title: PTP1B, α-glucosidase, and DPP-IV inhibitory effects for chromene derivatives from the leaves of Smilax china L.
abstract: Two new flavonoids, bismilachinone (11) and smilachinin (14), were isolated from the leaves of Smilax china L. together with 14 known compounds. Their structures were elucidated using spectroscopic methods. The PTP1B, α-glucosidase, and DPP-IV inhibitory activities of compounds 1-16 were evaluated at the molecular level. Among them, compounds 4, 7, and 10 showed moderate DPP-IV inhibitory activities with IC50 values of 20.81, 33.12, and 32.93 μM, respectively. Compounds 3, 4, 6, 11, 12, and 16 showed strong PTP1B inhibitory activities, with respective IC50 values of 7.62, 10.80, 0.92, 2.68, 9.77, and 24.17 μM compared with the IC50 value for the positive control (ursolic acid: IC50 = 1.21 μM). Compounds 2-7, 11, 12, 15, and 16 showed potent α-glucosidase inhibitory activities, with respective IC50 values of 8.70, 81.66, 35.11, 35.92, 7.99, 26.28, 11.28, 62.68, 44.32, and 70.12 μM. The positive control, acarbose, displayed an IC50 value of 175.84 μM. In the kinetic study for the PTP1B enzyme, compounds 6, 11, and 12 displayed competitive inhibition with Ki values of 3.20, 8.56, and 5.86 μM, respectively. Compounds 3, 4, and 16 showed noncompetitive inhibition with Ki values of 18.75, 5.95, and 22.86 μM, respectively. Molecular docking study for the competitive inhibitors (6, 11, and 12) radically corroborates the binding affinities and inhibition of PTP1B enzymes. These results indicated that the leaves of Smilax china L. may contain compounds with anti-diabetic activity.
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea.
authors.forename: Bing Tian
authors.initials: BT
authors.lastname: Zhao
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea.
authors.forename: Duc Dat
authors.initials: DD
authors.lastname: Le
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea; Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Hanoi, Vietnam.
authors.forename: Phi Hung
authors.initials: PH
authors.lastname: Nguyen
authors.affiliation: Department of Food Science & Nutrition, Pukyong National University, Busan 48513, Republic of Korea.
authors.forename: Md Yousof
authors.initials: MY
authors.lastname: Ali
authors.affiliation: Department of Food Science & Nutrition, Pukyong National University, Busan 48513, Republic of Korea.
authors.forename: Jae-Sue
authors.initials: JS
authors.lastname: Choi
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea.
authors.forename: Byung Sun
authors.initials: BS
authors.lastname: Min
authors.affiliation: Department of Physiology, College of Oriental Medicine, Dongguk University, Seoul 04620, Republic of Korea.
authors.forename: Heung Mook
authors.initials: HM
authors.lastname: Shin
authors.affiliation: Department of Biotechnology, Kangwon National University, Chuncheon, Gangwon 24341, Republic of Korea.
authors.forename: Hae Ik
authors.initials: HI
authors.lastname: Rhee
authors.affiliation: College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea. Electronic address: woomh@cu.ac.kr.
authors.forename: Mi Hee
authors.initials: MH
authors.lastname: Woo
mesh_terms: D001578:Benzopyrans / Q000737:chemistry* / Q000378:metabolism; D001665:Binding Sites; D018819:Dipeptidyl Peptidase 4 / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D017434:Protein Structure, Tertiary; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D032281:Smilax / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001578:Benzopyrans; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1; D018819:Dipeptidyl Peptidase 4
keywords: DPP-IV; Molecular docking; PTP1B; Smilax china L.; α-Glucosidase inhibitor