A Pair of Enantiomeric Bis- seco-abietane Diterpenoids from Cryptomeria fortunei

Lu Feng, Attila Mándi, Chunping Tang, T. Kurtán, Shuai Tang, Chang Qiang Ke, Ning Shen, Ge Lin, Sheng Yao, Yang Ye

Research output: Contribution to journalArticle

Abstract

(±)-Cryptomeriolide, a pair of racemic bis-seco-abietane diterpenoids, were isolated from the bark of Cryptomeria fortunei. The separation of enantiomers was achieved by using chiral stationary phase HPLC. Their structures including the absolute configuration and conformations in solution and solid state were determined by extensive analysis of spectroscopic data, single-crystal X-ray diffraction, and comparison of calculated and experimental electronic circular dichroism data. A bioinspired one-pot enantiomeric synthesis of 1a and 1b was accomplished via a readily made intermediate orthoquinone from sugiol. All compounds including the synthetic intermediates were assayed for their cytotoxic activities on human cancer cell lines HL-60, A549, and SGC7901.

Original languageEnglish
Pages (from-to)2667-2672
Number of pages6
JournalJournal of Natural Products
Volume81
Issue number12
DOIs
Publication statusPublished - Dec 28 2018

Fingerprint

Abietane Diterpenes
Cryptomeria
Enantiomers
Diterpenes
Circular Dichroism
Human Activities
X-Ray Diffraction
Conformations
High Pressure Liquid Chromatography
Cells
Single crystals
Cell Line
X ray diffraction
Neoplasms
sugiol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

A Pair of Enantiomeric Bis- seco-abietane Diterpenoids from Cryptomeria fortunei. / Feng, Lu; Mándi, Attila; Tang, Chunping; Kurtán, T.; Tang, Shuai; Ke, Chang Qiang; Shen, Ning; Lin, Ge; Yao, Sheng; Ye, Yang.

In: Journal of Natural Products, Vol. 81, No. 12, 28.12.2018, p. 2667-2672.

Research output: Contribution to journalArticle

Feng, L, Mándi, A, Tang, C, Kurtán, T, Tang, S, Ke, CQ, Shen, N, Lin, G, Yao, S & Ye, Y 2018, 'A Pair of Enantiomeric Bis- seco-abietane Diterpenoids from Cryptomeria fortunei', Journal of Natural Products, vol. 81, no. 12, pp. 2667-2672. https://doi.org/10.1021/acs.jnatprod.8b00482
Feng, Lu ; Mándi, Attila ; Tang, Chunping ; Kurtán, T. ; Tang, Shuai ; Ke, Chang Qiang ; Shen, Ning ; Lin, Ge ; Yao, Sheng ; Ye, Yang. / A Pair of Enantiomeric Bis- seco-abietane Diterpenoids from Cryptomeria fortunei. In: Journal of Natural Products. 2018 ; Vol. 81, No. 12. pp. 2667-2672.
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