A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity

  • Bioorg Med Chem Lett. 2014 Sep 1;24(17):4120-4. doi: 10.1016/j.bmcl.2014.07.057.
Bui Thi Thuy Luyen  1 Bui Huu Tai  2 Nguyen Phuong Thao  2 Seo Young Yang  1 Nguyen Manh Cuong  3 Young In Kwon  4 Hae Dong Jang  4 Young Ho Kim  5
Affiliations
  • 1. College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
  • 2. College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea; Institute of Marine Biochemistry (IMBC), Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
  • 3. Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
  • 4. Department of Food and Nutrition, Hannam University, Daejeon 305-811, Republic of Korea.
  • 5. College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea. Electronic address: [email protected].
Abstract

Two new compounds, piperoside (1) and isoheptanol 2(S)-O-β-D-xylopyranosyl (1→6)-O-β-D-glucopyranoside (11), along with 10 known compounds 3,4-dihydroxyallylbenzene (2), 1,2-di-O-β-D-glucopyranosyl-4-allylbenzene (3), tachioside (4), benzyl-O-β-D-glucopyranoside (5), icariside F2 (6), dihydrovomifoliol-3'-O-β-D-glucopyranoside (7), isopropyl O-β-D-glucopyranoside (8), isopropyl primeveroside (9), n-butyl O-β-D-glucopyranoside (10), isoheptanol 2(S)-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside (12), were isolated from the leaves of Piper retrofractum. Their structures were determined from 1D-NMR, 2D-NMR, and HR-ESI-MS spectral, a modified Mosher's method, and comparisons with previous reports. All of the isolated compounds showed modest α-glucosidase inhibitory (4.60±1.74% to 11.97±3.30%) and antioxidant activities under the tested conditions.

Keywords
Antioxidant; Isoheptanol 2(S)-O-β-d-xylopyranosyl (1→6)-O-β-d-glucopyranoside; Piper retrofractum; Piperoside; α-Glucosidase inhibitor.
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