Skip to main content
Top
Published in: Journal of Natural Medicines 1/2017

01-01-2017 | Original Paper

Constituents from the leaves of Clausena lansium and their anti-inflammatory activity

Authors: De-Yang Shen, Ping-Chung Kuo, Shiow-Chyn Huang, Tsong-Long Hwang, Yu-Yi Chan, Po-Chuen Shieh, Nguyen Thi Ngan, Tran Dinh Thang, Tian-Shung Wu

Published in: Journal of Natural Medicines | Issue 1/2017

Login to get access

Abstract

Five new acyclic amides, clausenalansamides C-G (15), clausenaline G (6) and (±)-5-(4-methylphenyl)-γ-valerolactone (7) reported from the natural source for the first time, were characterized from the leaves of Clausena lansium. Their structures were established by spectroscopic and spectrometric methods, and the absolute configurations of new compounds 15 were determined by electronic circular dichroism and single-crystal X-ray diffraction analyses. Eighteen compounds were evaluated for their anti-inflammatory activity and only imperatorin (11) and wampetin (12) displayed significant inhibition of fMLP/CB-induced superoxide anion generation with IC50 values of 1.7 ± 0.3 and 6.8 ± 1.1 μM, respectively.
Appendix
Available only for authorised users
Literature
1.
go back to reference Huang CC (1959) Preliminary Study on Chinese Rutaceae (3). Acta Phytotax Sin 8:69–124 Huang CC (1959) Preliminary Study on Chinese Rutaceae (3). Acta Phytotax Sin 8:69–124
2.
go back to reference Yang MH, Cao YH, Li WX, Yang YQ, Cheng YY, Huang L (1987) Isolation and structural elucidation of clausenamide from the leaves of Clausena lansium (Lour.) Skeels. Acta Pharm Sin B 22:33–40 Yang MH, Cao YH, Li WX, Yang YQ, Cheng YY, Huang L (1987) Isolation and structural elucidation of clausenamide from the leaves of Clausena lansium (Lour.) Skeels. Acta Pharm Sin B 22:33–40
3.
go back to reference Yang MH, Chen YY, Huang L (1987) Studies on the chemical constituents of Clausena lansium (Lour.) Skeels II: The isolation and structural elucidation of neoclausenamide and cycloclausenamide. Acta Chin Sin 45:1170–1174 Yang MH, Chen YY, Huang L (1987) Studies on the chemical constituents of Clausena lansium (Lour.) Skeels II: The isolation and structural elucidation of neoclausenamide and cycloclausenamide. Acta Chin Sin 45:1170–1174
4.
go back to reference Yang MH, Chen YY, Huang L (1988) Three novel cyclic amides from Clausena lansium. Phytochemistry 27:445–450CrossRef Yang MH, Chen YY, Huang L (1988) Three novel cyclic amides from Clausena lansium. Phytochemistry 27:445–450CrossRef
5.
go back to reference Lakshmi V, Raj K, Kapil RS (1998) Chemical constituents of Clausena lansium: Part III. Structure of lansamide-3 and 4. Indian J Chem Sect B Org Chem Incl Med Chem 37B:422–424 Lakshmi V, Raj K, Kapil RS (1998) Chemical constituents of Clausena lansium: Part III. Structure of lansamide-3 and 4. Indian J Chem Sect B Org Chem Incl Med Chem 37B:422–424
6.
go back to reference Ji X, van der Helm D, Lakshmi V, Agarwal SK, Kapil RS (1992) Structure of lansimide 2, a product from Clausena lansium. Acta Crystallogr Sect C Cryst Struct Commun 48:1082–1085CrossRef Ji X, van der Helm D, Lakshmi V, Agarwal SK, Kapil RS (1992) Structure of lansimide 2, a product from Clausena lansium. Acta Crystallogr Sect C Cryst Struct Commun 48:1082–1085CrossRef
7.
go back to reference Chokeprasert P, Charles AL, Sue KH, Huang TC (2007) Volatile components of the leaves, fruits and seeds of wampee [Clausena lansium (Lour.) Skeels]. J Food Compos Anal 20:52–56CrossRef Chokeprasert P, Charles AL, Sue KH, Huang TC (2007) Volatile components of the leaves, fruits and seeds of wampee [Clausena lansium (Lour.) Skeels]. J Food Compos Anal 20:52–56CrossRef
8.
go back to reference Wong KC, Wong SN, Sam TW, Chee SG (1998) Volatile constituents of Clausena lansium (Lour.) Skeels fruit. J Essent Oil Res 10:700–702CrossRef Wong KC, Wong SN, Sam TW, Chee SG (1998) Volatile constituents of Clausena lansium (Lour.) Skeels fruit. J Essent Oil Res 10:700–702CrossRef
9.
go back to reference Adebajo AC, Iwalewa EO, Obuotor EM, Ibikunle GF, Omisore NO, Adewunmi CO, Obaparusi OO, Klaes M, Adetogun GE, Schmidt TJ, Verspohl EJ (2009) Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects. J Ethnopharmacol 122:10–19CrossRefPubMed Adebajo AC, Iwalewa EO, Obuotor EM, Ibikunle GF, Omisore NO, Adewunmi CO, Obaparusi OO, Klaes M, Adetogun GE, Schmidt TJ, Verspohl EJ (2009) Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects. J Ethnopharmacol 122:10–19CrossRefPubMed
10.
go back to reference Shen DY, Chao CH, Chan HH, Huang GJ, Hwang TL, Lai CY, Lee KH, Thang TD, Wu TS (2012) Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers. Phytochemistry 82:110–117CrossRefPubMed Shen DY, Chao CH, Chan HH, Huang GJ, Hwang TL, Lai CY, Lee KH, Thang TD, Wu TS (2012) Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers. Phytochemistry 82:110–117CrossRefPubMed
11.
go back to reference Shen DY, Chan YY, Hwang TL, Juang SH, Huang SC, Kuo PC, Thang TD, Lee EJ, Damu AG, Wu TS (2014) Constituents of the roots of Clausena lansium and their potential anti-inflammatory activity. J Nat Prod 77:1215–1223CrossRefPubMed Shen DY, Chan YY, Hwang TL, Juang SH, Huang SC, Kuo PC, Thang TD, Lee EJ, Damu AG, Wu TS (2014) Constituents of the roots of Clausena lansium and their potential anti-inflammatory activity. J Nat Prod 77:1215–1223CrossRefPubMed
12.
go back to reference Shen DY, Nguyen TN, Wu SJ, Shiao YJ, Hung HY, Kuo PC, Kuo DH, Thang TD, Wu TS (2014) γ- and δ-Lactams from the leaves of Clausena lansium. J Nat Prod 78:2521–2530CrossRef Shen DY, Nguyen TN, Wu SJ, Shiao YJ, Hung HY, Kuo PC, Kuo DH, Thang TD, Wu TS (2014) γ- and δ-Lactams from the leaves of Clausena lansium. J Nat Prod 78:2521–2530CrossRef
13.
go back to reference Yang SC, Chung PJ, Ho CM, Kuo CY, Hung MF, Huang YT, Chang WY, Chang YW, Chan KH, Hwang TL (2013) Propofol inhibits superoxide production, elastase release, and chemotaxis in formyl peptide-activated human neutrophils by blocking formyl peptide receptor 1. J Immunol 190:6511–6519CrossRefPubMed Yang SC, Chung PJ, Ho CM, Kuo CY, Hung MF, Huang YT, Chang WY, Chang YW, Chan KH, Hwang TL (2013) Propofol inhibits superoxide production, elastase release, and chemotaxis in formyl peptide-activated human neutrophils by blocking formyl peptide receptor 1. J Immunol 190:6511–6519CrossRefPubMed
14.
go back to reference Yu HP, Hsieh PW, Chang YJ, Chung PJ, Kuo LM, Hwang TL (2011) 2-(2-Fluorobenzamido)benzoate ethyl ester (EFB-1) inhibits superoxide production by human neutrophils and attenuates hemorrhagic shock-induced organ dysfunction in rats. Free Radic Biol Med 50:1737–1748CrossRefPubMed Yu HP, Hsieh PW, Chang YJ, Chung PJ, Kuo LM, Hwang TL (2011) 2-(2-Fluorobenzamido)benzoate ethyl ester (EFB-1) inhibits superoxide production by human neutrophils and attenuates hemorrhagic shock-induced organ dysfunction in rats. Free Radic Biol Med 50:1737–1748CrossRefPubMed
15.
go back to reference Scott AI (1964) Interpretation ultraviolet spectra of natural products, 2nd edn. Pergamon Press, New York Scott AI (1964) Interpretation ultraviolet spectra of natural products, 2nd edn. Pergamon Press, New York
16.
go back to reference Maneerat W, Tha-in S, Cheenpracha S, Prawat U, Laphookhieo S (2011) New amides from the seeds of Clausana lansium. J Med Plant Res 5:2812–2815 Maneerat W, Tha-in S, Cheenpracha S, Prawat U, Laphookhieo S (2011) New amides from the seeds of Clausana lansium. J Med Plant Res 5:2812–2815
17.
go back to reference Song WW, Zeng GZ, Peng WW, Chen KX, Tan NH (2014) Cytotoxic amides and quinolones from Clausena lansium. Helv Chim Acta 97:298–305CrossRef Song WW, Zeng GZ, Peng WW, Chen KX, Tan NH (2014) Cytotoxic amides and quinolones from Clausena lansium. Helv Chim Acta 97:298–305CrossRef
18.
go back to reference Milner PH, Coates NJ, Gilpin ML, Spear SR, Eggleston DS (1996) SB-204900, a novel oxirane carboxamide from Clausena lansium. J Nat Prod 59:400–402CrossRef Milner PH, Coates NJ, Gilpin ML, Spear SR, Eggleston DS (1996) SB-204900, a novel oxirane carboxamide from Clausena lansium. J Nat Prod 59:400–402CrossRef
19.
go back to reference Teshima KI, Kaneko T, Ohtani K, Kasai R, Lhieochaiphant S, Picheansoonthon C, Yamasak K (1998) Sulfur-containing glucosides from Clinacanthus nutans. Phytochemistry 48:831–835CrossRef Teshima KI, Kaneko T, Ohtani K, Kasai R, Lhieochaiphant S, Picheansoonthon C, Yamasak K (1998) Sulfur-containing glucosides from Clinacanthus nutans. Phytochemistry 48:831–835CrossRef
20.
go back to reference Liu GT, Li WX, Chen YY, Wei HL (1996) Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice. Drug Dev Res 39:174–178CrossRef Liu GT, Li WX, Chen YY, Wei HL (1996) Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice. Drug Dev Res 39:174–178CrossRef
21.
go back to reference Sowmithran D, Prasad KJR (1986) Heterocycles 2: synthesis of 1-hydroxycarbazoles and mukonine isomers. Heterocycles 24:711–717CrossRef Sowmithran D, Prasad KJR (1986) Heterocycles 2: synthesis of 1-hydroxycarbazoles and mukonine isomers. Heterocycles 24:711–717CrossRef
22.
go back to reference Wang B, Shen YM, Shi Y (2006) Enantioselective synthesis of γ-aryl-γ-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer−Villiger oxidation. J Org Chem 71:9519–9521CrossRefPubMed Wang B, Shen YM, Shi Y (2006) Enantioselective synthesis of γ-aryl-γ-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer−Villiger oxidation. J Org Chem 71:9519–9521CrossRefPubMed
23.
go back to reference Yang MH, Chen YY, Huang L (1991) Studies on the chemical constituents of Clausena lansium (Lour.) Skeels. III. The structural elucidation of homo- and ζ- clausenamide. Chin Chem Lett 2:291–292 Yang MH, Chen YY, Huang L (1991) Studies on the chemical constituents of Clausena lansium (Lour.) Skeels. III. The structural elucidation of homo- and ζ- clausenamide. Chin Chem Lett 2:291–292
24.
go back to reference Yang L, Deng G, Wang DX, Huang ZT, Zhu JP, Wang MX (2007) Highly efficient and stereoselective N-vinylation of oxiranecarboxamides and unprecedented 8- endo-epoxy-arene cyclization: expedient and biomimetic synthesis of some Clausena alkaloids. Org Lett 9:1387–1390CrossRefPubMed Yang L, Deng G, Wang DX, Huang ZT, Zhu JP, Wang MX (2007) Highly efficient and stereoselective N-vinylation of oxiranecarboxamides and unprecedented 8- endo-epoxy-arene cyclization: expedient and biomimetic synthesis of some Clausena alkaloids. Org Lett 9:1387–1390CrossRefPubMed
25.
go back to reference Shen DY, Juang SH, Kuo PC, Huang GJ, Chan YY, Damu AG, Wu TS (2013) Chemical constituents from Andrographis echioides and their anti-inflammatory activity. Int J Mol Sci 14:496–514CrossRef Shen DY, Juang SH, Kuo PC, Huang GJ, Chan YY, Damu AG, Wu TS (2013) Chemical constituents from Andrographis echioides and their anti-inflammatory activity. Int J Mol Sci 14:496–514CrossRef
26.
go back to reference Lin J (1989) Cinnamamide derivatives from Clausena lansium. Phytochemistry 28:621–622CrossRef Lin J (1989) Cinnamamide derivatives from Clausena lansium. Phytochemistry 28:621–622CrossRef
27.
go back to reference Maneerat W, Ritthiwigrom T, Cheenpracha S, Laphookhieo S (2012) Carbazole alkaloids and coumarins from Clausena lansium roots. Phytochem Lett 5:26–28CrossRef Maneerat W, Ritthiwigrom T, Cheenpracha S, Laphookhieo S (2012) Carbazole alkaloids and coumarins from Clausena lansium roots. Phytochem Lett 5:26–28CrossRef
28.
go back to reference Kofinas C, Chinou I, Loukis A, Harvala C, Maillard M, Hostettmann K (1998) Flavonoids and bioactive coumarins of Tordilium apulum. Phytochemistry 48:637–641CrossRef Kofinas C, Chinou I, Loukis A, Harvala C, Maillard M, Hostettmann K (1998) Flavonoids and bioactive coumarins of Tordilium apulum. Phytochemistry 48:637–641CrossRef
29.
go back to reference Wu TS, Chan YY, Leu YL (1998) Sesquiterpenes from the root and stem of Aristolochia cucurbitafolia. J Nat Prod 61:511–514CrossRef Wu TS, Chan YY, Leu YL (1998) Sesquiterpenes from the root and stem of Aristolochia cucurbitafolia. J Nat Prod 61:511–514CrossRef
30.
go back to reference Ariza MR, Larsen TO, Petersen BO, Duus JØ, Barrero AF (2002) Penicillium digitatum metabolites on synthetic media and Citrus fruits. J Agric Food Chem 50:6361–6365CrossRefPubMed Ariza MR, Larsen TO, Petersen BO, Duus JØ, Barrero AF (2002) Penicillium digitatum metabolites on synthetic media and Citrus fruits. J Agric Food Chem 50:6361–6365CrossRefPubMed
31.
go back to reference Wu TS, Huang SC, Wu PL, Teng CM (1996) Carbazole alkaloids from Clausena excavata and their biological activity. Phytochemistry 43:133–140CrossRefPubMed Wu TS, Huang SC, Wu PL, Teng CM (1996) Carbazole alkaloids from Clausena excavata and their biological activity. Phytochemistry 43:133–140CrossRefPubMed
32.
go back to reference Vasskog T, Andersen JH, Hansen E, Svenson J (2012) Characterization and cytotoxicity studies of the rare 21:4 n-7 acid and other polyunsaturated fatty acids from the marine opisthobranch Scaphander lignarius, isolated using bioassay guided fractionation. Mar Drugs 10:2676–2690CrossRefPubMedPubMedCentral Vasskog T, Andersen JH, Hansen E, Svenson J (2012) Characterization and cytotoxicity studies of the rare 21:4 n-7 acid and other polyunsaturated fatty acids from the marine opisthobranch Scaphander lignarius, isolated using bioassay guided fractionation. Mar Drugs 10:2676–2690CrossRefPubMedPubMedCentral
33.
go back to reference Kuo PC, Yang ML, Hwang TL, Lai YY, Li YC, Thang TD, Wu TS (2013) Anti-inflammatory diterpenoids from Croton tonkinensis. J Nat Prod 76:230–236CrossRefPubMed Kuo PC, Yang ML, Hwang TL, Lai YY, Li YC, Thang TD, Wu TS (2013) Anti-inflammatory diterpenoids from Croton tonkinensis. J Nat Prod 76:230–236CrossRefPubMed
34.
go back to reference Wu TS, Huang SC, Wu PL (1996) Carbazole alkaloids from stem bark of Clausena excavata. Phytochemistry 43:1427–1429CrossRef Wu TS, Huang SC, Wu PL (1996) Carbazole alkaloids from stem bark of Clausena excavata. Phytochemistry 43:1427–1429CrossRef
35.
go back to reference Hargus JA, Fronczek FR, Vicente MGH, Smith KM (2007) Mono-(L)-aspartylchlorine-6. Photochem Photobiol 83:1006–1015CrossRefPubMed Hargus JA, Fronczek FR, Vicente MGH, Smith KM (2007) Mono-(L)-aspartylchlorine-6. Photochem Photobiol 83:1006–1015CrossRefPubMed
36.
go back to reference Cheng HH, Wang HK, Ito J, Bastow KF, Tachibana Y, Nakanishi Y, Xu Z, Luo TY, Lee KH (2001) Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum. J Nat Prod 64:915–919CrossRefPubMed Cheng HH, Wang HK, Ito J, Bastow KF, Tachibana Y, Nakanishi Y, Xu Z, Luo TY, Lee KH (2001) Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum. J Nat Prod 64:915–919CrossRefPubMed
37.
go back to reference Wu PL, Lin FW, Wu TS, Kuoh CS, Lee KH, Lee SJ (2004) Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. Chem Pharm Bull 52:345–349CrossRefPubMed Wu PL, Lin FW, Wu TS, Kuoh CS, Lee KH, Lee SJ (2004) Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. Chem Pharm Bull 52:345–349CrossRefPubMed
38.
go back to reference Machida K, Kikuchi M (1996) Norisoprenoids from Viburnum dilatatum. Phytochemistry 41:1333–1336CrossRef Machida K, Kikuchi M (1996) Norisoprenoids from Viburnum dilatatum. Phytochemistry 41:1333–1336CrossRef
39.
go back to reference Macías FA, Lacret R, Varela RM, Nogueiras C, Molinillo JMG (2008) Bioactive apocarotenoids from Tectona grandis. Phytochemistry 69:2708–2715CrossRefPubMed Macías FA, Lacret R, Varela RM, Nogueiras C, Molinillo JMG (2008) Bioactive apocarotenoids from Tectona grandis. Phytochemistry 69:2708–2715CrossRefPubMed
40.
go back to reference Adam W, Zhang A (2004) High π-facial selectivity through chelation of magnesium ions in the DMD epoxidation of α, β-unsaturated imides with chiral pyrrolidinone auxiliaries. Eur J Org Chem 2004:147–152CrossRef Adam W, Zhang A (2004) High π-facial selectivity through chelation of magnesium ions in the DMD epoxidation of α, β-unsaturated imides with chiral pyrrolidinone auxiliaries. Eur J Org Chem 2004:147–152CrossRef
41.
go back to reference Chen YR, Yang MH, Liu GT, Huang L (1989) 2,3-Dihydroxy-3-phenyl-N-(2-phenylethyl)- propionic acid amides derivatives thereof. US Patent 04826873 Chen YR, Yang MH, Liu GT, Huang L (1989) 2,3-Dihydroxy-3-phenyl-N-(2-phenylethyl)- propionic acid amides derivatives thereof. US Patent 04826873
Metadata
Title
Constituents from the leaves of Clausena lansium and their anti-inflammatory activity
Authors
De-Yang Shen
Ping-Chung Kuo
Shiow-Chyn Huang
Tsong-Long Hwang
Yu-Yi Chan
Po-Chuen Shieh
Nguyen Thi Ngan
Tran Dinh Thang
Tian-Shung Wu
Publication date
01-01-2017
Publisher
Springer Japan
Published in
Journal of Natural Medicines / Issue 1/2017
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-016-1033-x

Other articles of this Issue 1/2017

Journal of Natural Medicines 1/2017 Go to the issue