来自玛卡(秘鲁玛咖)的新型酰胺类化合物。

New alkamides from maca (Lepidium meyenii).

作者信息

Zhao Jianping, Muhammad Ilias, Dunbar D Chuck, Mustafa Jamal, Khan Ikhlas A

机构信息

Department of Pharmacognosy and National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA.

出版信息

J Agric Food Chem. 2005 Feb 9;53(3):690-3. doi: 10.1021/jf048529t.

Abstract

Maca (Lepidium meyenii) has been used as a food in Peru for thousands of years. More recently a wide array of commercial maca products have gained popularity as dietary supplements, with claims of anabolic and aphrodisiac effects, although the biologically active principles are not fully known. In an earlier chemical investigation, two new alkamides and a novel fatty acid, as well as the N-hydroxypyridine derivative, macaridine, were isolated from L. meyenii. Further examination has led to the isolation of five additional new alkamides, namely, N-benzyl-9-oxo-12Z-octadecenamide (1), N-benzyl-9-oxo-12Z,15Z-octadecadienamide (2), N-benzyl-13-oxo-9E,11E-octadecadienamide (3), N-benzyl-15Z-tetracosenamide (4), and N-(m-methoxybenzyl)hexadecanamide (5). Their structures were established by spectrometric and spectroscopic methods including ESI-HRMS, EI-MS, (1)H, (13)C, and 2D NMR, as well as (1)H-(15)N 2D HMBC experiments. In addition, the identity of N-benzyl-15Z-tetracosenamide (4) was confirmed by synthesis. These compounds have been found from only L. meyenii and could be used as markers for authentication and standardization.

摘要

玛咖(秘鲁玛咖)在秘鲁作为食物已有数千年历史。最近,各种各样的商业玛咖产品作为膳食补充剂广受欢迎,据称具有合成代谢和壮阳作用,尽管其生物活性成分尚未完全明确。在早期的化学研究中,从秘鲁玛咖中分离出了两种新的烷酰胺、一种新型脂肪酸以及N - 羟基吡啶衍生物玛咖啶。进一步研究又分离出另外五种新的烷酰胺,即N - 苄基 - 9 - 氧代 - 12Z - 十八碳烯酰胺(1)、N - 苄基 - 9 - 氧代 - 12Z,15Z - 十八碳二烯酰胺(2)、N - 苄基 - 13 - 氧代 - 9E,11E - 十八碳二烯酰胺(3)、N - 苄基 - 15Z - 二十四碳烯酰胺(4)和N - (间甲氧基苄基)十六酰胺(5)。通过光谱和波谱方法,包括电喷雾高分辨质谱(ESI - HRMS)、电子轰击质谱(EI - MS)、氢谱(¹H)、碳谱(¹³C)和二维核磁共振谱(2D NMR)以及¹H - ¹⁵N二维异核多键相关实验(¹H - ¹⁵N 2D HMBC)确定了它们的结构。此外,通过合成确认了N - 苄基 - 15Z - 二十四碳烯酰胺(4)的结构。这些化合物仅在秘鲁玛咖中发现,可作为鉴定和标准化的标志物。

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