Reaction of the Molluscicide Glaucolide B with Bentonite

Jimenez, Manuel; Ortega, Alfredo; Navarro, Arturo; Maldonado, Emma; Calsteren, M. R. Van; Jankowski, Chrystopher K.

doi:10.1021/np50117a012

J. Nat. Prod.

1995

DOI: 10.1021/np50117a012

|View full text |Cite

Reaction of the Molluscicide Glaucolide B with Bentonite

Manuel Jimenez¹,

Alfredo Ortega²,

Arturo Navarro³

et al.

Abstract: Glaucolide B [1] was transformed, under bentonite earth/EtOAc conditions, into compound3 ([lk,45,5i?,65,85,10i?]-8,10,13-triacetoxy-l(4)-epoxy-l,5-dihydroxygermacr-7(ll)-en-6(12)-olide. The structures of compound 3 and of its derivatives 4 and 5 were established by nmr spectroscopy.'Contribution No. 1291 of the Instituto de Química, U.N.A.M.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1997

2019

Publication Types

Select...

Article4

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

(1 citation statement)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[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

View full text Add to dashboard Cite

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)...

show abstract

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

View full text Add to dashboard Cite

show abstract

Antiproliferative, cytotoxic and apoptotic activity of the bentonite transformation of sesquiterpene lactone glaucolide B to 5β-hydroxy-hirsutinolide on tumor cell lines

Flores-Guzmán

Alvarado-Sansininea

López-Muñoz

et al. 2019

European Journal of Pharmacology

View full text Add to dashboard Cite

Sesquiterpene lactones from Vernonia scorpioides and their in vitro cytotoxicity

et al. 2010

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Reaction of the Molluscicide Glaucolide B with Bentonite

Cited by 4 publications

References 8 publications

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

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

Antiproliferative, cytotoxic and apoptotic activity of the bentonite transformation of sesquiterpene lactone glaucolide B to 5β-hydroxy-hirsutinolide on tumor cell lines

Sesquiterpene lactones from Vernonia scorpioides and their in vitro cytotoxicity

Contact Info

Product

Resources

About