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

14 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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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

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M3 - Article

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AN - SCOPUS:85048275803

SN - 0253-6269

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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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