Monomeric, Dimeric, and Trimeric Tropane Alkaloids from Pellacalyx saccardianus

Chan ZY 1 , Krishnan P 1 , Modaresi SM 1 , Hii LW , Mai CW 2 , Lim WM Show all authors , Leong CO , Low YY 3 , Wong SK 3 , Yong KT 4 , Leong AZ 1 , Lee MK 1 , Ting KN 1 , Lim KH 1

Affiliations 

  • 1 School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
  • 2 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
  • 3 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
  • 4 Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
J Nat Prod, 2021 08 27;84(8):2272-2281.
PMID: 34342431 DOI: 10.1021/acs.jnatprod.1c00374

Abstract

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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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