Analysis and antiproliferative activity of bark extractives of Betula neoalaskana and B. papyrifera. Synthesis of the most active extractive component - Betulin 3-caffeate

Natural Product Communications

Volumn 2, Issue 1, 2007, Pages 17-26

  Kolomitsyn, Igor V ^a   Holy, Jon ^b   Perkins, Edward ^b   Krasutsky, Pavel A ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

Antiproliferative; Betula neoalaskana; Betula papyrifera; Betulin; Betulin 3 caffeate; Betulinic acid; Birch bark; Lupeol; Oleanolic acid

Indexed keywords

EID: 67651113177     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0700200105     Document Type: Article

References (60)

1. Furlow JJ. (1997) Betulaceae Gray. Birch family. In: Flora of North America north of Mexico, New York, Oxford University press, 507-538.
2. Packee EC. (2004) Taxonomy and evolution of Alaska's birches. Agroborealis, 36, 20-30.
3. Safford LO, Bjorkbom, JC, Zasada, JC. (1990) Betula papyrifera Marsh. paper birch. In: Burns, Russell M.; Honkala, Barbara H., technical coordinators. Silvics of North America. Vol. 2. Hardwoods. Agric. Handb. U.S. Department of Agriculture, Forest Service, Washington, DC, 158-171.
4. Krasutsky PA. (2006) Birch bark research and development. Natural Product Report, 23, 919-942.
5. (a) Seshadri TR, Vedantham TNC. (1971) Chemical examination of the barks and heartwoods of Betula species of American origin. Phytochemistry, 10, 897-898;
6. (b) O'Connell MM, Bentley MD, Campbell CS, Cole BJW. (1988) Betulin and lupeol in bark from four white-barked birches. Phytochemistry, 27, 2175-2176.
7. Habiyaremye I, Stevanovic-Janezic T, Riedl B, Garneau F-X, Jean F-I. (2002) Pentacyclic triterpene constituents of yellow birch bark from Quebec. Journal of Wood Chemistry and Technology, 22, 83-91.
8. (a) Cole BJW, Bentley MD, Hua Y. (1991) Triterpenoid extractives in the outer bark of Betula lenta (black birch). Holzforschung, 45, 265-268;
9. (b) Hua Y, Bentley MD, Cole BJW, Murray KD, Alford AR. (1991) Triterpenes from the outer bark of Betula nigra. Journal of Wood Chemistry and Technology, 11, 503-516.
10. (a) Ekman R. (1983) Lipophilic extractives of the inner bark of birch, Betula verrucosa Ehrh. Finnish Chemical Letters, 162-165;
11. (b) Ekman R. (1983) The suberin monomers and triterpenoids from the outer bark of Betula verrucosa Ehrh. Holzforschung, 37, 205-211;
12. (c) Kislitsyn AN. (1994) Birch bark extractives: isolation, composition, properties, and application. Koksnes Khimiya, 3-28;
13. (d) Achrem-Achremowicz J, Janeczko Z. (2003) Betulin - a pentacyclic triterpene. Wiadomosci Chemiczne, 57, 223-246;
14. (e) Pokhilo ND, Uvarova NI. (1998) Triterpenoids of the dammarane series from various species of the Betula genus. Khimiya v Interesakh Ustoichivogo Razvitiya, 6, 461-467;
15. (f) Kamperdick C, Thuy TT, Van Sung T, Adam G. (1995) Triterpenoids from Betula alnoides. Planta Medica, 61, 486.
16. (a) Pan H, Lundgren LN, Andersson R. (1994) Triterpene caffeates from bark of Betula pubescens. Phytochemistry, 37, 795-799 ;
17. (b) Odinokova LE, Denisenko VA, Pokhilo ND, Uvarova NI. (1985) Oleanolic caffeate from the outer bark of Betula davurica. Khimiya Prirodnykh Soedinenii, 270-271;
18. (c) Fuchino H, Satoh T, Tanaka N. (1995) Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii. Chemical & Pharmaceutical Bulletin, 43, 1937-1942;
19. (d) Kochergina TY, Malinovskaya GV, Pokhilo ND, Denisenko VA, Uvarova NI. (1986) The composition of the outer bark of Betula mandschurica. Khimiya Prirodnykh Soedinenii, 647-648;
20. (e) Fuchino H, Konishi S, Satoh T, Yagi A, Saitsu K., Tatsumi T, Tanaka N. (1996) Chemical evaluation of Betula species in Japan. II. Constituents of Betula platyphylla var. japonica. Chemical & Pharmaceutical Bulletin, 44, 1033-1038;
21. (f) Fuchino H, Satoh T, Yokochi M, Tanaka N. (1998) Chemical evaluation of Betula species in Japan. V. Constituents of Betula ovalifolia. Chemical & Pharmaceutical Bulletin, 46, 169-170;
22. (g) Fuchino H, Satoh T, Shimizu M, Tanaka N. (1998) Chemical evaluation of Betula species in Japan. IV. Constituents of Betula davurica. Chemical & Pharmaceutical Bulleti, 46, 166-168;
23. (h) Fuchino H, Satoh T, Hida J, Terada M, Tanaka N. (1998) Chemical evaluation of Betula species in Japan. VI. Constituents of Betula schmidtii. Chemical & Pharmaceutical Bulletin, 46, 1051-1053.
24. Ekman R, Sjoholm R. (1983) Betulinol 3-caffeate in outer bark of Betula verrucosa Ehrh. Finnish Chemical Letters, 134-136.
25. Reichardt PB. (1981) Papyriferic acid: a triterpenoid from Alaskan paper birch. Journal of Organic Chemistry, 46, 4576-4578.
26. (a) Krasutsky PA, Carlson RM, Nesterenko VV, Kolomitsyn IV, Edwardson C. (2002) Birch bark processing and the isolation of natural products from birch bark. US patent # 6,392,070;
27. (b) Krasutsky PA, Carlson RM, Nesterenko VV, Kolomitsyn IV, Edwardson C. (2003) Birch bark processing and the isolation of natural products from birch bark. US patent # 6,634,575;
28. (c) Krasustky PA, Carlson RM, Kolomitsyn IV. (2004) Isolation of natural products from birch bark. US Patent # 6,768,016;
29. (d) Krasutsky PA, Carlson RM, Nesterenko VV, Kolomitsyn IV, Edwardson C. (2004) Birch bark processing and the isolation of natural products from birch bark. US patent # 6,815,553.
30. Eckerman C, Ekman R. (1985) Comparison of solvents for extraction and crystallization of betulinol from birch bark waste. Paperi ja Puu, 67, 100, 102-103, 105-106.
31. Fu L, Zhang S, Li N, Wang J, Zhao M, Sakai J, Hasegawa T, Mitsui T, Kataoka T, Oka S, Kiuchi M, Hirose K, Ando M. (2005) Three new triterpenes from Nerium oleander and biological activity of the isolated compounds. Journal of Natural Products, 68, 198-206.
32. Badria FA, Mikhaeil BR, Maatooq GT, Amer MMA. (2003) Immunomodulatory triterpenoids from the oleogum resin of Boswellia carterii Birdwood. Zeitschrift fuer Naturforschung, C: Journal of Biosciences, 58, 505-516.
33. Fujioka T, Kashiwada Y, Kilkuskie RE, Cosentino LM, Ballas LM, Jiang JB, Janzen WP, Chen IS, Lee KH. (1994) Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids. Journal of Natural Products, 57, 243-247.
34. Hata K, Hori K, Takahashi S. (2002) Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. Journal of Natural Products, 65, 645-648.
35. Naved T, Ansari SH, Mukhtar HM, Ali M. (2005) New triterpenic esters of oleanene-series from the flowers of Calendula officinalis Linn. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 44B, 1088-1091.
36. Patra A, Chaudhuri SK, Panda SK. (1988) Betulin-3-caffeate from Quercus suber. Carbon-13 NMR spectra of some lupenes. Journal of Natural Products, 51, 217-220.
37. (a) Saija A, Tomaino A, Trombetta D, De Pasquale A, Uccella N, Barbuzzi T, Paolino D, Bonina F. (2000) In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents. International Journal of Pharmaceutics, 199, 39-47;
38. (b) Muller RH, Wissing S, Mader K. (2001) Sunscreens containing UV radiation reflecting or absorbing agents, protecting against harmful UV radiation and reinforcing the natural skin barrier. Patent Cooperation Treaty, International Application WO 2001003652, 55 pp.
39. Krasutsky PA, Kolomitsyna O, Krasutskyy D.A, Kacharov OD, Kolomitsyn IV. (2005) Birch bark extract processing utilizing azeotropic distillation. Patent Cooperation Treaty, International Application WO 2005047304, 60 pp.
40. Hiroya K, Takahashi T, Miura N, Naganuma A, Sakamoto T. (2002) Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium. Bioorganic & Medicinal Chemistry, 10, 3229-3236.
41. Lee YJ, Liao PH, Chen WK, Yang CC. (2000) Preferential cytotoxicity of caffeic acid phenethyl ester analogues on oral cancer cells. Cancer Letters, 153, 51-56.
42. Nagaoka T, Banskota AH, Tezuka Y, Saiki I, Kadota S. (2002) Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-metastatic murine colon 26-L5 carcinoma cell line. Bioorganic & Medicinal Chemistry, 10, 3351-3359.
43. Symon AV, Kaplun AP, Vlasenkova NK, Gerasimova GK, Shon LB, Litvin EF, Kozlova LM, Surkova EL, Shvets VI. (2003) Epimerization of hydroxyl group in lupan series triterpenoids. Russian Journal of Bioorganic Chemistry (Translation of Bioorganicheskaya Khimiya), 29, 185-189.
44. Bankova V. (1990) Synthesis of natural esters of substituted cinnamic acids. Journal of Natural Products, 53, 821-824.
45. Krasutsky PA, Avilov DV, Sergeeva T, Krasutskyy DA, Kolomitsyna ON. (2004) Triterpene quaternary salts as biologically active surfactants. U.S. Patent Application 10/893147.
46. Krasutsky PA, Carlson RM, Nesterenko VV. (2001) Method for manufacturing betulinic acid. US Patent 6,232,481.
47. Pisha E, Chai H, Lee IS, Chagwedera TE, Farnsworth NR, Cordell GA, Beecher CW, Fong HH, Kinghorn AD, Brown DM. (1995) Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nature Medicine, 1, 1046-1051.
48. Zuco V, Supino R, Righetti SC, Cleris L, Marchesi E, Gambacorti-Passerini C, Formelli F. (2002) Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells. Cancer Letters, 175, 17-25.
49. (a) Noda Y, Kaiya T, Kohda K, Kawazoe Y. (1997) Enhanced cytotoxicity of some triterpenes toward leukemia L1210 cells cultured in low pH media: possibility of a new mode of cell killing. Chemical & Pharmaceutical Bulletin, 45, 1665-1670;
50. (b) Ehrhardt H, Fulda S, Fuehrer M, Debatin KM, Jeremias I. (2004) Betulinic acid-induced apoptosis in leukemia cells. Leukemia, 18, 1406-1412;
51. (c) Raghuvar Gopal DV, Narkar AA, Badrinath Y, Mishra KP, Joshi DS. (2005) Betulinic acid induces apoptosis in human chronic myelogenous leukemia (CML) cell line K-562 without altering the levels of Bcr-Abl. Toxicology Letters, 155, 343-351;
52. (d) Fulda S, Jeremias I, Steiner HH, Pietsch T, Debatin K-M. (1999) Betulinic acid: a new cytotoxic agent against malignant brain-tumor cells. International Journal of Cancer, 82, 435-441;
53. (e) Schmidt ML, Kuzmanoff KL, Ling-Indeck L, Pezzuto JM. (1997) Betulinic acid induces apoptosis in human neuroblastoma cell lines. European Journal of Cancer, 33, 2007-2010;
54. (f) Wick W, Grimmel C, Wagenknecht B, Dichgans J, Weller M. (1999) Betulinic acid-induced apoptosis in glioma cells: a sequential requirement for new protein synthesis, formation of reactive oxygen species, and caspase processing. Journal of Pharmacology and Experimental Therapeutics, 289, 1306-1312.
55. Karpova MB, Sanmun D, Henter J-I, Smirnov AF, Fadeel B. (2006) Betulinic acid, a natural cytotoxic agent, fails to trigger apoptosis in human Burkitt's lymphoma-derived B-cell lines. International Journal of Cancer, 118, 246-252.
56. Fulda S, Friesen C, Los M, Scaffidi C, Mier W, Benedict M, Nunez G, Krammer PH, Peter ME, Debatin KM. (1997) Betulinic acid triggers CD95 (APO-1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors. Cancer Research, 57, 4956-4964.
57. Zhang Y, Li J-X, Zhao J, Wang S-Z, Pan Y, Tanaka K, Kadota S. (2005) Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation. Bioorganic & Medicinal Chemistry Letters, 15, 1629-1632.
58. McBurney MW, Rogers BJ. (1982) Isolation of male embryonal carcinoma cells and their chromosome replication patterns. Developmental Biology, 89, 503-508.
59. Andrews PW. (1984) Retinoic acid induces neuronal differentiation of a cloned human embryonal carcinoma cell line in vitro. Developmental Biology, 103, 285-293.
60. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. Journal of the National Cancer Institute, 82, 1107-1112.