Synthesis and antimicrobial evaluation of pogostone and its analogues

Journal of Pharmacy and Pharmacology

Zhou

Zhu

et al. 2017

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Synthesis and preclinical pharmacokinetic study of DHA-10, a novel potential antifungal pogostone analogue

Journal of Pharmacy and Pharmacology

Zhou

Zhu

et al. 2017

“…17 The dried aerial parts of P. cablin (9.0 kg) were exhaustively extracted through water-steam distillation and the white PO crystal (372.8 mg, yield 0.0041%) was obtained by crystallization. Its chemical structure was identified by comparing its spectral data (MS, 1 H and 13 C-NMR) with those published previously, 18 and its purity was above 98% as determined by HPLC using a previously described method. 19 …”

Section: Extraction and Isolation Of Pomentioning

confidence: 99%

The gastroprotective effect of pogostone from Pogostemonis Herba against indomethacin-induced gastric ulcer in rats

Chen

et al. 2015

Exp Biol Med (Maywood)

Self Cite

Pogostemonis Herba, known as ''Guang-Huo-Xiang'' in Chinese, has been widely used in the treatment of gastrointestinal dysfunction. Pogostone is one of the major constituents of Pogostemonis Herba. The aim was to scientifically evaluate the possible gastroprotective effect and the underlying mechanisms of pogostone against indomethacin-induced gastric ulcer in rats. Rats were orally treated with vehicle, lansoprazole (30 mg/kg) or pogostone (10, 20 and 40 mg/kg) and subsequently exposed to acute gastric lesions induced by indomethacin. Gross evaluation, histological observation, gastric mucosal superoxide dismutase activity, glutathione content, catalase activity, malonaldehyde level and prostaglandin E2 production were performed. Immunohistochemistry and reverse transcription polymerase chain reaction for cyclooxygenase-1 and cyclooxygenase-2, as well as terminal deoxynucleotidyltransferase-mediated dUTP nick-end labeling assay, immunohistochemistry for heat-shock protein 70, B-cell lymphoma-2 and Bax were conducted. Results indicated that rats pretreated with pogostone showed remarkable protection from the gastric mucosa damage compared to vehicle-treated rats based on the ulcer index and inhibition percentage. Histologically, oral administration of pogostone resulted in observable improvement of gastric injury, characterized by reduction of necrotic lesion, flattening of gastric mucosa and alleviation of submucosal edema with hemorrhage. Pogostone pretreatment significantly raised the depressed activities of superoxide dismutase, glutathione and catalase, while reduced the elevated malonaldehyde level compared with indomethacin-induced group. Pogostone-pretreated group induced a significant increase in gastric mucosal prostaglandin E2 level and obvious up-regulation of protein levels and mRNA expressions of cyclooxygenase-1 and cyclooxygenase-2. Furthermore, antiapoptotic effect of pogostone was verified by terminal deoxynucleotidyltransferase-mediated dUTP nick-end labeling assay, and the apoptotic process triggered by pogostone involved the up-expression of heat-shock protein70 and B-cell lymphoma-2 protein, and suppression of Bax protein expressions in the ulcerated tissues. It is speculated that the gastroprotective effect of pogostone against indomethacin-induced gastric ulceration might be associated with its stimulation of cyclooxygenase-mediated prostaglandin E2, antioxidant and antiapoptotic effect.

“…It is commonly used for the treatment of common cold, diarrhea, fever, etc. As one of the secondary metabolites from Herba Pogostemonis [1], pogostone (PO) exhibits extensive biological activities, such as potential anti-bacterial, anti-candida, anti-fungal, insecticidal, anti-inflammatory, and immunosuppressive activities [2][3][4]. Recently, Huang et al [5] have reported that PO had strong insecticidal activity against Spodoptera litura and Spodoptera exigua, especially in the aspect of antifeedant, larvicidal, growth inhibitory, etc.…”

Section: Introductionmentioning

confidence: 99%

“…Due to PO's low output of direct extraction from natural product, more concern turns to the chemical synthesis. Up to present, only one literature reported the synthesis of PO to solve the limitation of natural resource (Scheme 1) [1]. However, the reactive condition of nitrogen protection and the use of hydrogenator in the process of synthesis were not suitable for many labs and factories.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pogostone by one-step

Chen

Zhou

Journal of Asian Natural Products Research

et al. 2016

Self Cite

Pogostone, isolated from Pogostemon cablin, has many biological activities such as potential antibacterial, anticandida, and antifungal. Traditional extraction leads to low output of PO about 17.6 mg/kg from Herba Pogostemonis. The previous literature had reported a synthetic study and the yield had reached 4.48% with strictly controlled reaction conditions. The two methods above cannot meet the large demand of PO; we report a new synthesis method. 4-hydroxy-6-methyl-2-pyrone (1) was added in toluene, with the existence of acylation catalyst 4-dimethylaminopyridine (DMAP), 4-methylvaleric acid (2), and condensing agent dicyclohexylcarbodiimide (DCC), PO was synthesized after the combination of 3-carbon of (1) with 1-OH of (2) in the acylation reaction. The purity had reached 98%, determined by HPLC. The structure was confirmed by spectroscopic methods including infrared, electron ionization mass spectrometry, and nuclear magnetic resonance spectroscopy. PO was totally synthesized in one step including cyclization, with total yield of 27.2%.