Syzysamalactone, an Unusual 11-Carbon δ-Lactone Derivative from the Fresh Ripe Fruits of Syzygium samarangense (Wax Apple)

  • J Nat Prod. 2022 Aug 26;85(8):2100-2103. doi: 10.1021/acs.jnatprod.1c01114.
Yan-Ping Liu  1  2  3 ,  Zhen Xie  1 ,  Ruo-Qing Guan  1 ,  Meng-Ran Du  1 ,  Ze-Hua Qiao  1 ,  Xin-Yuan Suo  1 ,  Ze-Yu Liu  1 ,  Yuan Bian  1 ,  Lei Qiang  3 ,  Yan-Hui Fu  1  4  5
Affiliations
  • 1. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, People's Republic of China.
  • 2. Key Laboratory of Research and Development of Tropical Fruit and Vegetable of Haikou City, Hainan Normal University, Haikou 571158, People's Republic of China.
  • 3. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
  • 4. Engineering Research Center for Industrialization of Southern Medicinal Plants Resources of Hainan Province, Hainan Normal University, Haikou 571158, People's Republic of China.
  • 5. Key Laboratory of Southern Medicinal Plants Resources of Haikou City, Hainan Normal University, Haikou 571158, People's Republic of China.
PMID: 35968659 DOI: 10.1021/acs.jnatprod.1c01114
Abstract

To study the chemical constituents from the ripe fresh fruits of Syzygium samarangense (wax apple) and their potential health effects, a phytochemical investigation was undertaken. A new δ-lactone derivative, syzysamalactone (1), along with a known biogenetically related δ-lactone derivative, 6-pentyl-α-pyrone (2), were isolated from the fresh ripe fruits of S. samarangense. Syzysamalactone (1) is an unusual 11-carbon δ-lactone derivative, and its chemical structure and absolute configuration were elucidated by spectroscopic data analysis. A plausible biogenetic pathway for 1 was also proposed. Furthermore, the potential neuroprotective effects of compounds 1 and 2 were assessed. As a result, compounds 1 and 2 displayed notable neuroprotective effects with EC50 values of 0.29 ± 0.03 and 1.28 ± 0.06 μM, respectively, using the SH-SY5Y human neuroblastoma cell line. This is the first report of δ-lactone derivatives showing significant neuroprotective activities.