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Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii.

ABSTRACT: Chemical investigation of the 90% acetone extract of the branches and leaves of Sabina gaussenii led to the isolation of two new cinnamyl isovalerate derivatives (1-2) and eighteen known compounds (3-20). Their structures were determined mainly by means of MS, 1D- and 2D-NMR data, and this is the first time these compounds have been reported from this plant. The biological activity test results indicated that the 90% acetone extract showed cytotoxicity against the human lung adenocarcinoma (A549) cell line (IC50 = 0.98 ± 0.1 ?g/mL), compound 6 showed cytotoxicities against human cervical carcinoma (HeLa) (IC50 = 0.4 ± 0.1 ?M ) and human gastric carcinoma (BGC-823) (IC50 = 0.9 ± 0.2 ?M) cancer cell lines, and compound 19 showed cytotoxicities against HeLa (IC50 = 1.5 ± 0.4 ?M), BGC-823 (IC50 = 7.0 ± 0.8 ?M ), and A549 (IC50 = 10.6 ± 1.5 ?M ) cancer cell lines.

SUBMITTER: Sun ZH

PROVIDER: S-EPMC6273497 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii.

Sun Zhang-Hua ZH Tan Ning-Hua NH Zeng Guang-Zhi GZ Zhang Yu-Mei YM

Molecules (Basel, Switzerland) 20160429 5

Chemical investigation of the 90% acetone extract of the branches and leaves of Sabina gaussenii led to the isolation of two new cinnamyl isovalerate derivatives (1-2) and eighteen known compounds (3-20). Their structures were determined mainly by means of MS, 1D- and 2D-NMR data, and this is the first time these compounds have been reported from this plant. The biological activity test results indicated that the 90% acetone extract showed cytotoxicity against the human lung adenocarcinoma (A549 ...[more]

PMID: 27136522

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Project description:The dark-colored viologen radical cations are unstable in air and easily fade, thus greatly limiting their applications. If a suitable substituent is introduced into the structure, it will have the dual function of chromism and luminescence, which will broaden its application field. Here, Vio1·2Cl and Vio2·2Br were synthesized by introducing aromatic acetophenone and naphthophenone substituents into the viologen structure. The keto group (-CH2CO-) on the substituents is prone to isomerize into the enol structure (-CH[double bond, length as m-dash]COH-) in organic solvents, especially in DMSO, resulting in a larger conjugated system to stabilize the molecular structure and enhance fluorescence. The time-dependent fluorescence spectrum shows obvious keto-to-enol isomerization-induced fluorescence enhancement. The quantum yield also increased significantly (T = 1 day, ΦVio1 = 25.81%, ΦVio2 = 41.44%; T = 7 days, ΦVio1 = 31.48%, and ΦVio2 = 54.40%) in DMSO. The NMR and ESI-MS data at different times further confirmed that the fluorescence enhancement was caused by isomerization, and no other fluorescent impurities were produced in solution. DFT calculations show that the enol form is almost coplanar throughout the molecular structure, which is conducive to stabilizing the structure and enhancing fluorescence. The fluorescence emission peaks of the keto and enol structures of Vio12+ and Vio22+ were at 416-417 nm and 563-582 nm, respectively. The fluorescence relative oscillator strength of Vio12+ and Vio22+ enol structures is significantly higher than that of keto structures (f value changes from 1.53 to 2.63 for Vio12+ and from 1.62 to 2.81 for Vio22+), indicating stronger fluorescence emission of the enol structure. The calculated results are in good agreement with the experimental results. Vio1·2Cl and Vio2·2Br are the first examples of isomerization-induced fluorescence enhancement of viologen derivatives, which shows strong solvatofluorochromism under UV light, making up for the disadvantage that it is easy for a viologen radical to fade in air, and providing a new strategy for designing and synthesizing viologen materials with strong fluorescence.

Dataset Information

Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii.

Publications

Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii.

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