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

  • Bioorg Med Chem Lett. 2015 Jan 15;25(2):254-8. doi: 10.1016/j.bmcl.2014.11.059.
Nguyen Xuan Nhiem  1 ,  Nguyen Thi Thu Hien  1 ,  Bui Huu Tai  2 ,  Hoang Le Tuan Anh  1 ,  Dan Thi Thuy Hang  1 ,  Tran Hong Quang  1 ,  Phan Van Kiem  1 ,  Chau Van Minh  1 ,  Wonmin Ko  3 ,  Seungjun Lee  3 ,  Hyuncheol Oh  3 ,  Seung Hyun Kim  4 ,  Young Ho Kim  5
Affiliations
  • 1. Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
  • 2. Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam; College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
  • 3. College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea.
  • 4. College of Pharmacy, Yonsei Institute of Pharmaceutical Science, Yonsei University, Incheon 406-840, Republic of Korea. Electronic address: [email protected].
  • 5. College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea. Electronic address: [email protected].
PMID: 25499882 DOI: 10.1016/j.bmcl.2014.11.059
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±0.01μM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39±0.12μM and 0.32±0.04μM, respectively.

Keywords
Annona glabra; Annonaceae; Anti-inflammation; ent-Kaurane diterpene.
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