Tumor inhibitors. 111. Structure and stereochemistry of jatrophone, a novel macrocyclic diterpenoid tumor inhibitor

Kupchan, S. Morris; Sigel, Carl W.; Matz, M; Gilmore, C. J.; Bryan, R. F.

doi:10.1021/ja00424a050

Cited by 116 publications

(45 citation statements)

References 6 publications

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“…X-Ray photographs, recorded on a single crystal with Cu Ko~ radiation, gave unit cell parameters in good agreement with those reported and the same space group [3 ]. Mass spectra agreed with the presence of the Jatrophone molecule.…”

Section: Methodssupporting

confidence: 84%

“…In fact, extracts ofJatropha gossypiifolia and related species have been employed in the treatment of tumors [2]. The stereochemistry and structure of Jatrophone was elucidated by chemical and X-ray crystallographic studies [3] and the strategy for total synthesis reported [4]. c~.Methylene ~,-lactone function is essential to the tumor inhibitor activity 20 16/.…”

Section: Introductionmentioning

confidence: 99%

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On the interaction between jatrophone and DNA

1981

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Section: Methodssupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

On the interaction between jatrophone and DNA

1981

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“…For instance, from the roots ofJ. gossypifolia, jatrophone (a macrocyclic diterpenoid) and 2~-and 2fl-hydroxyjatrophone were isolated [6,7], and from J. macrorrhiza acetylaleuritolic acid (a triterpenoid) and jatropham (a lactam), which all displayed antileukemic activity [8,9].…”

Section: Introductionmentioning

confidence: 99%

Curcacycline A — a novel cyclic octapeptide isolated from the latex of Jatropha curcas L

et al. 1995

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From the latex of Jatropha curcas L. (Euphorbiaceae) a novel cyclic octapeptide was isolated, which we named curcacycline A. The compound was found to contain one threonine, one valine, two glycine, and four leucine residues. By two-dimensional ~H-NMR spectroscopy (HOHAHA and ROESY), its sequence was determined to be GiyLLeu2-Leu3-Gly4-ThrS-Val6-LeuT-Leu sGly% Curcacycline A displays a moderate inhibition of (i) classical pathway activity of human complement and (ii) proliferation of human T-cells.and two-dimensional 1H-NMR spectroscopy (HOHAHA and ROESY). Experimental Plant materialJatropha curcas L. plants grown as hedges in Jepara (near Kudus, Java, Indonesia) were identified. Crude latex was obtained by cutting off leaf stalks, adding a few drops of EtOH to prevent the latex from excessive foaming. The latex was stored at -20°C until use.

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Section: )mentioning

confidence: 99%

“…2,4,5) This substance has been the object of several scientific investigations, and, in Brazil, results have included reports on molluscidal activity, 6) relaxant action in rat portal veins, 7) inhibition of insulin, 8) and inhibition of plateled rich plasma aggregation. 9) Most of the Jatropha elliptica in "cachaça" used in Brazil have no information on their exact composition in relation as substances presents or on the recommended dosages, imposing serious risks to public health.…”

Section: )mentioning

confidence: 99%

Quantitative Determination of Jatrophone in "Cachaca" Prepared with Jatropha elliptica

Brum

Cardoso

Honda

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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The genus Jatropha (Euphorbiaceae) are used in medicinal plant therapy against skin diseases.1) Jatropha elliptica according to popular wisdom can be used in the form of a tincture prepared by maceration of subterranean stems in a sugar-cane derived spirit "cachaça", administered orally, for the treatment of venomous snake bites. Other uses include as an anti-inflammatory, and an anticholestheremic. Studies phytochemical in ethanolic extract of the subterranean stems showed identification of the diterpene jatrophone ( Fig. 1) and also others substances.2) Other studied in dichloromethanic extract was determined d-selinene. 3)Jatrophone is considered cytotoxic and tumor-inhibitory agent. 2,4,5) This substance has been the object of several scientific investigations, and, in Brazil, results have included reports on molluscidal activity, 6) relaxant action in rat portal veins, 7) inhibition of insulin, 8) and inhibition of plateled rich plasma aggregation. 9)Most of the Jatropha elliptica in "cachaça" used in Brazil have no information on their exact composition in relation as substances presents or on the recommended dosages, imposing serious risks to public health.HPLC equipment is widely disseminated in Brazil. We have developed an analytical procedure suitable for sample preparation and HPLC-UV analysis of jatrophone contents in "cachaça".The HPLC technique has been shown to be a very efficient system separating complex mixtures plants. HPLC methods have been reported for the determination of substances in callus cultures, vitro culture, serum, dermis, plants, citrus, essential oils and phytomedicines, but only the most recent published methods report assay validation. [10][11][12][13][14][15][16][17][18][19][20][21] There are no descriptions in the literature about sample preparation and determination quantitative of jatrophone present in "cachaça" prepared with Jatropha elliptica employed in Brazil.The sensitivity, linearity, accuracy, precision were evaluated. The efficiency of the analytical procedure was assessed through calculation of recovery values. ExperimentalPlant Material The samples were collected from the "cerrado" of the Mato Grosso do Sul State, Brazil. A voucher specimen was deposited in the herbarium CCBS/UFMS, in Campo Grande/MS, Brazil.Chemicals Spectroscopy-grade acetonitrile, hexane, acetone, chloroform and methanol were purchased from Tedia Company/U.S.A. Water was purified using a Milli-Q system (Millipore). Jatrophone were isolated and purified by chromatography and recrystallization in Chemical Laboratories of the Mato Grosso do Sul Federal University. The identity of the standard was confirmed by MS, IR, and 1 H-and 13 C-NMR and their purity evaluated with HPLC-UV was 97.7% (Fig. 2). The "cachaça" (a commercial product containing distillates of sugar-cane, sugar and water) had and alcohol content of 38%). Stock mixtures of standard were made from the individual solutions in water-acetonitrile (13 : 7) and used as external standards.TLC Condition The chloroform fractions and the jatrop...

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Tumor inhibitors. 111. Structure and stereochemistry of jatrophone, a novel macrocyclic diterpenoid tumor inhibitor

Cited by 116 publications

References 6 publications

On the interaction between jatrophone and DNA

On the interaction between jatrophone and DNA

Curcacycline A — a novel cyclic octapeptide isolated from the latex of Jatropha curcas L

Quantitative Determination of Jatrophone in "Cachaca" Prepared with Jatropha elliptica

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