Dengratiols A-D, four new bibenzyl derivatives from Dendrobium gratiossimum

Jiawei Sun; Jimei Liu; Yuyu Liu; Ridao Chen; Yan Li; Shan Cen; Xiaomei Chen; Shunxing Guo; Jungui Dai

doi:10.1016/j.fitote.2021.104926

Dengratiols A-D, four new bibenzyl derivatives from Dendrobium gratiossimum

Fitoterapia. 2021 Jul:152:104926. doi: 10.1016/j.fitote.2021.104926. Epub 2021 May 13.

Authors

Jiawei Sun¹, Jimei Liu¹, Yuyu Liu¹, Ridao Chen¹, Yan Li¹, Shan Cen², Xiaomei Chen³, Shunxing Guo³, Jungui Dai⁴

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, CAMS Key Laboratory of Enzyme and Biocatalysis of Natural Drugs, and NHC Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China.
² Department of Immunology, Institute of Medicinal Biotechnology, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, China.
³ Institute of Medicinal Plants, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100193, China.
⁴ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, CAMS Key Laboratory of Enzyme and Biocatalysis of Natural Drugs, and NHC Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China. Electronic address: jgdai@imm.ac.cn.

PMID: 33991602
DOI: 10.1016/j.fitote.2021.104926

Abstract

Dengratiol A (1), an unprecedented bibenzyl derivative bearing a tropolone unit together with three pairs of bibenzyl enantiomers (±)-dengratiols B-D [(±)-2-(±)-4], were isolated from Dendrobium gratiossimum Rchb.f. The resolution of enantiomers was performed with chiral HPLC. Their structures were characterized by extensive spectroscopic data analysis and calculated electronic circular dichroism (ECD). A hypothetical biosynthetic pathway for 1 is proposed. Biological assay revealed that (-)-2 showed moderate antiviral effect against IAV with IC₅₀ value of 6.3 μM, and (±)-2 displayed cytotoxic activities against five human tumor cell lines with IC₅₀ values ranging from 15.5 to 42.5 μM.

Keywords: Bibenzyls; Dendrobium gratiossimum; Dengratiols; Tropolone.

MeSH terms

Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Bibenzyls / isolation & purification
Bibenzyls / pharmacology*
Cell Line, Tumor
China
Dendrobium / chemistry*
Humans
Molecular Structure
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Stems / chemistry

Substances

Antineoplastic Agents, Phytogenic
Bibenzyls
Phytochemicals