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Alpha-amylase inhibitory activity and phytochemical study of Zhumeria majdae Rech. f. and Wendelbo.

Mirshafie B, Mokhber-Dezfouli N, Manayi A, Saeidnia S, Ajani Y, Gohari AR - Pharmacognosy Res (2014 Oct-Dec)

Bottom Line: Three flavonoid glycosides: Linarin (1), hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) were successfully identified in the extract.The activity of alpha amylase enzyme was dose-dependently suppressed by the butanol extract.The inhibitory concentrations of 50% for the extract and acarbose were calculated at 24.5 ± 2.1 and 6.6 ± 3.1 mg/mL, respectively.

View Article: PubMed Central - PubMed

Affiliation: Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran.

ABSTRACT

Background: Zhumeria majdae (Lamiaceae) is an endemic species growing in the South parts of Iran especially Hormozgan province. The plant is so-called Mohrekhosh locally and widely used for medicinal purposes including stomachache and dysmenorrhea.

Objective: In order to separation and identification of the main flavonoid glycosides of the plant (aerial parts including leaves, stems, flowers, and fruits were used) and evaluation of its alpha-amylase inhibitory (AAI) activity, methanolic extract was prepared and fractionated to botanolic portion.

Materials and methods: Isolation of the main compounds of the butanol extract of the plant have been performed using different column chromatography methods such as high-performance liquid chromatography (C18 column) and Sephadex LH-20 as well. The isolated compounds were identified by Hydrogen-1 nuclear magnetic resonance and Carbon-13 nuclear magnetic resonance spectra and comparison with those reported in previous literature. Moreover, inhibitory activity of the butanolic extract of the plant against alpha-amylase enzyme was examined in different concentrations (15-30 mg/mL), where acarbose used as a positive control.

Results: Three flavonoid glycosides: Linarin (1), hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) were successfully identified in the extract. The activity of alpha amylase enzyme was dose-dependently suppressed by the butanol extract. The extract exhibited the highest inhibition at 30 mg/mL toward enzyme (77.9 ± 2.1%), while acarbose inhibited the enzyme at 20 mg/mL by 73.9 ± 1.9%. The inhibitory concentrations of 50% for the extract and acarbose were calculated at 24.5 ± 2.1 and 6.6 ± 3.1 mg/mL, respectively.

Conclusion: Z. majdae contains glycosylated flavones and could be a good candidate for anti-diabetic evaluations in animal and clinical trials due to possessing AAI activity.

No MeSH data available.


Related in: MedlinePlus

Chemical structures of the compounds 1–3 isolated from Zhumeria majdae
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Figure 1: Chemical structures of the compounds 1–3 isolated from Zhumeria majdae

Mentions: Isolation of the main compounds of the plant Z. majdae via chromatographic process resulted in identification of three flavonoid glycosides, named linarin (1),[10] hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3)[1112] based on the spectroscopic spectra (1H-NMR, 13C-NMR) compared to the known standard compounds [Figure 1], which reported in the literature. 13C-NMR data of the compounds 1–3 in DMSO-d6 is reported in Table 1. 1H-NMR of the compounds 1–3 is also indicated at Table 2. The compound 1, linarin, has recently been isolated from the aerial parts of Linaria reflexa Desf. (Scrophulariaceae), which employed in North African folk medicine for treatment of certain skin diseases.[10] The NMR data of the present study are in good agreement with those reported by Cheriet et al.,[10] However, this is the first report of the isolation of this compound from Zhumeria genus and Lamiaceae family. The aglycone of the two other flavonoids 2 and 3 is a well-known methoxylated flavone named hispidulin. The mentioned aglycone has previously been reported from Scoparia dulcis Linn. (Scrophulariaceae) and was found to be inactive against HIV-1/IIIB in MT-4 cells, whereas the same test on the aqueous extract of the plant was positive.[13] However, it showed other pharmacological activities. For instance, it is a benzodiazepine receptor ligand with positive allosteric properties abled to traverse the blood-brain barrier and exhibit anticonvulsive effects.[14] Furthermore, hepatoprotective activity has been reported from this compound.[15] So far, different glycosides of the aglycone “hispidulin” have been reported from other plant species. For example, chromatographic separation of the butanolic fraction of the methanol extract of Cirsium japonicum var. ussuriense resulted in the isolation of hispidulin 7-neohesperidoside together with the known cirsimaritin 4’- glucoside and acacetin 7-rutinoside.[12] However, to the best of our knowledge, hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) have not yet been separated from Zhumeria or other relative genus in Lamiaceae family.


Alpha-amylase inhibitory activity and phytochemical study of Zhumeria majdae Rech. f. and Wendelbo.

Mirshafie B, Mokhber-Dezfouli N, Manayi A, Saeidnia S, Ajani Y, Gohari AR - Pharmacognosy Res (2014 Oct-Dec)

Chemical structures of the compounds 1–3 isolated from Zhumeria majdae
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4660508&req=5

Figure 1: Chemical structures of the compounds 1–3 isolated from Zhumeria majdae
Mentions: Isolation of the main compounds of the plant Z. majdae via chromatographic process resulted in identification of three flavonoid glycosides, named linarin (1),[10] hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3)[1112] based on the spectroscopic spectra (1H-NMR, 13C-NMR) compared to the known standard compounds [Figure 1], which reported in the literature. 13C-NMR data of the compounds 1–3 in DMSO-d6 is reported in Table 1. 1H-NMR of the compounds 1–3 is also indicated at Table 2. The compound 1, linarin, has recently been isolated from the aerial parts of Linaria reflexa Desf. (Scrophulariaceae), which employed in North African folk medicine for treatment of certain skin diseases.[10] The NMR data of the present study are in good agreement with those reported by Cheriet et al.,[10] However, this is the first report of the isolation of this compound from Zhumeria genus and Lamiaceae family. The aglycone of the two other flavonoids 2 and 3 is a well-known methoxylated flavone named hispidulin. The mentioned aglycone has previously been reported from Scoparia dulcis Linn. (Scrophulariaceae) and was found to be inactive against HIV-1/IIIB in MT-4 cells, whereas the same test on the aqueous extract of the plant was positive.[13] However, it showed other pharmacological activities. For instance, it is a benzodiazepine receptor ligand with positive allosteric properties abled to traverse the blood-brain barrier and exhibit anticonvulsive effects.[14] Furthermore, hepatoprotective activity has been reported from this compound.[15] So far, different glycosides of the aglycone “hispidulin” have been reported from other plant species. For example, chromatographic separation of the butanolic fraction of the methanol extract of Cirsium japonicum var. ussuriense resulted in the isolation of hispidulin 7-neohesperidoside together with the known cirsimaritin 4’- glucoside and acacetin 7-rutinoside.[12] However, to the best of our knowledge, hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) have not yet been separated from Zhumeria or other relative genus in Lamiaceae family.

Bottom Line: Three flavonoid glycosides: Linarin (1), hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) were successfully identified in the extract.The activity of alpha amylase enzyme was dose-dependently suppressed by the butanol extract.The inhibitory concentrations of 50% for the extract and acarbose were calculated at 24.5 ± 2.1 and 6.6 ± 3.1 mg/mL, respectively.

View Article: PubMed Central - PubMed

Affiliation: Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran.

ABSTRACT

Background: Zhumeria majdae (Lamiaceae) is an endemic species growing in the South parts of Iran especially Hormozgan province. The plant is so-called Mohrekhosh locally and widely used for medicinal purposes including stomachache and dysmenorrhea.

Objective: In order to separation and identification of the main flavonoid glycosides of the plant (aerial parts including leaves, stems, flowers, and fruits were used) and evaluation of its alpha-amylase inhibitory (AAI) activity, methanolic extract was prepared and fractionated to botanolic portion.

Materials and methods: Isolation of the main compounds of the butanol extract of the plant have been performed using different column chromatography methods such as high-performance liquid chromatography (C18 column) and Sephadex LH-20 as well. The isolated compounds were identified by Hydrogen-1 nuclear magnetic resonance and Carbon-13 nuclear magnetic resonance spectra and comparison with those reported in previous literature. Moreover, inhibitory activity of the butanolic extract of the plant against alpha-amylase enzyme was examined in different concentrations (15-30 mg/mL), where acarbose used as a positive control.

Results: Three flavonoid glycosides: Linarin (1), hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) were successfully identified in the extract. The activity of alpha amylase enzyme was dose-dependently suppressed by the butanol extract. The extract exhibited the highest inhibition at 30 mg/mL toward enzyme (77.9 ± 2.1%), while acarbose inhibited the enzyme at 20 mg/mL by 73.9 ± 1.9%. The inhibitory concentrations of 50% for the extract and acarbose were calculated at 24.5 ± 2.1 and 6.6 ± 3.1 mg/mL, respectively.

Conclusion: Z. majdae contains glycosylated flavones and could be a good candidate for anti-diabetic evaluations in animal and clinical trials due to possessing AAI activity.

No MeSH data available.


Related in: MedlinePlus