title: Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus.
abstract: Phytochemical analysis of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of two new alkylphloroglucinols, gallomyrtucommulone E and F (1 and 2), along with four other known alkylphloroglucinol derivatives, gallomyrtucommulone A (3), endoperoxide G3 (4), myrtucommulone B (5), callistenone B (6) and five known triterpenoids, including betulinic acid (7), 3β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), diospyrolide (10) and ursolic acid (11). The structures of the natural compounds were determined from the spectroscopic evidences including 1D-/2D-NMR and HR-MS spectrometry. All the isolated compounds were assessed for the effects on the sEH inhibitory activity. The acylphloroglucinols myrtucommulone B (5)/callistenone B (6) (in mixture), and two triterpenoids, ursolic acid (11) and 3β-hydroxy-urs-11-en-13(28)-olide (9) displayed strong inhibition of sEH activity, with IC50 values of 0.7, 11.2 and 24.8 μM, respectively.
authors.affiliation: Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam.
authors.forename: Pham Ngoc
authors.initials: PN
authors.lastname: Khanh
authors.affiliation: Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen Str., 47000 Hue, Viet Nam.
authors.forename: Ho Viet
authors.initials: HV
authors.lastname: Duc
authors.affiliation: Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam.
authors.forename: Tran Thu
authors.initials: TT
authors.lastname: Huong
authors.affiliation: Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam.
authors.forename: Ninh The
authors.initials: NT
authors.lastname: Son
authors.affiliation: Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam.
authors.forename: Vu Thi
authors.initials: VT
authors.lastname: Ha
authors.affiliation: Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam.
authors.forename: Doan Thi
authors.initials: DT
authors.lastname: Van
authors.affiliation: College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors.forename: Bui Huu
authors.initials: BH
authors.lastname: Tai
authors.affiliation: College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors.forename: Ji Eun
authors.initials: JE
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors.forename: Ah Reum
authors.initials: AR
authors.lastname: Jo
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
authors.affiliation: Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, 122100 CauGiay, Hanoi, Viet Nam. Electronic address: nmcuong_inpc@yahoo.com.vn.
authors.forename: Nguyen Manh
authors.initials: NM
authors.lastname: Cuong
mesh_terms: D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D004851:Epoxide Hydrolases / Q000037:antagonists & inhibitors*; D006801:Humans; D015394:Molecular Structure; D027822:Myrtaceae / Q000737:chemistry*; D010696:Phloroglucinol / Q000737:chemistry* / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D011994:Recombinant Proteins; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D004791:Enzyme Inhibitors; D011994:Recombinant Proteins; D014315:Triterpenes; D010696:Phloroglucinol; D004851:Epoxide Hydrolases
keywords: Alkylphloroglucinol; Callistemon citrinus; Gallomyrtucommulone; Soluble epoxide hydroxylase (sEH); betulinic acid (PubChem CID: 64971); diospyrolide (PubChem CID: 3037455); endoperoxide G3 (PubChem CID: 11207902); gallomyrtucommulone A (PubChem CID: 11505110); ursolic acid (PubChem CID: 64945)