title: New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages.
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.
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Nguyen Xuan
authors.initials: NX
authors.lastname: Nhiem
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Nguyen Thi Thu
authors.initials: NT
authors.lastname: Hien
authors.affiliation: 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.
authors.forename: Bui Huu
authors.initials: BH
authors.lastname: Tai
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Hoang Le Tuan
authors.initials: Hle T
authors.lastname: Anh
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Dan Thi Thuy
authors.initials: DT
authors.lastname: Hang
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Tran Hong
authors.initials: TH
authors.lastname: Quang
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Phan Van
authors.initials: PV
authors.lastname: Kiem
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Chau Van
authors.initials: CV
authors.lastname: Minh
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea.
authors.forename: Wonmin
authors.initials: W
authors.lastname: Ko
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea.
authors.forename: Seungjun
authors.initials: S
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea.
authors.forename: Hyuncheol
authors.initials: H
authors.lastname: Oh
authors.affiliation: College of Pharmacy, Yonsei Institute of Pharmaceutical Science, Yonsei University, Incheon 406-840, Republic of Korea. Electronic address: kimsh11@yonsei.ac.kr.
authors.forename: Seung Hyun
authors.initials: SH
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea. Electronic address: yhk@cnu.ac.kr.
authors.forename: Young Ho
authors.initials: YH
authors.lastname: Kim
mesh_terms: D000818:Animals; D031041:Annona; D045786:Diterpenes, Kaurane / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005638:Fruit; D008070:Lipopolysaccharides / Q000633:toxicity; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D045786:Diterpenes, Kaurane; D008070:Lipopolysaccharides; D010936:Plant Extracts; D009569:Nitric Oxide
keywords: Annona glabra; Annonaceae; Anti-inflammation; ent-Kaurane diterpene