Halogenated chamigrane sesquiterpenes from Bornean Laurencia majuscula

  • Takashi Kamada
  • Chin-Soon Phan
  • Vivian Shi-Ting Sien
  • Charles Santhanaraju Vairappan
8th Asian Pacific Phycological Forum

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.

Keywords

Laurencia majuscula Rhodomelaceae Red alga Cytotoxicity Halogenated chamigrane Chemical race 

Notes

Acknowledgments

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

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Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Laboratory of Natural Products Chemistry, Institute for Tropical Biology and ConservationUniversiti Malaysia SabahKota KinabaluMalaysia

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