Structure and stereochemistry of (−)-odorinol, an antileukemic diamide from Aglaia odorata

Hayashi, Nanao; Lee, Kuo Hsiung̀; Hall, Iris H.; McPhail, Andrew T.; Huang, Huan Chang

doi:10.1016/0031-9422(82)85208-4

Cited by 39 publications

(51 citation statements)

References 3 publications

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“…Several cinnamic acid-derived bisamides have been reported from the above genus. Aglaia, Odorinol exhibited antileukemic activity in the P-388 system (Hayashi et al 1982).…”

Section: Resultsmentioning

confidence: 95%

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Balachandran¹,

Kumar²,

Arun

et al. 2014

Appl Nanosci

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N-Benzyl-2,2,2-trifluoroacetamide was obtained by acylation of benzylamine with trifluoroacetic anhydride using Friedel-Crafts acylation method. The synthesised compound was confirmed by spectroscopic and crystallographic techniques. N-Benzyl-2,2,2-trifluoroacetamide was assessed for its antimicrobial, antioxidant, cytotoxic and molecular docking properties. It showed good antifungal activity against tested fungi and moderate antibacterial activity. The minimum inhibitory concentration values of Nbenzyl-2,2,2-trifluoroacetamide against fungi were 15.62 lg/ mL against A. flavus, 31.25 lg/mL against B. Cinerea and 62.5 lg/mL against T. mentagrophytes, Scopulariopsis sp., C. albicans and M. pachydermatis. N-Benzyl-2,2,2-trifluoroacetamide showed 78.97 ± 2.24 of antioxidant activity at 1,000 lg/mL. Cupric ion reducing antioxidant capacity of N-benzyl-2,2,2-trifluoroacetamide was dependent on the concentration. Ferric reducing antioxidant power assay of N-benzyl-2,2,2-trifluoroacetamide showed (1.352 ± 0.04 mM Fe(II)/g) twofold higher value compared to the standard. N-Benzyl-2,2,2-trifluoroacetamide showed 75.3 % cytotoxic activity at the dose of 200 lg/mL with IC 50 (54.7 %) value of 100 lg/mL. N-Benzyl-2,2,2-trifluoroacetamide was subjected to molecular docking studies for the inhibition AmpC beta-lactamase, Glucosamine-6-Phosphate Synthase and lanosterol 14 alpha-demethylase (CYP51) enzymes which are targets for antibacterial and antifungal drugs. Docking studies of N-benzyl-2,2,2-trifluoroacetamide showed low docking energy. N-Benzyl-2,2,2-trifluoroacetamide can be evaluated further for drug development.

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“…Several cinnamic acid-derived bisamides have been reported from the above genus. Aglaia, Odorinol exhibited antileukemic activity in the P-388 system (Hayashi et al 1982).…”

Section: Resultsmentioning

confidence: 95%

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Balachandran¹,

Kumar²,

Arun

et al. 2014

Appl Nanosci

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“…From the results of these two-stage carcinogenesis tests, it was concluded that odorine and odorinol inhibited both the initiation and promotion stages of two-stage skin carcinogenesis. The present cancer chemopreventive activity of odorine and odorinol together with the direct anti-leukemic activity of odorinol 3) show that these compounds might be valuable anti-carcinogenic agents in chemical carcinogenesis. Investigations on the details of the inhibitory mechanisms of these compounds on chemical carcinogenesis are being studied.…”

Section: Resultsmentioning

confidence: 94%

“…and the flowers are also used for scenting tea on account of its fragrance. 1) From this plant, the aminopyrrolidine-diamides odorine and odorinol (ϭ2-hydroxyodorine), 2,3) and other constituents, [4][5][6][7] had been isolated. In addition, the anti-leukemic activity of odorinol against P-388 lymphocytic leukemia of mice has already been reported.…”

mentioning

confidence: 99%

“…In addition, the anti-leukemic activity of odorinol against P-388 lymphocytic leukemia of mice has already been reported. 3) As part of our search for possible cancer chemopreventive agents from natural sources, we have already reported a primary in vitro assay indicating the inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). [8][9][10][11] Because chemical carcinogenesis is a two-stage or multi-stage process, including initiation, promotion, and progression stages, anti-tumor promoters and initiators have been regarded as most promising agents for the chemoprevention of cancer.…”

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confidence: 99%

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Cancer Chemopreventive Activity of Odorine and Odorinol from Aglaia odorata.

Inada

Nishino

Kuchide

et al. 2001

Biological & Pharmaceutical Bulletin

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The leaves and flowers of Aglaia odorata LOUR. (Meliaceae) are used in China as a herbal remedy for treatment of bruises, vertigo, cough etc. and the flowers are also used for scenting tea on account of its fragrance.1) From this plant, the aminopyrrolidine-diamides odorine and odorinol (ϭ2-hydroxyodorine), 2,3) and other constituents, 4-7) had been isolated. In addition, the anti-leukemic activity of odorinol against P-388 lymphocytic leukemia of mice has already been reported.3) As part of our search for possible cancer chemopreventive agents from natural sources, we have already reported a primary in vitro assay indicating the inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). [8][9][10][11] Because chemical carcinogenesis is a two-stage or multi-stage process, including initiation, promotion, and progression stages, anti-tumor promoters and initiators have been regarded as most promising agents for the chemoprevention of cancer. 12)As a result, we have characterized the potent anti-tumor promoting activity of odorine and odorinol isolated from A. odorata. 6) In the present study, we carried out in vivo twostage carcinogenesis tests of these compounds on mouse skin using 7,12-dimethylbenz[a]anthracene (DMBA)/TPA, 13) since many compounds inhibiting EBV-EA activation have been shown to act as inhibitors of tumor promotion in in vivo systems.14-17) Further, on the basis of experimental proof that nitric oxide (NO) strongly initiated carcinogenesis [18][19][20] on mouse skin, the inhibitory effects of odorine and odorinol on tumor-initiation by NO donors such as (Ϯ)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexenamide (NOR-1) 19) and peroxynitrite 20) were also investigated. MATERIALS AND METHODSChemicals DMBA and TPA were purchased from Nacalai Tesque (Kyoto, Japan). NOR-1 and peroxynitrite were obtained from Dojindo Laboratories (Kumamoto, Japan).Animals Specific pathogen-free female ICR-(6-weekold) and SENCAR-mice (6-week-old) were obtained from Japan SLC Inc. (Shizuoka, Japan). These animals were housed, five per polycarbonate cage, in a temperature-controlled room at 24Ϯ2°C and given food and water ad libitum. Isolation of Odorine and Odorinol from Aglaia odorata Leaves of A. odorata (700 g) were harvested in January, 1993 in the Herbarium Bogoriense (Bogor, Indonesia). The ethyl acetate-soluble fraction was prepared (47.6 g from 78.0 g of the MeOH extract) and aminopyrrolidine-diamides, odorine (160 mg) and odorinol (230 mg), were isolated in 99.9% purity from the crude fraction by the previously reported method. 6) Two-Stage Mouse Skin Carcinogenesis TestInduced by DMBA/TPA The animals (female ICR mice, 6-week-old) were divided into three experimental groups of 15 mice each. The back of each mouse was shaved with surgical clippers, and the mice were carcinogenically initiated with DMBA (100 mg, 390 nmol) in acetone (0.1 ml) as an initiation treatment. For group I (positive control group), one week after ...

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“…The leaves have been used for treatment of headache (Mabberley et al, 1995). Some of benzofuran derivatives from Aglaia genus show interesting biological activities including antiviral (Joshi et al, 1987;Zhou et al, 2013), antileukemic (Hayashi et al, 1982), and insecticidal activities (Ishibashi et al, 1993).…”

Section: Introductionmentioning

confidence: 99%

Anti-HIV-1 integrase effect of compounds fromAglaia andamanicaleaves and molecular docking study with acute toxicity test in mice

Puripattanavong

Tungcharoen

Chaniad

et al. 2015

Pharmaceutical Biology

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Structure and stereochemistry of (−)-odorinol, an antileukemic diamide from Aglaia odorata

Cited by 39 publications

References 3 publications

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Cancer Chemopreventive Activity of Odorine and Odorinol from Aglaia odorata.

Anti-HIV-1 integrase effect of compounds fromAglaia andamanicaleaves and molecular docking study with acute toxicity test in mice

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