New acylphloroglucinol-sesquiterpenoid adducts with antiviral activities from Dryopteris atrata.

Jihui Zhang, Jinghao Wang, Wei Tang, Xi Shen, Jinlin Chen, Huilin Ou, Qianyi Situ, Yaolan Li, Guocai Wang, Yubo Zhang, Nenghua Chen
Author Information
  1. Jihui Zhang: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
  2. Jinghao Wang: Department of Pharmacy, The First Affiliated Hospital, Jinan University, Guangzhou 510630, China; The Guangzhou Key Laboratory of Basic and Translational Research on Chronic Diseases, Jinan University, Guangzhou 510630, China.
  3. Wei Tang: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
  4. Xi Shen: Guangdong Clinical Translational Center for Targeted Drug, Department of Pharmacology, School of Medicine, Jinan University, Guangzhou 510632, China.
  5. Jinlin Chen: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
  6. Huilin Ou: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
  7. Qianyi Situ: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
  8. Yaolan Li: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
  9. Guocai Wang: Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China; The Guangzhou Key Laboratory of Basic and Translational Research on Chronic Diseases, Jinan University, Guangzhou 510630, China. Electronic address: twangguocai@jnu.edu.cn.
  10. Yubo Zhang: The Guangzhou Key Laboratory of Basic and Translational Research on Chronic Diseases, Jinan University, Guangzhou 510630, China; Guangdong Clinical Translational Center for Targeted Drug, Department of Pharmacology, School of Medicine, Jinan University, Guangzhou 510632, China. Electronic address: ybzhang99@126.com.
  11. Nenghua Chen: Department of Pharmacy, The First Affiliated Hospital, Jinan University, Guangzhou 510630, China; The Guangzhou Key Laboratory of Basic and Translational Research on Chronic Diseases, Jinan University, Guangzhou 510630, China. Electronic address: chennenghua@jnu.edu.cn.

Abstract

Seven novel acylphloroglucinol-sesquiterpenoid adducts, designated as dryatraols J-P (1-7), were isolated from the rhizomes of Dryopteris atrata (Wall. ex Kunze) Ching. The structures, including absolute configurations, were elucidated using comprehensive spectroscopic data, calculated C Nuclear Magnetic Resonance-Diastereotopic Probability Assignment Plus (C NMR-DP4+) probability analysis, and ECD calculations. These structures represent a rare subclass of carbon skeleton of acylphloroglucinol-sesquiterpenoid adducts with a furan ring connecting the acylphloroglucinol and sesquiterpenoid moieties. Notably, compounds 1-6 are the first reported examples of acylphloroglucinol-sesquiterpenoid adducts with dimeric acylphloroglucinol incorporated into the aristolane- or rulepidanol-type sesquiterpene, while compound 7 features a hydroxylated monomeric acylphloroglucinol motif. A preliminary evaluation of their antiviral activities revealed that compounds 1-6 exhibited more potent activities against respiratory syncytial virus (RSV) with IC values ranging from 0.75 to 3.12 ��mol��L compared to the positive control (ribavirin).

Keywords

MeSH Term

Antiviral Agents
Phloroglucinol
Sesquiterpenes
Molecular Structure
Dryopteris
Rhizome
Respiratory Syncytial Viruses
Humans

Chemicals

Antiviral Agents
Phloroglucinol
Sesquiterpenes

Word Cloud

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