Ant-repellent triterpenoids from Cordia alliodora

Chen, Ted K.; Ales, Diane C.; Baenziger, N. C.; Wiemer, David F.

doi:10.1021/jo00168a030

Cited by 92 publications

(67 citation statements)

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“…(Table 1), which are typical of the olean-12-en-27-oic acid series. 4,8) Except for the hydroxymethylene at d C 67.2 in 2, its 13 C-NMR data were similar to those of 3-oxoolean-12-en-27-oic acid (3). The position C-23 for the hydroxymethylene was confirmed by comparing the chemical shifts of (Fig.…”

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confidence: 58%

Cytotoxicity of Triterpenes Isolated from Aceriphyllum rossii

Lee

Yoo

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Aceriphyllum rossii ENGLER (Saxifragaceae), an endemic species in Korea, is a perennial herb growing on damp rocks along valleys, usually to a height of 30 cm. It has deeply lobed maple-like leaves and thick brown rhizomes. Clusters of small white flowers bloom on an upright stem in spring. The young leaflets and stems have been used for food. 1) Only a few studies have been carried out on the chemical constituents and biological activities of this plant. Triterpenes and flavonol glycosides have been reported as constituents of this plant and have been found to inhibit ACAT (acyl-CoA: cholesterol acyltransferase) and to possess antioxidant activity.2,3) In our continuing study for the discovery of novel antitumor agents from natural sources, we have found that a MeOH extract of the whole plant of A. rossii had cytotoxicity (Ͼ70% inhibition at 30 mg/ml) against the human leukemia HL-60 cell line. The cytotoxicity of the MeOH extract was concentrated in the hexane-and EtOAc-soluble fractions. Further phytochemical study on these fractions resulted in the isolation of two new triterpenes (1, 2), together with six known triterpenes (3-8). The present paper reports the isolation and structural elucidation of these triterpenes and their in vitro cytotoxicity against the K562 and HL-60 cell lines. Results and DiscussionThe MeOH extract of the whole plant of A. rossii was suspended in H 2 O and successively partitioned with hexane, EtOAc, and BuOH. The hexane-and EtOAc-soluble fractions, with cytotoxicity against both the K562 and HL-60 cell lines, were subjected to silica gel column chromatography to give several fractions that were further purified with column chromatography on silica gel to afford eight triterpenes, including the new compounds, 3a,23-isopropylidenedioxyolean-12-en-27-oic acid (1) and 23-hydroxy-3-oxoolean-12-en-27-oic acid (2), as well as six known triterpenes, 3-oxoolean-12-en-27-oic acid (3), 4) 3a-hydroxyolean-12-en-27-oic acid (4), 4) b-peltoboykinolic acid (5), 5) aceriphyllic acid A (6),2) oleanolic acid (7), 6) and gypsogenic acid (8) 7 Bioassay-guided fractionation of a MeOH extract of the whole plant of Aceriphyllum rossii (Saxifragaceae) led to the isolation of two new triterpenes, 3a a,23-isopropylidenedioxyolean-12-en-27-oic acid (1) and 23-hydroxy-3-oxoolean-12-en-27-oic acid (2), together with six known triterpenes, 3-oxoolean-12-en-27-oic acid (3), 3a a-hydroxyolean-12-en-27-oic acid (4), b b-peltoboykinolic acid (5), aceriphyllic acid A (6), oleanolic acid (7), and gypsogenic acid (8). The structures of these compounds were elucidated on the basis of physicochemical and spectroscopic analyses. These compounds were evaluated for in vitro cytotoxicity against the K562 and HL-60 cell lines. Olean-12-en-27-oic acid derivatives (1-6) exhibited considerable cytotoxicity against K562 and HL-60 cell lines with IC 50 values ranging from 12.2 to 28.7 m mM and from 12.1 to 25.8 m mM, respectively.

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confidence: 58%

Cytotoxicity of Triterpenes Isolated from Aceriphyllum rossii

Lee

Yoo

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A majority of the triterpenoid compounds were identified from leaves and other few from root, stem, seed, fruit and aerial parts. As per structural characteristics, they are classified into four classes: (1) oleanane type isolated from C. alliodora, C. cylindrostachya, C. piauhiensis, C. latifolia and C. multispicata [74][75][76][77][78] ; (2) lupane type identified from C. obliqua and C. gilletii [79][80][81] ; (3) ursane type reported from C. retusa, C. obliqua, C. rothii and C. multispicata [80,[82][83][84][85] ; and (4) dammarane type found in C. spinescens, C. multispicata and C. verbenacea. [86][87][88] [58] C. fragrantissima [59] Heartwood Timber Alliodorol (2) C. alliodora [58] Heartwood Allioquinol C (3) C. alliodora [58] Heartwood Cordiachrome A (4) C. alliodora [58] Heartwood Cordiachrome A (5) C. fragrantissima [59] Timber Cordiachrome B (6) C. fragrantissima [59] Timber Cordiachrome C (7)…”

Section: Triterpenoidsmentioning

confidence: 99%

Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

Oza

Kulkarni

2017

Journal of Pharmacy and Pharmacology

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Objectives Cordia (family Boraginaceae) is a genus of deciduous flowering trees or shrubs comprising more than 300 species distributed widely in the tropical regions. The aim of this review was to provide exhaustive scientific information on traditional uses, phytochemistry and pharmacological activities of the 36 important species with medicinal value from the genus Cordia, to divulge prospects for further research on its therapeutic potential. Key findings Leaves, fruit, bark and seed of a majority of the species were found to possess abundant ethnomedicinal value, but leaves were found to be used most frequently to treat many ailments such as respiratory disorders, stomach pain, wound, inflammation, myalgia, cough, dysentery and diarrhoea. The phytochemical investigation of 36 species resulted in isolation of 293 chemical constituents from various chemical classes. The crude extracts, fractions, essential oils and pure compounds isolated from various Cordia species were reported to have a varied range of pharmacological activities. Summary Many of the traditional uses of the genus Cordia were supported by the results obtained from pharmacological studies performed using various extracts or pure compounds. More attention should be given to the biological evaluation using pure phytochemicals and to identify the mechanism of actions and exploring this genus for new drug discovery.

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“…In addition, the 1 Hand 13 The isolates were evaluated for in vitro cytotoxic activity against cancer cell lines A549, LLC, HL-60, and MCF-7 using the MTT assay method. 27,28) As the results in Table 3 Extraction and Isolation The air-dried stem barks of C. japonica (5.2 kg) was extracted with MeOH (15 l) at room temperature for 72 h and the process was repeated three times. After the evaporation of the solvent under reduced pressure, the crude MeOH extract (378.0 g) was obtained.…”

Section: Resultsmentioning

confidence: 99%

“…Cytotoxic activity was measured using a modified MTT assay. 27,28) Viable cells were seeded in the growth medium (100 ml) into 96 well microtiter plates (1ϫ10 4 cells per well) and incubated at 37°C in a 5% CO 2 incubator. The test sample was dissolved in DMSO and adjusted to final sample concentrations ranging from 5.0 to 150 mM by diluting with the growth medium.…”

Section: Resultsmentioning

confidence: 99%