Profiling of the resin glycoside content of Mexican Jalap roots with purgative activity

Journal of Natural Products

Volumn 69, Issue 10, 2006, Pages 1460-1466

  Pereda Miranda, Rogelio ^a   Fragoso Serrano, Mabel ^a   Escalante Sánchez, Edgar ^a   Hernández Carlos, Beatriz ^a   Linares, Edelmira ^b   Bye, Robert ^b  

^a Universidad Nacional Autonoma de Mexico Facultad de Quimica   (Mexico)

^b DEPARTAMENTO DE ZOOLOGÍA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; IPOMOEA ORIZABENSIS EXTRACT; IPOMOEA PURGA EXTRACT; IPOMOEA STANS EXTRACT; LAXATIVE; OPERCULINIC ACID B; PLANT EXTRACT; PURGIC ACID A; PURGIC ACID B; RESIN; SCAMMONIC ACID A;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IPOMOEA; IPOMOEA ORIZABENSIS; IPOMOEA PURGA; IPOMOEA STANS; MEDICINAL PLANT; METHYLATION; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; QUALITY CONTROL; SAPONIFICATION;

CATHARTICS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOSIDES; IPOMOEA; MEDICINE, TRADITIONAL; MEXICO; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT ROOTS; PLANTS, MEDICINAL; RESINS, PLANT;

CONVOLVULACEAE; CONVOLVULUS SCAMMONIA; IPOMOEA; IPOMOEA ORIZABENSIS; IPOMOEA PURGA; IPOMOEA STANS;

EID: 33845474326     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np060295f     Document Type: Article

References (41)

1. Dr. Francisco Hernández (1515-1587), King Phillip II's chief medical officer in the Spanish colonies in the New World (1570-1577), was the first trained scientist to gather ethnobotanical information directly from Aztec healers and to assess the medicinal usefulness of the natural resources found in the highland central area of Mexico. He described the properties of the "cacamótic tlanoquiloni" or purgative potatoes (Mexican jalap roots) as being "benign remedies" to purge the stomach "with wonderful gentleness and safety, and furthermore they remove bilious and other humors from the veins". Selective sections in English from his The Natural History of New Spain can be found in: Hernández, F. The Mexican Treasury: the Writings of Dr. Francisco Hernández; Varey, S., Ed.; Stanford University Press: Stanford, CA, 2000; pp 117-156.
2. Hernández, F. Historia Natural de Nueva España; Universidad Nacional Autónoma de México: Mexico City, 1959; Vol. II, pp 133-135.
3. A medicinal plant complex consists of an assemblage of herbal drugs that are taxonomically different at the specific, generic, and/or familial level but that share (a) one or more key morphological features; (b) a common name; (c) certain organoleptic characteristics; and (d) at least one therapeutic application. Within the complex, usually one species (called dominant or signature) is considered to have the most effective properties and is widely employed and distributed beyond its natural geographic range. Subordinate species are those considered to be of lesser quality and usually applied when the dominant species is not available, but they are not necessarily adulterants. For some examples in Mexico and the adjacent United States, see: Linares, E.; Bye, R. J. Ethnopharmacol. 1987, 19, 153-183.
4. Valdés, J.; Flores, H. In Francisco Hernández. Obras Completas; Universidad Nacional Autónoma de México: Mexico City, 1985; Vol. VII, pp 9-222.
5. Purgatives along with diaphoretics, diuretics, and emetics were basic attributes of prehispanic herbal remedies since the Aztecs viewed diseases as being caused by phlegm that needed to be discharged. For Aztec medicinal concepts and practices, see: Ortiz de Montellano, B. R. Aztec Medicine, Health, and Nutrition; Rutgers University Press: New Brunswick, NJ, 1990; pp 189-192.
6. (a) Gunther, R. T. The Greek Herbal of Dioscorides; Hafner: New York, 1968; p 571.
7. (b) von Bingen, H. Hildegard's Healing Plants: from her Medieval Classic Physica; Beacon: Boston, 2001; p 177.
8. Gerard, J. The Herbal or General History of Plants; Dover: New York, 1975; pp 866-869.
9. Libellus de Medicinalibus Indorum Herbis (Little Book of Indian Medicinal Herbs) is a treasury of Aztec herbal remedies and the first medical text known to have been written in the New World. The author of this valuable document was Martín de la Cruz, an Aztec physician, who originally dictated it in Nahuatl, the language of the Aztecs, and which was later translated into Latin by the Aztec nobleman Juan Badiano in 1552. One illustration in this herbal (Folio 32 recto) represents a bindweed called "Uelicpahtli" (Nahuatl language, uelic = savory, pahtli = medicine). It appears as a red-flowered Ipomoea with a large tuberous root. The legend accompaning this miniature reads "purgatio ventris" (purging the abdomen). Its therapeutical descriptions is similar to that given by Dr. Francisco Hernández for the "cacamótic tlanoquiloni", suggesting it is the jalap root (I. purga). For transcription, translation, and contemporary botanical interpretations of this centuries-old Aztec remedy, see: (a) Emmart, E. W. The Badianus Manuscript (Codex Barberini, Latin 241). An Aztec Herbal of 1552; The Johns Hopkins Press: Baltimore, 1940; p 260.
10. (b) Gates, W. An Aztec Herbal. The Classic Codex of 1552; Dover: New York, 2000; p 55.
11. (c) Miranda, F.; Valdés, J. In Libellus de Medicinalibus Indorum Herbis; Instituto Mexicano del Seguro Social: Mexico City, 1964; pp 243-282.
12. (a) Williams, L. O. Econ. Bot. 1970, 24, 399-401.
13. (b) Comisión Permanente de la Farmacopea de los Estados Unidos Mexicanos. Extrafarmacopea Herbolaria de los Estados Unidos Mexicanos; Secretaría de Salud: Mexico City, 2001; pp 18-19.
14. (a) Noriega, J. M. Curso de Historia de Drogas; Instituto Médico Nacional: Mexico City, 1902; pp 372-373.
15. (b) Herrera, A. L. Farmacopea Latino-Americana; Herrero Hermanos: Mexico City, 1921; pp 658-659.
16. The root of "tumbavaquero", a Spanish composite word that literally means "knock the cowboy over" or "cowboy stunner", is used in combination with orange flowers (Citrus sinensis), "flor de manita" (hand flower, Chiranthodendron pectadactylon), heart flower (Talauma mexicana), "palo brasil" (logwood, Haematoxylum brasiletto), "salvia de bolita" (butterfly bush, Buddleja perfoliata), and tila flower (Ternstroemia spp.); one cup of the infusion to be drunk in the morning and at night. For origin and description of this herbal drug, see: Linares, E.; Bye, R.; Flores, B. Medicinal Plants of Mexico: Traditional Uses and Remedies; Instituto de Biología, Universidad Nacional Autónoma de México: Mexico City, 1999; pp 118-119.
17. Martínez, M. Las Plantas Medicinales de México; Ediciones Botas: Mexico City, 1989; pp 276-279.
18. The recommended dosages of jalap root (to a liter of water) are 1-3 g if a powder, 0.2-0.4 g if an extract, 0.1-0.6 g if a resin, and 10 to 20 drops every 4 h if a tincture; if given in sugar or jelly, this remedy is a safe purge for children. A teaspoon of the root, cut small or granulated, to a cup of boiling water. For preparation of home remedies, see: http://electrocomm.tripod. com/jalapa-jalapa.html.
19. In the 1940s, the Xico region in Veracruz cultivated and exported about 40 tons of dried jalap root (I. purga) to the United States per year, maintaining this level up to the 1990s, after which it dwindled to nearly zero. However, the use of wild I. orizabensis as a substitute for cultivated jalap root has never been documented, so no official trade records exist, although in pharmaceutical commerce it is currently available as liquid alcoholic extracts and resin. The commercial demand for jalap roots has declined in Mexico due to the use of other laxatives derived from psyllium fruits (Plantago spp.) and cassia leaves (Senna spp.) as well as the domination of the world market by Italian and German herbal drug traders who import resins of the Brazilian jalap (I. operculata). For the traditional production system of jalap root, see: Linajes, A.; Rico-Gray, V.; Carrión, G. Econ. Bot. 1994, 48, 84-89.
20. Davidow, J. Infusions of Healing. A Treasury of Mexican-American Herbal Remedies; Fireside: New York, 1999; pp 134-135.
21. The attempts of taxonomists to classify the diversity of Mexican jalaps has resulted in considerable confusion in both the commercial names and the scientific nomenclature. In addition, other plants were used as "jalap" and employed as substitutes or adulterants; they included Phytolacca octandra L. and Mirabilis jalapa L., species totally unrelated taxonomically to Ipomoea.
22. Pereda-Miranda, R.; Bah, M. Curr. Top. Med. Chem. 2003, 3, 111-131.
23. (a) Hernández-Carlos, B.; Bye, R.; Pereda-Miranda, R. J. Nat. Prod. 1999, 62, 1096-1100.
24. (b) Pereda-Miranda, R.; Hernández-Carlos, B. Tetrahedron 2002, 58, 3145-3154.
25. High-purity oligosaccharides are required for structure elucidation by NMR or MS and for use as substrates to determine their biological activity. For an example of the biological activities of oligosaccharides, see; Pereda-Miranda, R.; Kaatz, G. W.; Gibbons, S. J. Nat. Prod. 2006, 69, 406-409.
26. A mixture of minor glycosidic acids, differing from the major saponification product in having a substitution or elimination of one sugar unit in the oligosaccharide core, has also been obtained. For examples, see: (a) Bah, M.; Pereda-Miranda, R. Tetrahedron 1996, 52, 13063-13080.
27. (b) Bah, M.; Pereda-Miranda, R. Tetrahedron 1997, 53, 9007-9022.
28. (c) Pereda-Miranda, R.; Escalante-Sánchez, E.; Escobedo-Martínez, C. J. Nat. Prod. 2005, 68, 226-230.
29. (d) Chérigo, L.; Pereda-Miranda, R. J. Nat. Prod. 2006, 69, 595-599.
30. Neue, U. D. HPLC Columns. Theory, Technology, and Practice; Wiley-VCH: New York, 1997; pp 217-223.
31. The chromatographic mode is partition, and retention time increases with the polarity of the analyte and decreases with the polarity of the mobile phase.
32. I. orizabensis yields 10-18% of resin glycosides; root of "tumbava-quero" (I. stans) < 1%.
33. (a) Reynolds, W. F.; Yu, M.; Enríquez, R. G.; González, H.; León, I.; Magos, G.; Villarreal, M. L. J. Nat. Prod. 1995, 58, 1730-1734.
34. (b) León, I.; Enríquez, R. G.; Gnecco, D.; Villarreal, M. L.; Cortés, D. A.; Reynolds, W. F.; Yu, M. J. Nat. Prod. 2004, 67, 1552-1556.
35. The voucher cited identifies the specimen used for chemical investigations as Ipomoea stans Cav. (IMSSM voucher 2691). This material was collected on June 18, 1982, from Km 93 on the Puebla-Orizaba Highway, Mexico. Confusion arises because it is not clear whether the authors collected the plant material and saved it until the early 1990s to work on or they re-collected plant material from the same location and merely used the 1982 voucher herbarium for purposes of plant identification.
36. (a) Noda, N.; Kogetsu, H.; Kawasaki, T.; Miyahara, K. Phytochemistry 1990, 29, 3565-3569.
37. (b) Kogetsu, H.; Noda, N.; Kawasaki, T.; Miyahara, K. Phytochemistry 1991, 30, 957-963.
38. Ono, M.; Kawasaki, T.; Miyahara, K. Chem. Pharm. Bull. 1989, 37, 3209-3213.
39. MacLeod, J. K.; Ward, A. J. Nat. Prod. 1997, 60, 467-471.
40. Duus, J. Ø.; Gotfredsen, H.; Block, K. Chem. Rev. 2000, 100, 4589-4614.
41. Ono, M.; Yamada, F.; Noda, N.; Kawasaki, T.; Miyahara, K. Chem. Pharm. Bull. 1993, 41, 1023-1026.