Research articles
ScienceAsia 51 (2025):ID 2025066 1-8 |doi:
10.2306/scienceasia1513-1874.2025.066
Rapid separation of L-gossypol using chiral derivatizing
reagent combined with ultrasonic crystallizatio
Yun Zhoua,b,?, Yizhuo Lia,?, Ke Lib, Junfeng Zhangb, Xueping Lib,*, Daocheng Wuc,*
ABSTRACT: Gossypol, a natural polyphenolic compound, has notable medicinal and economic value due to its strong
antitumor activity. Its primary active form, levorotatory gossypol (L-gossypol), exhibits optical activity. However, the
existing methods for separating L-gossypol face challenges such as complexity, low yield, and high costs. Traditional
techniques like column chromatography are unsuitable for industrial-scale production. While the crystallization
separation could achieve gram-scale yields with relatively lower overall costs, ensuring purity required several days for
one production cycle. In this study, we innovatively employed a combination of a chiral derivatizing reagent (CDR) and
ultrasonic crystallization to achieve a rapid and cost-effective separation of L-gossypol. Ultrasonic crystallization uses
ultrasound-induced cavitation to drive crystallization. The method involves the use of an economical chiral resolving
agent, specifically (S)-1-(p-nitrophenyl)-1,3-dihydroxypropanamine, which reacts with racemic gossypol to produce
derivatives with distinct physical properties. Ultrasonic crystallization in ethyl acetate serves to efficiently crystallize
L-gossypol derivatives. Acid hydrolysis is then employed to remove the chiral resolving agent, resulting in high-purity
L-gossypol products. Notably, this streamlined process reduces the separation duration from 4 days, as reported in
existing literature, to a single day. Establishing a cyclic process enables continuous production of substantial amounts
of high-purity L-gossypol. Within 24 h, crystal yield reached 43.80% with 97.89% optical purity; after hydrolysis, the
total yield was 40.45% with 97.07% optical purity. Furthermore, the separated L-gossypol samples exhibit significant
antitumor activity. The developed approach offers a promising application prospect for enhancing the efficiency and
scalability of L-gossypol production in industrial settings.
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| a |
College of Clinical Medicine, Xi?an Medical University, Xi?an 710021 China |
| b |
Xi?an Key Laboratory for Prevention and Treatment of Common Aging Diseases, Translational and Research Centre
for Prevention and Therapy of Chronic Disease, Institute of Basic and Translational Medicine, Xi?an Medical
University, Xi?an 710021 China |
| c |
Key Laboratory of Biomedical Information, Engineering of Education Ministry, School of Life Science and
Technology, Xi?an Jiaotong University, Xi?an 710049 China |
* Corresponding author, E-mail: wudaocheng@mail.xjtu.edu.cn, lxp_lucy@qq.com
Received 20 Feb 2024, Accepted 0 0000
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