ScienceDirect, DOAJ, and Web of Science, were searched to present the best review. In this review, we clearly represent the active constituents responsible for each and every pharmacological activity, plausible mechanism of action, and maximum inhibitory concentrations, as well as IC50 values. Approximately 400 different bioactive compounds, including alkaloids, terpenoids, quinines, phenylpropanoids, polyphenolic compounds, flavonoids, coumarins, anthocyanins, carotenoids, neolignans, fatty acids, polycosanols, tocopherols, and sitosterols, have been reported in the leaves, seeds, roots, and aerial parts of P. frutescens. The bioactive constituents of P. frutescens exhibited different enzyme-inhibition properties, including antihyaluronidase effects and aldose reductase inhibitory, α-glucosidase inhibitory, xanthine oxidase inhibitory, and tyrosinase inhibitory properties. P. frutescens showed strong anti-inflammatory, antidepressant, anti-spasmodic, anticancer, antioxidant, antimicrobial, insecticidal, neuroprotective, and hepatoprotective effects. Hence, the active constituents of P. frutescens used in the treatment of diabetes and diabetic complications (retinopathy, neuropathy, and nephropathy), prevention of hyperuricemia in gout patients, hyper pigmentation, allergic conditions, skin inflammation, skin allergy, atopic dermatitis, periodontosis, androgenic alopecia, gastric inflammation, oesophagitis, carcinogenesis, cardiovascular, Alzheimer’s, Parkinson’s, and cerebral ischemic disorders. Furthermore, we revealed the most active constituents and possible mechanisms of the pharmacological properties of P. frutescens.

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Perillanolides A and B, new monoterpene glycosides from the leaves of Perilla frutescens

Cited by 10 publications

References 17 publications

Identification of inhibitors from a functional food-based plant Perillae Folium against hyperuricemia via metabolomics profiling, network pharmacology and all-atom molecular dynamics simulations

Identification of inhibitors from a functional food-based plant Perillae Folium against hyperuricemia via metabolomics profiling, network pharmacology and all-atom molecular dynamics simulations

Efficacy of Perilla frutescens (L.) Britton var. frutescens extract on mild knee joint pain: A randomized controlled trial

Perilla frutescens: A Rich Source of Pharmacological Active Compounds

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