Isolation and Identification of Trachyloban-19-Oic and (-)-Kaur-16-en-19-Oic Acids as Antimicrobial Agents from the Prairie Sunflower, Helianthus annuus

Mitscher, L. A.; Rao, G. Seshagiri; Veysoglu, Tarik; Drake, Steven D.; Haas, Tucuch

doi:10.1021/np50029a024

Cited by 50 publications

(30 citation statements)

References 9 publications

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“…Many reports have extensively shown that kaurane-type diterpenes exhibit several important biological properties, including antiparasitic effects (Batista et al 2007;Da Costa et al, 1996), antispasmodic and relaxant actions on the smooth muscle (Ambrosio et al, 2006;Tirapelli et al, 2004), as well as analgesic and antiinflammatory activities (Okuyama et al, 1991;Paiva et al, 2002). Members of this class of diterpenes have been reported to have cytotoxic effects, (Hanson, 2006;Ghisalberti, 1997), antiproliferative action on tumour cell cultures (Mongelli et al, 2002), and significant antimicrobial activity against Gram-positive and Gram-negative bacteria and yeasts, including Bacillus subtilis (Ghisalberti, 1997;Slimestad et al, 1995), Staphylococcus aureus, Mycobacterium smegmatis (Ghisalberti, 1997;Mitscher et al, 1983), Saccharomyces cerevisiae, Escherichia coli, Cladosporium herbarum, Candida albicans (Ghisalberti, 1997), among others. Moreover, a previous screening using Brazilian plants against oral pathogens performed in our laboratories showed that plant extracts rich in kaurane diterpenes are very effective against these microorganisms.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Kaurane Diterpenes against Oral Pathogens

Ambrósio

Furtado

Oliveira

et al. 2008

Zeitschrift Für Naturforschung C

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Two kaurane diterpenes, ent-kaur-16(17)-en-19- , respectively. Our results show that KA has potential to be used as a prototype for the discovery of new effective anti-infection agents against microorganisms responsible for caries and periodontal diseases. Moreover, these results allow to conclude that minor structural differences among these diterpenes significantly influence their antimicrobial activity, bringing new perspectives to studies on the structure-activity relationship of this type of metabolites with respect to caries and periodontal diseases.

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Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Kaurane Diterpenes against Oral Pathogens

Ambrósio

Furtado

Oliveira

et al. 2008

Zeitschrift Für Naturforschung C

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“…Since their first identification, they have been isolated from a wide range of families and genus of plants, but mainly from Asteraceae (Helianthus), Labiateae (Sideritis), Annonaceae (Xylopia) and Euphorbiaceae (Croton) (5). The bioactivities of most trachylobanes have not been explored, although some trachylobane diterpenes have been shown to possess antimicrobial, antifeedant and antifungal properties (6)(7)(8)(9)(10)(11).…”

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confidence: 99%

Cytotoxic and Antitumor Potentialities of Aporphinoid Alkaloids

Stevigny

Bailly²,

Quetin-Leclercq³

2005

CMCACA

152

113

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Aporphinoids form an important group of plant secondary metabolites. Some of these compounds are used for a long time in traditional medicine for the treatment of various diseases, from benign syndromes to more severe illnesses. More than 500 aporphine alkaloids have been isolated from various plant families and many of these compounds display potent cytotoxic activities which may be exploited for the design of anticancer agents. Here we review the origin, biosynthesis, structure and cytotoxic properties of the prominent members of this class of compounds. Simple aporphinoids (boldine, dicentrine) as well as oxo-, pro-and dehydroaporphines, and dimeric forms such as thalicarpine, are discussed here. Their mechanisms of action are not well known but DNA-manipulating enzymes such as polymerases and topoisomerases are among the most frequently cited targets for these benzylisoquinoline compounds. This review presents an updated view of the cytotoxic properties of the aporphinoids and ...

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“…Ent-kaur-16-en-19-oic acid 1 is a natural ent-kaurane-type diterpenoid that can be isolated in a good yield from many plants, such as Wedelia [1], Mikania [2], Annona [3], Xylopia [4] and Helianthus genera, especially from sunfl ower (Helianthus annuus sp) [5][6][7][8][9][10][11][12][13][14][15][16]. A wide spectrum of bioactivities of ent-kaur-16-en-19-oic acid 1 and its derivatives has been reported, including the following effects: trypanocidal [2], embryotoxic [17], cytotoxic [12,17] anti-HIV, anti-infl ammatory, anti-fertility, antibacterial, antifungal, molluscicidal [18], anti-feedant [19], anti-platelet aggregation [20], anti-cancer [21], anti-plasmodic and relaxant activities [22], anti-Alzheimer and antioxidant [23]; acid 1 was also used as remedy for the treatment of type 2 diabetes and obesity [24].…”

Section: Introductionmentioning

confidence: 99%

Synthetic Transformations of Ent-Kaurenoic Acid

Morarescu¹

2015

ChemJMold

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Abstract. This paper presents a review on kaurane diterpenes, covering various aspects of chemical and microbiological transformations of native ent-kaurenoic acid, namely, its reactions via COOH groups, double bonds and rearrangements of the carbon skeleton that lead to a wide range of natural and synthetic derivatives with potential biologic activities and can present convenient synthons for the syntheses of other native ent-kauranes. Ent-kaur-16-en-19-oic acid 1 is one of the intermediate compounds, which is involved in the biosynthesis of diverse ent-kaurane diterpenes, including gibberellins, a group of growth phyto-hormones. Therefore, it is not surprising that many ent-kauranes and their derivatives act as growth regulators in plants [25]. KeywordsThe broad spectrum of presented by the ent-kaurane diterpenes biological activities has motivated countless studies of structural modifi cations of the skeleton, aiming at obtaining the new potentially bioactive substances. These structural transformations have been achieved either chemically or microbiologically, by using microorganism cultures.

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Isolation and Identification of Trachyloban-19-Oic and (-)-Kaur-16-en-19-Oic Acids as Antimicrobial Agents from the Prairie Sunflower, Helianthus annuus

Cited by 50 publications

References 9 publications

Antimicrobial Activity of Kaurane Diterpenes against Oral Pathogens

Antimicrobial Activity of Kaurane Diterpenes against Oral Pathogens

Cytotoxic and Antitumor Potentialities of Aporphinoid Alkaloids

Synthetic Transformations of Ent-Kaurenoic Acid

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