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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Nat. Prod. 2021, 84, 8, 2272-2281
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Monomeric, Dimeric, and Trimeric Tropane Alkaloids from Pellacalyx saccardianus

  • Zi-Yang Chan
    Zi-Yang Chan
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
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    • , 
  • Premanand Krishnan
    Premanand Krishnan
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
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    • , 
  • Sayed Mohammadhossein Modaresi
    Sayed Mohammadhossein Modaresi
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
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    • , 
  • Ling-Wei Hii
    Ling-Wei Hii
    School of Pharmacy  and  Centre for Cancer and Stem Cells Research, Institute for Research, Development and Innovation, International Medical University, 57000 Kuala Lumpur, Malaysia
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    • , 
  • Chun-Wai Mai
    Chun-Wai Mai
    Centre for Cancer and Stem Cells Research, Institute for Research, Development and Innovation, International Medical University, 57000 Kuala Lumpur, Malaysia
    State Key Laboratory of Oncogenes and Related Genes, Renji-Med X Clinical Stem Cell Research Center, Department of Urology, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China
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    • , 
  • Wei-Meng Lim
    Wei-Meng Lim
    School of Pharmacy  and  Centre for Cancer and Stem Cells Research, Institute for Research, Development and Innovation, International Medical University, 57000 Kuala Lumpur, Malaysia
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    • , 
  • Chee-Onn Leong
    Chee-Onn Leong
    School of Pharmacy  and  Centre for Cancer and Stem Cells Research, Institute for Research, Development and Innovation, International Medical University, 57000 Kuala Lumpur, Malaysia
    More by Chee-Onn Leong
    • , 
  • Yun-Yee Low
    Yun-Yee Low
    Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
    More by Yun-Yee Low
    Orcidhttps://orcid.org/0000-0002-7429-4238
    • , 
  • Soon-Kit Wong
    Soon-Kit Wong
    Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
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    • , 
  • Kien-Thai Yong
    Kien-Thai Yong
    Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
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    • , 
  • Alyssa Zi-Xin Leong
    Alyssa Zi-Xin Leong
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
    More by Alyssa Zi-Xin Leong
    • , 
  • Mei-Kee Lee
    Mei-Kee Lee
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
    More by Mei-Kee Lee
    • , 
  • Kang-Nee Ting
    Kang-Nee Ting
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
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    • , and 
  • Kuan-Hon Lim*
    Kuan-Hon Lim
    School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
    *Email: [email protected]
    More by Kuan-Hon Lim
    Orcidhttps://orcid.org/0000-0003-1462-3324
Cite this: J. Nat. Prod. 2021, 84, 8, 2272–2281
Publication Date (Web):August 3, 2021
https://doi.org/10.1021/acs.jnatprod.1c00374
Copyright © 2021 American Chemical Society and American Society of Pharmacognosy
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Abstract

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Seven new tropane alkaloids, including five monomeric (1–5), one dimeric (6), and one trimeric (7) 3α-nortropane ester, along with two known monomeric nortropane alkaloids (8 and 9), were isolated from the leaves and bark of Pellacalyx saccardianus. Their structures, including the absolute configuration of the enantiomeric pair of (±)-6, were elucidated by comprehensive spectroscopic analyses. Alkaloids 6 and 7 showed cytotoxicity toward human pancreatic cancer cell lines (AsPC-1, BxPC3, PANC-1, and SW1990). Alkaloids 1, 4, and 9 induced a smooth muscle relaxation effect comparable to that of atropine (Emax 106.1 ± 7.5%, 97.0 ± 5.2%, 100.9 ± 1.4%, 111.7 ± 1.7%, respectively) on isolated rat tracheal rings.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jnatprod.1c00374.

  • 1H NMR, 13C NMR, and HRMS for compounds 1–7; chiral-phase HPLC chromatograms of (±)-6 and (±)-7; Cartesian coordinates for the lowest-energy conformer of (−)-6 (II-3′S); cumulative concentration–response curves of compounds 1, 4, 6, 8, 9, and atropine on isolated rat tracheal rings (PDF)

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Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 1 publications.

  1. Ivan M. Novitskiy, Andrei G. Kutateladze. DU8ML: Machine Learning-Augmented Density Functional Theory Nuclear Magnetic Resonance Computations for High-Throughput In Silico Solution Structure Validation and Revision of Complex Alkaloids. The Journal of Organic Chemistry 2022, 87 (7) , 4818-4828. https://doi.org/10.1021/acs.joc.2c00169

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