New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages

Nguyen Xuan Nhiem, Nguyen Thi Thu Hien, Bui Huu Tai, Hoang Le Tuan Anh, Dan Thi Thuy Hang, Tran Hong Quang, Phan Van Kiem, Chau Van Minh, Wonmin Ko, Seungjun Lee, Hyuncheol Oh, Seung Hyun Kim, Young Ho Kim

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12 Citations (Scopus)

Abstract

Three new ent-kaurane diterpenoids, 7β,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-d-glucopyranoside ester (2), 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16β,17-dihydroxy-ent-kaurane (6), 16β,17-dihydroxy-ent-kauran-19-al (7), and 16β,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01 ± 0.01 μM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39 ± 0.12 μM and 0.32 ± 0.04 μM, respectively.

Original languageEnglish
Pages (from-to)254-258
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number2
DOIs
Publication statusPublished - 2015 Jan 15

Bibliographical note

Funding Information:
This work was financially supported by Vietnam Academy of Science and Technology (VAST 04.04.13-14). This work was also supported by a grant from the Priority Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2009-0093815 ), Republic of Korea. The authors are grateful to Mr. Dang Vu Luong, Institute of Chemistry, VAST for recording the NMR and mass spectra.

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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