Structural Characterization and Assessment of the Cytotoxicity of 2,3-Dihydro-1H-indene Derivatives and Coumarin Glucosides from the Bark of Streblus indicus

Ruijie He; Xishan Huang; Yanjun Zhang; Liangdeng Wu; Hui Nie; Dexiong Zhou; Buming Liu; Shengping Deng; Ruiyun Yang; Shuai Huang; Zhijie Nong; Jun Li; Yan Huang

doi:10.1021/acs.jnatprod.6b00306

Structural Characterization and Assessment of the Cytotoxicity of 2,3-Dihydro-1H-indene Derivatives and Coumarin Glucosides from the Bark of Streblus indicus

J Nat Prod. 2016 Oct 28;79(10):2472-2478. doi: 10.1021/acs.jnatprod.6b00306. Epub 2016 Oct 5.

Authors

Ruijie He^{1

2}, Xishan Huang³, Yanjun Zhang¹, Liangdeng Wu¹, Hui Nie¹, Dexiong Zhou¹, Buming Liu⁴, Shengping Deng¹, Ruiyun Yang¹, Shuai Huang¹, Zhijie Nong¹, Jun Li¹, Yan Huang⁴

Affiliations

¹ State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmacy, Guangxi Normal University , Guilin 541004, People's Republic of China.
² Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany , Guilin 541006, People's Republic of China.
³ School of Chemistry and Chemical Engineering, Sun Yat-sen University , Guangzhou 510275, People's Republic of China.
⁴ Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards , Nanning 530022, People's Republic of China.

PMID: 27704822
DOI: 10.1021/acs.jnatprod.6b00306

Abstract

A pair of enantiomers and a pair of 2,3-dihydro-1H-indene epimers, rac-indidene A (rac-1), indidenes B and C (2, 3); four new coumarin glucosides (4-7); and four known coumarin glucosides (8-11) were isolated from the bark of Streblus indicus (Bur.) Corner. The structures of 1-11 were defined by physical data analyses, including MS, NMR, and single-crystal X-ray diffraction. The absolute configurations of the 2,3-dihydro-1H-indene derivatives were defined via experimental and calculated ECD data. rac-Indidene A and indidenes B and C showed inhibitory activity against A549 and MCF-7 tumor cells with IC₅₀ values in the range of 2.2 ± 0.1 to 7.2 ± 0.9 μM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

A549 Cells
Chromatography, High Pressure Liquid
Coumarins / chemistry
Coumarins / isolation & purification*
Coumarins / pharmacology*
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification*
Drugs, Chinese Herbal / pharmacology*
Glucosides / chemistry
Glucosides / isolation & purification*
Glucosides / pharmacology*
Humans
Indenes / chemistry
Indenes / isolation & purification*
Indenes / pharmacology*
Inhibitory Concentration 50
MCF-7 Cells
Molecular Structure
Moraceae / chemistry*
Nuclear Magnetic Resonance, Biomolecular
Plant Bark / chemistry*
Stereoisomerism

Substances

Coumarins
Drugs, Chinese Herbal
Glucosides
Indenes