Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

Srijan Shrestha; Pradeep Paudel; Su Hui Seong; Byung Sun Min; Eun Kyoung Seo; Hyun Ah Jung; Jae Sue Choi

doi:10.1007/s12272-018-1044-0

Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

Srijan Shrestha
, Pradeep Paudel
, Su Hui Seong
, Byung Sun Min
, Eun Kyoung Seo
, Hyun Ah Jung
, Jae Sue Choi

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

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).

Original language	English
Pages (from-to)	737-742
Number of pages	6
Journal	Archives of Pharmacal Research
Volume	41
Issue number	7
DOIs	https://doi.org/10.1007/s12272-018-1044-0
State	Published - 1 Jul 2018

Bibliographical note

Funding Information:
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).

Publisher Copyright:
© 2018, The Pharmaceutical Society of Korea.

Keywords

Advanced glycation end-products
Cassia obtusifolia
Naphthalenic lactone glycosides

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10.1007/s12272-018-1044-0

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title = "Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds",

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",

author = "Srijan Shrestha and Pradeep Paudel and Seong, \{Su Hui\} and Min, \{Byung Sun\} and Seo, \{Eun Kyoung\} and Jung, \{Hyun Ah\} and Choi, \{Jae Sue\}",

note = "Funding Information: 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). Publisher Copyright: {\textcopyright} 2018, The Pharmaceutical Society of Korea.",

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doi = "10.1007/s12272-018-1044-0",

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T1 - Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

AU - Shrestha, Srijan

AU - Paudel, Pradeep

AU - Seong, Su Hui

AU - Min, Byung Sun

AU - Seo, Eun Kyoung

AU - Jung, Hyun Ah

AU - Choi, Jae Sue

N1 - Funding Information: 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). Publisher Copyright: © 2018, The Pharmaceutical Society of Korea.

PY - 2018/7/1

Y1 - 2018/7/1

N2 - 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).

AB - 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).

KW - Advanced glycation end-products

KW - Cassia obtusifolia

KW - Naphthalenic lactone glycosides

UR - https://www.scopus.com/pages/publications/85048275803

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DO - 10.1007/s12272-018-1044-0

M3 - Article

C2 - 29948771

AN - SCOPUS:85048275803

SN - 0253-6269

VL - 41

SP - 737

EP - 742

JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

IS - 7

ER -

Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds

Abstract

Bibliographical note

Keywords

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