Scientific Reports (Jun 2024)

Albiflorenes A–L, polyoxygenated cyclohex(a/e)ne diterpene esters from Kaempferia albiflora

  • Pornpuk Booranaseensuntorn,
  • Jutatip Boonsombat,
  • Sanit Thongnest,
  • Paratchata Batsomboon,
  • Nanthawan Reuk-Ngam,
  • Panita Khlaychan,
  • Saroj Ruchisansakun,
  • Prasat Kittakoop,
  • Supanna Techasakul,
  • Chulabhorn Mahidol,
  • Somsak Ruchirawat

DOI
https://doi.org/10.1038/s41598-024-64889-6
Journal volume & issue
Vol. 14, no. 1
pp. 1 – 17

Abstract

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Abstract Twelve polyoxygenated cyclohex(a/e)ne diterpene esters, named albiflorenes A–L (1–12), were isolated from the whole plants of Kaempferia albiflora, known as “Prao Mang Mum.” Their structures and relative stereochemistry were determined by extensive spectroscopic analysis. Furthermore, the comparison of experimental electronic circular dichroism (ECD) curves with the curves predicted by TDDFT was used to determine the absolute configurations. Albiflorenes contain polyoxygenated cyclohexane (or cyclohexene) derivatives, which are linked to either isopimarane or abietane diterpene acid units. The discovery marks the first occurrence of a conjugate between polyoxygenated cyclohexane (or cyclohexene) rings and diterpenoids. Among the isolates, albiflorene C specifically exhibited antibacterial activity against Bacillus cereus with MIC and MBC values of 3.13 and 6.25 μg/mL, respectively.