Isolation of 5-(8′Z-heptadecenyl)-resorcinol from etiolated rice seedlings as an antifungal agent

Suzuki, Yukiko; Esumi, Yasuaki; Hyakutake, Hiroshi; Kono, Yoshiki; Sakurai, Akira

doi:10.1016/0031-9422(95)00809-8

Cited by 65 publications

(39 citation statements)

References 14 publications

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“…Compounds 4, 5 and 6 were identified as 5-n-pentadecyl-1,3-benzenediol, 15) its 8ЈZ-enyl congener 15) and 5-(8ЈZ,11ЈZ-heptadecadienyl)-1,3-benzenediol, 16) respectively, by NMR and FAB-MS/MS analyses ( Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

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Ardisiphenols and Other Antioxidant Principles from the Fruits of Ardisia colorata.

Sumino

Sekine

Ruangrungsi

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Novel alkylphenols, ardisiphenols A-C (1-3) and a novel bergenin derivative, demethoxybergenin (10) were isolated from the fruits of Ardisia colorata (Myrsinaceae), together with known alkylresorcinols (4-6), embelin (7), myricetin (8), quercetin (9), bergenin (11), norbergenin (12), kaempferol (13), quercetin-3-O-b b-D-glucopyranoside (14) and gallic acid (15). Their structures were determined by NMR, MS(/MS) analyses and other spectroscopic methods. Ardisiphenols showed moderate scavenging activities toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and showed cytotoxicity against the murine breast cancer cell line, FM3A.

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Section: Resultsmentioning

confidence: 99%

“…The activity of alkylresorcinols (4-6) was not directly proportional to the concentra- tion, and that made it impossible to calculate the Trolox equivalent values. Quercetin (9), norbergenin (12) and gallic acid (15) showed strong activity. Embelin (7), the major constituent of this plant, showed activity comparable to Trolox.…”

Section: )mentioning

confidence: 99%

Ardisiphenols and Other Antioxidant Principles from the Fruits of Ardisia colorata.

Sumino

Sekine

Ruangrungsi

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Both of these two compounds are reported to be associated with antibacterial 19,20 and anticancer 21,22 properties. Resorcinol structure is present in large number of compounds of therapeutic value showing anticancer 23,24 and antifungal activity 25,26 . A novel series of quinols with heteroaromatic or (arylsulphonyl) indole substitution at 4 position has been reported to show in vitro antitumour activity 27 .…”

Section: Short Communicationmentioning

confidence: 99%

Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest

Chamoli

Rawat

Jacob

2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Compounds 4 and 5 were identified as 5-pentadecyl-1,3-benzenediol 8) and its 8ЈZ-enyl congener, 8) respectively, by spectroscopic methods (Fig. 3).…”

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Ardisiphenols A-C, Novel Antioxidants from the Fruits of Ardisia colorata.

Sumino

Sekine

Ruangrungsi

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Novel alk(en)ylphenols, named ardisiphenols A-C (1-3) were isolated from the fruits of Ardisia colorata, together with known alk(en)ylresorcinols (4-6). Their structures were determined by the NMR and MS/MS analyses. All compounds showed scavenging activities towards 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and cytotoxicities against murine breast cancer cell line, FM3A.Key words Ardisia colorata; Myrsinaceae; ardisiphenol; alk(en)ylphenol; cytotoxicity Ardisia colorata ROXB. (Myrsinaceae) is used as a folk medicine for liver disease, cough and diarrhoea in Thailand. A previous phytochemical investigation on this species resulted in the isolation of rapanone and ilexol.1) No further detailed study has been reported. In the course of the screening for antioxidants in Thai medicinal plants, A. colorata showed a scavenging activity towards DPPH radical in TLC autographic assay.2) This paper deals with the structure elucidation of the newly isolated alk(en)ylphenols and known alk(en)ylresorcinols, and their cytotoxicities against murine breast cancer cell line, FM3A.The 75% ethanol extract of the dried fruits of A. colorata (500 g) was partitioned by successive extraction with organic solvents of increasing polarity. Initially the attention was paid to the antioxidative compounds in n-hexane fraction, then repeated silica gel chromatographies (CHCl 3 -MeOH, n-hexaneAcOEt) and HPLC (MeOH-0.2% AcOH, 85 : 15) were performed to give new compounds 1-3 (0.043, 0.084, 0.058%, respectively) and known compounds 4-6 (0.022, 0.053, 0.037%, respectively). The six compounds were all positive for ferric chloride test and showed scavenging activities towards DPPH radical in TLC autographic assay.Ardisiphenol A (1) has a molecular formula C 23 H 38 O 4 from high-resolution (HR)-FAB-MS. The 1 H-NMR spectrum of 1 showed signals of two meta coupled aromatic protons at d 6.13 (d, Jϭ2.7 Hz, H-5) and 6.21 (d, Jϭ2.7 Hz, H-3), and signals due to a long alkyl side chain at d 0.89 (3H, t, Jϭ7.0 Hz, H-15Ј), 1.28 (24H, overlapped, H-3Ј--14Ј), 1.50 (homobenzyl 2H, m) and 2.35 (benzyl 2H, t, Jϭ7.3 Hz). The 13 C-NMR spectrum of 1 showed signals for tetra-substituted benzene at d 131. 6, 150.6, 102.4, 156.5, 107.9 and 137.4, and signals for an alkyl side chain which were assigned as shown in Fig. 1 by two-dimensional (2D)-NMR spectra. Signals of acetoxyl group were also observed at d 2.25 (3H, s), 20.5 (OCOCH 3 ) and 171.6 (OCOCH 3 ). Electron impact (EI)-MS showed a base peak at m/z 139 corresponding to a benzylic fragmentation of deacetylated ion of 1 and an intense peak of deacetylated ion of 1 at 335 (MϪAc) ϩ . Therefore, it was suspected that 1 was a benzene derivative tetra-substituted by two hydroxyl groups, an acetoxyl group and an unbranched C 15 alkyl chain. However, the position of the acetoxyl group was not deduced from above experimental data and the nuclear Overhauser effect (NOE) enhancement was not observed between the acetyl group and any other protons. To locate hydroxyl groups on the benzene ring, the 13 C-NMR of 1 was caref...

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Isolation of 5-(8′Z-heptadecenyl)-resorcinol from etiolated rice seedlings as an antifungal agent

Cited by 65 publications

References 14 publications

Ardisiphenols and Other Antioxidant Principles from the Fruits of Ardisia colorata.

Ardisiphenols and Other Antioxidant Principles from the Fruits of Ardisia colorata.

Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest

Ardisiphenols A-C, Novel Antioxidants from the Fruits of Ardisia colorata.

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