Antitumoral and Antimicrobial Activities of Bitter Sesquiterpene Lactones of<i>Vernonia amygdalina</i>, a Possible Medicinal Plant Used by Wild Chimpanzees

Jisaka, Mitsuo; Ohigashi, Hajime; Takegawa, Kazunori; Huffman, Michael A.; Koshimįzu, Koichi

doi:10.1271/bbb.57.833

Cited by 75 publications

(51 citation statements)

References 4 publications

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“…The 1 H and 13 C NMR spectral data of vernolide were in good agreement with published data (Rabe et al, 2002) (Table 1). This compound has previously been reported from the aerial parts of Vernonia amygdalina Del., Vernonia colorata willd, and Vernonia hindei S. Moore (Jisaka et al, 1993;Zdero et al, 1991;Rabe et al, 2002).…”

Section: Structural Identification Of Sesquiterpene Lactonessupporting

confidence: 55%

“…The 1 H NMR spectral data of vernodalol were in agreement with the earlier report of this compound by Asaka et al (1977) (Table 1). Jisaka et al (1993) reported vernodalol to be an artifact of vernodalin, presumed to be the product of methanol and extract solvolysis reaction during the extraction process. However, a recent report by Erasto et al (2006) confirmed the identity of this compound.…”

Section: Structural Identification Of Sesquiterpene Lactonesmentioning

confidence: 99%

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Antioxidant Constituents inVernonia amygdalina. Leaves

Erasto

Grierson

Afolayan

2007

Pharmaceutical Biology

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Vernonia amygdalina Del. (Asteraceae) is a plant widely used both for nutritional and medicinal purposes throughout the tropical Africa. The health-promoting ability of this plant species might be related to the antioxidative effect of its constituents. In this study,the antioxidant activity of this plant was evaluated by comparing the reducing capacity and the DPPH radical scavenging of two previously isolated sesquiterpene lactones (vernolide and vernodalol) with the ethanol extract from which the two compounds were isolated. Results indicated that vernolide had a higher reducing power than vernodalol and the ethanol extract. At 0.25 mg=mL, vernolide had an absorbance value of 0.15 while vernolide and the ethanol extract had absorbencies of 0.042 and 0.144, respectively. Catechin (a standard antioxidant compound), however, exhibited a higher reducing power than all the three samples. In the DPPH radical scavenging, both the sesquiterpene lactones and the ethanol extract exhibited appreciable activity. At 0.25 mg=mL, the activity order was ethanol extract > vernodalol > vernolide. At all concentrations, the ethanol extract had higher radical scavenging activity than the sesquiterpene lactones, suggesting a possible synergistic effect of these and any other antioxidant constituents.

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Section: Structural Identification Of Sesquiterpene Lactonessupporting

confidence: 55%

Section: Structural Identification Of Sesquiterpene Lactonesmentioning

confidence: 99%

Antioxidant Constituents inVernonia amygdalina. Leaves

Erasto

Grierson

Afolayan

2007

Pharmaceutical Biology

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“…Among the Vernonia species, some cytotoxicity has been described for isolated sesquiterpene lactones from V. cinerea (15), V. lasiopus (16) and V. amygdalina (27). Some active Vernonia extracts have also been found, such as the water-soluble extract of edible V. amygdalina leaves (9), and the water extract from the roots of V. kotschyana (20) and V. anthelmintica (10).…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic activity of the dichloromethane fraction from Vernonia scorpioides (Lam.) Pers. (Asteraceae) against Ehrlich's tumor cells in mice

Pagno

Blind

Biavatti

et al. 2006

Braz J Med Biol Res

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Vernonia scorpioides has been widely used in Brazil to treat skin problems and chronic wounds, such as ulcers of the lower limbs and diabetic lesions. In the present study, we investigated the effect of a dichloromethane (DCM) fraction of V. scorpioides leaf extract on Ehrlich ascitic and solid tumor-bearing mice. The animals were treated once a day with the DCM fraction at a concentration of 5 mg/kg, administered ip during and after the development of the tumor. The lifespan, weight, number and type of leukocytes, number of tumor cells, volume of solid and ascitic tumors were measured. The development of the tumor with pre-treated tumor cells in vitro with the DCM fraction (5 mg/kg) was analyzed and the animals were sacrificed after 7 days. The DCM fraction (5 mg/kg) totally inhibited tumor development when in direct contact with tumor cells, and also ascitic tumor development with in vitro treatment or when administered ip, in loco (after 7 days). Animals treated with the DCM fraction increased their lifespan ca. 2 weeks and maintained their body weight for 30 days. When applied immediately after the inoculation of the tumor cells in vivo, it totally abolished tumor development, with tumor development only decreasing when treatment was started 3 days after the tumor challenge. These data suggest an antineoplastic activity of the fraction. Oral or ip administration of DCM fraction (5 mg/kg) for 7 days did not reduce the solid tumor volume. The cytotoxic activity described here differs from the conventional immune suppressing profile of standard chemotherapy because it increases neutrophil influx to the peritoneal cavity. These results show that, besides exhibiting a tumoricidal activity, the DCM fraction also exhibits inflammatory activity.

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“…7-9) Glaucolides have been reported to elicit molluscicidal, antitumoral, and antimicrobial properties 5,10,11) ; but their effects on smooth muscle have not been investigated previously. Parthenolide, a structurally related sesquiterpene lactone (Fig.…”

mentioning

confidence: 99%

“…[3][4][5][6] However, several hirsutinolides might be artifacts formed from glaucolides on exposure to acidic adsorbents during chromatography. [7][8][9] Glaucolides have been reported to elicit molluscicidal, antitumoral, and antimicrobial properties 5,10,11) ; but their effects on smooth muscle have not been investigated previously. Parthenolide, a structurally related sesquiterpene lactone (Fig.…”

mentioning

confidence: 99%

Relaxation of Uterine and Aortic Smooth Muscle by Glaucolides D and E from Vernonia liatroides.

Campos

Oropeza

Fernández

et al. 2003

Biological & Pharmaceutical Bulletin

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Vernonia spp. (Asteraceae) are reported in Mexican herbolaria for used in menstrual disorders, hair regeneration, dysentery, and as a coagulant.1) Brazilian folk medicine has shown that the crude extract prepared from leaves of V. condensata prevents stomach and liver disturbances (sic).2) Several of these applications suggest presence of compounds active on smooth muscle. Sesquiterpene lactones, mainly glaucolide-and hirsutinolide-type, have been isolated from Vernonia spp. -sensu latu-.3-6) However, several hirsutinolides might be artifacts formed from glaucolides on exposure to acidic adsorbents during chromatography.7-9) Glaucolides have been reported to elicit molluscicidal, antitumoral, and antimicrobial properties 5,10,11) ; but their effects on smooth muscle have not been investigated previously. Parthenolide, a structurally related sesquiterpene lactone (Fig. 1D) bearing also a germacra-1(10),4-diene-4-epoxide skeleton is known to inhibit smooth muscle contractility likely due to the amethylene g-lactone moiety.12) Therefore, the effects of glaucolides D (Fig. 1A) and E (Fig. 1B) on vascular and uterine smooth muscle contraction were studied. The effect of a hirsutinolide type sesquiterpene lactone (Fig. 1C) lacking both germacrane skeleton and a-methylene g-lactone was also investigated. We have assayed the action of these compounds on smooth muscle pre-contracted with either depolarizing high-KCl solution or an agonist (noradrenaline for aorta and oxytocin for uterus). This model was selected as mean to indicate whether glaucolides D and E are able to relax the contraction dependent on different pathways of calcium influx. MATERIALS AND METHODSCompounds Glaucolides D (Fig. 1A) and E (Fig. 1B) were isolated from Vernonia liatroides by chromatography and identified by spectroscopic methods as previously described. 3) The hirsutinolide [1R,4S,5R,6S,8S,10R]-8,10,13-triacetoxy-1(4)-epoxy-1,5-dihydroxygermacr-7(11)-en-6(12)-olide ( Fig. 1C) Animals Sprague-Dawley rats, female for uterine experiments and male for aorta experiments, body weight approximately 300 g, were used. Virgin female rats received a subcutaneous injection of estradiol benzoate (40 mg/kg) 24 h prior to the experiment. Animal experiments were performed following the recommendations of the Policies on Animal Experimentation of the Scientific Committee of the Instituto Mexicano del Seguro Social; animals were decapitated, and uterus or descending thoracic aorta were isolated, fat and connective tissue were removed, and tissues were placed in Krebs-Ringer bicarbonate solution.Uterus Experiments Uterine rings (5-7 mm long) were placed in a 5 ml organ bath containing Krebs-Ringer bicarbonate (KRb) solution with the following composition (mM): NaCl, 120; KCl, 4.6; CaCl 2 , 1.5; NaHCO 3 , 20; KH 2 PO 4 , 1.2; MgSO 4 , 1.2, and glucose 11, maintained at 37°C and bubbled with a mixture of 95% O 2 -5% CO 2 (pHϭ7.4). Contractions were recorded isometrically by a force-displacement transducer (Grass, FT03) connected to a Grass polygraph (model 7B)...

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Antitumoral and Antimicrobial Activities of Bitter Sesquiterpene Lactones ofVernonia amygdalina, a Possible Medicinal Plant Used by Wild Chimpanzees

Cited by 75 publications

References 4 publications

Antioxidant Constituents inVernonia amygdalina. Leaves

Antioxidant Constituents inVernonia amygdalina. Leaves

Cytotoxic activity of the dichloromethane fraction from Vernonia scorpioides (Lam.) Pers. (Asteraceae) against Ehrlich's tumor cells in mice

Relaxation of Uterine and Aortic Smooth Muscle by Glaucolides D and E from Vernonia liatroides.

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