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菊苣种子中的一个新三萜糖苷和其他生物活性成分。

A novel terpenoid glycoside and other bioactive constituents from the seeds of Cichoriumintybus.

机构信息

School of Pharmacy, College of Pharmacy and Nursing, University of Nizwa, Oman.

Phytochemistry Research Laboratory, Department of Pharmacognosy & Phytochemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi, India.

出版信息

Carbohydr Res. 2023 Feb;524:108745. doi: 10.1016/j.carres.2023.108745. Epub 2023 Jan 13.

DOI:10.1016/j.carres.2023.108745
PMID:36680966
Abstract

Phytochemical investigation of the seeds of Cichorium intybus L (C. intybus) led to isolate n-hexacosane (CI-1), an aliphatic higher ketone, n-nonacosan-3-one (CI-2), two aliphatic acid esters characterized as n-octacosanyl decanoate (CI-3) and n-tricosanyl hexadecanoate (CI-4), two mixed glycerides identified as as glyceryl-1-(hexadec-7- enoyl)-2- tetradecanoyl-3-hexadecanoate (Cl-5) and glyceryl-1- (eicos-9-enoyl)-2,3, bis-eicosanoate (Cl-6), and three e steroidal constituents and their structures were elucidated as as stigmast-5, 22-dien-3β -ol-21-oic acids (Cl-7), stigmasterol-3β-d-glucopyranoside (Cl-8) and stigmast-5, 22-dien-3-β-ol-3-β-d-glucuronopyranoside (Cl-9). The dry seeds powder was defatted and finally extracted with ethanol by using a maceration method. The ethanol was evaporated near to dryness and silica gel was added to the extract and a slurry with the help of methanol solvent was prepared. The slurry was loaded to the column by using petroleum ether and was eluted with a mixture of chloroform and methanol. A series of test tubes were collected and each test tube with 2 mL eluents was collected. Based on the thin layer chromatography (TLC) the content of nine test tubes were considered as pure compounds. The solvent was evaporated from the test tube at room temperature. All the nine compounds from the column were characterized by using Infrared (IR), Nuclear Magnetic Resonance (NMR) and Mass spectrometry (MS). Eight compounds were previously isolated from the plant and they showed various biological activities. A new compound was isolated for the first time from the plant kingdoms. Based on the chromatographic and spectroscopic analysis the new compound was characterized as stigmasterol carboxylic acid (CI-9). The isolated new compound could be used to treat liver and cardiac diseases.

摘要

对菊苣(Cichorium intybus L.,C. intybus)种子的植物化学研究导致分离出一种脂肪族高酮,正二十六烷(CI-1),一种正壬烷-3-酮(CI-2),两种脂肪酸酯,鉴定为正二十八烷酸癸酯(CI-3)和正二十三烷酸二十六烷酯(CI-4),两种混合甘油酯,鉴定为甘油-1-(十六碳-7-烯酰基)-2-十四烷酰基-3-十六烷酯(Cl-5)和甘油-1-(二十碳-9-烯酰基)-2,3, 双二十烷酸酯(Cl-6),以及三种甾体成分,其结构被阐明为豆甾-5,22-二烯-3β-醇-21-酸(Cl-7)、豆甾醇-3β-D-吡喃葡萄糖苷(Cl-8)和豆甾-5,22-二烯-3β-醇-3-β-D-吡喃葡萄糖醛酸苷(Cl-9)。将干种子粉末脱脂,最后用浸渍法用乙醇提取。将乙醇在近干状态下蒸发,并将硅胶加入提取物中,在甲醇溶剂的帮助下制备浆液。将浆液装入柱中,用石油醚洗脱,并用氯仿和甲醇的混合物洗脱。收集一系列试管,每管收集 2 mL 洗脱液。根据薄层色谱(TLC),有 9 个试管的含量被认为是纯化合物。在室温下从试管中蒸发溶剂。从柱上分离出的 9 种化合物均通过红外(IR)、核磁共振(NMR)和质谱(MS)进行鉴定。其中 8 种化合物之前已从该植物中分离得到,它们表现出各种生物活性。一种新化合物首次从植物王国中分离得到。根据色谱和光谱分析,新化合物被鉴定为豆甾醇羧酸(CI-9)。分离得到的新化合物可用于治疗肝脏和心脏疾病。

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