New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages

Nguyen Xuan Nhiem; Nguyen Thi Thu Hien; Bui Huu Tai; Hoang Le Tuan Anh; Dan Thi Thuy Hang; Tran Hong Quang; Phan Van Kiem; Chau Van Minh; Wonmin Ko; Seungjun Lee; Hyuncheol Oh; Seung Hyun Kim; Young Ho Kim

doi:10.1016/j.bmcl.2014.11.059

New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages

Nguyen Xuan Nhiem, Nguyen Thi Thu Hien, Bui Huu Tai, Hoang Le Tuan Anh, Dan Thi Thuy Hang, Tran Hong Quang, Phan Van Kiem, Chau Van Minh, Wonmin Ko, Seungjun Lee, Hyuncheol Oh, Seung Hyun Kim, Young Ho Kim

Department of Pharmacy

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

17 Citations (Scopus)

Abstract

Three new ent-kaurane diterpenoids, 7β,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-d-glucopyranoside ester (2), 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16β,17-dihydroxy-ent-kaurane (6), 16β,17-dihydroxy-ent-kauran-19-al (7), and 16β,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC₅₀ value of 0.01 ± 0.01 μM; compounds 1 and 7 showed significant inhibitory NO production with the IC₅₀ values of 0.39 ± 0.12 μM and 0.32 ± 0.04 μM, respectively.

Original language	English
Pages (from-to)	254-258
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2014.11.059
Publication status	Published - 2015 Jan 15

Bibliographical note

Funding Information:
This work was financially supported by Vietnam Academy of Science and Technology (VAST 04.04.13-14). This work was also supported by a grant from the Priority Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2009-0093815 ), Republic of Korea. The authors are grateful to Mr. Dang Vu Luong, Institute of Chemistry, VAST for recording the NMR and mass spectra.

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2014.11.059

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Nhiem, N. X., Hien, N. T. T., Tai, B. H., Anh, H. L. T., Hang, D. T. T., Quang, T. H., Kiem, P. V., Minh, C. V., Ko, W., Lee, S., Oh, H., Kim, S. H., & Kim, Y. H. (2015). New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. Bioorganic and Medicinal Chemistry Letters, 25(2), 254-258. https://doi.org/10.1016/j.bmcl.2014.11.059

@article{e2eb3da214504a4094304aeee467173c,

title = "New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages",

abstract = "Three new ent-kaurane diterpenoids, 7β,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-d-glucopyranoside ester (2), 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16β,17-dihydroxy-ent-kaurane (6), 16β,17-dihydroxy-ent-kauran-19-al (7), and 16β,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01 ± 0.01 μM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39 ± 0.12 μM and 0.32 ± 0.04 μM, respectively.",

author = "Nhiem, {Nguyen Xuan} and Hien, {Nguyen Thi Thu} and Tai, {Bui Huu} and Anh, {Hoang Le Tuan} and Hang, {Dan Thi Thuy} and Quang, {Tran Hong} and Kiem, {Phan Van} and Minh, {Chau Van} and Wonmin Ko and Seungjun Lee and Hyuncheol Oh and Kim, {Seung Hyun} and Kim, {Young Ho}",

note = "Funding Information: This work was financially supported by Vietnam Academy of Science and Technology (VAST 04.04.13-14). This work was also supported by a grant from the Priority Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2009-0093815 ), Republic of Korea. The authors are grateful to Mr. Dang Vu Luong, Institute of Chemistry, VAST for recording the NMR and mass spectra. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2015",

month = jan,

day = "15",

doi = "10.1016/j.bmcl.2014.11.059",

language = "English",

volume = "25",

pages = "254--258",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "2",

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Nhiem, NX, Hien, NTT, Tai, BH, Anh, HLT, Hang, DTT, Quang, TH, Kiem, PV, Minh, CV, Ko, W, Lee, S, Oh, H, Kim, SH & Kim, YH 2015, 'New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages', Bioorganic and Medicinal Chemistry Letters, vol. 25, no. 2, pp. 254-258. https://doi.org/10.1016/j.bmcl.2014.11.059

TY - JOUR

T1 - New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages

AU - Nhiem, Nguyen Xuan

AU - Hien, Nguyen Thi Thu

AU - Tai, Bui Huu

AU - Anh, Hoang Le Tuan

AU - Hang, Dan Thi Thuy

AU - Quang, Tran Hong

AU - Kiem, Phan Van

AU - Minh, Chau Van

AU - Ko, Wonmin

AU - Lee, Seungjun

AU - Oh, Hyuncheol

AU - Kim, Seung Hyun

AU - Kim, Young Ho

N1 - Funding Information: This work was financially supported by Vietnam Academy of Science and Technology (VAST 04.04.13-14). This work was also supported by a grant from the Priority Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2009-0093815 ), Republic of Korea. The authors are grateful to Mr. Dang Vu Luong, Institute of Chemistry, VAST for recording the NMR and mass spectra. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2015/1/15

Y1 - 2015/1/15

N2 - Three new ent-kaurane diterpenoids, 7β,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-d-glucopyranoside ester (2), 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16β,17-dihydroxy-ent-kaurane (6), 16β,17-dihydroxy-ent-kauran-19-al (7), and 16β,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01 ± 0.01 μM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39 ± 0.12 μM and 0.32 ± 0.04 μM, respectively.

AB - Three new ent-kaurane diterpenoids, 7β,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-d-glucopyranoside ester (2), 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16β,17-dihydroxy-ent-kaurane (6), 16β,17-dihydroxy-ent-kauran-19-al (7), and 16β,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01 ± 0.01 μM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39 ± 0.12 μM and 0.32 ± 0.04 μM, respectively.

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New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages

Abstract

Bibliographical note

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