2. Academic Validation
  3. Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities

Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities

  • Chin J Nat Med. 2024 Oct;22(10):929-936. doi: 10.1016/S1875-5364(24)60723-5.
Jie Dong 1,  Haibo Li 2,  Mi Zhou 1,  Xinsheng Yao 3,  Jianliang Geng 4,  Yang Yu 5
Affiliations

Affiliations

  • 1 Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy; International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China; and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China.
  • 2 State Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture, Jiangsu Kanion Pharmaceutical Co., Ltd., Lianyungang 222001, China.
  • 3 Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy; International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China; and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China. Electronic address: tyaoxs@jnu.edu.cn.
  • 4 School of Chinese Materia Medica, Guangdong Pharmaceutical University, Guangzhou 510006, China. Electronic address: gengjianliang8521@126.com.
  • 5 Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy; International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China; and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China. Electronic address: 1018yuyang@163.com.
PMID: 39428184 DOI: 10.1016/S1875-5364(24)60723-5
Abstract

Four previously unreported diarylheptanoids (1a/1b-2a/2b), one undescribed sesquiterpenoid (8), one new diterpenoid (12), and twelve known analogs were isolated from the fruits of Alpinia oxyphylla. The structural elucidation of these compounds was achieved through a comprehensive analysis of spectroscopic data, single-crystal X-ray diffraction, electronic circular dichroism (ECD), and modified Mosher's method. Enantiomeric mixtures (1a/1b, 2a/2b, 3a/3b, 4a/4b, and 5a/5b) were separated on a chiral column using acetonitrile-water mixtures as eluents. Among them, compounds 3a/3b and 4a/4b were isolated as optically pure enantiomers in the initial chiral separation. Furthermore, most of the isolates were evaluated for their inhibitory effects against the production of nitric oxide (NO) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. Interestingly, 2 and 4 showed significant inhibitory activities against NO production with IC50 values of 33.65 and 9.88 μmol·L-1 (hydrocortisone: IC50 34.26 μmol·L-1), respectively. Additionally, they also partially reduced the secretion of IL-6.

Keywords

Alpinia oxyphylla; Anti-inflammatory activity; Diarylheptanoids; Structural elucidation; Terpenoids.

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