2. Academic Validation
  3. Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

  • Arch Pharm Res. 2018 Jul;41(7):737-742. doi: 10.1007/s12272-018-1044-0.
Srijan Shrestha 1,  Pradeep Paudel 1,  Su Hui Seong 1,  Byung Sun Min 2,  Eun Kyoung Seo 3,  Hyun Ah Jung 4,  Jae Sue Choi 5
Affiliations

Affiliations

  • 1 Department of Food and Life Science, Pukyong National University, Busan, 48513, Republic of Korea.
  • 2 Drug Research and Development Center, College of Pharmacy, Daegu Catholic University, Gyeongbuk, 38430, Republic of Korea.
  • 3 Graduate School of Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, 120-750, Republic of Korea.
  • 4 Department of Food and Life Science, Pukyong National University, Busan, 48513, Republic of Korea. jungha@jbnu.ac.kr.
  • 5 Department of Food Science and Human Nutrition, Chonbuk National University, Jeonju, 54896, Republic of Korea. choijs@pknu.ac.kr.
PMID: 29948771 DOI: 10.1007/s12272-018-1044-0
Abstract

Two new naphthalenic lactone glycosides, (3S)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-benzo[g]isochromene-3-carboxylic acid 9-O-β-D-glucopyranoside (1) and (3R)-cassialactone 9-O-β-D-glucopyranoside (2) were isolated from seeds of Cassia obtusifolia Linn., along with five known compounds: (3R)-cassialactone 9-O-β-D-gentiobioside (3), emodin 1-O-β-gentiobioside (4), 1-hydroxyl-2-acetyl-3,8-dimethoxy-naphthalene 6-O-β-D-apiofuranosyl-(1 → 2)-β-D-glucopyranoside (5), rubrofusarin 6-O-β-D-gentiobioside (6), rubrofusarin 6-O-β-D-triglucoside (7). Structures of 1 and 2 were elucidated by NMR and HR-ESI-MS spectroscopic analysis. Their stereochemistry was determined by CD experiment. All compounds were tested for their ability to inhibit the formation of advanced glycation end-products in vitro. Compounds 1, 2, 3, 5, and 6 showed significant in vitro inhibitory activities (IC50 values of 11.63, 23.40, 7.32, 89.03, and 38.89 µM, respectively).

Keywords

Advanced glycation end-products; Cassia obtusifolia; Naphthalenic lactone glycosides.

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