Gigantecin: a Novel Antimitotic and Cytotoxic Acetogenin, with Nonadjacent Tetrahydrofuran Rings, from Goniothalamus Giganteus (Annonaceae)

Overview

Journal Experientia

Specialty Science

Date 1990 May 15

PMID 2347408

Citations 3

Authors

A Alkofahi

J K Rupprecht

Y M Liu

C J Chang

D L Smith

J L McLaughlin

Affiliations

Soon will be listed here.

Abstract

Gigantecin (I), a novel tetrahydroxy-di-tetrahydrofuran fatty acid gamma-lactone (acetogenin), was isolated from an ethanolic extract of the stem bark of Goniothalamus giganteus Hook. f., Thomas (Annonaceae), by means of activity-directed fractionation (brine shrimp lethality test). This new compound is extremely cytotoxic to human tumor cells, inhibits crown gall tumors on potato discs, and is active in an assay designed to detect antimitotic agents (9 ASK).

Citing Articles

Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes.

Spurr I, Brown R Molecules. 2010; 15(1):460-501.

PMID: 20110904 PMC: 6257053. DOI: 10.3390/molecules15010460.

Recent progress on the total synthesis of acetogenins from Annonaceae.

Li N, Shi Z, Tang Y, Chen J, Li X Beilstein J Org Chem. 2009; 4:48.

PMID: 19190742 PMC: 2633664. DOI: 10.3762/bjoc.4.48.

Goniothalamus species: a source of drugs for the treatment of cancers and bacterial infections?.

Wiart C Evid Based Complement Alternat Med. 2007; 4(3):299-311.

PMID: 17965760 PMC: 1978243. DOI: 10.1093/ecam/nem009.

References

Hui Y, Rupprecht J, Liu Y, Anderson J, Smith D, Chang C . Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata. J Nat Prod. 1989; 52(3):463-77. DOI: 10.1021/np50063a002. View

Alkofahi A, Rupprecht J, Smith D, Chang C, McLaughlin J . Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae). Experientia. 1988; 44(1):83-5. DOI: 10.1007/BF01960258. View

Meyer B, Ferrigni N, Putnam J, Jacobsen L, Nichols D, McLaughlin J . Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med. 1982; 45(1):31-4. View

Ferrigni N, Putnam J, Anderson B, Jacobsen L, Nichols D, Moore D . Modification and evaluation of the potato disc assay and antitumor screening of euphorbiaceae seeds. J Nat Prod. 1982; 45(6):679-86. DOI: 10.1021/np50024a005. View