Alkaloids and Polyacetylenes from Hippobroma longiflora with Antiangiogenesis Properties

Tzu-Yi Ke; Shih-Wei Wang; Shu-Rong Chen; Dong-Ming Huang; Yun-Sheng Lin; Tsong-Long Hwang; Wen-Chun Sun; Yuan-Bin Cheng

doi:10.1021/acs.jnatprod.2c00853

Alkaloids and Polyacetylenes from Hippobroma longiflora with Antiangiogenesis Properties

J Nat Prod. 2023 Apr 28;86(4):719-729. doi: 10.1021/acs.jnatprod.2c00853. Epub 2023 Apr 6.

Authors

Tzu-Yi Ke^{1

2}, Shih-Wei Wang^{3

4

5}, Shu-Rong Chen², Dong-Ming Huang⁶, Yun-Sheng Lin⁷, Tsong-Long Hwang^{8

9

10}, Wen-Chun Sun^{3

11}, Yuan-Bin Cheng²

Affiliations

¹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
² Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
³ Institute of Biomedical Sciences, MacKay Medical College, New Taipei City 25245, Taiwan.
⁴ Department of Medicine, MacKay Medical College, New Taipei City 25245, Taiwan.
⁵ School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁶ Institute of Biomedical Engineering and Nanomedicine, National Health Research Institutes, Miaoli 35053, Taiwan.
⁷ Department of Biological Science and Technology, Meiho University, Pingtung 91202, Taiwan.
⁸ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan.
⁹ Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33303, Taiwan.
¹⁰ Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 33305, Taiwan.
¹¹ Division of Colon and Rectal Surgery, Department of Surgery, MacKay Memorial Hospital, Taipei 104217, Taiwan.

PMID: 37023532
DOI: 10.1021/acs.jnatprod.2c00853

Abstract

Four new alkaloids, hippobrines A-D (1-4), along with three new polyacetylenes, hippobrenes A-C (5-7), were isolated from Hippobroma longiflora. Compounds 1-3 possess an unprecedented carbon skeleton. All of the new structures were determined by analyzing their mass and NMR spectroscopic data. The absolute configurations of 1 and 2 were confirmed by single-crystal X-ray analyses, and the absolute configurations of 3 and 7 were deduced using their ECD spectra. Plausible biogenetic pathways of 1 and 4 were proposed. In regard to bioactivities, all compounds (1-7) exhibited weak antiangiogenic activity against human endothelial progenitor cells, with IC₅₀ values ranging from 21.1 ± 1.1 to 44.0 ± 2.3 μg/mL.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids* / chemistry
Alkaloids* / pharmacology
Humans
Molecular Structure
Polyacetylene Polymer

Substances

Polyacetylene Polymer
Alkaloids