Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors.
Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors.
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DOI：
10.1021/acs.jnatprod.0c01055
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发表时间：
2021-04-23
影响因子：
5.1
通讯作者：
McCurdy CR
中科院分区：
文献类型：
--
作者：
Chear NJ;León F;Sharma A;Kanumuri SRR;Zwolinski G;Abboud KA;Singh D;Restrepo LF;Patel A;Hiranita T;Ramanathan S;Hampson AJ;McMahon LR;McCurdy CR
从马来西亚绣线菊（Mitragynaspeciosa，Kratom）的新鲜叶片中分离得到10个吲哚和羟吲哚生物碱（1-10）。这些化合物的化学结构是建立在广泛的1D和2D NMR和HRMS数据分析的基础上。本文首次报道了mitragynine oxindole B（4）的光谱数据。通过单晶X射线衍射确定了mitragynine oxindole B（4）的空间构型。同时定量测定了M.从马来西亚半岛北方地区的不同位置收集的大羽花叶样品也使用UPLC-MS/MS进行。评价羟吲哚生物碱（1-4）和吲哚生物碱（10）对阿片受体的结合亲和力。Corynoxine（1）对μ-阿片受体表现出高亲和力，Ki值为16.4 nM。此外，corynoxine（1）是1.8倍更有效的比吗啡在大鼠受到伤害性热板试验。这些发现对于评价次要羟吲哚生物碱在M. speciosa。
Ten indole and oxindole alkaloids (1–10) were isolated from the freshly collected leaves of Malaysian Mitragyna speciosa (Kratom). The chemical structures of these compounds were established on the basis of extensive 1D and 2D NMR and HRMS data analysis. The spectroscopic data of mitragynine oxindole B (4) are reported herein for the first time. The spatial configuration of mitragynine oxindole B (4) was confirmed by single-crystal X-ray diffraction. Simultaneous quantification of the isolated alkaloids in the M. speciosa leaf specimens collected from different locations in the northern region of Peninsular Malaysia was also performed using UPLC-MS/MS. The oxindole alkaloids (1–4) and the indole alkaloid (10) were assessed for binding affinity at opioid receptors. Corynoxine (1) showed high binding affinity to μ-opioid receptors with a Ki value of 16.4 nM. Further, corynoxine (1) was 1.8-fold more potent than morphine in rats subjected to a nociceptive hot plate assay. These findings have important implications for evaluating the combined effects of the minor oxindole alkaloids in the overall therapeutic activity of M. speciosa.
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