Six New Chalcones from<i>Angelica keiskei</i>Inducing Adiponectin Production in 3T3-L1 Adipocytes

Ohnogi, Hiromu; Kudo, Yoko; Tahara, Kazukuni; Sugiyama, Katsumi; Enoki, Tatsuji; Hayami, Shoko; Sagawa, Hiroaki; Tanimura, Yuko; Aoi, Wataru; Naito, Yuji; Kato, Ikunoshin; Yoshikawa, Toshikazu

doi:10.1271/bbb.110976

Cited by 24 publications

(23 citation statements)

References 32 publications

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“…Compound C reversed the anti-adipogenic effects of the chalcones, further supporting the involvement of 1 and 2 in AMPK activation [26]. Adiponectin helps to improve insulin resistance, so compounds aiding in adiponectin production may be useful in inhibiting the development of metabolic syndrome [27]. In one study, the effects of compounds 1, 2, and 15-19 were assessed for their effects on adiponectin production in 3T3-L1 adipocytes.…”

Section: Antidiabetic and Antiobesity Activitiesmentioning

confidence: 87%

“…All chalcones upregulated the expression of adiponectin mRNA, particularly compounds 17 (7.80-fold induction) and 18 (8.27-fold induction). Compounds 1, 2, and 15-19 also significantly enhanced adiponectin production [27]. Absolute configuration at points marked with an asterisk (*) were not specified in original articles.…”

Section: Antidiabetic and Antiobesity Activitiesmentioning

confidence: 99%

“…Ashitaba, as is typical with members of the Apiaceae family, contains bioactive furanocoumarins (25) and dihydrofuranocoumarin analogs (23,27). In fact, compound 25 has illustrated phototoxic and photogenotoxic effects in a number of studies [48,49].…”

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confidence: 99%

“…Additionally, toxicological analyses on isolated compounds should be conducted. In particular, the toxicological profiles of prenylated chalcones , the representative structural class of ashitaba, as well as those of furanocoumarins (23,25,27), must be thoroughly characterized to determine ranges of toxicity.…”

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confidence: 99%

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A Review of the Medicinal Uses and Pharmacology of Ashitaba

Caesar

Cech

2016

Planta Med

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Medicinal plants are commonly employed for therapeutic purposes throughout the world. A recent National Health Interview Survey estimated that nearly 18 % of adults in the United States regularly took non-vitamin, non-mineral dietary supplements in 2012 [1]. Because of the popularity of herbal medicines, it is important to understand the chemical basis behind the purported activities of botanicals. Angelica, a member of the Apiaceae (Umbelliferae) family, is a large genus comprised of over 60 species. Members of the genus have been utilized as medicines across the world, most notably in Asia, to treat numerous ailments, including influenza, hepatitis, arthritis, indigestion, fever, and microbial infections [2]. An increasing number of studies are being conducted on a medicinally promising member of the genus, Angelica keiskei Koidzumi (Apiaceae), or ashitaba. This large leafy perennial plant native to the Pacific coast of Japan is used throughout Asia for its diuretic, laxative, stimulant, and galactagogue properties [3]. In the past decade, several active constituents representing chalcones, flavanones, and coumarins have been isolated and characterized from ashitaba, and several bioactiv-ities have been described. This review presents the current progress on ashitaba pharmacological studies, with a focus on isolated secondary metabolites, biological activity, toxicological data, and clinical relevance. Bioactive Metabolites Isolated from Ashitaba ! Chalcones Most of the literature on the bioactive metabolites from ashitaba concerns the diverse activity of various chalcones (l " Table 1 and Fig. 1), which are most abundant in the root bark of the plant [4]. Chalcones are formed from phenylpropanoid starter units, extended with three malonyl-CoA molecules. The resulting polyketide is folded by the enzyme chalcone synthase to promote Claisen condensations and subsequent enolizations [5]. Interestingly, the bioactive chalcones found in ashitaba are prenylated at the 5′-position (l " Fig. 1), indicating that these molecules have undergone multiple biosynthetic steps, travelling through the acetate, shikimate, and isoprenoid pathways.

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Section: Antidiabetic and Antiobesity Activitiesmentioning

confidence: 87%

Section: Antidiabetic and Antiobesity Activitiesmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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A Review of the Medicinal Uses and Pharmacology of Ashitaba

Caesar

Cech

2016

Planta Med

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“…A. keiskei contains such nutrients as vitamin A, vitamin K, and dietary fiber in its leaves, stems, and roots. 26 It has also been reported that A. keiskei is rich in chalcones, such as 4-hydroxyderricin and xanthoangelol, which are considered to have biological functions. 16,27 Chalcones are the starting material for biosynthesis of flavonoids found in usual dietary intake of humans.…”

Section: Discussionmentioning

confidence: 99%

Chalcones fromAngelica keiskeiAttenuate the Inflammatory Responses by Suppressing Nuclear Translocation of NF-κB

Chang

Lee

Ryu

2014

Journal of Medicinal Food

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The ethyl acetate-soluble fraction from the ethanolic extract of Angelica keiskei showed potent inhibitory activity against the production of nitric oxide (NO) in lipopolysaccharide (LPS)-activated RAW 264.7 cells. We identified seven chalcones (1-7) from EtOAc-soluble fractions through the activity-guided separation. Four active principles, identified as 4-hydroxyderrcine (1), xanthoangelol E (2), xanthokeismin A (4), and xanthoangelol B (5), inhibited the production of NO and the expression of proinflammatory cytokines, interleukin (IL)-1β and IL-6, in LPS-activated macrophages. Western blotting and reverse transcription-polymerase chain reaction analysis demonstrated that these chalcones attenuated protein and mRNA levels of inflammatory enzymes such as inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Moreover, these active compounds suppressed the degradation of inhibitory-κBα (I-κBα) and the translocation of nuclear factor κB (NF-κB) into nuclei of LPS-activated macrophages. These data demonstrate that four chalcones (1, 2, 4, and 5) from A. keiskei can suppress the LPS-induced production of NO and the expression of iNOS/COX-2 genes by inhibiting the degradation of I-κBα and nuclear translocation of NF-κB. Taken together, four chalcones from A. keiskei may have efficacy as anti-inflammatory agents.

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The neuroprotective effects of Chalcones from Ashitaba on cuprizone‐induced demyelination via modulation of brain‐derived neurotrophic factor and tumor necrosis factor α

Rowhanirad

Taherianfard

2023

Brain and Behavior

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IntroductionMultiple sclerosis (MS) is the most common demyelinating disease of the central nervous system. However, the limitations of available therapeutic strategies are frustrating, both in terms of their low efficacy and multiple side effects. Previous studies showed that natural compounds such as Chalcones possess neuroprotective effects on neurodegenerative disorders. However, few studies have so far been published on the potential effects of Chalcones on treating demyelinating disease. The present study was designed to investigate the effects of Chalcones from Ashitaba (ChA) on cuprizone‐induced noxious changes in the C57BL6 mice model of MS.MethodsThe mice received normal diets (Control group: CNT), or Cuprizone‐supplemented diets either without ChA (Cuprizone group: CPZ) or with low or high (300, 600 mg/kg/day) doses of ChA (ChA‐treated groups: CPZ+ChA300/600). Brain‐derived neurotrophic factor (BDNF) and tumor necrosis factor alpha (TNFα) levels, demyelination scores in the corpus callosum (CC), and cognitive impairment were evaluated using the enzyme‐linked immunosorbent assay, histological, and Y‐maze tests, respectively.ResultsThe findings showed that ChA Co‐treatment significantly reduced the extent of demyelination in the CC and the serum and brain levels of TNFα in the ChA‐treated groups compared to the CPZ group. Besides, treatment with a higher dose of ChA significantly improved the behavioral responses and BDNF levels in the serum and brain of the CPZ+ChA600 group when compared with the CPZ group.ConclusionThe present study provided evidence for the neuroprotective effects of ChA on cuprizone‐induced demyelination and behavioral dysfunction in C57BL/6 mice, possibly by modulating TNFα secretion and BDNF expression.

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Six New Chalcones fromAngelica keiskeiInducing Adiponectin Production in 3T3-L1 Adipocytes

Cited by 24 publications

References 32 publications

A Review of the Medicinal Uses and Pharmacology of Ashitaba

A Review of the Medicinal Uses and Pharmacology of Ashitaba

Chalcones fromAngelica keiskeiAttenuate the Inflammatory Responses by Suppressing Nuclear Translocation of NF-κB

The neuroprotective effects of Chalcones from Ashitaba on cuprizone‐induced demyelination via modulation of brain‐derived neurotrophic factor and tumor necrosis factor α

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