Higenamine 4′-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor

Kato, Eisuke; Inagaki, Yoshishige; Kawabata, Jun

doi:10.1016/j.bmc.2015.04.054

Cited by 32 publications

(16 citation statements)

References 19 publications

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“…We previously reported the isolation of higenamine 4′- O -β- d -glucoside ( 1 ) from lotus plumule as a glucose uptake inducer against muscle cells, and indicated that its stereochemistry is ( S ) [ 17 ]. However, during a following research related to the structure-activity relationship study of 1 , a question arose about the stereochemistry of natural 1 isolated from lotus plumule, and the above reports have inspired us to precisely examine the stereochemistry of natural 1 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers

2017

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Higenamine is a tetrahydroisoquinoline present in several plants that has β-adrenergic receptor agonist activity. Study of the biosynthesis of higenamine has shown the participation of norcoclaurine synthase, which controls the stereochemistry to construct the (S)-isomer. However, when isolated from nature, higenamine is found as the racemate, or even the (R)-isomer. We recently reported the isolation of higenamine 4′-O-β-d-glucoside. Herein, its (R)- and (S)-isomers were synthesized and compared to precisely determine the stereochemistry of the isolate. Owing to their similar spectral properties, determination of the stereochemistry based on NMR data was considered inappropriate. Therefore, a high-performance liquid chromatography method was established to separate the isomers, and natural higenamine 4′-O-β-d-glucoside was determined to be a mixture of isomers.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers

2017

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“…In people with type II diabetes, insulin-induced stimulation of hepatic, muscle, and adipose tissue glucose uptake is impaired [32,33,34,35]. Among numerous structurally diverse natural products affecting glucose uptake [35,36,37,38,39,40,41,42,43,44,45], flavonoids are a predominant factor [36,37,38,39,40]. Among isolates 1 – 24 , compounds 1 – 3 are flavonol derivatives and quercetin ( 3 ) was identified in our study as the most active single component of purple I. batatas leaves.…”

Section: Resultsmentioning

confidence: 99%

Characterization of Secondary Metabolites from Purple Ipomoea batatas Leaves and Their Effects on Glucose Uptake

Lee

Chen

et al. 2016

Molecules

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Ipomoea batatas has long been used in folk medicine for the treatment of hyperglycemia or as a food additive for the prevention of type 2 diabetes. However, neither the plant extract nor its active components have been evaluated systematically. In this work four crude extracts, including n-hexane-(IBH), 95% MeOH-(IBM), n-BuOH-(IBB), and H 2 O-soluble (IBW) fractions, were prepared by fractionation of a methanolic extract of purple I. batatas leaves. Twenty-four pure compounds 1-24 were then isolated by various chromatographic techniques and their structures identified from NMR and MS data. Glucose uptake assays in differentiated 3T3-L1 adipocytes and rat primary hepatocytes, as well as western blot analysis, were carried out to evaluate the antidiabetic activity of this species. The IBH crude fraction, with methyl decanoate (22) as a major and active compound, showed the greatest effect on glucose uptake, most likely via activation of Glut4 and regulation of the PI3K/AKT pathway. Quercetin 3-O-β-D-sophoroside (1), quercetin (3), benzyl β-d-glucoside (10), 4-hydroxy-3-methoxybenzaldehyde (12), and methyl decanoate (22) could be important components contributing to the antidiabetic effects. We conclude that purple I. batatas leaves have potential as an antidiabetic plant source and the active constituents 1, 3, 10, 12, and 22 are promising lead candidates for future investigation.

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“…NMR is difficult to cover the non-nutrient metabolites occurring at low concentrations ( Scalbert et al, 2014 ). The major applications of NMR in lotus seed metabolomics focused on the structure identification of pure compounds of alkaloids ( Kato et al, 2015 ). GC–MS have an excellent separation capability, and a large pool of databases for metabolite identification.…”

Section: Metabolomics Study On the Lotus Seedsmentioning

confidence: 99%

Current Advances in the Metabolomics Study on Lotus Seeds

2016

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Lotus (Nelumbo nucifera), which is distributed widely throughout Asia, Australia and North America, is an aquatic perennial that has been cultivated for over 2,000 years. It is very stimulating that almost all parts of lotus have been consumed as vegetable as well as food, especially the seeds. Except for the nutritive values of lotus, there has been increasing interest in its potential as functional food due to its rich secondary metabolites, such as flavonoids and alkaloids. Not only have these metabolites greatly contributed to the biological process of lotus seeds, but also have been reported to possess multiple health-promoting effects, including antioxidant, anti-amnesic, anti-inflammatory, and anti-tumor activities. Thus, comprehensive metabolomic profiling of these metabolites is of key importance to help understand their biological activities, and other chemical biology features. In this context, this review will provide an update on the current technological platforms, and workflow associated with metabolomic studies on lotus seeds, as well as insights into the application of metabolomics for the improvement of food safety and quality, assisting breeding, and promotion of the study of metabolism and pharmacokinetics of lotus seeds; meanwhile it will also help explore new perspectives and outline future challenges in this fast-growing research subject.

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Higenamine 4′-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor

Cited by 32 publications

References 19 publications

Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers

Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers

Characterization of Secondary Metabolites from Purple Ipomoea batatas Leaves and Their Effects on Glucose Uptake

Current Advances in the Metabolomics Study on Lotus Seeds

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