Planta Med 2014; 80(06): 498-501
DOI: 10.1055/s-0034-1368352
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antimycobacterial Furofuran Lignans from the Roots of Anemopsis californica

Robert O. Bussey III
1   Department of Chemistry and Biochemistry, University of North Carolina Greensboro, Greensboro, NC, USA
,
Arlene A. Sy-Cordero
1   Department of Chemistry and Biochemistry, University of North Carolina Greensboro, Greensboro, NC, USA
,
Mario Figueroa
2   Facultad de Química, Universidad Nacional Autónoma de México, Mexico DF, Mexico
,
Fredrick S. Carter
1   Department of Chemistry and Biochemistry, University of North Carolina Greensboro, Greensboro, NC, USA
,
Joseph O. Falkinham III
3   Department of Biological Sciences and Virginia Tech Center for Drug Discovery and Development, Virginia Tech., Blacksburg, VA, USA
,
Nicholas H. Oberlies
1   Department of Chemistry and Biochemistry, University of North Carolina Greensboro, Greensboro, NC, USA
,
Nadja B. Cech
1   Department of Chemistry and Biochemistry, University of North Carolina Greensboro, Greensboro, NC, USA
› Author Affiliations
Further Information

Publication History

received 25 November 2013
revised 19 February 2014

accepted 24 February 2014

Publication Date:
31 March 2014 (online)

Abstract

Topical preparations of Anemopsis californica have been used by Native American tribes in the southwestern United States and northern Mexico to treat inflammation and infections. We report results of bioassay-guided isolation conducted on a sample of A. californica roots. The furofuran lignans sesamin (1) and asarinin (2) were isolated and shown to have MIC values ranging from 23 to 395 µM against five different species of environmental nontuberculous mycobacteria. These findings are significant given that these bacteria can cause skin, pulmonary, and lymphatic infections. Crude A. californica extracts were analyzed by liquid chromatography-mass spectrometry, and it was determined that sesamin and asarinin were extracted at relatively high levels from the roots (1.7–3.1 g/kg and 1.1–1.7 g/kg, respectively), but at lower levels from the leaves (0.13 g/kg for both compounds). Our findings suggest that the majority of activity of crude A. californica root extracts against nontuberculous mycobacteria can be attributed to the presence of sesamin and asarinin. This paper is the first to report the isolation of these compounds from a member of the Saururaceae family, and the first to describe their activity against nontuberculous mycobacteria.

Supporting Information

 
  • References

  • 1 Newman DJ, Cragg GM. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod 2012; 75: 311-335
  • 2 Train P, Henrichs JR, Archer WA. Medicinal uses of plants by Indian tribes of Nevada (Bioactive plants, Vol. 1). Quarterman Publications: Lawrence; 1978: 19-20
  • 3 Curtin LSM. By the prophet of the earth: ethnobotany of the Pima. Tucson: University of Arizona Press; 1984: 156
  • 4 Romero JB. The botanical lore of the California Indians. New York: Vintage Press; 1954: 15
  • 5 Bocek BR. Ethnobotany of Costanoan Indians, California, based on collections by John P. Harrington. Econ Bot 1984; 38: 240-255
  • 6 Medina AL, Lucero ME, Holguin FO, Estell RE, Posakony JJ, Simon J, OʼConnell MA. Composition and antimicrobial activity of Anemopsis californica leaf oil. J Agric Food Chem 2005; 53: 8694-8698
  • 7 Dimayuga RE, Garcia SR. Antimicrobial screening of medicinal plants from Baja California Sur, Mexico. J Ethnopharmacol 1991; 31: 181-192
  • 8 Medina-Holguin AL, Micheletto S, Holguin FO, Rodriguez J, OʼConnell MA. Environmental influences on essential oils in roots of Anemopsis californica . Hortscience 2007; 42: 1578-1583
  • 9 Medina-Holguin AL, Holguin FO, Micheletto S, Goehle S, Simon JA, OʼConnell MA. Chemotypic variation of essential oils in the medicinal plant, Anemopsis californica . Phytochemistry 2008; 69: 919-927
  • 10 Kaminski CN, Ferrey SL, Lowrey T, Guerra L, Van Slambrouck S, Steelant WFA. In vitro anticancer activity of Anemopsis californica . Oncol Lett 2010; 1: 711-715
  • 11 Daniels AL, Van Slambrouck S, Lee RK, Arguello TS, Browning J, Pullin MJ, Kornienko A, Steelant WF. Effects of extracts from two Native American plants on proliferation of human breast and colon cancer cell lines in vitro . Oncol Rep 2006; 15: 1327-1331
  • 12 Timbrook J. Virtuous herbs: plants in Chumash medicine. J Ethnobiol 1987; 7: 171-180
  • 13 Falkinham III JO. Nontuberculous mycobacteria from household plumbing of patients with nontuberculous mycobacteria disease. Emerg Infect Dis 2011; 17: 419-424
  • 14 De Groote MA, Pace NR, Fulton K, Falkinham III JO. Relationships between Mycobacterium isolates from patients with pulmonary mycobacterial infection and potting soils. Appl Environ Microbiol 2006; 72: 7602-7606
  • 15 Billinger ME, Olivier KN, Viboud C, Montes de Oca R, Steiner C, Holland SM, Prevots DR. Nontuberculous mycobacteria-associated lung disease, United States in hospitalized persons, 1998–2005. Emerg Infect Dis 2009; 15: 1562-1569
  • 16 Griffith DE, Aksamit T, Brown-Elliott BA, Catanzaro A, Daley C, Gordin F, Holland SM, Horsburgh R, Huitt G, Iademarco MF, Iseman M, Olivier K, Ruoss S, von Reyn CF, Wallace RJ, Winthrop K, Subcommittee AMD. An official ATS/IDSA statement: diagnosis, treatment, and prevention of nontuberculous mycobacterial diseases. Amer J Resp Critical Care Med 2007; 175: 367-416
  • 17 Collier SA, Stockman LJ, Hicks LA, Garrison LE, Zhou FJ, Beach MJ. Direct healthcare costs of selected diseases primarily or partially transmitted by water. Epidemiol Infect 2012; 140: 2003-2013
  • 18 Bussey III RO, Cech NB, Sy-Cordero AA, Falkinham JO, Oberlies NH. Sesamin from the roots of Yerba mansa (Anemopsis californica). Planta Med 2012; 78: 1111
  • 19 Li CY, Chow TJ, Wu TS. The epimerization of sesamin and asarinin. J Nat Prod 2005; 68: 1622-1624
  • 20 Tocher JF. Isolation of another substance from sesame oil. Amer J Pharm 1891; 63: 143-146
  • 21 Haller HL, LaForge FB, Sulivan WN. Some compounds related to sesamin: their structures and their synergistic effect with pyrethrum insecticides. J Org Chem 1942; 7: 185-188
  • 22 Nissanka APK, Karunaratne V, Bandara BMR, Kumar V, Nakanishi T, Nishi M, Inada A, Tillekeratne LMV, Wijesundara DSA, Gunatilaka AAL. Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum . Phytochemistry 2001; 56: 857-861
  • 23 Eberhard EG. Prickly ash bark. Am J Pharm 1890; 71: 231-236
  • 24 Christov R, Bankovaa V, Tsvetkova I, Kujumgiev A, Delgado Tejerac A. Antibacterial furofuran lignans from Canary Islands propolis. Fitoterapia 1999; 70: 89-92
  • 25 Yang GZ, Hu Y, Yang B, Chen Y. Lignans from the bark of Zanthoxylum planispinum . Helv Chim Acta 2009; 92: 1657-1664
  • 26 Zloh M, Gibbons S. The role of small molecule-small molecule interactions in overcoming biological barriers for antimicrobial drug action. Theor Chem Acc 2007; 117: 231-238
  • 27 Rangkaew N, Suttisri R, Moriyasu M, Kawanishi K. A new acyclic diterpene acid and bioactive compounds from Knema glauca . Arch Pharmacal Res 2009; 32: 685-692
  • 28 Gu JQ, Graf TN, Lee D, Chai HB, Mi Q, Kardono LB, Setyowati FM, Ismail R, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kroll DJ, Falkinham III JO, Wall ME, Wani MC, Kinghorn AD, Oberlies NH. Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. J Nat Prod 2004; 67: 1156-1161
  • 29 Beggs ML, Crawford JT, Eisenach KD. Isolation and sequencing of the replication region of Mycobacterium avium plasmid pLR7. J Bacteriol 1995; 177: 4836-4840
  • 30 Falkinham JO, Macri RV, Maisuria BB, Actis ML, Sugandhi EW, Williams AA, Snyder AV, Jackson FR, Poppe MA, Chen L, Ganesh K, Gandour RD. Antibacterial activities of dendritic amphiphiles against nontuberculous mycobacteria. Tuberculosis 2011; 92: 173-181
  • 31 Sugandhi EW, Macri RV, Williams AA, Kite BL, Slebodnick C, Falkinham III JO, Esker AR, Gandour RD. Synthesis, critical micelle concentrations, and antimycobacterial properties of homologous, dendritic amphiphiles. Probing intrinsic activity and the “cutoff” effect. J Med Chem 2007; 50: 1645-1650