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Anthelmintic flavonoids and other compounds from Combretum glutinosum Perr. ex DC (Combretaceae) leaves


Toklo, Placide M; Yayi Ladekan, Eléonore; Linden, Anthony; Hounzangbe-Adote, Sylvie; Kouam, Siméon F; Gbenou, Joachim D (2021). Anthelmintic flavonoids and other compounds from Combretum glutinosum Perr. ex DC (Combretaceae) leaves. Acta Crystallographica. Section C: Structural Chemistry, 77(9):505-512.

Abstract

A chemical study of the hydro-ethanol extract of the leaves of Combretum glutinosum resulted in the isolation of nine com­pounds, including 5-de­methyl­sin­en­se­tin (1), umuhengerin (2), (20S,24R)-ocotillone (3), lupeol (4), β-sitosterol (5), oleanolic acid (6), betulinic acid (7), corymbosin (8) and β-sito­sterol glucoside (9). Four com­pounds have been isolated for the first time from the genus Combretum [viz. (1), (2), (3) and (8)]. The crystal structures of flavonoid (2), C20H20O8, Z′ = 2, and triterpene (3), C30H50O3, Z′ = 1, have been determined for the first time; the latter confirmed the absolute configuration of native (20S,24R)-ocotillone previously derived from the crystal structures of related derivatives. The mol­ecules of (3) are linked into supra­molecular chains by inter­molecular O—H⋯O hydrogen bonds. The crude extracts obtained by aqueous decoction and hydro-ethano­lic maceration, as well as the nine isolated com­pounds, were tested for their anthelmintic activity on the larvae and adult worms of Haemonchus contortus, a hematophage that causes parasitic disorders in small ruminants. The evaluated anthelmintic activity showed that the extracts at different doses, as well as all the com­pounds tested at 150 µg ml−1, inhibited the migration of the larvae and the motility of the adult worms of the parasite com­pared with the phosphate buffer solution negative reference control. The best activity was obtained with flavonoids (1), (2) and (8) on both stages of the parasite. The flavones that showed good activity can be used for the further development of other derivatives, which could increase the anthelmintic efficacy.

Abstract

A chemical study of the hydro-ethanol extract of the leaves of Combretum glutinosum resulted in the isolation of nine com­pounds, including 5-de­methyl­sin­en­se­tin (1), umuhengerin (2), (20S,24R)-ocotillone (3), lupeol (4), β-sitosterol (5), oleanolic acid (6), betulinic acid (7), corymbosin (8) and β-sito­sterol glucoside (9). Four com­pounds have been isolated for the first time from the genus Combretum [viz. (1), (2), (3) and (8)]. The crystal structures of flavonoid (2), C20H20O8, Z′ = 2, and triterpene (3), C30H50O3, Z′ = 1, have been determined for the first time; the latter confirmed the absolute configuration of native (20S,24R)-ocotillone previously derived from the crystal structures of related derivatives. The mol­ecules of (3) are linked into supra­molecular chains by inter­molecular O—H⋯O hydrogen bonds. The crude extracts obtained by aqueous decoction and hydro-ethano­lic maceration, as well as the nine isolated com­pounds, were tested for their anthelmintic activity on the larvae and adult worms of Haemonchus contortus, a hematophage that causes parasitic disorders in small ruminants. The evaluated anthelmintic activity showed that the extracts at different doses, as well as all the com­pounds tested at 150 µg ml−1, inhibited the migration of the larvae and the motility of the adult worms of the parasite com­pared with the phosphate buffer solution negative reference control. The best activity was obtained with flavonoids (1), (2) and (8) on both stages of the parasite. The flavones that showed good activity can be used for the further development of other derivatives, which could increase the anthelmintic efficacy.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Condensed Matter Physics
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Inorganic Chemistry
Physical Sciences > Materials Chemistry
Uncontrolled Keywords:Materials Chemistry, Inorganic Chemistry, Physical and Theoretical Chemistry, Condensed Matter Physics
Language:English
Date:1 September 2021
Deposited On:30 Aug 2021 13:07
Last Modified:27 Sep 2022 11:50
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:2053-2296
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1107/s2053229621007841
Project Information:
  • : FunderSNSF
  • : Grant ID206021_164018
  • : Project TitleDual X-ray Wavelength Single-Crystal Diffractometer
  • : FunderDAAD
  • : Grant ID57316173
  • : Project Title
  • : FunderYaounde- Bielefeld Bilateral Graduate School
  • : Grant ID
  • : Project TitleNatural Products with Antiparasite and Anti-bacterial Activity (YaBiNaPA) project
  • : FunderWest African Research Association
  • : Grant ID
  • : Project TitleBiological testing

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