Abstract
From the leaves and bark of Zanthoxylum monophyllum, a new lignan, 3-methoxy-3′,4′-methylenedioxylignan-4,8,9,9′-tetraol (1), has been isolated along with 22 known compounds (2–23), fifteen of them reported for the first time from Z. monophyllum. Their chemical structures were elucidated using detailed spectroscopic studies and
chemical analysis. All compounds were evaluated for antimicrobial and antiprotozoal
activities. Alkaloids bis-[6-(5,6-dihydro-chelerythrinyl)] ether (2) and 6-ethoxy-chelerythrine (4) exhibited strong activity against Aspergillus fumigatus and methicillin-resistant Staphylococcus aureus (MRSA). Compound 4-methoxy-N-methyl-2-quinolone (9) exhibited significant activity against MRSA (IC50 value of 8.0 µM) while compound 5,8,4′-trihydroxy-3,7,3′-trimethoxyflavone (10) showed weak activity against Plasmodium falciparum.
Key words
Zanthoxylum monophyllum
- Rutaceae - lignans - alkaloids - antimicrobial - antimalarial activities
References
- 1 Little Jr E L, Wadsworth F H. Rue family (Rutaceae). Common trees of Puerto Rico
and the Virgin Islands; Agricultural handbook No. 249. Washington; U.S. Department
of Agriculture, Forest Service, U.S. Government Printing Office 1964: 232-233
- 2
De Garcia L A, Calle J, Reguero M T, Joseph-Nathan P.
Phytochemical study of Zanthoxylum monophyllum.
Fitoterapia.
1989;
60
447-450
- 3
Stermitz F R, Sharifi I A.
Alkaloids of Zanthoxylum monophyllum and Z. punctatum.
Phytochemistry.
1977;
16
2003-2006
- 4
Stermitz F R, Caolo M A, Swinehart J A.
Alkaloids and other constituents of Zanthoxylum williamsii, Z. monophyllum, and Z. fagara.
Phytochemistry.
1980;
19
1469-1472
- 5
Cuca S L E, Martinez V J C, Delle Monache F.
Constituyentes químicos de Zanthoxylum monophyllum.
Rev Col Quím.
1998;
27
17-27
- 6
MacRae W D, Tower G H N.
Biological activities of lignans.
Phytochemistry.
1984;
23
1207-1220
- 7
Bastos J K, Carvalho J C T, De Souza G H B.
Antiinflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo.
J Ethnopharmacol.
2001;
75
279-282
- 8
Borsato M L C, Grael C F F, Souza G E P, Lopes N P.
Analgesic activity of the lignans from Lychnophora ericoides.
Phytochemistry.
2000;
55
809-813
- 9
Achenbach H, Waibel R, Addae-Mensah I.
Lignans and other constituents from Carissa edulis.
Phytochemistry.
1983;
22
749-753
- 10
Son J K, Lee S H, Nagarapu L, Jahng Y.
A simple synthesis of nordihydroguaiaretic acid and its derivatives.
Bull Korean Chem Soc.
2005;
26
1117-1120
- 11
Dostál J, Táborská E, Slavík J, Potáček M, De Hoffmann E.
Structure of chelerythrine base.
J Nat Prod.
1995;
58
723-729
- 12
Mitscher L A, Park Y H, Clark D, Clark III G W.
Antimicrobial agents from higher plants. An investigation of Hunnemannia fumariaefolia pseudoalcoholates of sanguinarine and chelerythrine.
Lloydia.
1978;
41
145-150
- 13
Bernhard H O, Thiele K.
Isolierung von (±)-Tembamid aus Zanthoxylum tingoassuiba L. (Rutaceae).
Helv Chim Acta.
1978;
61
2269-2272
- 14
Chen C H, Chen T M, Lee C.
Thalifaurine and dehydrodiscretine, new quaternary protoberberines from Thalictrum fauriei.
J Pharm Sci.
1980;
69
1061-1065
- 15
Hussain R A, Kim J, Beecher C W W, Kinghorn A D.
Unambiguous carbon-13 NMR assignments of some biologically active protoberberine alkaloids.
Heterocycles.
1989;
29
2257-2260
- 16
He W, Van Puyvelde L, De Kimpe N, Verbreuggen L, Anthonissen K, Van der Flaas M, Bosselaers J,
Mathenge S G, Mudida F P.
Chemical constituents and biological activities of Zanthoxylum usambarense.
Phytother Res.
2002;
16
66-70
- 17
Coppola G M, Kahle A D, Shapiro M J.
Carbon-13 NMR investigation of some heteroring substituted 2- and 4-quinolone systems.
Org Magn Reson.
1981;
17
242-245
- 18
Horie T, Ohtsuru Y, Shibata K, Yamashita K, Tsikamaya M, Kawamura Y.
13C NMR spectral assignment of the A-ring of polyoxygenated flavones.
Phytochemistry.
1998;
47
865-874
- 19
Rao G N, Kumar P M, Hayashi T.
Constituents of Cassia auriculata.
Fitoterapia.
2000;
71
82-83
- 20
Okunda A L, Wiemer D F.
(−)-Loliolide, an ant-repellent compound from Zanthoxylum stulosum.
J Nat Prod.
1985;
48
472-473
- 21
Hisamichi S, Yoshizaki F, Kondo Y.
Studies on the Shikon. The colorless substances isolated from Lithospermum erythrorhizon Sieb. et Zucc.
Shoyakugaku Zasshi.
1982;
365
170-172
- 22
Marcos M, Jimenez C, Villaverde M C, Riguera R, Castedo L, Stremitz F.
Lignans and other constituents from south and central American Zanthoxylum species.
Planta Med.
1990;
56
89-91
- 23
Bickii J, Tchouya G R, Tchouankeu J C, Tsamo F.
Antiplasmodial agents of the stem bark of Entandrophragma angolense (Meliacea).
Afr J Tradit Complement Alternat Med.
2007;
4
135-139
- 24
Baharate S B, Khan S I, Yunus N A, Chaulhe S K, Jacob M R, Tekwani B.
Antiprotozoal and antimicrobial activites of O-alkylated and formylated acylphloroglucinols.
Bioorg Med Chem.
2007;
15
87-96
- 25
Radwan M M, Manly S P, Ross S A.
Two new sulfated sterols from the marine sponge Lendenfeldia dendyi.
Nat Prod Commun.
2007;
2
901-903
Prof. Dr. Samir A. Ross
National Center for Natural Products Research and Department of Pharmacognosy
School of Pharmacy, The University of Mississippi
University, MS 38677
USA
Phone: +1 66 29 15 10 31
Fax: +1 66 29 15 79 89
Email: sross@olemiss.edu
