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

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

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.

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