Isolation, characterization and antiplasmodial activity of steroidal alkaloids from Funtumia elastica (Preuss) Stapf

Zirihi, Guédé Noël; Grellier, Philippe; Guédé-Guina, F.; Bodo, Bernard; Mambu, Lengo

doi:10.1016/j.bmcl.2005.03.021

Cited by 58 publications

(41 citation statements)

References 9 publications

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“…The only published characterizations of Funtumia elastica describes the isolation of steroidal alkaloids from its leaves and bark with antiplasmodial [52] or antifungal activity [53]. Steroids may also be one component involved in the anecdotal effect of Yamoa™ on asthma, but our data suggesting immunostimulatory effects of Yamoa™ are inconsistent with anti-inflammatory effects attributed to steroids.…”

Section: Discussionmentioning

confidence: 71%

Polysaccharides derived from Yamoa™ (Funtumia elastica) prime γδ T cells in vitro and enhance innate immune responses in vivo

Graff

Kimmel

Freedman

et al. 2009

International Immunopharmacology

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Yamoa™ (ground bark of Funtumia elastica tree) is marketed and sold as a dietary supplement with anecdotal therapeutic effects in the treatment of asthma and hay fever. We determined that Yamoa™ and Yamoa™-derived polysaccharides affected innate immunity, in part, by priming γδ T cells. Gene expression patterns in purified bovine γδ T cells and monocytes induced by Yamoa™ were similar to those induced by ultrapure lipopolysaccharide (uLPS). In the presence of accessory cells, Yamoa™ had priming effects that were similar to those of LPS on bovine and murine γδ T cells, but much more potent than LPS on human γδ T cells. The bioactive component of Yamoa™ was delineated to a complex polysaccharide fraction (Yam-I). Intraperitoneal injection of Yamoa™ and Yam-I in mice induced rapid increases in peritoneal neutrophils directed by changes in chemokine expression. In support of a unique agonist found in Yam-I, similar peritonitis responses were also observed in TLR4-and MyD88-deficient mice. Therapeutic treatment with Yam-I resulted in decreased bacterial counts in feces from mice with Salmonella enterica serotype Typhimurium (ST)-induced enterocolitis. This characterization of the immune stimulatory properties of polysaccharides derived from Yamoa™ suggests mechanisms for the anecdotal positive effects of its ingestion and that these polysaccharides show potential for application in innate protection from disease.

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Section: Discussionmentioning

confidence: 71%

Polysaccharides derived from Yamoa™ (Funtumia elastica) prime γδ T cells in vitro and enhance innate immune responses in vivo

Graff

Kimmel

Freedman

et al. 2009

International Immunopharmacology

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“…4) In continuation to our previous attempt on the isolation of novel molecules from the Himalayan bioresource, 5-8) a new steroidal alkaloid was isolated and characterized, designated as holadysenterine (1), together with three known steroidal alkaloids, conessine (2), isoconessimine (3) and kurchessine (4) from the stem bark of H. antidysenterica.…”

mentioning

confidence: 92%

“…3) Recently, the antiplasmodial activity of conessine and isoconessine has been reported against the chloroquine-resistant strain FcB1 of Plasmodium falciparum. 4) In continuation to our previous attempt on the isolation of novel molecules from the Himalayan bioresource, [5][6][7][8] a new steroidal alkaloid was isolated and characterized, designated as holadysenterine (1), together with three known steroidal alkaloids, conessine (2), isoconessimine (3) and kurchessine (4) from the stem bark of H. antidysenterica.…”

mentioning

confidence: 98%

Steroidal Alkaloids from Holarrhena antidysenterica (L.) WALL.

Kumar

Singh

Bhandari

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Holarrhena antidysenterica (L.) WALL. (Apocynaceae) is a medicinal plant, found throughout the Indian subcontinent. Stem bark of the plant, commercially known as "kurchi", has been extensively investigsted due to its traditional use in the treatment of amoebic dysentery, diarrhea, asthma, bronchopneumonia and malaria.2) Stem bark and seeds of the plant are reported to contain a number of steroidal alkaloids, such as conanines, 3-aminoconanines, 20-aminoconanines, 3-aminopregnans, 3,20-diaminopregnanes and their derivatives. 3) Being the principle alkaloid, conessine is mostly studied for its antidiarrhoel properties.3) Recently, the antiplasmodial activity of conessine and isoconessine has been reported against the chloroquine-resistant strain FcB1 of Plasmodium falciparum. 4) In continuation to our previous attempt on the isolation of novel molecules from the Himalayan bioresource, 5-8) a new steroidal alkaloid was isolated and characterized, designated as holadysenterine (1), together with three known steroidal alkaloids, conessine (2), isoconessimine (3) and kurchessine (4) from the stem bark of H. antidysenterica. Results and DiscussionAlkaloidal fraction (1.19%) isolated from the stem bark (1 kg) of the plant was chromatographed over basic alumina, led to the isolation of compounds 1-4.Compound 1 was obtained as an amorphous powder. Its high-resolution mass spectrum in positive-ion FAB-MS showed a [MϩH] ϩ at m/z 391.2892 (Calcd for C 23 H 39 N 2 O 3 391.2961) corresponded to the molecular formula C 23 H 38 N 2 O 3 , indicating six degrees of unsaturation in the molecule. Four of these were accounted for a tetracyclic structure of pregnane-type skeleton and two were due to endocyclic double bond and acetamide functionality at the C-20 position. The IR spectrum showed absorption at 1618 (CϭC), 1680 (amide carbonyl), 3410 (OH) and 3540 (NH) cm Ϫ1. The 1 H-NMR spectrum of 1 (Table 1) included two doublets at d 3.41 (1H, d, Jϭ11.7 Hz) and 3.75 (1H, d, Jϭ11.7 Hz) and were assigned to the C-13 hydroxymethylene protons. The vinylic proton was recorded at d 5.46 as a broad singlet. Two wide multiplets at d 2.92 and 3.53 were assigned to H-3a-and H-20b-, respectively. The b-orientation of H-20 was deduced by comparing the spectral values with published data for steroidal alkaloids [9][10][11][12][13][14][15][16][17][18][19] and biogenetic considerations keeping in view of the fact that all pregnane-type steroidal alkloids are biosynthesized from cholesterol via pregnenolone. 10,20) The H-21 (3H, d, Jϭ 6.6 Hz) and H-19 (3H, s) methyl groups appeared at d 1.38 and 1.09, respectively. A three proton singlet at d 1.97 was due to the presence of acetamide methyl protons. A D 2 O exchangeable proton singlet due to N-hydroxyl at d 4.95 appeared to be overlapped with solvent (CD 3 OD) signal. 21)However, on D 2 O exchange the C-21 methyl proton signal shielded to d 1.11 which suggested the position of hydroxyl group at amine functional of side chain. 21)The 13 C-NMR spectrum of 1 (Table 1) showed 22 resonances, while ...

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“…It has useful antioxidant, antifungal, anti-biotic, and anti-inflammatory properties and is traditionally used to treat allergies and respiratory issues. The therapeutic ability of FE is attributable to the phytochemical constituents therein, and Such compounds as ascorbic acid (AA), conessine (CS) and methyl ursolate have been shown to be the active constituents of the extract [17,18]. The structures are presented in Fig.…”

Section: Introductionmentioning

confidence: 98%

Inhibitory Action ofFuntumia elasticaExtracts on the Corrosion of Q235 Mild Steel in Hydrochloric Acid Medium: Experimental and Theoretical Studies

Chidiebere

Oguzie

Liu

et al. 2014

Journal of Dispersion Science and Technology

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The inhibiting effect of aqueous extracts of Funtumia elastica (FE) on mild steel corrosion in 1 M HCl solution was investigated using electrochemical and surface characterization techniques. The results revealed that FE effectively inhibited the corrosion reaction. Polarization data reveal that the extract functioned as a mixed-type inhibitor, while impedance results show that the extract organic matter adsorbed on the metal/solution interface. FT-IR, SEM and AFM results confirmed the formation of a protective layer of extract adsorbed on the mild steel surface. Adsorption of some organic constituents of FE on mild steel was theoretically described by quantum chemical computations and molecular dynamics simulations, in the framework of the density functional theory (DFT).

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Isolation, characterization and antiplasmodial activity of steroidal alkaloids from Funtumia elastica (Preuss) Stapf

Cited by 58 publications

References 9 publications

Polysaccharides derived from Yamoa™ (Funtumia elastica) prime γδ T cells in vitro and enhance innate immune responses in vivo

Polysaccharides derived from Yamoa™ (Funtumia elastica) prime γδ T cells in vitro and enhance innate immune responses in vivo

Steroidal Alkaloids from Holarrhena antidysenterica (L.) WALL.

Inhibitory Action ofFuntumia elasticaExtracts on the Corrosion of Q235 Mild Steel in Hydrochloric Acid Medium: Experimental and Theoretical Studies

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