New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. Issue 2 (15th January 2015)

• Record Type: Journal Article
• Authors: Nhiem, Nguyen Xuan; Hien, Nguyen Thi Thu; Tai, Bui Huu; Anh, Hoang Le Tuan; Hang, Dan Thi Thuy; Quang, Tran Hong; Kiem, Phan Van; Minh, Chau Van; Ko, Wonmin; Lee, Seungjun; Oh, Hyuncheol; Kim, Seung Hyun; Kim, Young Ho
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 2(2015)
• Page Start: 254
• Page End: 258
• Publication Date: 2015-01-15
• Subjects: Annona glabra -- Annonaceae -- ent-Kaurane diterpene -- Anti-inflammation; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2014.11.059
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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, compound3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01 ± 0.01 μM; compounds1 and7 showed significant inhibitory NO production with the IC50 values of 0.39 ± 0.12 μM and 0.32 ± 0.04 μM, respectively.