Literature DB >> 2778448

Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata.

Y H Hui1, J K Rupprecht, Y M Liu, J E Anderson, D L Smith, C J Chang, J L McLaughlin.   

Abstract

Screening of crude extracts of the bark of Annona bullata showed cytotoxic and pesticidal activities. By monitoring with brine-shrimp lethality, two novel, extremely potent acetogenins, bullatacin [1] and bullatacinone [2], were isolated. Spectral and chemical methods identified bullatacin as a diastereomer of asimicin. Bullatacinone represents bullatacin with the lactone cleaved and reformed at the 4-OH. Compounds 1 and 2 show selective cytotoxicities in human tumor cell lines, and certain susceptible cells give ED50 values as low as 10(-12)-10(-15) micrograms/ml. Bullatacin was pesticidal at concentrations as low as 1 ppm, but bullatacinone lacked pesticidal activities. The known compounds liriodenine and (-)-kaur-16-en-19-oic acid were also isolated and were lethal to brine shrimp but were not significantly cytotoxic.

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Year:  1989        PMID: 2778448     DOI: 10.1021/np50063a002

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  11 in total

1.  Antiproliferative acetogenins from a Uvaria sp. from the Madagascar dry forest.

Authors:  Yumin Dai; Liva Harinantenaina; Peggy J Brodie; Martin W Callmander; Richard Randrianaivo; Stephan Rakotonandrasana; Etienne Rakotobe; Vincent E Rasamison; Yongchun Shen; Karen TenDyke; Edward M Suh; David G I Kingston
Journal:  J Nat Prod       Date:  2011-12-02       Impact factor: 4.050

2.  Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Authors:  Jennifer M Tinsley; Eric Mertz; Pek Y Chong; Robert-André F Rarig; William R Roush
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

Review 3.  Sylvaticin: a new cytotoxic and insecticidal acetogenin from Rollinia sylvatica (Annonaceae).

Authors:  K J Mikolajczak; R V Madrigal; J K Rupprecht; Y H Hui; Y M Liu; D L Smith; J L McLaughlin
Journal:  Experientia       Date:  1990-03-15

4.  Gigantecin: a novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, from Goniothalamus giganteus (Annonaceae).

Authors:  A Alkofahi; J K Rupprecht; Y M Liu; C J Chang; D L Smith; J L McLaughlin
Journal:  Experientia       Date:  1990-05-15

5.  16 alpha-hydroxy-(-)-kauranoic acid: a selectively cytotoxic diterpene from Annona bullata.

Authors:  Y H Hui; C J Chang; D L Smith; J L McLaughlin
Journal:  Pharm Res       Date:  1990-04       Impact factor: 4.200

Review 6.  Probing the ubiquinone reduction site in bovine mitochondrial complex I using a series of synthetic ubiquinones and inhibitors.

Authors:  H Miyoshi
Journal:  J Bioenerg Biomembr       Date:  2001-06       Impact factor: 2.945

7.  Synthesis and anti-tumor activity of carbohydrate analogues of the tetrahydrofuran containing acetogenins.

Authors:  Stewart Bachan; K A Tony; Akira Kawamura; Diego Montenegro; Anjali Joshi; Himanshu Garg; David R Mootoo
Journal:  Bioorg Med Chem       Date:  2013-08-29       Impact factor: 3.641

8.  Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I).

Authors:  M Degli Esposti; A Ghelli; M Ratta; D Cortes; E Estornell
Journal:  Biochem J       Date:  1994-07-01       Impact factor: 3.857

9.  Bullatacin--in vivo and in vitro experience in an ovarian cancer model.

Authors:  C H Holschneider; M T Johnson; R M Knox; A Rezai; W J Ryan; F J Montz
Journal:  Cancer Chemother Pharmacol       Date:  1994       Impact factor: 3.333

10.  Bullatacin triggers immunogenic cell death of colon cancer cells by activating endoplasmic reticulum chaperones.

Authors:  Fangtian Fan; Peiliang Shen; Yue Ma; Wangbo Ma; Hongyan Wu; Hao Liu; Qing An
Journal:  J Inflamm (Lond)       Date:  2021-06-10       Impact factor: 4.981

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