Studies on Bignoniaceae: Newbouldiosides D – F, Minor Phenylethanoid Glycosides from Newbouldia laevis, and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata ^{[ # ]}

 

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Abstract

Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, and β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 2)-6-O-E-sinapoyl-β-D-glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7-O-(2″-O-formyl)-β-D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety.

^# Dedicated to Professor Arnold Vlietinck on the occasion of his 80th birthday.

Publication History

Received: 06 July 2020

Accepted after revision: 15 September 2020

Article published online:
06 November 2020

© 2020. Thieme. All rights reserved.

Georg Thieme Verlag KG
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• References

• 1 Olmsteadt RG, Zjhra ML, Lohmann LG, Grose SO, Eckart AJ. A molecular phylogeny and classification of Bignoniaceae. Am J Bot 2009; 96: 1731-1743
  CrossrefPubMedGoogle Scholar
• 2 Gafner S, Wolfender JL, Nianga M, Stoeckli-Evans H, Hostettmann K. Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots. Phytochemistry 1996; 42: 1315-1320
  CrossrefPubMedGoogle Scholar
• 3 Gafner S, Wolfender JL, Nianga M, Hostettmann K. Phenylpropanoid glycosides from Newbouldia laevis roots. Phytochemistry 1997; 44: 687-690
  CrossrefPubMedGoogle Scholar
• 4 Kernan MR, Amarquaye A, Chen JL, Chan J, Sesin DF, Parkinson N, Ye Z, Barrett M, Bales C, Stoddart CA, Sloan B, Blanc P, Limbach C, Mrisho S, Rozhon EJ. Antiviral phenylpropanoid glycosides from the medicinal plant Markhamia lutea . J Nat Prod 1998; 61: 564-570
  CrossrefPubMedGoogle Scholar
• 5 Kanchanapoom T, Kasai R, Yamasaki K. Phenolic glycosides from Markhamia stipulata . Phytochemistry 2002; 59: 557-563
  CrossrefPubMedGoogle Scholar
• 6 Adesanya SA, Nia R, Fontaine C, Pais M. Pyrazole alkaloids from Newbouldia laevis . Phytochemistry 1994; 35: 1053-1055
  CrossrefPubMedGoogle Scholar
• 7 Aladesanmi AJ, Nia R, Nahrstedt A. New pyrazole alkaloids from the root bark of Newbouldia laevis . Planta Med 1998; 64: 90-91
  Article in Thieme ConnectPubMedGoogle Scholar
• 8 Khan MR, Mlungwana SM. γ-Sitosterol, a cytotoxic sterol from Markhamia zanzibarica and Kigelia africana . Fitoterapia 1999; 70: 96-97
  CrossrefPubMedGoogle Scholar
• 9 El-Hela AA. Phenolics from Spathodea acuminata (P. Beauvais) leaves. Al-Azhar J Pharm Sci 2001; 27: 152-162
  PubMedGoogle Scholar
• 10 El-Hela AA. A new iridoid glucoside from Spathodea acuminata (P. Beauvais) leaves. Al-Azhar J Pharm Sci 2001; 27: 115-120
  PubMedGoogle Scholar
• 11 Ngouela S, Tsamo E, Sondengam BL. Extractives from Bignoniaceae. Constituents of the stembark of Spathodea campanulata . Planta Med 1988; 54: 476
  Article in Thieme ConnectPubMedGoogle Scholar
• 12 Ngouela S, Nyasse B, Tsamo E, Sondengam BL, Conolly JD. Spathodic acid: a triterpene acid from the stem bark of Spathodea campanulata . Phytochemistry 1990; 29: 3559-3561
  CrossrefPubMedGoogle Scholar
• 13 Burkill HM. The useful Plants of West tropical Africa. 2nd edition, Vol. 1. Kew, London: Royal Botanic Gardens; 1985: 440-446
  Google Scholar
• 14 Azuine MA. Cancer and Ethnobotany of Nigeria. Aachen: Shaker; 1999: 115-116
  Google Scholar
• 15 Gormann R, Kaloga M, Li XC, Ferreira D, Bergenthal D, Kolodziej H. Furanonaphthoquinones, atraric acid and a benzofuran from the stembarks of Newbouldia laevis . Phytochemistry 2003; 64: 583-587
  CrossrefPubMedGoogle Scholar
• 16 Gormann R, Kaloga M, Ferreira D, Marais JPJ, Kolodziej H. Newbouldiosides A–C, phenylethanoid glycosides from the stem bark of Newbouldia laevis . Phytochemistry 2006; 67: 805-811
  CrossrefPubMedGoogle Scholar
• 17 Gormann R, Schreiber L, Kolodziej H. Cuticular wax profiles of leaves of some traditionally used African Bignoniaceae. Z Naturforsch 2004; 59c: 631-635
  CrossrefPubMedGoogle Scholar
• 18 Zou JM, Wang LS, Niu XM, Sun HD, Guo YJ. Phenylethanoid glycosides from Picria felterrae Lour. J Integr Plant Biol 2005; 47: 632-636
  CrossrefPubMedGoogle Scholar
• 19 Sugiyama M, Kikuchi M. Phenylethanoid glycosides from Osmanthus asiaticus . Phytochemistry 1995; 32: 1553-1555
  CrossrefPubMedGoogle Scholar
• 20 Xue Z, Yang B. Phenylethanoid glycosides: Research advances in their phytochemistry, pharmacological activity and pharmacokinetics. Molecules 2016; 21: 991
  CrossrefPubMedGoogle Scholar
• 21 Kyriakopoulou I, Magiatis P, Skaltsounis AL, Aligiaris A, Harvala C. Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia . J Nat Prod 2001; 64: 1095-1097
  CrossrefPubMedGoogle Scholar
• 22 Harborne JB. Comparative biochemistry of the flavonoids – VI.: Flavonoid patterns in the Bignoniaceae and the Gesneriaceae. Phytochemistry 1967; 6: 1643-1651
  CrossrefPubMedGoogle Scholar
• 23 Hegnauer R. Chemotaxonomie der Pflanzen, Vol. VIII. Basel: Birkhäuser; 1989: 128-138
  CrossrefGoogle Scholar
• 24 Blatt CTT, Santos M, Salatino A. Flavonoids of Bignoniaceae from the “cerrado” and their possible taxonomic significance. Plant Syst Evol 1998; 210: 289-292
  CrossrefPubMedGoogle Scholar
• 25 Mansoor A, Neeru J, Mohammad K, Mohammad I. Isolation and characterization of two new flavanone disaccharides from the leaves of Tecoma grandiflora, Bignoniaceae. J Chem Res Synop 1991; 5: 10
  PubMedGoogle Scholar
• 26 Foo LY. Configuration and conformation of dihydroflavonols from Acacia melanoxylon . Phytochemistry 1987; 26: 813-817
  CrossrefPubMedGoogle Scholar
• 27 Slimestad R, Andersen ØM, Francis GW. Ampelopsin 7-glucoside and other dihydroflavonol 7-glucosides from needles of Picea abies . Phytochemistry 1994; 35: 550-552
  CrossrefPubMedGoogle Scholar
• 28 Judelicato JM, Stewart BA, Engel GL. Formylation of glucose by cefamandole nafate at alkaline pH. J Pharm Sci 1980; 69: 1183-1188
  CrossrefPubMedGoogle Scholar
• 29 Foo LY, Karchesy JJ. Polyphenolic glycosides from Douglas fir inner bark. Phytochemistry 1989; 28: 1237-1240
  CrossrefPubMedGoogle Scholar
• 30 Baderschneider B, Winterhalter P. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from riesling wine and screening for antioxidant activity. J Agric Food Chem 2001; 49: 2788-2798
  CrossrefPubMedGoogle Scholar
• 31 Von Poser GL, Schripsema J, Henriques AT, Rosendahl J. The distribution of iridoids in Bignoniaceae. Biochem Syst Ecol 2000; 28: 351-366
  CrossrefPubMedGoogle Scholar
• 32 Guiso M. Pondraneoside, a new iridoid glucoside from Pondranea ricasoliana . J Nat Prod 1982; 45: 462-465
  CrossrefPubMedGoogle Scholar
• 33 Guiso M, Marra C, Piccioni F, Nicoletti M. Iridoid and phenylglucoside from Tecoma capensis . Phytochemistry 1997; 45: 193-194
  CrossrefPubMedGoogle Scholar
• 34 Bianco A, Passacantilli P, Righi G. New iridoid glycosides from Tecoma capensis . J Nat Prod 1983; 46: 314-319
  CrossrefPubMedGoogle Scholar