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Halogenated chamigrane sesquiterpenes from Bornean Laurencia majuscula

Abstract

The red alga genus Laurencia (Rhodomelaceae, Ceramiales) is known to produce and contain a rich diversity of halogenated secondary metabolites. These compounds are dominated by two major biosynthetic groups: terpenes (sesquiterpenes, diterpenes, and triterpenes) and C15-acetogenins. In the course of our investigation on red algae genus Laurencia from North Borneo Island, three new halogenated chamigranes, 7-aldehydelaurencenone B (1), 2-chloro-3-methoxy-α-chamigren-9-one (2), and laureborneone (3) along with five known halogenated derivatives such as [1(15)Z,2Z,4R,8S,9R]-8,15-dibromochamigra-1(15),2,11(12)-trien-9-ol (4), [1(15)E,2Z,4R,8S,9R]-8,15-dibromochamigra-1(15),2,11(12)-trien-9-ol (5), ma’ilion (6), laurencenone B (7), and 2-chloro-3-hydroxy-α-chamigren-9-one (8) were isolated from Laurencia majuscula. The structures of these compounds were determined based on spectroscopic data which consisted of infrared (FT-IR), H1-NMR, C13-NMR, H1-H1-COSY, HSQC, HMBC, and NOESY. In addition, high-resolution electrospray ionization mass spectrometry (HRESIMS) was done to calculate their molecular formula and unsaturation index. The anticancer potentials of these compounds were tested against three cancer cell lines, and their IC50 values were determined.

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Acknowledgments

We are grateful to the Sabah Parks for the support and assistance during field survey.

Funding

This work was financially supported by the Sabah Biodiversity Centre [GL0070].

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Correspondence to Charles Santhanaraju Vairappan.

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Kamada, T., Phan, CS., Sien, V.ST. et al. Halogenated chamigrane sesquiterpenes from Bornean Laurencia majuscula. J Appl Phycol 30, 3373–3378 (2018). https://doi.org/10.1007/s10811-018-1452-z

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Keywords

  • Laurencia majuscula
  • Rhodomelaceae
  • Red alga
  • Cytotoxicity
  • Halogenated chamigrane
  • Chemical race