New Terpenylated Dihydrochalcone Derivatives Isolated from <i>Mitrella kentii</i>

Benosman, A.; Oger, Jean-Michel; Richomme, Pascal; Bruneton, J.; Roussakis, Christos; Bosch, Simone; Sévenet, Thierry; Ito, K.; Ichino, Kunio; Hadi, A. Hamid A.

doi:10.1021/np9700331

Cited by 17 publications

(9 citation statements)

References 14 publications

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“…Experimentally, the plant showed anti-inflammatory activity [10]. Previous chemical studies on M. kentii resulted in the isolation of isoquinoline alkaloids [11], terpenylated dihydrochalcones [12] and four other benzoic acids [10]. As a continuation of our research for biologically active compounds for the treatment of gastric ulcer from the Malaysian flora, a hexane extract of the bark of this plant was selected for phytochemical investigations.…”

Section: Introductionmentioning

confidence: 99%

RETRACTED ARTICLE: Gastroprotective effect of desmosdumotin C isolated from Mitrella kentii against ethanol-induced gastric mucosal hemorrhage in rats: possible involvement of glutathione, heat-shock protein-70, sulfhydryl compounds, nitric oxide, and anti-Helicobacter pylori activity

Sidahmed

Azizan

Mohan

et al. 2013

BMC Complement Altern Med

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BackgroundMitrella kentii (M. kentii) (Bl.) Miq, is a tree-climbing liana that belongs to the family Annonaceae. The plant is rich with isoquinoline alkaloids, terpenylated dihydrochalcones and benzoic acids and has been reported to possess anti-inflammatory activity. The purpose of this study is to assess the gastroprotective effects of desmosdumotin C (DES), a new isolated bioactive compound from M. kentii, on gastric ulcer models in rats.MethodsDES was isolated from the bark of M. kentii. Experimental rats were orally pretreated with 5, 10 and 20 mg/kg of the isolated compound and were subsequently subjected to absolute ethanol-induced acute gastric ulcer. Gross evaluation, mucus content, gastric acidity and histological gastric lesions were assessed in vivo. The effects of DES on the anti-oxidant system, non-protein sulfhydryl (NP-SH) content, nitric oxide (NO)level, cyclooxygenase-2 (COX-2) enzyme activity, bcl-2-associated X (Bax) protein expression and Helicabacter pylori (H pylori) were also investigated.ResultsDES pre-treatment at the administered doses significantly attenuated ethanol-induced gastric ulcer; this was observed by decreased gastric ulcer area, reduced or absence of edema and leucocytes infiltration compared to the ulcer control group. It was found that DES maintained glutathione (GSH) level, decreased malondialdehyde (MDA) level, increased NP-SH content and NO level and inhibited COX-2 activity. The compound up regulated heat shock protein-70 (HSP-70) and down regulated Bax protein expression in the ulcerated tissue. DES showed interesting anti-H pylori effects. The efficacy of DES was accomplished safely without any signs of toxicity.ConclusionsThe current study reveals that DES demonstrated gastroprotective effects which could be attributed to its antioxidant effect, activation of HSP-70 protein, intervention with COX-2 inflammatory pathway and potent anti H pylori effect.

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Section: Introductionmentioning

confidence: 99%

RETRACTED ARTICLE: Gastroprotective effect of desmosdumotin C isolated from Mitrella kentii against ethanol-induced gastric mucosal hemorrhage in rats: possible involvement of glutathione, heat-shock protein-70, sulfhydryl compounds, nitric oxide, and anti-Helicobacter pylori activity

Sidahmed

Azizan

Mohan

et al. 2013

BMC Complement Altern Med

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“…While most DHCs found in nature are derived from phloretin, some plants, such as Uvaria angolensis (Hufford and Oguntimein, 1980) or Mitrella kentia (Benosman et al, 1997), accumulate also DHC structures lacking the 4-hydroxy group. This means they are most likely derived from pinocembrin DHC and are produced by CHS from dihydrocinnamoyl-CoA and three units of malonyl-CoA.…”

Section: Resultsmentioning

confidence: 99%

Metabolic engineering of Saccharomyces cerevisiae for de novo production of dihydrochalcones with known antioxidant, antidiabetic, and sweet tasting properties

Eichenberger

Lehka

Folly

et al. 2017

Metabolic Engineering

101

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Dihydrochalcones are plant secondary metabolites comprising molecules of significant commercial interest as antioxidants, antidiabetics, or sweeteners. To date, their heterologous biosynthesis in microorganisms has been achieved only by precursor feeding or as minor by-products in strains engineered for flavonoid production. Here, the native ScTSC13 was overexpressed in Saccharomyces cerevisiae to increase its side activity in reducing p-coumaroyl-CoA to p-dihydrocoumaroyl-CoA. De novo production of phloretin, the first committed dihydrochalcone, was achieved by co-expression of additional relevant pathway enzymes. Naringenin, a major by-product of the initial pathway, was practically eliminated by using a chalcone synthase from barley with unexpected substrate specificity. By further extension of the pathway from phloretin with decorating enzymes with known specificities for dihydrochalcones, and by exploiting substrate flexibility of enzymes involved in flavonoid biosynthesis, de novo production of the antioxidant molecule nothofagin, the antidiabetic molecule phlorizin, the sweet molecule naringin dihydrochalcone, and 3-hydroxyphloretin was achieved.

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“…These observations together with the CH 2 and CH 1 H, 1 H-correlation shown in Fig. 3 suggested that 3 is a 3-substituted menthene derivative with a freely rotating side-chain [10] [11]. The olefinic H-atoms at d(H) 7.38 (HÀC(7)) and 6.77 (HÀC(6)) correlated with a quaternary C-atom at d(C) 158.8 (C(5)) and the aromatic C-atom at d(C) 137.2 (C(8)).…”

Section: (¼ (2e)-1-{24-dihydroxy-3-[(1s2e5s)-5-hydroxy-17-bis(4-hmentioning

confidence: 99%

New Diarylheptanoids and Kavalactone from Alpinia katsumadaiHayata

Chou

Wang

2010

Helvetica Chimica Acta

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Two new diarylheptanoids, katsumains A (1) and B (2), and one new kavalactone, katsumadain (3), together with the three known compounds (4E,6E)-1,7-diphenylhepta-4,6-dien-3-one (4), (5R,6E)-1,7diphenyl-5-hydroxyhept-6-en-3-one (5), and cardamonin (6), were isolated from the seeds of Alpinia katsumadai Hayata. Their structures were elucidated mainly by spectroscopic methods (1D-and 2D-NMR) and by mass spectrometry (HR-ESI-MS). Besides, the erroneous nomenclatures for (þ)linderatin and (þ)-neolinderatin as given in [10] [11] were corrected to be 2',4',6'-trihydroxy-3'-[(3R,4R)-4-isopropyl-1-methylcyclohex-1-en-3-yl]dihydrochalcone for (þ)-linderatin and 2',4',6'-trihydroxy-3',5'bis[(3R,4R)-4-isopropyl-1-methylcyclohex-1-en-3-yl]dihydrochalcone for (þ)-neolinderatin, respectively.

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New Terpenylated Dihydrochalcone Derivatives Isolated from Mitrella kentii

Cited by 17 publications

References 14 publications

RETRACTED ARTICLE: Gastroprotective effect of desmosdumotin C isolated from Mitrella kentii against ethanol-induced gastric mucosal hemorrhage in rats: possible involvement of glutathione, heat-shock protein-70, sulfhydryl compounds, nitric oxide, and anti-Helicobacter pylori activity

RETRACTED ARTICLE: Gastroprotective effect of desmosdumotin C isolated from Mitrella kentii against ethanol-induced gastric mucosal hemorrhage in rats: possible involvement of glutathione, heat-shock protein-70, sulfhydryl compounds, nitric oxide, and anti-Helicobacter pylori activity

Metabolic engineering of Saccharomyces cerevisiae for de novo production of dihydrochalcones with known antioxidant, antidiabetic, and sweet tasting properties

New Diarylheptanoids and Kavalactone from Alpinia katsumadaiHayata

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