Diterpenoids

Hanson, James R.

doi:10.1039/b807311m

Cited by 94 publications

(49 citation statements)

References 384 publications

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“…More importantly, these fascinating structures often possess useful and unique biological activities that inspire new therapeutic approaches 1–5 . Gibberellin 6 and ent -kaurane derivatives 7, 8 are two diterpene natural products 9 with a complex tetracyclic molecular architecture (Figure 1) featuring, most prominently, a bicyclo[3.2.1]octane system, which has been the focus of significant recent synthetic efforts 10, 11 . Both gibberellins and ent -kauranes have noteworthy biological activity; the gibberellins as plant hormones and growth regulators 12–14 , and the ent -kauranes in a wide array of therapies.…”

Section: Introductionmentioning

confidence: 99%

The enantioselective construction of tetracyclic diterpene skeletons with Friedel–Crafts alkylation and palladium-catalyzed cycloalkenylation reactions

et al. 2015

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Due to the profound extent to which natural products inspire medicinal chemists in drug discovery, there is demand for innovative syntheses of these often complex materials. This article describes the synthesis of tricarbocyclic natural product architectures through an extension of the enantioselective Birch-Cope sequence with intramolecular Friedel-Crafts alkylation reactions. Additionally, palladium-catalyzed enol silane cycloalkenylation of the tricarbocyclic structures afforded the challenging bicyclo[3.2.1]octane C/D ring system found in the gibberellins and the ent-kauranes, two natural products with diverse medicinal value. In the case of the ent-kaurane derivative, an unprecedented alkene rearrangement converted four alkene isomers to one final product.

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Section: Introductionmentioning

confidence: 99%

The enantioselective construction of tetracyclic diterpene skeletons with Friedel–Crafts alkylation and palladium-catalyzed cycloalkenylation reactions

et al. 2015

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“…Traditional Chinese medicines have a number of advantages, including fewer side effects and combination treatment to increase efficiency (3,4). Diterpene acid is one of the numerous traditional Chinese medicines that has a long history of recordation and clinical application (5). Diterpene acid has antiviral, anti-inflammatory, antitumor, antifungal and immunosuppressive effects (6)(7)(8)(9).…”

Section: Introductionmentioning

confidence: 99%

Role of pseudolaric acid B in A549 lung cancer cell proliferation and apoptosis

Guan

Yang

2013

Molecular Medicine Reports

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Abstract. Recently, traditional Chinese medicine has gained attention for its potential use as a chemotherapeutic agent. Pseudolaric acid B (PAB) is a diterpene acid isolated from Pseudolarix kaempferi and possesses antifungal, antimicrobial, antifertility and antiangiogenic properties. It was also reported that PAB may inhibit proliferation and induce apoptosis in various types of cancer. However, its effects on A549 lung cancer cells remain to be determined. The present study aimed to determine the potential roles of PAB in the proliferation and apoptosis of A549 cells. The results showed that PAB inhibited A549 cell proliferation in a time-and dose-dependent manner. Fluorescence microscopy results showed that cells treated with 20 µmol/l PAB for 24 h exhibited karyorrhexis and apoptotic body formation. In addition, A549 cells were treated with 5, 10, 20, 40 or 80 µmol/l PAB for 24 h and apoptosis was analyzed using Annexin-V/propidium iodide kit. The apoptosis rates were 8. 95, 18.71, 24.66, 35.02 and 43.64%, respectively, in PAB-treated cells and 0.80% in the control group. Furthermore, western blot analysis showed that PAB treatment upregulated the protein levels of Bax, Bad and downregulated Bcl-2 and Bcl-xl expression. In conclusion, PAB may serve as a potent chemotherapeutic agent against human lung cancer.

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“…Vinyl 16 carbamoylbenzamides of methyl lambertianate obtained from azlactone of methyl 16 formyllambertianate showed the properties of cytostatic polychemotherapy correctors [10,11]. Recently, an active search for immunomodulating and antitumor agents among the diterpenoid derivatives containing the fragments of various amino acids has been conducted [12].…”

Section: Introductionmentioning

confidence: 99%

Synthetic transformations of higher terpenoids. XXVI. 16-acetylaminomethyllabdanoids and their cytotoxicity

et al. 2012

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Condensation of methyl 16-aminomethyllambertianate with N-Boc-omega-amino acids leads smoothly to 16-(N-Boc-aminononan)- and 16-(N-Boc-aminoundecan)amidomethyllabdanoids. The amide of bicyclo[2.2.1]heptan-1,2-dicarbocylic acid with a labdanoid substituent was obtained under the reaction of methyl aminomethyllambertianate with bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride. Intereaction of methyl 16-aminomethyllambertianate with chloroacetyl chloride leads to methyl 16-(chloroacetylaminomethyl)lambertianate; condensation of this compound with amino acid methyl ethers the corresponding amides of methyl lambertianate was obtained. The resulting compounds are more (compared with lambertianic acid) cytotoxicity in the cell lines CEM-13, MT-4 and U-937 with an CCID50 concentration of 3.9-9.9 microM.

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Diterpenoids

Cited by 94 publications

References 384 publications

The enantioselective construction of tetracyclic diterpene skeletons with Friedel–Crafts alkylation and palladium-catalyzed cycloalkenylation reactions

The enantioselective construction of tetracyclic diterpene skeletons with Friedel–Crafts alkylation and palladium-catalyzed cycloalkenylation reactions

Role of pseudolaric acid B in A549 lung cancer cell proliferation and apoptosis

Synthetic transformations of higher terpenoids. XXVI. 16-acetylaminomethyllabdanoids and their cytotoxicity

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