Phytochemistry of cimicifugic acids and associated bases in Cimicifuga racemosa root extracts

Phytochemical Analysis

Volumn 20, Issue 2, 2009, Pages 120-133

  Gödecke, Tanja ^a   Nikolic, Dejan ^a   Lankin, David C ^a   Chen, Shao Nong ^a   Powell, Sharla L ^a   Dietz, Birgit ^a   Bolton, Judy L ^a   van Breemen, Richard B ^a   Farnsworth, Norman R ^a   Pauli, Guido F ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

1H NMR full spin analysis; Centrifugal partition chromatography (CPC); Cimicifuga (Actaea) racemosa; Cimicifugic acids; Counter current chromatography (CCC); N methylserotonin; PH zone refinement counter current chromatography (pHZR CCC); Serotonergic activity

Indexed keywords

CENTRIFUGATION; LIQUID CHROMATOGRAPHY;

1H NMR FULL SPIN ANALYSE; CENTRIFUGAL PARTITION CHROMATOGRAPHY; CIMICIFUGA (ACTAEA) RACEMOSA; CIMICIFUGIC ACID; COUNTER-CURRENT CHROMATOGRAPHY; COUNTERCURRENT CHROMATOGRAPHY; NΩ-METHYLSEROTONIN; PH ZONE REFINEMENT COUNTER-CURRENT CHROMATOGRAPHY; SEROTONERGIC ACTIVITY;

BIOASSAY;

ALKALOID; BASE; CIMICIFUGA RACEMOSA EXTRACT; CIMICIFUGIC ACID; CIMIPRONIDINE; CINNAMIC ACID DERIVATIVE; N METHYLSEROTONIN; UNCLASSIFIED DRUG; CAFFEIC ACID DERIVATIVE; PHENYLACETIC ACID DERIVATIVE; PLANT EXTRACT;

ARTICLE; BIOASSAY; CHROMATOGRAPHY; CIMICIFUGA RACEMOSA; COMPLEX FORMATION; CONTROLLED STUDY; DISSOCIATION; HYPOTHESIS; ISOLATION PROCEDURE; METHODOLOGY; NONHUMAN; PH; PHYTOCHEMISTRY; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; CHEMISTRY; CHO CELL; CIMICIFUGA; CRICETULUS; ELECTROSPRAY MASS SPECTROMETRY; HAMSTER; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CIMICIFUGA DAHURICA; CIMICIFUGA RACEMOSA;

ANIMALS; CAFFEIC ACIDS; CHO CELLS; CIMICIFUGA; CRICETINAE; CRICETULUS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PHENYLACETATES; PLANT EXTRACTS; PLANT ROOTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 65249168309     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.1106     Document Type: Article

References (47)

1. Albertazzi P. 2006. A review of non-hormonal options for the relief of menopausal symptoms. Treat Endocrinol 5: 101-113.
2. Bashir A, Hamburger M, Msonthi JD and Hostettmann K. 1993. Sinapic acid from Polygala virgata. Phytochemistry 32: 741-745.
3. Berthod A, Friesen JB, Inui T and Pauli GF. 2007. Elution-extrusion countercurrent chromatography: theory and concepts in metabolic analysis. Anal Chem 79: 3371-3382.
4. Blondeau P, Segura M, Perez-Fernandez R and de Mendoza J. 2007. Molecular recognition of oxoanions based on guanidinium receptors. Chem Soc Rev 36: 198-210.
5. Bodinet C and Freudenstein J. 2002. Influence of Cimicifuga racemosa on the proliferation of estrogen receptor-positive human breast cancer cells. Breast Cancer Res Treat 76: 1-10.
6. Bolle P, Mastrangelo S, Perrone F and Evandri MG. 2007. Estrogen-like effect of a Cimicifuga racemosa extract sub-fraction as assessed by in vivo, ex vivo and in vitro assays. J Steroid Biochem Mol Biol 107: 262-269.
7. Burdette J. 2003. Biological evaluation of botanical dietary supplements for the alleviation of menopausal symptoms. Ph.D. Dissertation. University of Illinois at Chicago.
8. Burdette JE, Chen SN, Lu ZZ, Xu H, White BE, Fabricant DS, Liu J, Fong HH, Farnsworth NR, Constantinou AI, Van Breemen RB, Pezzuto JM and Bolton JL. 2002. Black cohosh (Cimicifuga racemosa L.) protects against menadione-induced DNA damage through scavenging of reactive oxygen species: bioassay-directed isolation and characterization of active principles. J Agric Food Chem 50: 7022-7028.
9. Burdette JE, Liu J, Chen SN, Fabricant DS, Piersen CE, Barker EL, Pezzuto JM, Mesecar A, van Breemen RB, Farnsworth NR and Bolton JL. 2003. Black cohosh acts as a mixed competitive ligand and partial agonist of the serotonin receptor. J Agric Food Chem 51: 5661-5670.
10. Chen B, Piletsky S and Turner AP. 2002. High molecular recognition: design of 'Keys'. Comb Chem High Throughput Screen 5: 409-427.
11. Dixon-Shanies D and Shaikh N. 1999. Growth inhibition of human breast cancer cells by herbs and phytoestrogens. Oncol Rep 6: 1383-1387.
12. Fabricant DS. 2006. Pharmacognostic investigation of black cohosh ( Cimicifuga racemosa (L.) Nutt.). Ph.D. Dissertation. University of Illinois at Chicago.
13. Fabricant D, Nikolic D, Lankin DC, Chen S-N, Jaki B, Krunic A, van Breemen RB, Fong HHS, Farnsworth NR and Pauli GF. 2005. Cimipronidine: A novel cyclic guanidine alkaloid from Cimicifuga racemosa (L.) Nutt. J Nat Prod 68: 1266-1270.
14. Foster S. 1999. Black cohosh: Cimicifuga racemosa - a literature review. HerbalGram 4: 35-55.
15. Friesen JB and Pauli GF. 2007a. Rational development of solvent system families in counter-current chromatography. J Chromatogr A 1151: 51-59.
16. Friesen JB and Pauli GF. 2007b. Reciprocal symmetry plots as a representation of countercurrent chromatograms. Anal Chem 79: 2320-2324.
17. Hasa Y and Tazaki H. 2004. Biosynthesis of fukinolic acid isolated from Petasites japonicus. Biosci Biotechnol Biochem 68: 2212-2214.
18. Hostanska K, Nisslein T, Freudenstein J, Reichling J and Saller R. 2004. Evaluation of cell death caused by triterpene glycosides and phenolic substances from Cimicifuga racemosa extract in human MCF-7 breast cancer cells. Biol Pharm Bull 27: 1970-1975.
19. Hunter CA and Sanders JKM. 1990. The nature of π-π interactions. J Am Chem Soc 112: 5525-5534.
20. Ito Y. 1996. pH-peak-focusing and pH-zone-refining countercurrent chromatography. Chem Anal 132: 121-175.
21. Jarry H, Metten M, Spengler B, Christoffel V and Wuttke W. 2003. In vitro effects of the Cimicifuga racemosa extract BNO 1055. Maturitas 44: S31-38.
22. Joffe H, Soares CN, Petrillo LF, Viguera AC, Somley BL, Koch JK and Cohen LS. 2007. Treatment of depression and menopause-related symptoms with the serotonin-norepinephrine reuptake inhibitor duloxetine. J Clin Psychiat 68: 943-950.
23. 1H-NMR chemical shifts of aromatic protons in sampangine derivatives. Spectrosc Lett 36: 477-485.
24. Kruse S-O. 2000. Phytochemische Arbeiten zu Cimicifuga racemosa (L.) Nutt. - Gewinnung und Analytik wirksamer Fraktionen und Inhaltsstofee. Ph.D. Dissertation. Westfälische Wilhelms University.
25. Kruse SO, Löhning A, Pauli GF, Winterhoff H and Nahrstedt A. 1999. Fukiic and piscidic acid esters from the rhizome of Cimicifuga racemosa and the estrogenic activity of fukinolic acid. Planta Med 65: 763-764.
26. Kusano A, Shibano M, Tsukamoto D and Kusano G. 2001. Studies on the constituents of Cimicifuga species. XXVIII. Cycloart-7-enol glycosides from the underground parts of Cimicifuga simplex Wormsk. Chem Pharm Bull 49: 437-441.
27. Li W, Sun Y, Liang W, Fitzloff JF and van Breemen RB. 2003. Identification of caffeic acid derivatives in Actea racemosa (Cimicifuga racemosa, black cohosh) by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 17: 978-982.
28. Liu JH, Burdette JE, Xu HY, Gu CG, van Breemen RB, Bhat KPL, Booth N Constantinou AI, Pezzuto JM, Fong HHS, Farnsworth NR and Bolton JL. 2001. Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms. J Agric Food Chem 49: 2472-2479.
29. Martin R, Lilley TH, Bailey NA, Falshaw CP, Haslam E, Magnolato D and Begley MJ. 1986. Polyphenol-caffeine complexation. J Chem Soc Chem Comm 105-106.
30. 1H-NMR studies: a caveat in the investigations of molecular recognition and structure elucidation. Tetrahedron 54: 15489-15498.
31. Mukhopadhyay S and Cordell GA. 1981. Catharanthus alkaloids. XXXVI. Isolation of vincaleukoblastine (VLB) and periformyline from Catharanthus trichophyllus and pericyclivine from Catharanthus roseus. J Nat Prod 44: 335-339.
32. Nuntanakorn P, Jiang B, Einbond LS, Yang H, Kronenberg F, Weinstein IB and Kennelly EJ. 2006. Polyphenolic constituents of Actaea racemosa. J Nat Prod 69: 314-318.
33. Powell SL, Gödecke T, Nikolic D, Chen S-N, Dietz B, Farnsworth NR, van Breemen RB, Lankin DC, Pauli GF and Bolton JL. 2008. In vitro serotonergic activity of black cohosh (Cimicifuga racemosa) and identification of a potential active constituent, N-methylserotonin. J Agric Food Chem DOI: 10.1021/ jf0803298z.
34. Rossouw JE, Anderson GL, Prentice RL, LaCroix AZ, Kooperberg C, Stefanick ML, Jackson RD, Beresford SA, Howard BV, Johnson KC, Kotchen JM and Ockene J. 2002. Risks and benefits of estrogen plus progestin in healthy postmenopausal women: principal results from the Women's Health Initiative randomized controlled trial. JAMA 288: 321-333.
35. Sakamura S, Yoshihara T and Toyoda K. 1973. Constituents of Petasites japonicus. Structures of fukiic acid and fukinolic acid. Agric Biol Chem 37: 1915-1921.
36. Shefter E. 1969. Structural studies on complexes. IV. Crystal structure of a 1:1 5-chlorosalicylic acid and theophylline complex. J Pharm Sci 58: 710-714.
37. Sipe K, Leventhal L, Burroughs K, Cosmi S, Johnston GH and Deecher DC. 2004. Serotonin 2A receptors modulate tail-skin temperature in two rodent models of estrogen deficiency-related thermoregulatory dysfunction. Brain Res 1028: 191-202.
38. Stromeier S. 2003. Phytochemische Untersuchungen und Prüfung auf estrogene Aktivität von phenolischen Inhaltsstoffen aus Cimicifuga racemosa (L.) Nutt. (syn. Actaea racemosa L.). Westfälische Wilhelms University.
39. Stromeier S, Petereit F and Nahrstedt A. 2005. Phenolic esters from the rhizomes of Cimicifuga racemosa do not cause proliferation effects in MCF-7 cells. Planta Med 71: 495-500.
40. Svoboda GH. 1961. Alkaloids of Vincea rosea (Catharanthus roseus). IX. Extraction and characterization of leurosidine and leurocristine. Lloydia 24: 173-178.
41. Takahira M, Kusano A, Shibano M, Kusano G and Miyase T. 1998a. Constituents of Cimicifuga spp. 24. Phenolics of Cimicifuga spp. 2. Piscidic acid and fukiic acid esters from Cimicifuga simplex. Phytochemistry 49: 2115-2119.
42. Takahira M, Kusano A, Shibano M, Kusano G, Sakurai N, Nagai M and Miyase T. 1998b. Three new fukiic acid esters, cimicifugic acids A, B and C, from Cimicifuga simplex Wormsk. Chem Pharm Bull 46: 362-365.
43. Ternai B and Markham KR. 1976. Carbon-13 NMR studies of flavonoids - I - flavonoes and flavonols. Tetrahedron 32: 556-569.
44. Viereck V, Emons G and Wuttke W. 2005. Black cohosh: just another phytoestrogen?, Trends in Endocrinology and Metabolism 16: 214-221.
45. Zanardi R, Rossini D, Magri L, Malaguti A, Colombo C and Smeraldi E. 2007. Response to SSRIs and role of the hormonal therapy in postmenopausal depression. Eur Neuropsychopharmacol 17: 400-405.
46. Zhao XH, Chen DH, Si JY, Pan RL and Shen LG. 2002. Studies on the phenolic acid constituents from Chinese medicine 'sheng-ma', rhizome of Cimicifuga foetidaL., Acta Pharm Sin 37: 535-538.
47. Zierau O, Bodinet C, Kolba S, Wulf M and Vollmer G. 2002. Antiestrogenic activities of Cimicifuga racemosa extracts. J Steroid Biochem Mol Biol 80: 125-130.