Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils

Tsung Hsien Chou; Ih Sheng Chen; Tsong Long Hwang; Tai Chi Wang; Zong-Huei Li; Lin Yang Cheng; Ya Chih Chang; Jui Ying Cho; Jih Jung Chen

doi:10.1021/np8004503

Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils

Tsung Hsien Chou, Ih Sheng Chen, Tsong Long Hwang, Tai Chi Wang, Zong-Huei Li, Lin Yang Cheng, Ya Chih Chang, Jui Ying Cho, Jih Jung Chen

School of Pharmacy

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

42 Citations (Scopus)

Abstract

Six new phthalides, (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (1), (S)-3-ethyl-7-hydroxy-5,6-dimethoxyphthalide (2), (S)-3-ethyl-5,6,7- trimethoxyphfhalide (3), (R)-3-ethyl-7-hydroxy-6-methoxyphthalide (4), (Z)-3-ethylidene-7-hydroxy-6-methoxyphthalide (5), and (Z)-3-ethylidene-6,7- dimethoxyphthalide (6), have been isolated from the root of Pittosporum illicioides var. illicioides, together with seven known compounds. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1-4 exhibited inhibition (IC₅₀ ≤ 29.8 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 5 and 6 inhibited fMLP/CB-induced elastase release with IC₅₀ values of 38.6 ± 4.3 and 33.9 ± 3.9 μM, respectively.

Original language	English
Pages (from-to)	1692-1695
Number of pages	4
Journal	Journal of Natural Products
Volume	71
Issue number	10
DOIs	https://doi.org/10.1021/np8004503
Publication status	Published - Oct 2008

ASJC Scopus subject areas

Complementary and alternative medicine
Molecular Medicine
Organic Chemistry
Analytical Chemistry
Pharmaceutical Science
Pharmacology
Drug Discovery

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10.1021/np8004503

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title = "Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils",

abstract = "Six new phthalides, (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (1), (S)-3-ethyl-7-hydroxy-5,6-dimethoxyphthalide (2), (S)-3-ethyl-5,6,7- trimethoxyphfhalide (3), (R)-3-ethyl-7-hydroxy-6-methoxyphthalide (4), (Z)-3-ethylidene-7-hydroxy-6-methoxyphthalide (5), and (Z)-3-ethylidene-6,7- dimethoxyphthalide (6), have been isolated from the root of Pittosporum illicioides var. illicioides, together with seven known compounds. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1-4 exhibited inhibition (IC50 ≤ 29.8 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 5 and 6 inhibited fMLP/CB-induced elastase release with IC50 values of 38.6 ± 4.3 and 33.9 ± 3.9 μM, respectively.",

author = "Chou, {Tsung Hsien} and Chen, {Ih Sheng} and Hwang, {Tsong Long} and Wang, {Tai Chi} and Zong-Huei Li and Cheng, {Lin Yang} and Chang, {Ya Chih} and Cho, {Jui Ying} and Chen, {Jih Jung}",

year = "2008",

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doi = "10.1021/np8004503",

language = "English",

volume = "71",

pages = "1692--1695",

journal = "Journal of Natural Products",

issn = "0163-3864",

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T1 - Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils

AU - Chou, Tsung Hsien

AU - Chen, Ih Sheng

AU - Hwang, Tsong Long

AU - Wang, Tai Chi

AU - Li, Zong-Huei

AU - Cheng, Lin Yang

AU - Chang, Ya Chih

AU - Cho, Jui Ying

AU - Chen, Jih Jung

PY - 2008/10

Y1 - 2008/10

N2 - Six new phthalides, (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (1), (S)-3-ethyl-7-hydroxy-5,6-dimethoxyphthalide (2), (S)-3-ethyl-5,6,7- trimethoxyphfhalide (3), (R)-3-ethyl-7-hydroxy-6-methoxyphthalide (4), (Z)-3-ethylidene-7-hydroxy-6-methoxyphthalide (5), and (Z)-3-ethylidene-6,7- dimethoxyphthalide (6), have been isolated from the root of Pittosporum illicioides var. illicioides, together with seven known compounds. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1-4 exhibited inhibition (IC50 ≤ 29.8 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 5 and 6 inhibited fMLP/CB-induced elastase release with IC50 values of 38.6 ± 4.3 and 33.9 ± 3.9 μM, respectively.

AB - Six new phthalides, (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (1), (S)-3-ethyl-7-hydroxy-5,6-dimethoxyphthalide (2), (S)-3-ethyl-5,6,7- trimethoxyphfhalide (3), (R)-3-ethyl-7-hydroxy-6-methoxyphthalide (4), (Z)-3-ethylidene-7-hydroxy-6-methoxyphthalide (5), and (Z)-3-ethylidene-6,7- dimethoxyphthalide (6), have been isolated from the root of Pittosporum illicioides var. illicioides, together with seven known compounds. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1-4 exhibited inhibition (IC50 ≤ 29.8 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 5 and 6 inhibited fMLP/CB-induced elastase release with IC50 values of 38.6 ± 4.3 and 33.9 ± 3.9 μM, respectively.

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Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils

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