Aristolactams from roots of Ottonia anisum (Piperaceae)

Natural Product Communications

Volumn 6, Issue 7, 2011, Pages 939-942

  Marques, André M ^a   Velozo, Leosvaldo S M ^a   Moreira, Davyson De L ^b   Guimarães, Elsie F ^c   Kaplan, Maria Auxiliadora C ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

^c INSTITUTO DE PESQUISAS JARDIM BOTÂNICO DO RIO DE JANEIRO   (Brazil)

Author keywords

Alkaloids; Aristolactams; Ottonia anisum; Piperaceae

Indexed keywords

ARISTOLACTAM AII; ARISTOLACTAM BIII; ARISTOLOLACTAM; ARISTOLOLACTAM BII; GONIOTHALACTAM; PIPEROLACTAM C; PLANT MEDICINAL PRODUCT; STIGMALACTAM; UNCLASSIFIED DRUG;

ARTICLE; BIOCHEMICAL COMPOSITION; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; MASS FRAGMENTOGRAPHY; OTTONIA ANISUM; PHYTOCHEMISTRY; PIPERACEAE; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

PIPERACEAE;

EID: 80052882604     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1100600704     Document Type: Article

References (34)

1. (a) Yunker TG. (1972) The Piperacee of Brazil. Hoehnea, 2, 19-366;
2. rd Ed., UFV, Viçosa, MG;
3. (c) Guimarães EF, Giordano LCS. (2004) Piperaceae do Nordeste brasileiro I: estado do Ceará. Rodriguesia, 55, 21-46.
4. (a) Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, Tyagi OD, Prasad AK, Wengel J, Olsen CE, Boll PM. (1997) Phytochemistry of the genus Piper. Phytochemistry, 46, 597-673;
5. (b) Antunes PA, Chierice GO, Constantino CJL, Aroca RF. (2001) Spectroscopic characterization of N-isobutyl-6-(p-methoxyphenyl)-2E,4E- hexedieneamide extracted from Ottonia propinqua. Vibrational Spectroscopy, 27, 175-181;
6. (c) Salazar KJM, Paredes GED, Lluncor LR, Young MCM, Kato MJ. (2005) Chromenes of polyketide origin from Peperomia villipetiola. Phytochemistry, 66, 573-579;
7. (d) Naumov P, Dragull K, Yoshioka M, Tang Chung-Shih, Ng SW. (2008) Structural characterization of genuine (-)-pipermethystine, (-)- epoxypipermethystine, (+)-dihydromethysticin and yangonin from the kava plant (Piper methysticum). Natural Product Communications, 3, 1333-1336;
8. (e) Ferreira MGPR, Kayano AM, Silva-Jardim I, Silva TO, Zuliani JP, Facundo VA, Calderon LA, Almeida-e-Silva A, Ciancaglini P, Stábeli RG. (2010) Antileishmanial activity of 3-(3,4,5-trimethoxyphenyl) propanoic acid purified from Amazonian Piper tuberculatum Jacq., Piperaceae, fruits. Revista Brasileira de Farmacognosia, 29, 3910-3913.
9. (a) Moreira DL, Guimarães EF, Kaplan MAC. (1998) Non-polar constituents from Piper lhotzkyanum. Phytochemistry, 49, 1054-1057;
10. (b) Moreira DL, Guimarães EF, Kaplan MAC. (2000) A C-glucosylflavone from Leaves of Piper lhotzkyanum. Phytochemistry, 55, 783-786;
11. (c) Velozo LS M, Ferreira MJP, Santos MIRS, Moreira DL, Emerenciano VP, Kaplan MAC. (2006) Unusual chromenes from Peperomia blanda. Phytochemistry, 67, 492-496. (Pubitemid 43213054)
12. Marques AM, Velozo LSM, Guimarães EF, Kaplan MAC. (2008) Caracterização de derivado arilbutanoídico em folhas e raízes de Ottonia anisum Sprengel. Revista Brasileira de Farmacognosia, 18, 709-712.
13. Kim JK, Kim YH, Nam HT, Kim BT, Heo JN. (2008) Total synthesis of aristolactams via a one-pot Suzuki-Miyaura Coupling/Aldol condensation Cascade reaction. Organic Letters, 10, 3543-3546.
14. (a) Desai SJ, Chaturvedi R, Mulchandani NB. (1990) Piperolactam D, a new aristolactam from indian Piper species. Journal of Natural Products, 53, 496-497;
15. (b) Mix DB, Guinaudeau H, Shamma M. (1982) The aristolochic acids and aristolactams. Journal of Natural Products, 45, 657-666. (Pubitemid 13180942)
16. (a) Tabopda TK, Ngoupayo J, Liu J, Anne-Claire Mitaine A. (2008) Bioactive aristolactams from Piper umbellatum. Phytochemistry, 69, 1726-1731;
17. (b) Chia YC, Chang FR, Teng CM, Wu YC. (2000) Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii. Journal of Natural Products, 63, 1160-1163;
18. (c) Wu PL, Su GC, Wu TS. (2003) Constituents from the stems of Aristolochia manshuriensis. Journal of Natural Products, 66, 996-998;
19. (d) Kumar V, Prasad AK, Parmar VS. (2003) Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities. Natural Products Reports, 20, 565-583;
20. (a) Sun NJ, Antoun M, Hang CJ, Cassadyx JM. (1987) New cytotoxic aristolactams from Pararistolochia flos-avis. Journal of Natural Products, 50, 843-846;
21. (b) Jinbin Y, Qian L, Weifeng Z, Li D, Fei T, Shouzhuo Y. (2008) Simultaneous analysis of six aristolochic acids and five aristolactams in herbal plants and their preparations by high-performance liquid chromatography-diode array detection-fluorescence detection. Journal of Chromatography A, 1182, 85-92;
22. (c) Tao CH, Ahmed M, Kang SS, Waller DP, Bingel AS, Lankin DC, Cordell GA, Soejarto DD, Fong HH. (1984) Studies on Aristolochia III. Isolation and biological evaluation of constituents of Aristolochia Indica roots for fertility-regulating activity. Journal of Natural Products, 47, 331-341;
23. (d) Stiborova M, Frei E,Wiessler M, Schmeiser HH. (2001) Human enzymes involved in the metabolic activation of carcinogenic aristolochic acids: Evidence for reductive activation by cytochromes P450 1A1 and 1A2. Chemical Research in Toxicology, 14, 1128-1137;
24. (e) Nguyen NT, Pham VC, Litaudon M, Gueritte F, Grellier F, Nguyen VT, Nguyen VH. (2008) Antiplasmodial alkaloids from Desmos rostrata. Journal of Natural Products, 71, 2057-2059.
25. (a) Chia YC, Chang FR, Teng CM, Wu YC. (2000) Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii. Journal of Natural Products, 63, 1160-1163;
26. (b) Mix DB, Guinaudeau H, Shamma M. (1982) The aristolochic acids and aristolactams. Journal of Natural Products, 45, 657-666;
27. (c) Sun NJ, Antoun M, Hang CJ, Cassadyx JM. (1987) New cytotoxic aristolactams from Pararistolochia flos-avis. Journal of Natural Products, 50, 843-846.
28. (a) Attaluri S, Bonala RR, Yang Y, Lukin M, Wen Y, Grollman AP, Moriya M, Johnson F. (2010) DNA adducts of aristolochic acid II: total synthesis and site-specific mutagenesis studies in mammalian cells. Nucleic Acids Research, 38, 339-352;
29. (b) Yuana J, Luo X, Guo M, Wu J, Yang W. (2009) Determination of aristolochic acid I and its metabolites in cell culture with a hyphenated high-performance liquid chromatographic technique for cell toxicology. Talanta, 78, 1141-1147;
30. (c) Elban MA, Chapuis JC, Li M, Hecht SM. (2007) Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines. Bioorganic Medicinal Chemistry Letters, 15, 6119-6125;
31. (d) wolfgang Pfau W, Schmeiser HH, Wiessler M. (1991) N6-Adenyl arylation of DNA by aristolochic acid II and a synthetic model for the putative proximate carcinogen. Chemical Research in Toxicoloy, 4, 581- 586;
32. (e) Desai SJ, Chaturvedi R, Mulchandani NB. (1990) Piperolactam D, a new aristolactam from indian Piper species. Journal of Natural Products, 53, 496-497;
33. (f) Couture A, Deniau E, Grandclaudon P, Rosen HR, Leonce S, Pfeiffer B, Renard P. (2002) Synthesis and biological evaluation of aristolactams. Bioorganic Medicinal Chemistry Letters, 12, 3557-3559. (Pubitemid 35346488)
34. Choi YL, Kim JK, Choi SU, Min YK, Myung BA, Kim BT, Heo JN. (2009) Synthesis of aristolactam analogues and evaluation of their antitumor activity. Bioorganic Medicinal Chemistry Letters, 19, 3036-3040.