A guanidine derivative from seeds of Plantago asiatica

Goda, Yukihiro; Kawahara, Nobuo; Kiuchi, Fumiyuki; Hirakura, Kazuhiro; Kikuchi, Yoshihiro; Nishimura, Hiroaki; Takao, Masaki; Marumoto, Masahiko; Kitazaki, Hironori

doi:10.1007/s11418-008-0275-7

Cited by 18 publications

(13 citation statements)

References 9 publications

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“…Previous studies report the herb extracts rich in phenylpropanoid glycosides have anti-obesity effects on diet-induced mice, and the possible mechanisms were demonstrated as stimulating leptin expression and cholesterol catabolism, suppressing fatty acid synthesis, and accelerating fatty acid β-oxidation [ 39 , 40 ]. Plantagoguanidinic acid A is a newly found guanidine derivative from P. asiatica L. seeds, and improves glucose metabolism in alloxan-induced diabetic mice [ 29 , 41 , 42 ]. Other guanidine derivatives were also reported to have potential anti-inflammatory and anti-hyperglycemic effects in in vitro pharmacological studies through inhibition of cyclooxygenase-2 activity and suppression of hepatic gluconeogenesis [ 43 , 44 ].…”

Section: Discussionmentioning

confidence: 99%

Plantago asiatica L. Seed Extract Improves Lipid Accumulation and Hyperglycemia in High-Fat Diet-Induced Obese Mice

Yang

Tong

et al. 2017

IJMS

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Obesity and its common association with type 2 diabetes, dyslipidemia, and cardiovascular diseases are worldwide epidemics. Currently, to prevent or treat obesity and associated metabolic disorders, herbal dietary supplements or medicines have attracted more and more attention owing to their relative effectiveness with fewer significant side effects. We investigate the therapeutic effects and underlying mechanisms of Plantago asiatica L. seed extract (PSE) on obesity and associated metabolic disorders in high-fat (HF) diet-induced mice. Our results displayed that PSE did not modify food intake or body weight but decreased abdominal white adipose tissue ratio, white/brown adipocyte size, serum total cholesterol, triglyceride (TG), low density lipoprotein cholesterol, free fatty acid, and hepatic TG concentrations when compared with the HF group. The levels of fasting blood glucose and glucose tolerance were improved in the PSE group when compared with the HF group. Furthermore, PSE upregulated mRNA expressions of peroxisome proliferator activated receptors (PPARs) and target genes related to fatty acid metabolism and energy expenditure in liver and adipose tissue of obese mice when compared with the HF group. PSE treatment effectively improved lipid and glucose metabolism in HF diet-induced obese mice. These effects might be attributed to the upregulation of PPAR signaling

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Section: Discussionmentioning

confidence: 99%

Plantago asiatica L. Seed Extract Improves Lipid Accumulation and Hyperglycemia in High-Fat Diet-Induced Obese Mice

Yang

Tong

et al. 2017

IJMS

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“…The structures of plantagoguanidinic acid and plumbagine D were confirmed by standard compounds. Plantagoguanidinic acid was first isolated from PAL seeds . The fragment ion of plantagoguanidinic acid at m / z 208.1445 was generated by the elimination of H 2 O from the carboxyl (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Guanidine derivatives are a group of novel alkaloids that have potential hypoglycemic effect . The three species of Plantaginis Semen showed similar contents of Plantagoguanidinic acid and Plumbagine D, while PAL and PML displayed higher amounts of total guanidine derivatives (Table ).…”

Section: Resultsmentioning

confidence: 99%

Comprehensive metabolite profiling of Plantaginis Semen using ultra high performance liquid chromatography with electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry coupled with elevated energy technique

Wang

Yang

et al. 2016

J of Separation Science

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“…Plantaginis Semen is a well‐known traditional Chinese medicine with diuretic, antioxidant, antidiabetic, expectorant, antioxidant and anti‐inflammatory effects (Doan et al, ; Harput, Genc, & Saracoglu, ; Hu, Nie, Li, & Xie, ; Samuelsen, ), including major constituents such as alkaloids, flavonoids, iridoids and phenylethanoid glycosides (Gao et al, ; Nhiem et al, ; Qi, Xiong, Geng, Yang, & Wang, ). Plantagoguanidinic acid (PGA), a guanidine alkaloid which was first isolated from Plantago asiatica L. seeds by Goda et al (), is an active constituent in Plantaginis Semen.…”

Section: Introductionmentioning

confidence: 99%

A simple and selective UHPLC–MS/MS method for quantification of plantagoguanidinic acid in rat plasma and its application to a pharmacokinetic study

Zhong

Zheng

et al. 2017

Biomedical Chromatography

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A simple, sensitive and specific UHPLC-MS/MS method for quantification of plantagoguanidinic acid (PGA) in rat plasma was applied to investigate the pharmacokinetic behavior in vivo, using protopine as internal standard. The chromatography was separated on a Phenomenex® Luna-C column (2.1 × 150 mm, 3.0 μm) within 7.0 min using a mobile phase consisting of acetonitrile-0.1% formic acid solution under gradient elution at a flow rate of 0.4 mL/min. Prepared samples were monitored by multiple reaction monitoring mode, with the target fragmentions m/z 226.2 → 84.2 for PGA and m/z 354.2 → 188.9 for IS in positive electrospray ionization. The calibration curve of PGA was linear throughout the range 1-1000 ng/mL (r = 0.9962). The lower limit of quantitation in plasma for PGA was 0.1 ng/mL, and the recovery was >88.6%. Intra- and interday accuracy ranged from -8.6 to 4.9%. Furthermore, this validated method was successfully used for a pre-clinical pharmacokinetic study of PGA at a single dose of 20 and 5 mg/kg in rats via oral and intravenous administration. The study showed that PGA was absorpted rapidly and eliminated gradually with a greater absolute oral bioavailability of 70.1% in rats.

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A guanidine derivative from seeds of Plantago asiatica

Abstract: A new guanidine derivative named plantago-guanidinic acid was isolated from the seeds of Plantago asiatica. The structure was elucidated by two-dimensional (2D) nuclear magnetic resonance (NMR) spectral and other spectral methods.

Cited by 18 publications

References 9 publications

Plantago asiatica L. Seed Extract Improves Lipid Accumulation and Hyperglycemia in High-Fat Diet-Induced Obese Mice

Plantago asiatica L. Seed Extract Improves Lipid Accumulation and Hyperglycemia in High-Fat Diet-Induced Obese Mice

Comprehensive metabolite profiling of Plantaginis Semen using ultra high performance liquid chromatography with electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry coupled with elevated energy technique

A simple and selective UHPLC–MS/MS method for quantification of plantagoguanidinic acid in rat plasma and its application to a pharmacokinetic study

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