Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects

Akihisa, Toshihiro; Tokuda, Harukuni; Ukiya, Motohiko; Iizuka, Masaaki; Schneider, Stefan; Ogasawara, Kazuya; Mukainaka, Teruo; Iwatsuki, Kenji; Suzuki, Takashi; Nishino, Hoyoku

doi:10.1016/s0304-3835(03)00466-x

Cited by 117 publications

(98 citation statements)

References 12 publications

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“…In a previous study, compounds 1, 2, 7, 9, 23, 24, 26, 28, 29, 31, 35, 37, and 39 also showed potent inhibitor effects, ranging from 92-100 % inhibition at 1000 mol ratio, and 51-84% at 500 mol ratio. In Raji cells, inhibitors 1, 14, 35, 37, and 39 were more potent than the reference compound β-carotene [17]. Compound 27 was also found to have TPA-inhibiting properties [16].…”

Section: Chemopreventive Activitymentioning

confidence: 92%

“…Nitric oxide (NO) is another mutagen that affects microbial and mammalian cells due to the production of free radicals. When tested against Chang liver cells, compounds 7, 10, 11, 14, 24, 26, 28-31, 33, 34, and 38 showed inhibitory effects on NO almost equal to the reference compound glyzyrrhizin [3,17]. In another study, compounds 1 and 2 were also shown to suppress the production of NO in RAW264 macrophages, with negligible effects on cellular function [32].…”

Section: Oxidative Stress Relief and Anti-inflammatory Activitymentioning

confidence: 95%

“…Coumarins isolated from a number of plant species have been shown to possess anti-inflammatory and chemopreventive properties [14,15]. Indeed, coumarins isolated from ashitaba have demonstrated cytotoxic properties [3,16,17] in addition to antidiabetic [18], antiobesity [12], and blood pressure-reducing effects [19].…”

Section: Coumarinsmentioning

confidence: 99%

“…These compounds have been shown to possess radical scavenging, anti-inflammatory, and chemopreventive effects [21]. Flavanones in ashitaba, though less studied than the chalcones 1 and 2, have been studied most for their potential as chemopreventive agents [17].…”

Section: Flavanonesmentioning

confidence: 99%

“…Several researchers have studied the inhibitory effects of ashitaba compounds on the induction of the Epstein-Barr virus Early Antigen (EBV-EA) by 12-O-tetradecanoyl phorbol 13-acetate (TPA). EBV is associated with numerous diseases, including types of lymphoma and cancer, and the inhibitory effects on its induction are often used to evaluate antitumor-promoting activity in preliminary studies [3,17,30]. In Raji cells, compounds 10, 11, 14, 30, 34, 36, and 38 were more potent inhibitors than retinoic acid, the reference compound, with IC 50 values ranging from 215-320 mol ratio 32 pmol −1 TPA [3].…”

Section: Chemopreventive Activitymentioning

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: Chemopreventive Activitymentioning

confidence: 92%

Section: Oxidative Stress Relief and Anti-inflammatory Activitymentioning

confidence: 95%

Section: Coumarinsmentioning

confidence: 99%

Section: Flavanonesmentioning

confidence: 99%

Section: Chemopreventive Activitymentioning

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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Domino Reactions in the Total Synthesis of Natural Products

2013

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Xanthoangelols isolated from Angelica keiskei inhibit inflammatory‐induced plasminogen activator inhibitor 1 (PAI‐1) production

et al. 2011

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The folk medicine Angelica keiskei (Ashitaba) exhibits antitumor, antioxidant and antidiabetic activities and it has recently attracted attention as a health food. Ashitaba is thought to have antithrombotic properties, but this has not yet been scientifically proven. The elevation of plasma plasminogen activator inhibitor 1 (PAI-1), an inhibitor of fibrinolysis results in a predisposition to the risk of thrombosis. The present study showed that Ashitaba exudates injected intraperitoneally and orally administered over long-term suppressed the lipopolysaccharide (LPS) induced PAI-1 increase in mouse plasma. We also found that xanthoangelol, xanthoangelols B and D, the components of Ashitaba exudates, significantly inhibited TNFα-induced PAI-1 production from human umbilical vein endothelial cells (HUVECs). These findings suggest that Ashitaba can decrease elevated PAI-1 production, and that daily consumption of Ashitaba product might maintain anticoagulant status by inhibiting elevations in PAI-1 under inflammatory conditions.

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Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects

Cited by 117 publications

References 12 publications

A Review of the Medicinal Uses and Pharmacology of Ashitaba

A Review of the Medicinal Uses and Pharmacology of Ashitaba

Domino Reactions in the Total Synthesis of Natural Products

Xanthoangelols isolated from Angelica keiskei inhibit inflammatory‐induced plasminogen activator inhibitor 1 (PAI‐1) production

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