Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities
A pair of new 3,4;9,10-seco-cycloartane type triterpenoid stereoisomerides: 24R,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (1) named Illiciumolide A and 24S,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (2) named Illiciumolide B were isolated from the stem bark of Illicium difen...
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doaj-f48fe7e8a6c34331aec818fdc60785b42020-11-24T22:56:20ZengHindawi LimitedEvidence-Based Complementary and Alternative Medicine1741-427X1741-42882013-01-01201310.1155/2013/942541942541Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory ActivitiesChuntong Li0Fengmin Xi1Junling Mi2Zhijun Wu3Wansheng Chen4Department of Pharmacy, Shanghai Changzheng Hospital, Second Military Medical University, Fengyang Road 415, Shanghai 200003, ChinaDepartment of Pharmacy, Shanghai Changzheng Hospital, Second Military Medical University, Fengyang Road 415, Shanghai 200003, ChinaSchool of Pharmacy, Chengdu University of Traditional Chinese Medicine, Liutai Road 1166, Chengdu, Sichuan 611137, ChinaDepartment of Pharmacy, Shanghai Changzheng Hospital, Second Military Medical University, Fengyang Road 415, Shanghai 200003, ChinaDepartment of Pharmacy, Shanghai Changzheng Hospital, Second Military Medical University, Fengyang Road 415, Shanghai 200003, ChinaA pair of new 3,4;9,10-seco-cycloartane type triterpenoid stereoisomerides: 24R,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (1) named Illiciumolide A and 24S,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (2) named Illiciumolide B were isolated from the stem bark of Illicium difengpi, as well as five known biogenetically related triterpenoids, including sootepin E (3), betulinic acid (4), lupeol (5), (all-Z)-1,5,9,13,17,21-hexamethyl-1,5,9,13,17,21-cyclotertracosahexaene (6), and (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene (7). The structures of two new compounds were determined on the basis of spectroscopic analysis including 1D-, 2D-NMR, and MS techniques. Two assays were conducted: inhibition of tumor necrosis factor-alpha (TNF-α) and inhibition of nuclear factor kappa B (NF-κB) in RAW264. 7 cells induced by lipopolysaccharide (LPS). It was observed that compounds 1, 2 and 7 showed significant inhibition of TNF-α production and NF-κB release. The molecule docking results showed that compounds 1 and 2 got high fitness scores with dual specificity mitogen-activated protein kinase kinase 1 (MPKK1), whose activation plays a pivotal role between TNF-α and activation of NF-κB. The anti-HIV-1 potency of compounds 1–5 was also discussed, in addition to the results of computer-aided screening for targets.http://dx.doi.org/10.1155/2013/942541 |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Chuntong Li Fengmin Xi Junling Mi Zhijun Wu Wansheng Chen |
spellingShingle |
Chuntong Li Fengmin Xi Junling Mi Zhijun Wu Wansheng Chen Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities Evidence-Based Complementary and Alternative Medicine |
author_facet |
Chuntong Li Fengmin Xi Junling Mi Zhijun Wu Wansheng Chen |
author_sort |
Chuntong Li |
title |
Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities |
title_short |
Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities |
title_full |
Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities |
title_fullStr |
Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities |
title_full_unstemmed |
Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities |
title_sort |
two new 3,4;9,10-seco-cycloartane type triterpenoids from illicium difengpi and their anti-inflammatory activities |
publisher |
Hindawi Limited |
series |
Evidence-Based Complementary and Alternative Medicine |
issn |
1741-427X 1741-4288 |
publishDate |
2013-01-01 |
description |
A pair of new 3,4;9,10-seco-cycloartane type triterpenoid stereoisomerides: 24R,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (1) named Illiciumolide A and 24S,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (2) named Illiciumolide B were isolated from the stem bark of Illicium difengpi, as well as five known biogenetically related triterpenoids, including sootepin E (3), betulinic acid (4), lupeol (5), (all-Z)-1,5,9,13,17,21-hexamethyl-1,5,9,13,17,21-cyclotertracosahexaene (6), and (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene (7). The structures of two new compounds were determined on the basis of spectroscopic analysis including 1D-, 2D-NMR, and MS techniques. Two assays were conducted: inhibition of tumor necrosis factor-alpha (TNF-α) and inhibition of nuclear factor kappa B (NF-κB) in RAW264. 7 cells induced by lipopolysaccharide (LPS). It was observed that compounds 1, 2 and 7 showed significant inhibition of TNF-α production and NF-κB release. The molecule docking results showed that compounds 1 and 2 got high fitness scores with dual specificity mitogen-activated protein kinase kinase 1 (MPKK1), whose activation plays a pivotal role between TNF-α and activation of NF-κB. The anti-HIV-1 potency of compounds 1–5 was also discussed, in addition to the results of computer-aided screening for targets. |
url |
http://dx.doi.org/10.1155/2013/942541 |
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