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

Research output: Contribution to journalArticle

8 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 languageEnglish
Pages (from-to)254-258
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number2
DOIs
Publication statusPublished - 2015 Jan 15

Fingerprint

Kaurane Diterpenes
Annona
Macrophages
Fruits
Fruit
Nitric Oxide
Acids
Inhibitory Concentration 50
Esters
Diterpenes

All Science Journal Classification (ASJC) codes

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

Cite this

Nhiem, Nguyen Xuan ; Hien, Nguyen Thi Thu ; Tai, Bui Huu ; Anh, Hoang Le Tuan ; Hang, Dan Thi Thuy ; Quang, Tran Hong ; Kiem, Phan Van ; Minh, Chau Van ; Ko, Wonmin ; Lee, Seungjun ; Oh, Hyuncheol ; Kim, Seung Hyun ; Kim, Young Ho. / New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. In: Bioorganic and Medicinal Chemistry Letters. 2015 ; Vol. 25, No. 2. pp. 254-258.
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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}",
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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

New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. / Nhiem, Nguyen Xuan; Hien, Nguyen Thi Thu; Tai, Bui Huu; Anh, Hoang Le Tuan; Hang, Dan Thi Thuy; Quang, Tran Hong; Kiem, Phan Van; Minh, Chau Van; Ko, Wonmin; Lee, Seungjun; Oh, Hyuncheol; Kim, Seung Hyun; Kim, Young Ho.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 2, 15.01.2015, p. 254-258.

Research output: Contribution to journalArticle

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

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.

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