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New 14-membered cyclopeptide alkaloids from Zizyphus oxyphylla Edgew.

Kaleem WA, Nisar M, Qayum M, Zia-Ul-Haq M, Adhikari A, De Feo V - Int J Mol Sci (2012)

Bottom Line: Two new 14-membered cyclopeptide alkaloids, Oxyphylline B (4) and Oxyphylline C (5), along with three known 13-membered cyclopeptide alkaloids, were isolated from stem and roots of Zizyphus oxyphylla Edgew.The compounds were tested for antibacterial activity.Oxyphylline B (4) showed comparatively better antibacterial activities against Escherichia coli (MIC, 5 μg/mL) than other compounds.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacy, Abdul Wali Khan University Mardan, Anbar Campus 23200, Pakistan; E-Mail: waqar679@yahoo.co.uk.

ABSTRACT
Two new 14-membered cyclopeptide alkaloids, Oxyphylline B (4) and Oxyphylline C (5), along with three known 13-membered cyclopeptide alkaloids, were isolated from stem and roots of Zizyphus oxyphylla Edgew. The compounds were tested for antibacterial activity. Oxyphylline B (4) showed comparatively better antibacterial activities against Escherichia coli (MIC, 5 μg/mL) than other compounds. This compound also exhibited weak antimicrobial activities against Staphylococcus aureus (MIC, 25 μg/mL), Pseudomonas aeruginosa (MIC, 50 μg/mL) and Salmonella typhi (MIC, 50 μg/mL).

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f4-ijms-13-11520: Schematic diagram indicating study design.

Mentions: The air-dried root powder of Zizyphus oxyphylla (8 kg) was macerated in methanol (3 × 7 days × 20 L). After removal of the solvent under vacuum at 35 °C–40 °C, the crude extract (372 g) was obtained. This extract was partitioned between water and dichloromethane. Dichloromethane extract (2.5 g) was subjected to column chromatography over silica gel with hexane/acetone/diethyl amine (75:25:0.1, 10 L) mixture to afford eight fractions (A–H). Compounds 1 (10.2 mg) and 2 (8.7 mg) were obtained from fractions D (41.3 mg) and E (53.4 mg) by preparative TLC (hexane/acetone/diethyl amine, 15:10:1). The air-dried stem powder of Zizyphus oxyphylla (8 kg) was macerated in methanol (3 × 7 days × 20 L). Solvent was removed under reduced pressure at 35 °C–40 °C to give the crude extract (375 g), which was partitioned between water and chloroform. Chloroform extract (11.0 g) was purified by column chromatography over silica gel with hexane/acetone/diethyl amine mixture (75:25:0.1, 10 L) to give eight fractions (A–H). Fraction C (202 mg) was subjected to preparative TLC (hexane/acetone/diethyl amine, 15:10:1) to obtain compound 3 (6.1 mg). Fraction D (1.89 g) was subjected to column chromatography over silica gel using chloroform/methanol (89:11) gradient. Compounds 4 (Oxyphylline B, 13 mg) and 5 (Oxyphylline C, 19 mg) were recovered. (See Figure 4.)


New 14-membered cyclopeptide alkaloids from Zizyphus oxyphylla Edgew.

Kaleem WA, Nisar M, Qayum M, Zia-Ul-Haq M, Adhikari A, De Feo V - Int J Mol Sci (2012)

Schematic diagram indicating study design.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3472760&req=5

f4-ijms-13-11520: Schematic diagram indicating study design.
Mentions: The air-dried root powder of Zizyphus oxyphylla (8 kg) was macerated in methanol (3 × 7 days × 20 L). After removal of the solvent under vacuum at 35 °C–40 °C, the crude extract (372 g) was obtained. This extract was partitioned between water and dichloromethane. Dichloromethane extract (2.5 g) was subjected to column chromatography over silica gel with hexane/acetone/diethyl amine (75:25:0.1, 10 L) mixture to afford eight fractions (A–H). Compounds 1 (10.2 mg) and 2 (8.7 mg) were obtained from fractions D (41.3 mg) and E (53.4 mg) by preparative TLC (hexane/acetone/diethyl amine, 15:10:1). The air-dried stem powder of Zizyphus oxyphylla (8 kg) was macerated in methanol (3 × 7 days × 20 L). Solvent was removed under reduced pressure at 35 °C–40 °C to give the crude extract (375 g), which was partitioned between water and chloroform. Chloroform extract (11.0 g) was purified by column chromatography over silica gel with hexane/acetone/diethyl amine mixture (75:25:0.1, 10 L) to give eight fractions (A–H). Fraction C (202 mg) was subjected to preparative TLC (hexane/acetone/diethyl amine, 15:10:1) to obtain compound 3 (6.1 mg). Fraction D (1.89 g) was subjected to column chromatography over silica gel using chloroform/methanol (89:11) gradient. Compounds 4 (Oxyphylline B, 13 mg) and 5 (Oxyphylline C, 19 mg) were recovered. (See Figure 4.)

Bottom Line: Two new 14-membered cyclopeptide alkaloids, Oxyphylline B (4) and Oxyphylline C (5), along with three known 13-membered cyclopeptide alkaloids, were isolated from stem and roots of Zizyphus oxyphylla Edgew.The compounds were tested for antibacterial activity.Oxyphylline B (4) showed comparatively better antibacterial activities against Escherichia coli (MIC, 5 μg/mL) than other compounds.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacy, Abdul Wali Khan University Mardan, Anbar Campus 23200, Pakistan; E-Mail: waqar679@yahoo.co.uk.

ABSTRACT
Two new 14-membered cyclopeptide alkaloids, Oxyphylline B (4) and Oxyphylline C (5), along with three known 13-membered cyclopeptide alkaloids, were isolated from stem and roots of Zizyphus oxyphylla Edgew. The compounds were tested for antibacterial activity. Oxyphylline B (4) showed comparatively better antibacterial activities against Escherichia coli (MIC, 5 μg/mL) than other compounds. This compound also exhibited weak antimicrobial activities against Staphylococcus aureus (MIC, 25 μg/mL), Pseudomonas aeruginosa (MIC, 50 μg/mL) and Salmonella typhi (MIC, 50 μg/mL).

Show MeSH
Related in: MedlinePlus