Anti-Hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action

Shimoda, Hiroshi; Ninomiya, Kiyofumi; Nishida, Norihisa; Yoshino, Tomoe; Morikawa, Toshio; Matsuda, Hisashi; Yoshikawa, Masayuki

doi:10.1016/s0960-894x(02)00889-2

Cited by 138 publications

(96 citation statements)

References 13 publications

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“…[16][17][18][19][20] Additionally, inhibitory effects on GE by chakasaponins I (2) and II (3), 21) but not 4 and 5, on GE were reported. Therefore, effects of 2-5 on GE in mice were compared.…”

Section: Effects Of 2-5 On Gastric Emptying (Ge) In Micementioning

confidence: 99%

Medicinal Flowers. XXXIII. Anti-hyperlipidemic and Anti-hyperglycemic Effects of Chakasaponins I–III and Structure of Chakasaponin IV from Flower Buds of Chinese Tea Plant (<i>Camellia sinensis</i>)

Matsuda

Hamao

Nakamura

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Effects of principal saponins, chakasaponins I-III, from the flower buds of Camellia sinensis cultivated in Fujian province, China on plasma triglyceride (TG) and glucose levels in olive oil or sucrose-loaded mice were examined. Chakasaponins I-III at 50 and 100 mg/kg significantly inhibited increases in plasma TG and glucose levels. Furthermore, they prevented gastric emptying, suggesting that the former inhibitory effect is partly dependent on the inhibition of gastric emptying. In addition, the chemical structure of a new acylated oleanane-type triterpene oligoglycoside, chakasaponin IV, was elucidated on the basis of chemical and physicochemical evidence.

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Section: Effects Of 2-5 On Gastric Emptying (Ge) In Micementioning

confidence: 99%

Medicinal Flowers. XXXIII. Anti-hyperlipidemic and Anti-hyperglycemic Effects of Chakasaponins I–III and Structure of Chakasaponin IV from Flower Buds of Chinese Tea Plant (<i>Camellia sinensis</i>)

Matsuda

Hamao

Nakamura

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In fact cynaropicrin (162), aguerin B (160) and grosheimin (264) significantly suppressed serum TG elevation at 50 and 100 mg/kg during the early stage (2 h after olive oil administration), whereas dehydrocostus lactone (142) and 11b, 13-dihydro-deacylcynaropicrin (190) had a weaker activity (Shimoda et al, 2003).…”

Section: Other Activitiesmentioning

confidence: 99%

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

et al. 2013

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“…scolymus or Cynara cardunculus var scolymus), which originated in the Mediterranean basin (Sonnante et al, 2007), is an edible plant used in medicine since ancient times. Artichoke extracts possess many medicinal properties, including anticarcinogenic, anti-Human immunodeficiency virus, antioxidative, cholesterol-lowering, bile-expelling, hepatoprotective, and diuretic activities, as well as antifungal and antibacterial properties (Agarwal and Mukhtar, 1996;Gebhardt, 1997;Kraft, 1997;Brown and Rice-Evans, 1998;McDougall et al, 1998;Shimoda et al, 2003;Zhua et al, 2005). The high antioxidant capacity of artichoke is due primarily to flavonoids and phenolic acids, particularly 5-caffeoylquinic acid, also known as chlorogenic acid (CGA), 1,3-dicaffeoylquinic acid (cynarin), 1,5-dicaffeoylquinic acid, and caffeic acid, which are abundant in artichoke and bioavailable to humans through their diet (Azzini et al, 2007).…”

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Novel Hydroxycinnamoyl-Coenzyme A Quinate Transferase Genes from Artichoke Are Involved in the Synthesis of Chlorogenic Acid

Sonnante

D'Amore²,

Blanco³

et al. 2010

Plant Physiology

120

114

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Artichoke (Cynara cardunculus subsp. scolymus) extracts have high antioxidant capacity, due primarily to flavonoids and phenolic acids, particularly chlorogenic acid (5-caffeoylquinic acid [CGA]), dicaffeoylquinic acids, and caffeic acid, which are abundant in flower bracts and bioavailable to humans in the diet. The synthesis of CGA can occur following different routes in plant species, and hydroxycinnamoyl-coenzyme A transferases are important enzymes in these pathways. Here, we report on the isolation and characterization of two novel genes both encoding hydroxycinnamoyl-coenzyme A quinate transferases (HQT) from artichoke. The recombinant proteins (HQT1 and HQT2) were assayed after expression in Escherichia coli, and both showed higher affinity for quinate over shikimate. Their preferences for acyl donors, caffeoyl-coenzyme A or p-coumaroylcoenzyme A, were examined. Modeling and docking analyses were used to propose possible pockets and residues involved in determining substrate specificities in the HQT enzyme family. Quantitative real-time polymerase chain reaction analysis of gene expression indicated that HQT1 might be more directly associated with CGA content. Transient and stable expression of HQT1 in Nicotiana resulted in a higher production of CGA and cynarin (1,3-dicaffeoylquinic acid). These findings suggest that several isoforms of HQT contribute to the synthesis of CGA in artichoke according to physiological needs and possibly following various metabolic routes.

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Anti-Hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action

Cited by 138 publications

References 13 publications

Medicinal Flowers. XXXIII. Anti-hyperlipidemic and Anti-hyperglycemic Effects of Chakasaponins I–III and Structure of Chakasaponin IV from Flower Buds of Chinese Tea Plant (<i>Camellia sinensis</i>)

Medicinal Flowers. XXXIII. Anti-hyperlipidemic and Anti-hyperglycemic Effects of Chakasaponins I–III and Structure of Chakasaponin IV from Flower Buds of Chinese Tea Plant (<i>Camellia sinensis</i>)

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

Novel Hydroxycinnamoyl-Coenzyme A Quinate Transferase Genes from Artichoke Are Involved in the Synthesis of Chlorogenic Acid

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