Download PDF
CC BY-NC-ND 4.0 · Planta Medica International Open 2017; 4(03): e104-e107
DOI: 10.1055/s-0043-120070
Original Papers
Eigentümer und Copyright ©Georg Thieme Verlag KG 2018

Mayombensin, a New Azadirachtin I Derivative with Unusual Structure from Guarea mayombensis

Charlie Djeukeu
1   Faculty of Science, Department of Chemistry, University of Douala, Douala, Cameroon
,
Michel Feussi Tala
2   University of Göttingen, Institute of Organic and Biomolecular Chemistry, Göttingen, Germany
,
Carine Mvot Akak
1   Faculty of Science, Department of Chemistry, University of Douala, Douala, Cameroon
,
Anatole Guy Blaise Azebaze
1   Faculty of Science, Department of Chemistry, University of Douala, Douala, Cameroon
,
Alain Francois Kamdem Wafo
1   Faculty of Science, Department of Chemistry, University of Douala, Douala, Cameroon
,
Jean Duplex Wansi
1   Faculty of Science, Department of Chemistry, University of Douala, Douala, Cameroon
,
Juliette Catherine Vardamides
1   Faculty of Science, Department of Chemistry, University of Douala, Douala, Cameroon
,
Hartmut Laatsch
2   University of Göttingen, Institute of Organic and Biomolecular Chemistry, Göttingen, Germany
› Author Affiliations
Further Information

Publication History

received 18 February 2017
revised 07 June 2017

accepted 08 September 2017

Publication Date:
22 November 2017 (online)

   Permissions and Reprints

Abstract

A new highly oxidized tetranortriterpenoid, named mayombensin (1), was isolated from the twigs of Guarea mayombensis together with five known compounds and, further, two ceramides, 3,4-dimethyl-secotirucalla-4(28),7,24-trien-3,21-dioic acid (3), the glucosides of stigmasterol and β-sitosterol, and the respective aglyca. The structure of 1 was elucidated by detailed NMR analysis and confirmed as a novel azadirachtin homologue.

Key words

Guarea mayombensis - Meliaceae - tetranortriterpenoid - mayombensin - azadirachtin homologue

Supporting Information

 

  • References

  • 1 D'Arcy WC. Flora de Panama. Check list and index, Part 1. Saint Louis, MO: Missouri Botanical Garden; 1987: 672
    Search in Google Scholar
  • 2 Schultes RE, Raffauf RF. The healing forest: medicinal and toxic plants of the North West Amazonia. Portland, OR: Dioscorides Press; 1990
    Search in Google Scholar
  • 3 Pereira C, Barreto Júnior CB, Kuster RM, Simas NK, Sakuragui CM, Porzel A, Wessjohann L. Flavonoids and neolignan glucoside from Guarea macrophylla . Quim Nova 2012; 35: 1123-1126
    CrossrefPubMedSearch in Google Scholar
  • 4 Oga S, Sertie JA, Brasile AC, Hanada S. Anti-inflammatory effect of a crude extract from Guarea guidonia . Planta Med 1981; 42: 310-312
    Thieme ConnectPubMedSearch in Google Scholar
  • 5 Weniger B, Robledo S, Arango GJ, Deharo E, Aragón R, Muñoz V, Callapa J, Lobstein A, Anton R. Antiprotozoal activities of Colombian plants. J Ethnopharmacol 2001; 78: 193-200
    CrossrefPubMedSearch in Google Scholar
  • 6 Simoni IC, Munford V, Felicio JD, Lins AP. Antiviral activity of crude extracts of Guarea guidonia . Braz J Med Biol Res 1996; 29: 647-650
    PubMedSearch in Google Scholar
  • 7 Garcez FR, Nuñez CV, Garcez WS, Almeida RM, Roque NF. Sesquiterpenes, limonoids and coumarins from the wood bark of Guarea guidonia . Planta Med 1998; 64: 79-80
    Thieme ConnectPubMedSearch in Google Scholar
  • 8 Akinniyi JA, Connolly JD, Rycroft DS, Sondengam BL, Ifeadike NP. Tetranortriterpenoids and related compounds. Part 25. Two 3,4-secotirucallane derivates and 2’-hydroxyrohitukin from the bark of Guarea cedrata . Canadian J Chem 1980; 58: 1865-1868
    CrossrefPubMedSearch in Google Scholar
  • 9 Furlan M, Lopes MN, Fernandes JB, Pirani JR. Diterpenes from Guarea trichilioides . Phytochemistry 1996; 41: 1159-1161
    CrossrefPubMedSearch in Google Scholar
  • 10 Moutoo BS, Jativa C, Tinto WF, Reynolds WF, McLean S. Ecuadorin, a novel tetranortriterpenoid of Guarea kunthiana: structure elucidation by 2D-NMR spectroscopy. Canadian J Chem 1992; 70: 1260-126
    CrossrefPubMedSearch in Google Scholar
  • 11 Kubo I, Mataumoto A, Mataumoto T. New insect ecdysis inhibitory limonoid diacetylazadirachtinol isolated from Azadirachta indica (Meliaceae) oil. Tetrahedron 1985; 42: 485-496
    PubMedSearch in Google Scholar
  • 12 Govindachari TR, Sandhya G, Ganesh Raj SP. Azadirachtins H and I: two new tetranortriterpenoids from Azadirachta indica. J Nat Prod 1992; 55: 596-601
    CrossrefPubMedSearch in Google Scholar
  • 13 Taylor DAH. Azadirachtin: A study in the methodology of structure determination. Tetrahedron 1987; 43: 2779-2787
    CrossrefPubMedSearch in Google Scholar
  • 14 Bilton JN, Broughton HB, Jones P, Ley SV, Lidert Z, Horgan ED, Rzepa HS, Sheppard RN, Slawin AMZ, Williams DJ. An X-ray crystallographic, mass spectroscopic and NMR study of the limonoid insect antifeedant azadirachtin and related derivatives. Tetrahedron 1987; 43: 2805-2815
    CrossrefPubMedSearch in Google Scholar
  • 15 Heasley B. Synthesis of limonoid natural products. Eur J Org Chem 2011; 1: 19-46
    PubMedSearch in Google Scholar
  • 16 Khatun M, Billah M, Quader MA. Sterols and sterol glucosides from Phyllanthus species . Dhaka Univ J Sci 2012; 60: 5-10
    PubMedSearch in Google Scholar