| 摘要: | Rutaceae、Zanthoxylum avicennae、Melastomataceae、Pachy centria formosana、Scrophulariaceae、Limnophila rugosa、anti-inflammatory activity、anti-platelet aggregation activity
Zanthoxylum avicennae (Lam.) DC (Rutaceae) is an evergreen shrub distributed in Vietnam, Philippines, southern China, and Taiwan. Pachycentria formosana Hayata (Melastomataceae) is an endemic creeping shrub distributed in 300–2100 m forests throughout Taiwan. Limnophila rugosa (Roth) Merill (Scrophulariaceae) is a perennial herb grows swampy places and rice fields of Taiwan and is also distributed in Ryukyus, Malesia, Indochina, and Polynesia. In our studies on the anti-inflammatory and anti-platelet aggregation constituents of Formosan plants, many species have been screened for in vitro anti-inflammatory and anti-platelet aggregation activity. Among them, Z. avicennae, P. formosana and L. rugosa exhibited anti-inflammatory activity. In addition, L. rugosa also showed anti-platelet aggregation activity.
In our search for compounds with anti-inflammatory activities, five new coumarins, 5′-methoxyauraptene (1), 6,5′-dimethoxyauraptene (2), 5′-methoxycollinin (3), 7-((2′E,5′E)-7′-methoxy-3′,7′-dimethylocta-2′,5′- dienyloxy)coumarin (4), and 6-methoxy-7-((2′E,5′E)-7′-methoxy-3′,7′- dimethylocta-2′,5′-dienyloxy)coumarin (5), and 36 known compounds (6–41) have been isolated and identified from the leaves of Z. avicennae.
Investigation of CH2Cl2-soluble fraction of the leaves and twigs of P. formosana led to the isolation of a new ferulic acid ester derivative, tetracosane-1,24-diyl di[(Z)-ferulate] (42), and a new ellagic acid derivative, 3,4:3′,4′-bis(O,O-methylene)ellagic acid (43), along with 17 known compounds (44–60).
In addition, investigation of n-hexane and EtOAc-soluble fractions of the leaves of L. rugosa has led to the isolation of two new flavonoids limnorugosin A (61) and limnorugosin B (62), and a new benzoic aicd, (R)-3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoic acid (63), and 17 known compounds (33, 56, 57, 64–80). The structures of all isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures.
Among the isolated compounds, cedrelopsin (12), alloxanthoxyletin (13), 3,4-dihydroxybenzoic acid (21), methyl 4-hydroxybenzoate (22), skimmianine (31), diosmetin (35), (–)-syringaresinol (41), oleanolic acid (50), betulinic acid (52), isothymusin (66), and 3-farnesyl-4-hydroxy- benzoic acid (74) exhibited potent inhibition (IC50 values ≤ 3.96 μg/mL) on superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/ CB).
Cedrelopsin (12), alloxanthoxyletin (13), oleanolic acid (50), betulinic acid (52), (3R)-5-methylmellein (59), 4-hydroxy-3-(3′-methyl- 2′-butenyl)benzoic acid (72), 3-geranyl-4-hydroxybenzoic acid (73),and 3-farnesyl-4-hydroxybenzoic acid (74) also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 3.96 μg/mL.
In addition, pectolinarigenin (67) inhibited thrombin, arachidonic acid, and U46619-induced platelet aggregation with IC50 values of 6.91 ± 0.22, 6.04 ± 0.30, and 30.28 ± 0.22 μM?zrespectively.
狗花椒(Zanthoxylum avicennae)，為芸香科(Rutaceae)之常綠灌木，分佈於越南、菲律賓、中國南方及台灣。台灣厚距花(Pachycentria formosana)為野牡丹科(Melastomataceae)台灣特有之匍匐性附生灌木，分佈於全省300–2100公尺海拔森林中。而大葉石龍尾(Limnophila rugosa)為玄參科(Scrophulariaceae)之多年生草本植物，生長於台灣的濕地及稻田，也分佈於琉球群島，吉隆坡，馬來西亞，印度支那和波利尼西亞。對台灣產植物進行抗發炎與抗血小板凝集活性篩選，其中狗花椒、台灣厚距花與大葉石龍尾具有抗發炎活性，另外，大葉石龍尾亦具有抗血小板凝集活性。
由狗花椒葉部之EtOAc可溶部，目前已分離出五個新的coumarins: 5′-methoxyauraptene (1), 6,5′-dimethoxyauraptene (2), 5′-methoxycollinin (3), 7-((2′E,5′E)-7′-methoxy-3′,7′-dimethylocta-2′,5′- dienyloxy)coumarin (4) 及6-methoxy-7-((2′E,5′E)-7′-methoxy-3′,7′- dimethylocta-2′,5′-dienyloxy)coumarin (5)，以及36個已知化合物(6~41)。
由台灣厚距花枝葉之CH2Cl2可溶部，目前已分離出一個新的ferulic acid ester derivative: tetracosane-1,24-diyl di[(Z)-ferulate] (42)及一個新的ellagic acid derivative: 3,4:3′,4′-bis(O,O-methylene)ellagic acid (43)，以及17個已知化合物(42~60)。
另外自大葉石龍尾地上部之n-hexane及EtOAc可溶部，分離出兩個新的flavonoids: limnorugosin A (61)及limnorugosin B (62)，以及一個新的benzenoid: (R)-3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxy- benzoic acid (63)，以及 17個已知化合物(33, 56, 57, 61~80)。上述化合物之結構，經由各種圖譜分析及文獻數據比對予以確認。
目前分離所得到的化合物中，cedrelopsin (12), alloxanthoxyletin (13), 3,4-dihydroxybenzoic acid (21), methyl 4-hydroxybenzoate (22), skimmianine (31), diosmetin (35),(–)-syringaresinol (41), oleanolic acid (50), betulinic acid (52), isothymusin (66)及3-farnesyl-4-hydroxy- benzoic acid (74) 對於formyl-L-methionyl-L-leucyl-L-phenyl-alanine/ cytochalasin B (fMLP/CB)誘導人類嗜中性白血球產生超氧陰離子(O2•–)具有良好的抑制活性 (IC50 ≤ 3.96 μg/mL)。
另外，cedrelopsin (12), alloxanthoxyletin (13), oleanolic acid (50), betulinic acid (52), (3R)-5-methylmellein (59), 4-hydroxy-3-(3′-methyl- 2′-butenyl)benzoic acid (72), 3-geranyl-4-hydroxybenzoic acid (73)及3-farnesyl-4-hydroxybenzoic acid (74)對於fMLP/CB誘導彈性蛋白酶的釋放亦具有良好的抑制活性(IC50 ≤ 3.96 μg/mL)。
此外，pectolinarigenin (67)對於thrombin, arachidonic acid及U46619所誘導之血小板凝集亦具有良好的抑制作用，其IC50值為6.91 ± 0.22, 6.04 ± 0.30及30.28 ± 0.22 μM。 |
