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      Studying Mass Balance and the Stability of (Z)-Ligustilide from Angelica sinensis Helps to Bridge a Botanical Instability–Bioactivity Chasm

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          Abstract

          Numerous reports assigning ( Z) -ligustilide ( 1 ) the role of a major bioactive principle in Apiaceae botanicals are called into question by the recurrent demonstrations of 1 being an unstable, rapidly degrading compound, ultimately leading to dynamic Residual Complexity. While Angelica sinensis is recognized for its therapeutic value in (peri-)menopausal symptom management, its purported active principle, ligustilide, represents a typical example for the instability-bioactivity chasm of botanicals. To help bridge the gap, this study used both the essential oil and purified 1 obtained from A. sinensis to investigate the factors that influence the chemical transformation of 1 , the products formed, and the rationale for monitoring 1 in natural product preparations. Countercurrent separation was used to purify 1 from a supercritical fluid extract of A. sinensis , achieving 93.4% purity in a single step. Subsequent purification by preparative HPLC afforded 1 with a 98.0% purity. Providing a mass balance setting, we monitored chemical changes occurring to highly purified 1 under various conditions and at different time points, in sealed NMR tubes by quantitative 1 H NMR (qHNMR). The non-destructive nature of NMR enabled a comprehensive assessment of degradation products. Moreover, in being a mole-based determination, the total intensity (integral) of all NMR signals intrinsically represent the theoretical mass balance within the sample solution. The results demonstrated that 1 is most stable while within the original plant material. Exposure to light had a profound impact on the chemical transformation of 1 leading to the formation of ligustilide dimers and trimers, as verified by both NMR and LC-HRMS studies. Moreover, the results shown for 1 , augmented by other recent outcomes, have serious implications for the meaningful biological evaluation of NPs which exhibit instability/reactivity, while having a plethora of “promising” bioactivities reported in the literature and being frequently associated with unsubstantiated health claims.

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          Author and article information

          Journal
          Journal of Natural Products
          J. Nat. Prod.
          American Chemical Society (ACS)
          0163-3864
          1520-6025
          September 03 2019
          September 03 2019
          Affiliations
          [1 ]UIC/NIH Botanical Center, Program for Collaborative Research in the Pharmaceutical Sciences (PCRPS) and Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States
          [2 ]Department of Pharmacognosy, Faculty of Pharmacy, University of Sarajevo, Zmaja od Bosne 8, 71000 Sarajevo, Bosnia and Herzegovina
          [3 ]Center for Natural Product Technologies, Program for Collaborative Research in the Pharmaceutical Sciences (PCRPS) and Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States
          [4 ]Department of Physical Sciences, Rosary College of Arts and Sciences, Dominican University, River Forest, Illinois 60305, United States
          Article
          10.1021/acs.jnatprod.8b00962
          6930006
          31478376
          © 2019
          Product

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