Corresponding author (NCNPR): Jianping Zhao, jianping@olemiss.eduhttps://egrove.olemiss.edu/pharm_annual_posters/1008/thumbnail.jp

Chittiboyina, Amar G.

Khan, Ikhlas A.

Meng, Yonghai

Wang, Mei

Zhai, Chunmei

Zhao, Jianping

English

eGrove (Univ. of Mississippi)

University of Mississippi eGrove Annual Poster Session 2020 Annual Poster Session 10-23-2020 R09. New Atractylon Derivatives Generated in Processed Rhizomes of Atractylodes macrocephala Koidz Chunmei Zhai University of Mississippi; Heilongjiang University of Chinese Medicine, (People's Republic of China) Jianping Zhao University of Mississippi, jianping@olemiss.edu Amar G. Chittiboyina University of Mississippi Yonghai Meng University of Mississippi; Heilongjiang University of Chinese Medicine, (People's Republic of China) Mei Wang Natural Products Utilization Research Unit, ARS. Department of Agriculture See next page for additional authors Follow this and additional works at: https://egrove.olemiss.edu/pharm_annual_posters  Part of the Pharmacy and Pharmaceutical Sciences Commons Recommended Citation Zhai, Chunmei; Zhao, Jianping; Chittiboyina, Amar G.; Meng, Yonghai; Wang, Mei; and Khan, Ikhlas A., "R09. New Atractylon Derivatives Generated in Processed Rhizomes of Atractylodes macrocephala Koidz" (2020). Annual Poster Session 2020. 9. https://egrove.olemiss.edu/pharm_annual_posters/9 This Book is brought to you for free and open access by the Annual Poster Session at eGrove. It has been accepted for inclusion in Annual Poster Session 2020 by an authorized administrator of eGrove. For more information, please contact egrove@olemiss.edu. Authors Chunmei Zhai, Jianping Zhao, Amar G. Chittiboyina, Yonghai Meng, Mei Wang, and Ikhlas A. Khan This book is available at eGrove: https://egrove.olemiss.edu/pharm_annual_posters/9 Traditionally, most Chinese herbal medicines undergo elaborate processing inorder to become ingredients that are prescribed or utilized in the manufacturing ofTCM proprietary drugs [1,2]. Although the practice of processing has a longhistory, the underlying mechanisms largely remain unclear.Through the characterization of chemical profiles coupled with NMRmetabolomics approach, the chemical changes resulting from the traditionalprocessing protocol associated with RAM preparation were investigated. Five newchemical adducts, which were formed during processing RAM with wheat bran,were isolated and their structures were identified.The findings of this study may provide useful information for developingprocessing protocols and quality control standards for the processed RAMproducts.IntroductionThermally processed rhizomes of Atractylodes macrocephala (RAM)have a long history of use in Traditional Chinese medicine (TCM) for treatingvarious disorders, and have been an integral part of various traditional drugsand healthcare products. In TCM, herbal medicines are, in most cases,uniquely processed. Although it is thought that processing can alter theproperties and functions of herbal medicines so as to achieve desiredproperties, increase potency, and/or reduce side effects, the underlyingchemical changes remain unclear for most thermally processed Chinese herbalmedicines. In an attempt to shed some light on the scientific rationale behindthe processes involved in traditional medicine, the RAM processed by stir-frying with wheat bran was investigated for the change of chemicalcomposition. As a result, for the first time, five new chemical entities, alongwith ten known compounds, were isolated. Their chemical structures weredetermined by spectroscopic and spectrometric analyses. The possiblesynthetic pathway for the generation of such thermally-induced chemicalentities was also proposed.ResultsReferences 1. Zhao, Z., Liang, Z., Chan, K., Lu, G., Lee, E.L.M., Chen, H., Li, L. 2010 Planta med., 76(17), 1975-1986.2. Sheridan, H., Kopp, B., Krenn, L., Guo, D., Sendker, J. 2015. Science, 350(6262), S64-S66. AcknowledgmentThis work was supported in part by the Food and Drug Administration “Science Based Authentication ofBotanical Ingredients” grant number 2U01FD004246‐08, and the United States Department of Agriculture,Agricultural Research Service, Specific Cooperative Agreement No. 58-6060-6-015.The rhizomes of A. macrocephala were purchased from the HarbinMedicine Group Shiyitang Chinese Herbal Medicine Pharmaceutical Co.Following the processing protocol in the Chinese Pharmacopeia, the rhizomeswere cut into slices and air-dried to reach a constant weight. The wheat branwas first stir-fried in a cauldron with a temperature around 170 °C until smokeappeared. The rhizome slices were then added into the cauldron with a ratio ofthe rhizome to wheat bran of 1:4 (w/w), the mixture was stir-friedapproximately 26 mins until the slices turned to a yellow-brown color.NMR combined with chemometric analysis was applied for revealing thechange of chemical composition. NMR, TLC, flash chromatography wereapplied to identify, monitor, and isolate the components that showedsignificant changes during the processing.Fig. 2. Structures of compounds 1 – 15 isolated from theprocessed rhizomes of A. macrocephala.SummaryMaterial and MethodNew Atractylon Derivatives Generated in Processed Rhizomes of Atractylodes macrocephala KoidzChunmei Zhai 1,2, Jianping Zhao 1, Amar G. Chittiboyina 1, Yonghai Meng 1,2, Mei Wang3, Ikhlas A. Khan 11National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677; 2Heilongjiang University of Chinese Medicine, Harbin 150040, Heilongjiang. P. R. China; 3Natural Products Utilization Research Unit, ARS. Department of Agriculture, University, Mississippi 38677, USAThe University of MississippiTable 1. 1H (500 MHz) and 13C (125 MHz) NMR data ofcompounds 1 - 5 (recorded in CDCl3, ppm)Fig. 3. Proposed mechanism for the generation of compounds 1 – 5.A C EB D FFig. 1-A:Plant of Atractylodes macrocephala; B: Raw rhizomes of A. macrocephala (RAM); C：ProcessedRAM by stir-fried with earth; D: Processed RAM by stir-bake to brown; E: Processed RAM by stir-fried withwheat bran; F : Processed RAM by stir-fried. R= H, CH3, 2-furanyl, 5-hydroxymethl-2-furanylOO OHRORR-CHO-H2OORO1, 2, 3 or 4HHHHHCelluloseOCHOOCHOOHH CHOH3C CHOR-CHOPlausible mechanism:AtractylonABC                                                    -H2OOOOHAtractylon4 5   1   2   3   4   5  No. * δC δH δC δH δC δH δC δH δC δH 1, 1´, (1´´) 42.0 (t) 1.47, 1.68 (m, 4H) 41.9/42.0 (t) 1.49, 1.67 (m, 4H) 42.0 (t) 1.47, 1.66  (m, 4H) 41.9 (t) 1.48, 1.65  (m, 4H) 42.0 (t) 1.47, 1.67  (m, 6H) 2, 2´, (2´´) 23.6 (t) 1.57, 1.63 (m, 4H) 23.6 (t) 1.56, 1.63 (m, 4H) 23.6 (t) 1.55, 1.64 (m, 4H) 23.6 (t) 1.53, 1.63 (m, 4H) 23.6 (t) 1.54, 1.64 (m, 6H) 3, 3´, (3´´) 37.3 (t) 2.02, 2.37 (m, 4H)  37.4 (t) 2.02, 2.37 (m, 4H)  37.3 (t) 2.02, 2.38 (m, 4H)  37.3 (t) 2.02, 2.38 (m, 4H)  37.3/36.7 (t) 2.02, 2.37 (m, 6H)  4, 4´, (4´´) 150.0 (s)  150.0 (s)  149.9 (s)  149.9 (s)  149.9/150.0 (s)  5, 5´, (5´´) 45.7 (d) 2.10 (m, 2H) 45.7/45.8 (d) 2.10 (m, 2H) 45.7 (d) 2.10 (m, 2H) 45.6/45.7 (d) 2.09 (m, 2H) 45.6/45.7 (d) 2.10 (m, 3H) 6, 6´, (6´´) 21.2 (t) 2.25, 2.32 (m, 4H) 21.1 (t) 2.25, 2.32 (m, 4H) 21.1 (t) 2.27, 2.34 (m, 4H) 21.1 (t) 2.25, 2.32  (m, 4H) 21.1 (t) 2.25, 2.32  (m, 6H) 7, 7´, (7´´) 116.6 (s)  116.6 (s)  116.8 (s)  116.8 (s)  116.8/116.7 (s)  8, 8´, (8´´) 146.9 (s)  146.6 (s)  147.6 (s)  147.6 (s)  147.3/147.0 (s)  9, 9´, (9´´) 39.2 (t) 2.41  (m, 4H) 39.2/39.3 (t) 2.42 (m, 4H) 39.2 (t) 2.42 (m, 4H) 39.2 (t) 2.40 (m, 4H) 39.2/39.1 (t) 2.40/2.39 (m, 6H) 10, 10´, (10´´) 36.7 (s)  36.7 (s)  36.7 (s)  36.7 (s)  36.7/36.4 (s)  11, 11´, (11´´) 114.3 (s)  113.0 (s)  115.2 (s)  115.2 (s)  115.1/114.9 (s)  12, 12´, (12´´) 150.0 (s)  149.1 (s)  144.7 (s)  144.5 (s)  144.8/144.3 (s)  13, 13´, (13´´) 8.0 (q) 1.87  (s, 6H) 7.8/8.0 (q) 1.76/1.82  (s, 6H) 7.8/7.9 (q) 1.80/1.81  (s, 6H) 7.8/7.9 (q) 1.79/1.80  (s, 6H) 7.8/7.9/8.0 (q) 1.74/1.76/1.82  (s, 9H) 

R09. New Atractylon Derivatives Generated in Processed Rhizomes of Atractylodes macrocephala Koidz

https://egrove.olemiss.edu/cgi/viewcontent.cgi?article=1008&context=pharm_annual_posters

R09. New Atractylon Derivatives Generated in Processed Rhizomes of Atractylodes macrocephala Koidz

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