Phytochemistry2022,Vol.1999.DOI:10.1016/j.phytochem.2022.113174

Neolignans from Myristica fragrans seeds, revision of their absolute configurations, reduction products and biological activities

Kruakaew S. Singha S. Sutthivaiyakit S. Sangvichien E. Yahuafai J.
Phytochemistry2022,Vol.1999.DOI:10.1016/j.phytochem.2022.113174

Neolignans from Myristica fragrans seeds, revision of their absolute configurations, reduction products and biological activities

Kruakaew S. 1Singha S. 1Sutthivaiyakit S. 1Sangvichien E. 2Yahuafai J.3
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作者信息

  • 1. Department of Chemistry and Center of Excellence for Innovation in Chemistry Faculty of Science Ramkhamhaeng University
  • 2. Department of Biology Faculty of Science Ramkhamhaeng University
  • 3. Research Transfer and Academic Support Division National Cancer Institute
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Abstract

? 2022 Elsevier LtdChromatographic purification of the CH2Cl2 extract of Myristica fragrans seeds provided 19 known compounds, four dihydrofuran neolignans, licarines A, B and maceneolignans A, B were among the isolates. Prior to hydrogenation, in order to obtain their di- and tetrahydrogenated products, the absolute configuration of these compounds was thoroughly investigated based on their optical rotations and ECD spectra. This report provides evidences concerning the disagreement between the use of an aromatic quadrant rule and time-dependent density function theory calculation for the prediction of the absolute configurations at C-7 and C-8 in these dihydrobenzofuran neolignans. The absolute configurations of licarines A, B and maceneolignans A, B were subsequently redefined. The antimicrobial and cytotoxic activities of the isolates and reduction products of licarines A, B and maceneolignans A, B were also investigated.

Key words

Absolute configuration reassignment/Antimicrobial activity/Cytotoxicity/ECD calculation/Myristica fragrans Houtt./Myristicaceae/Reduction of neolignans. dihydrobenzofuran neolignans

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出版年

2022
Phytochemistry

Phytochemistry

CCR
ISSN:0031-9422
被引量1
参考文献量42
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