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来自柠檬桉的具有可溶性环氧化物水解酶抑制活性的烷基间苯三酚衍生物和三萜类化合物。

Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus.

作者信息

Khanh Pham Ngoc, Duc Ho Viet, Huong Tran Thu, Son Ninh The, Ha Vu Thi, Van Doan Thi, Tai Bui Huu, Kim Ji Eun, Jo Ah Reum, Kim Young Ho, Cuong Nguyen Manh

机构信息

Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam.

Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen Str., 47000 Hue, Viet Nam.

出版信息

Fitoterapia. 2016 Mar;109:39-44. doi: 10.1016/j.fitote.2015.10.013. Epub 2015 Nov 5.

DOI:10.1016/j.fitote.2015.10.013
PMID:26548595
Abstract

Phytochemical analysis of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of two new alkylphloroglucinols, gallomyrtucommulone E and F (1 and 2), along with four other known alkylphloroglucinol derivatives, gallomyrtucommulone A (3), endoperoxide G3 (4), myrtucommulone B (5), callistenone B (6) and five known triterpenoids, including betulinic acid (7), 3β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), diospyrolide (10) and ursolic acid (11). The structures of the natural compounds were determined from the spectroscopic evidences including 1D-/2D-NMR and HR-MS spectrometry. All the isolated compounds were assessed for the effects on the sEH inhibitory activity. The acylphloroglucinols myrtucommulone B (5)/callistenone B (6) (in mixture), and two triterpenoids, ursolic acid (11) and 3β-hydroxy-urs-11-en-13(28)-olide (9) displayed strong inhibition of sEH activity, with IC50 values of 0.7, 11.2 and 24.8 μM, respectively.

摘要

对红千层(Callistemon citrinus (Curtis) Skeels)叶和茎进行植物化学分析,分离得到两种新的烷基间苯三酚,即没食子酰桃金娘烯酮E和F(1和2),以及其他四种已知的烷基间苯三酚衍生物,没食子酰桃金娘烯酮A(3)、内过氧化物G3(4)、桃金娘烯酮B(5)、红千层烯酮B(6),还有五种已知的三萜类化合物,包括桦木酸(7)、3β-乙酰齐墩果酸(8)、3β-羟基-乌苏-11-烯-13(28)-内酯(9)、柿叶内酯(10)和熊果酸(11)。通过包括一维/二维核磁共振和高分辨质谱在内的光谱证据确定了这些天然化合物的结构。评估了所有分离出的化合物对可溶性环氧化物水解酶(sEH)抑制活性的影响。酰基间苯三酚桃金娘烯酮B(5)/红千层烯酮B(6)(混合物)以及两种三萜类化合物熊果酸(11)和3β-羟基-乌苏-11-烯-13(28)-内酯(9)对sEH活性表现出强烈抑制作用,IC50值分别为0.7、11.2和24.8 μM。

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