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Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from Zephyranthes candida

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Lipids

Abstract

Two novel ceramides, Candidamide A (1) with a phytosphingolipid structure, and Candidamide B (2) with a tertiary amide structure, together with 12 known compounds (3–14) have been isolated from the bulbs of Zephyranthes candida, The structures of 1 and 2 have been elucidated to be 1,3,5,6-tetrahydroxy-2-(2′-hydroxytetracosanoyl amino)-8-(E)-octadecadiene (1) and (2S,3S,4R,8E,2′R)-2-[N-(2′-hydroxyoctadecanoyl)-N-(1′′,2′′-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol (2) on the basis of spectroscopic evidence including IR, MS, NMR (1H-NMR, 13C-NMR, DEPT, 1H–1H COSY, HSQC, HMBC). The known compounds were identified as (2S)-3′,7-dihydroxy-4′-methoxyflavan (3), (2S)-4′-hydroxy-7-methoxyflavan (4), (2S)-4′,7-dihydroxyflavan (5), 7-hydroxy-3′, 4′-methylenedioxyflavan (6), ambrettolide (7), β-sitostero1 (8), β-daucosterin (9), rutin (10), pancratistatin (11), lycorine (12), haemanthidine (13), and haemanthamine (14). In the antimicrobial assay, candidamide A (1) and candidamide B (2) displayed moderate activities against bacteria Staphylococcus aureus and Escherichia coli, and fungi Aspergillus niger, Candida albicans and Trichophyton rubrum.

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Abbreviations

CC:

Column chromatography

COSY:

Correlation spectroscopy

DEPT:

Distortionless enhancement by polarization transfer

HMBC:

Heteronuclear multiple bond correlation

HSQC:

Heteronuclear single quantum correlation

HR:

High resolution

LCB:

Long chain base

FA:

Fatty acid

MICs:

Minimum inhibitory concentrations

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Acknowledgments

This work was financially supported in part by the Natural Science Foundation of Jiangsu Province (BK2004062). The authors wish to acknowledge Professor Y.-L. Wu at State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai China, for making suggestions on this paper.

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Authors and Affiliations

  1. Jiangsu Institute of Botany, Chinese Academy of Sciences, Nanjing Botanical Garden, Mem. Sun Yat-Sen, 210014, Nanjing, People’s Republic of China

    Zhi-ping Wu, Yu Chen, Bing Xia, Ming Wang, Yun-Fa Dong & Xu Feng

  2. College of Life Science, Nanjing Agricultural University, 210095, Nanjing, People’s Republic of China

    Zhi-ping Wu

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  1. Zhi-ping Wu
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  2. Yu Chen
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  3. Bing Xia
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  4. Ming Wang
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  5. Yun-Fa Dong
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  6. Xu Feng
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Correspondence to Xu Feng.

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Wu, Zp., Chen, Y., Xia, B. et al. Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from Zephyranthes candida . Lipids 44, 63–70 (2009). https://doi.org/10.1007/s11745-008-3246-6

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  • DOI: https://doi.org/10.1007/s11745-008-3246-6

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