Sulfated Naphthopyrones and Anthraquinones from the Vietnamese Crinoid Comanthus delicata

Chem Pharm Bull (Tokyo). 2022;70(5):408-412. doi: 10.1248/cpb.c21-00904.

Abstract

Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together with 6-methoxycomaparvin-5-methylether-8-O-sodium sulfate (6), 6-methoxycomaparvin-8-O-sodium sulfate (7), comaparvin-8-O-sodium sulfate (8), and 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone-6-O-sodium sulfate (9) were isolated from the Vietnamese crinoid Comanthus delicata. Their chemical structures were elucidated by extensive analysis of the one dimensional (1D) and 2D-NMR, high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra as well as calculation of optical rotation. In addition, significant cytotoxicity was observed for 6 against LNCaP (prostate cancer) cell line with IC50 value of 20.29 ± 2.43 µM, whereas moderate or weak cytotoxic effects were observed for 1-3 and 5-8 on SK-Mel-2 (melanoma) cell line and 7 and 8 against LNCaP cell line, with IC50 values ranging from 49.96 ± 1.74 to 76.92 ± 5.85 µM.

Keywords: Comanthus delicata; crinoid; cytotoxic activity; sulfated anthraquinone; sulfated naphthopyrone.

MeSH terms

  • Animals
  • Anthraquinones / chemistry
  • Anthraquinones / pharmacology
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Asian People
  • Echinodermata / chemistry
  • Humans
  • Neoplasms*

Substances

  • Anthraquinones
  • Antineoplastic Agents