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Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

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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).

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Acknowledgements

This research was supported by the Basic Science Research Program through the National. Research Foundation of Korea (NRF), and funded by the Ministry of Science, ICT & Future Planning (2015R1D1A1A01057156).

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Author notes

  1. Srijan Shrestha and Pradeep Paudel have contributed equally to this work.

Authors and Affiliations

  1. Department of Food and Life Science, Pukyong National University, Busan, 48513, Republic of Korea

    Srijan Shrestha, Pradeep Paudel, Su Hui Seong & Hyun Ah Jung

  2. Drug Research and Development Center, College of Pharmacy, Daegu Catholic University, Gyeongbuk, 38430, Republic of Korea

    Byung Sun Min

  3. Graduate School of Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, 120-750, Republic of Korea

    Eun Kyoung Seo

  4. Department of Food Science and Human Nutrition, Chonbuk National University, Jeonju, 54896, Republic of Korea

    Jae Sue Choi

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  1. Srijan Shrestha
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  2. Pradeep Paudel
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  3. Su Hui Seong
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  4. Byung Sun Min
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  5. Eun Kyoung Seo
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  6. Hyun Ah Jung
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  7. Jae Sue Choi
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Correspondence to Hyun Ah Jung or Jae Sue Choi.

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Shrestha, S., Paudel, P., Seong, S.H. et al. Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds. Arch. Pharm. Res. 41, 737–742 (2018). https://doi.org/10.1007/s12272-018-1044-0

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  • DOI: https://doi.org/10.1007/s12272-018-1044-0

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