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Planta Med 2013; 79(16): 1565-1571
DOI: 10.1055/s-0033-1350808
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Two New Flavonol Glycosides and a Metabolite Profile of Bryophyllum pinnatum, a Phytotherapeutic Used in Obstetrics and Gynaecology

Karin Fürer
1   Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
2   Department of Obstetrics, University Hospital Zurich, Zürich, Switzerland
,
Melanie Raith
1   Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
,
Rudolf Brenneisen
3   Department of Clinical Research, University of Bern, Bern, Switzerland
,
Monica Mennet
4   Weleda AG, Arlesheim, Switzerland
,
Ana Paula Simões-Wüst
5   Research Department, Paracelsus Hospital Richterswil, Richterswil, Switzerland
,
Ursula von Mandach
2   Department of Obstetrics, University Hospital Zurich, Zürich, Switzerland
,
Matthias Hamburger
1   Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
,
Olivier Potterat
1   Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
› Author Affiliations
Further Information

Publication History

received 28 February 2013
revised 11 June 2013

accepted 11 August 2013

Publication Date:
26 September 2013 (online)

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Abstract

Bryophyllum pinnatum is a succulent perennial plant native to Madagascar which is used in anthroposophical medicine to treat psychiatric disorders and as a tocolytic agent to prevent premature labour. We performed a metabolite profiling study in order to obtain a comprehensive picture of the constituents in B. pinnatum leaves and to identify chromatographic markers for quality control and safety assessment of medicinal preparations. Preliminary HPLC-PDA-ESIMS analyses revealed that flavonoid glycosides were the main UV-absorbing constituents in the MeOH extract of B. pinnatum. Two phenolic glucosides, syringic acid β-D-glucopyranosyl ester (1) and 4′-O-β-D-glucopyranosyl-cis-p-coumaric acid (2), as well as nine flavonoids (3-11) including kaempferol, quercetin, myricetin, acacetin, and diosmetin glycosides were unambiguously identified by 1H and 2D NMR analysis after isolation from a MeOH extract. The flavonol glycosides quercetin 3-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside 7-O-β-D-glucopyranoside (3) and myricetin 3-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside (4) were new natural products. With the aid of HPLC-PDA-APCIMS and authentic references isolated from the related species B. daigremontianum, the presence of four bufadienolides, bersaldegenin-1-acetate (12), bryophyllin A (13), bersaldegenin-3-acetate (14), and bersaldegenin-1,3,5-orthoacetate (15) was detected in B. pinnatum.

Key words

Bryophyllum pinnatum - Kalanchoe pinnata - Crassulaceae - HPLC-PDA-MS profiling - flavonoids - bufadienolides

Supporting Information

 

  • References

  • 1 Yadav NP, Dixit VK. Hepatoprotective activity of leaves of Kalanchoe pinnata Pers. J Ethnopharmacol 2003; 86: 197-202
    CrossrefPubMedGoogle Scholar
  • 2 Ajibesin KK. Ethnobotanical survey of plants used for skin diseases and related ailments in Akwa Ibom State, Nigeria. Ethnobot Res Appl 2012; 10: 463-522
    PubMedGoogle Scholar
  • 3 Ghasi S, Egwuibe C, Achukwu PU, Onyeanusi JC. Assessment of the medical benefit in the folkloric use of Bryophyllum pinnatum leaf among the Igbos of Nigeria for the treatment of hypertension. Afr J Pharm Pharmacol 2011; 5: 83-92
    PubMedGoogle Scholar
  • 4 Lans CA. Ethnomedicines used in Trinidad and Tobago for urinary problems and diabetes mellitus. J Ethnobiol Ethnomed 2006; 2: 45
    CrossrefPubMedGoogle Scholar
  • 5 Daems W, Kaufmann H, Titze O. Kurzgefasste Bryophyllum-Chronologie. Weleda Korrespondenzblätter für Ärzte 1982; 105: 5-11
    PubMedGoogle Scholar
  • 6 Hassauer W, Schreiber K, von der Decken D. Bryophyllum – Ein neuer Weg in der tokolytischen Therapie. Erfahrungsheilkunde 1985; 34: 683-687
    PubMedGoogle Scholar
  • 7 Plangger N, Rist L, Zimmermann R, von Mandach U. Intravenous tocolysis with Bryophyllum pinnatum is better tolerated than beta-agonist application. Eur J Obstet Gynecol Reprod Biol 2006; 124: 168-172
    CrossrefPubMedGoogle Scholar
  • 8 Simões-Wüst AP, Grãos M, Duarte CB, Brenneisen R, Hamburger M, Mennet M, Ramos MH, Schnelle M, Wächter R, Worel AM, von Mandach U. Juice of Bryophyllum pinnatum (Lam.) inhibits oxytocin-induced increase of the intracellular calcium concentration in human myometrial cells. Phytomedicine 2010; 17: 980-986
    CrossrefPubMedGoogle Scholar
  • 9 Wächter R, Brenneisen R, Hamburger M, Mennet M, Schnelle M, Worel AM, Simoes-Wust AP, von Mandach U. Leaf press juice from Bryophyllum pinnatum (Lamarck) Oken induces myometrial relaxation. Phytomedicine 2011; 19: 74-82
    CrossrefPubMedGoogle Scholar
  • 10 Schuler V, Suter K, Fürer K, Eberli D, Horst M, Betschart C, Brenneisen R, Hamburger M, Mennet M, Schnelle M, Simoes-Wust AP, von Mandach U. Bryophyllum pinnatum inhibits detrusor contractility in porcine bladder strips – a pharmacological study towards a new treatment option of overactive bladder. Phytomedicine 2012; 19: 947-951
    CrossrefPubMedGoogle Scholar
  • 11 Betschart C, von Mandach U, Seifert B, Scheiner D, Perucchini D, Fink D, Geissbuhler V. Randomized, double-blind placebo-controlled trial with Bryophyllum pinnatum versus placebo for the treatment of overactive bladder in postmenopausal women. Phytomedicine 2013; 20: 351-358
    CrossrefPubMedGoogle Scholar
  • 12 Muzitano MF, Tinoco LW, Guette C, Kaiser CR, Rossi-Bergmann B, Costa SS. The antileishmanial activity assessment of unusual flavonoids from Kalanchoe pinnata . Phytochemistry 2006; 67: 2071-2077
    CrossrefPubMedGoogle Scholar
  • 13 Pal S, Nag Chaudhuri AK. Studies on the anti-ulcer activity of a Bryophyllum pinnatum leaf extract in experimental animals. J Ethnopharmacol 1991; 33: 97-102
    CrossrefPubMedGoogle Scholar
  • 14 Ofokansi K, Esimone C, Anele C. Evaluation of the in vitro combined antibacterial effect of the leaf extracts of Bryophyllum pinnatum (Fam. Crassulaceae) and Ocimum gratissimum (Fam. Labiatae). Plant Prod Res J 2005; 9: 23-27
    PubMedGoogle Scholar
  • 15 Akinpelu DA. Antimicrobial activity of Bryophyllum pinnatum leaves. Fitoterapia 2000; 71: 193-194
    CrossrefPubMedGoogle Scholar
  • 16 Supratman U, Fujita T, Akiyama K, Hayashi H, Murakami A, Sakai H, Koshimizu K, Ohigashi H. Anti-tumor promoting activity of bufadienolides from Kalanchoe pinnata and K. daigremontiana x tubiflora . Biosci Biotechnol Biochem 2001; 65: 947-949
    CrossrefPubMedGoogle Scholar
  • 17 Almeida AP, Da Silva SA, Souza ML, Lima LM, Rossi-Bergmann B, de Moraes VL, Costa SS. Isolation and chemical analysis of a fatty acid fraction of Kalanchoe pinnata with a potent lymphocyte suppressive activity. Planta Med 2000; 66: 134-137
    Article in Thieme ConnectPubMedGoogle Scholar
  • 18 Ojewole J. Antinociceptive, anti-inflammatory and antidiabetic effects of Bryophyllum pinnatum (Crassulaceae) leaf aqueous extract. J Ethnopharmacol 2005; 99: 13-19
    CrossrefPubMedGoogle Scholar
  • 19 Kamboj A, Saluja A. Bryophyllum pinnatum (Lam.) Kurz.: Phytochemical and pharmacological profile: A Review. Pharmacogn Rev 2009; 3: 364-374
    PubMedGoogle Scholar
  • 20 Muzitano MF, Cruz EA, de Almeida AP, Da Silva SA, Kaiser CR, Guette C, Rossi-Bergmann B, Costa SS. Quercitrin: an antileishmanial flavonoid glycoside from Kalanchoe pinnata . Planta Med 2006; 72: 81-83
    Article in Thieme ConnectPubMedGoogle Scholar
  • 21 Yamagishi T, Haruna M, Yan XZ, Chang JJ, Lee KH. Antitumor agents, 110. Bryophyllin B, a novel potent cytotoxic bufadienolide from Bryophyllum pinnatum . J Nat Prod 1989; 52: 1071-1079
    CrossrefPubMedGoogle Scholar
  • 22 Wagner H, Lotter H, Fischer M. The toxic and sedative bufadienolides of Kalanchoe daigremontiana HAMET et PERR. Helv Chim Acta 1986; 69: 359-367
    CrossrefPubMedGoogle Scholar
  • 23 Muzitano MF, Bergonzi MC, De Melo GO, Lage CLS, Bilia AR, Vincieri FF, Rossi-Bergmann B, Costa SS. Influence of cultivation conditions, season of collection and extraction method on the content of antileishmanial flavonoids from Kalanchoe pinnata . J Ethnopharmacol 2011; 133: 132-137
    CrossrefPubMedGoogle Scholar
  • 24 El Abdellaoui S, Destandau E, Toribio A, Elfakir C, Lafosse M, Renimel I, Andre P, Cancellieri P, Landemarre L. Bioactive molecules in Kalanchoe pinnata leaves: extraction, purification, and identification. Anal Bioanal Chem 2010; 398: 1329-1338
    CrossrefPubMedGoogle Scholar
  • 25 Inoshiri S, Sasaki M, Kohda H, Otsuka H, Yamasaki K. Aromatic glycosides from Berchemia racemosa . Phytochemistry 1987; 26: 2811-2814
    CrossrefPubMedGoogle Scholar
  • 26 Rasmussen S, Wolff C, Rudolph H. 4′-O-beta-D-glucosyl-cis-p-coumaric acid – a natural constituent of Sphagnum fallax cultivated in bioreactors. Phytochemistry 1996; 42: 81-87
    CrossrefPubMedGoogle Scholar
  • 27 Zhong XN, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y. Three flavonol glycosides from leaves of Myrsine seguinii . Phytochemistry 1997; 46: 943-946
    CrossrefPubMedGoogle Scholar
  • 28 Soicke H, Gorler K, Waring H. Flavonol glycosides from Moghania faginea . Planta Med 1990; 56: 410-412
    Article in Thieme ConnectPubMedGoogle Scholar
  • 29 Neretina OV, Fedorov SV, Gromova AS, Lutskii VI, Elʼkin YN. Flavonoids of Hedysarum setigerum . Chem Nat Compd 2002; 38: 194-195
    CrossrefPubMedGoogle Scholar
  • 30 Wu J, Yi W, Jin L, Hu D, Song B. Antiproliferative and cell apoptosis-inducing activities of compounds from Buddleja davidii in Mgc-803 cells. Cell Div 2012; 7: 20
    CrossrefPubMedGoogle Scholar
  • 31 McKenzie RA, Franke FP, Dunster PJ. The toxicity to cattle and bufadienolide content of six Bryophyllum species. Aust Vet J 1987; 64: 298-301
    CrossrefPubMedGoogle Scholar
  • 32 Capon RJ, Macleod JK, Oelrichs PB. Bryotoxins B and C, toxic bufadienolide orthoacetates from the flowers of Bryophyllum tubiflorum (Crassulaceae). Aust J Chem 1986; 39: 1711-1715
    PubMedGoogle Scholar
  • 33 Yamagishi T, Yan XZ, Wu RY, McPhail DR, McPhail AT, Lee KH. Structure and stereochemistry of bryophyllin A, a novel potent cytotoxic bufadienolide orthoacetate from Bryophyllum pinnatum . Chem Pharm Bull 1988; 36: 1615-1617
    CrossrefPubMedGoogle Scholar
  • 34 Supratman U, Fujita T, Akiyama K, Hayashi H. New insecticidal bufadienolide, bryophyllin C, from Kalanchoe pinnata . Biosci Biotechnol Biochem 2000; 64: 1310-1312
    CrossrefPubMedGoogle Scholar