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Indole-3-carbinol
FOOD CHEMISTRY · 2022 · IF 9.231

Minor bioactive indoles from kimchi mirror the regioselectivity in indole-3-carbinol oligomerization

Jia Cheng Qian,Dan Liu,Li Ping Lin,Wen Jing Zhu,Ren Xiang Tan

Kimchi is a globally consumed food with diverse health-benefits, but the low-abundance bioactive compounds in kimchi remain largely neglected. Here we show that kimchi contains a family of low-abundance (0.5–1.6 μg/g, dried weight) high-order indole oligomers derived from indole-3-carbinol (I3C), a breakdown product released from cruciferous vegetables used for producing the traditional subsidiary food. The structure determination of such complex molecules was accomplished by synthesizing linear indole oligomers as standard materials followed by the LC–HR–MS analysis. One indole tetramer (LTe2) is substantially toxic to tumor MV4-11 (IC 50  = 1.94 μM) and THP-1 cells (IC 50  = 7.12 μM). Collectively, the work adds valuable information to the knowledge package about kimchi, and may inspire the generation of indole-based molecules, to which many drugs belong.

研究领域: 食品科学 · 药物化学 · 分子生物学
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Food Chemistry-X · 2024 · IF 6.5

Heating conversion of indole-3-carbinol into N-substituted oligomers with anti-melanoma effect

Jia Cheng Qian,Heng Peng Zhang,Yi Wang,Dan Liu

Cruciferous vegetables (CVs) are globally consumed with some health benefits believed to arise from indole-3-carbinol (I3C), a labile phytochemical liberated from indole glucosinolates, but few reports describe the effect of cooking on I3C reactions. Here, we present heat-promoted direct conversions of I3C in broccoli florets into indole derivatives, which are unique in the N -indolylmethylation and -hydroxymethylation of indole nuclei by 3-methyleneindole and formaldehyde formed in situ from the I3C dehydration and the dimerization of I3C to 3,3′-diindolylmethane (DIM), respectively. Such N -substituted indoles were found in a range of 0.4–4.6 μg per gram of steamed broccoli florets, with a novel compound N -(indol-3-ylmethyl)-3,3′-diindolylmethane (DIM-1) bio-evaluated to inhibit A375 cells with an IC 50 value of 1.87 μM. In aggregation, the investigation discloses the promoting effect of heating on the I3C transformation in CVs and identifies DIM-1 as an anti-cancer drug candidate, and thus updates the knowledge of I3C and bioactive derivatives thereof.

研究领域: 生物化学 · 药理学 · 癌症研究 · 食品科学
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MOLECULES · 2020 ·Vol. 25 ·期 9 ·2149 · IF 3.267

Extraction and Quantification of Sulforaphane and Indole-3-Carbinol from Rapeseed Tissues Using QuEChERS Coupled with UHPLC-MS/MS

Xu Yu,Fei Ma,Liangxiao Zhang,Peiwu Li

Rapeseed (Brassica napus L.) is rich in phenols, vitamins, carotenoids, and mineral elements, such as selenium. Additionally, it contains the active ingredients sulforaphane and indole-3-carbinol, which have been demonstrated to have pharmacological effects. In this study, sulforaphane and indole-3-carbinol were extracted and quantified from rapeseeds using quick, easy, cheap, effective, rugged and safe (QuEChERS) method coupled with ultra high performance liquid chromarography tandem mass spectrometry (UHPLC-MS/MS). The major parameters for extraction and purification efficiency were optimized, including the hydrolysis reaction, extraction condition and type and amount of purification adsorbents. The limit of detection (LOD) and the limit of quantification (LOQ) for sulforaphane were 0.05 μg/kg and 0.15 μg/kg, and for indole-3-carbinol were 5 μg/kg and 15 μg/kg, respectively. The developed method was used to successfully analyze fifty rapeseed samples. The QuEChERS coupled with UHPLC-MS/MS simultaneously detect sulforaphane and indole-3-carbinol in vegetable matrix and evaluate the quality and nutrition of rapeseed samples.Keywords:sulforaphane;indole-3-carbinol;QuEChERS;quantification;UHPLC-MS/MS

研究领域: 农业化学 · 分析化学 · 食品科学
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FOOD CHEMISTRY · 2022 · IF 9.231

Encapsulation of indole-3-carbinol in Pickering emulsions stabilized by OSA-modified high amylose corn starch: Preparation, characterization and storage stability properties

Wenxiu Zheng,Lin Ren,Wenzhuo Hao,Lei Wang,Changhong Liu,Lei Zheng

The stability of hydrophobic bioactive compound indole-3-carbinol (I3C) is a challenge for application. In this work, Pickering emulsions were prepared to encapsulate I3C. As the emulsifier, high amylose corn starch was pretreated by acid hydrolysis, afterwards modified by different concentrations of octenyl succinic anhydride (OSA), and their emulsions were evaluated. The XRD, SEM and FTIR results indicated the successful modification. ζ-potential, mean droplet size and emulsification index (EI) of the emulsions confirmed that modified starch with a higher degree of substitution (DS) was more effective for enhancing the storage stability. The results of encapsulation efficiency (EE) and retention degree of I3C after 14 d also proved the assumption. Moreover, the Pickering emulsions protected I3C against ultraviolet light and achieved controlled release in vitro . The food-grade Pickering emulsion loading I3C is promising to be used as a nutrient or dietary supplement for food applications.

CAS / MDL: 700-06-1
研究领域: 食品科学 · 材料科学 · 胶体化学 · 营养学
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