Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon.
Fitoterapia. 2013 Jun;87:37-42. doi: 10.1016/j.fitote.2013.03.017. Epub 2013 Mar 26.
Two new tryptophan derivatives, N-sulfonyl-L-tryptophan (tryptorheedei A) (1) and 3-(N-sulfonylindolyl)-D-lactic acid (tryptorheedei B) (2) together with the known 5-O-β-D-glucopyranosyl-2-hydroxyphenylacetic acid (3), 1-O-methylglucopyranoside, entadamide A, homogentisic acid and 3-O-β-D-glucopyranosyl-β-sitosterol, were isolated from the seed kernels of Entada rheedei (Mimosaceae). Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry and by comparison with spectroscopic data reported in the literature. Compounds 1 and 2 showed no toxicity to TZM and Human PBMC cells. Both compounds 1 and 2 were found to promote early infection events in HIV, likely by inhibiting the enzyme indolamine 2,3-dioxygenase (IDO) and preventing tryptophan depletion. Inhibition of IDO acutely in HIV infection inhibits viral replication, but chronic activation of IDO leads to immune impairment in AIDS. IDO is also the gatekeeper enzyme for kynurenine metabolism, a pathway involved in serotonin and melatonin biosynthesis and the regulation of glutamate and dopamine levels in the brain. Therefore inhibition of IDO might explain both the reported medicinal and neuropsychiatric effects of E. rheedei.
从扭黄茅（含羞草科）的种子中分离得到了两个新色氨酸衍生物，N-磺酰基-L-色氨酸（tryptorheedei A）（1）和 3-（N-磺酰基吲哚基）-D-乳酸（tryptorheedei B）（2），以及已知的 5-O-β-D-吡喃葡萄糖基-2-羟基苯乙酸（3）、1-O-甲基吡喃葡萄糖苷、entadamide A、高丝氨酸和 3-O-β-D-吡喃葡萄糖基-β-谷甾醇。它们的结构是通过 1D 和 2D NMR 光谱、质谱以及与文献中报道的光谱数据进行比较来确定的。化合物 1 和 2 对 TZM 和人 PBMC 细胞没有毒性。化合物 1 和 2 均能促进 HIV 的早期感染事件，可能通过抑制酶吲哚胺 2,3-双加氧酶（IDO）和防止色氨酸耗竭。在 HIV 感染中急性抑制 IDO 可抑制病毒复制，但慢性激活 IDO 会导致艾滋病的免疫损伤。IDO 也是犬尿氨酸代谢的守门员酶，犬尿氨酸代谢途径参与 5-羟色胺和褪黑素的生物合成以及大脑中谷氨酸和多巴胺水平的调节。因此，IDO 的抑制可能解释了扭黄茅的报道的医学和神经精神作用。
