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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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Related in: MedlinePlus

(A) Key COSY and NOESY interactions in oxyphylline C (5); (B) Key HMBC interactions in oxyphylline C (5).
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f3-ijms-13-11520: (A) Key COSY and NOESY interactions in oxyphylline C (5); (B) Key HMBC interactions in oxyphylline C (5).

Mentions: An HMBC experiment was used to assemble the different spin systems, functionalities and positions of hetero atoms (Table 1). The HMBC connectivity of H-7 (δ 3.95) to C-5 (δ 172.0), C-8 (δ 167.7), C-23 (δ 25.9), C-24 (δ 25.4) and C-25 (δ 47.9) confirmed the presence of a proline moiety in the cyclic ring. Similarly, H-3 (δ 5.80) exhibited HMBC connectivities with C-5 (δ 172.0), C-4 (δ 57.0), C-1 (δ 156.8), C-17 (δ 139.0), confirming the presence of a β-substituted phenylalanine unit. The correlation of H-10 (δ 6.55) with C-8 (δ 167.7), C-12 (δ 133.0) reconfirmed the presence of a styrylamine moiety. HMBC cross peaks for methine hydrogen (H-28) to C-27 (δ 169.7), C-37 (δ 166.4), C-29 (δ 37.0) and C-30 (δ 138.5), suggested the presence of an α-phenylalanine unit. Furthermore, H-38 displayed HMBC correlations with C-37 (δ 166.4) and C-40 (δ 136.2), indicating that cinnamoyl moiety joined to the α-phenylalanine unit. The NOESY spectrum indicated that the proline unit is part of a cyclic ring, through correlation between H-4 (δ 4.80) and H2-25 (δ 3.07 and 3.28). The NOESY correlation between H-38 (δ 6.65) and NH-36 (δ 7.11) reconfirmed the attachment of cinnamoyl moiety with α-phenylalanine unit. Key NOESY correlations are shown in Figure 3. The β-substituted phenylalanine moiety was identified as an erythro moiety on the basis of coupling constant (J3,4 = 7.2 Hz) [12].


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)

(A) Key COSY and NOESY interactions in oxyphylline C (5); (B) Key HMBC interactions in oxyphylline C (5).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f3-ijms-13-11520: (A) Key COSY and NOESY interactions in oxyphylline C (5); (B) Key HMBC interactions in oxyphylline C (5).
Mentions: An HMBC experiment was used to assemble the different spin systems, functionalities and positions of hetero atoms (Table 1). The HMBC connectivity of H-7 (δ 3.95) to C-5 (δ 172.0), C-8 (δ 167.7), C-23 (δ 25.9), C-24 (δ 25.4) and C-25 (δ 47.9) confirmed the presence of a proline moiety in the cyclic ring. Similarly, H-3 (δ 5.80) exhibited HMBC connectivities with C-5 (δ 172.0), C-4 (δ 57.0), C-1 (δ 156.8), C-17 (δ 139.0), confirming the presence of a β-substituted phenylalanine unit. The correlation of H-10 (δ 6.55) with C-8 (δ 167.7), C-12 (δ 133.0) reconfirmed the presence of a styrylamine moiety. HMBC cross peaks for methine hydrogen (H-28) to C-27 (δ 169.7), C-37 (δ 166.4), C-29 (δ 37.0) and C-30 (δ 138.5), suggested the presence of an α-phenylalanine unit. Furthermore, H-38 displayed HMBC correlations with C-37 (δ 166.4) and C-40 (δ 136.2), indicating that cinnamoyl moiety joined to the α-phenylalanine unit. The NOESY spectrum indicated that the proline unit is part of a cyclic ring, through correlation between H-4 (δ 4.80) and H2-25 (δ 3.07 and 3.28). The NOESY correlation between H-38 (δ 6.65) and NH-36 (δ 7.11) reconfirmed the attachment of cinnamoyl moiety with α-phenylalanine unit. Key NOESY correlations are shown in Figure 3. The β-substituted phenylalanine moiety was identified as an erythro moiety on the basis of coupling constant (J3,4 = 7.2 Hz) [12].

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