Isolation and Characterization of a New Triterpene from Iris missouriensis

Wong, Sui-Ming; Pezzuto, John M.; Fong, Harry H. S.; Farnsworth, Norman R.

doi:10.1021/np50044a024

Cited by 13 publications

(8 citation statements)

References 8 publications

(15 reference statements)

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“…These peaks existed intensely in the spectrum of the extract indicating the existence of these compounds in this extract. Furthermore, investigation of the downfield region of the three 13 C‐NMR spectra is in full agreement with GC/MS results too, by displaying very characteristic peaks of the olefinic carbons at δ (C) 109.32 and 151.00 ppm relating to lupeol, at δ (C) 107.12 and 154.74 ppm due to taraxasterol, at δ (C) 140.11 and 119.00 ppm concerning the pseudotaraxasterol and at δ (C) 121.53 and 145.28 ppm related to β‐ amyrin and/or their corresponding acetylated compounds.…”

Section: Resultssupporting

confidence: 83%

Hexane Extract of Echinops spinosissimus Turra subsp. spinosus from Tunisia: A Potential Source of Acetylated Sterols – Investigation of its Biological Activities

Bouattour

Fakhfakh

Dammak

et al. 2016

Chemistry & Biodiversity

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The hexane extract of Echinops spinosissimus Turra subsp. spinosus flower heads was analyzed for its fatty acid and sterol composition. Its physicochemical characteristics were also studied. The saponification, iodine and peroxide values were determined as 255 mg KOH/g, 42.57 g I /100 g and 110 m equiv. O /kg of oil, respectively. The oleic (C18:1; 61.14%), palmitic (C16:0; 21.36%) and linoleic (C18:2; 10.45%) acids were the dominant fatty acids. This extract was also found to contain high levels of β-sitosterol and stigmasterol (44.97% and 34.95% of total sterols, respectively). On the other hand, the identification of terpenoid compounds was investigated by using GC/MS, which revealed fourteen major terpenoids mainly taraxasterol, lupeol, pseudotaraxasterol, lup-22(29)-en-3-yl acetate, taraxasteryl acetate, α-amyrin, β-amyrin, pseudotaraxasteryl acetate, hop-20(29)-en3-β-ol, α-amirenone, along with β-sitosterol and stigmasterol. Moreover, we have evaluated the in vitro antibacterial and antifungal activities of the unsaponifiable matter and a fraction isolated from this extract. These activities were conducted using the diffusion disc methods and broth microdilution assay. The resulted fraction from this extract showed the highest antibacterial activity with significant minimum inhibitory concentrations (MIC) values 125.0 μg/ml against Staphylococcus aureus, Micrococcus luteus and Bacillus cereus. However, it did exhibit no substantial antifungal activity.

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Section: Resultssupporting

confidence: 83%

Hexane Extract of Echinops spinosissimus Turra subsp. spinosus from Tunisia: A Potential Source of Acetylated Sterols – Investigation of its Biological Activities

Bouattour

Fakhfakh

Dammak

et al. 2016

Chemistry & Biodiversity

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confidence: 99%

New Isoflavones from Iris nigricans

Al-Khalil¹,

Al‐Eisawi²,

Kato³

et al. 1994

J. Nat. Prod.

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From the rhizomes of Iris nigricans (Iridaceae), two new isoflavones, 4'hydroxy-5 -methoxy-6,7 -methy lenedioxy isoflavone [1] (nigricin) and 4'-hydroxy-5,3' -dimethoxy-6,7-methylenedioxyisoflavone [3] (nigricanin), were isolated and characterized, along with 5,4'dihydroxy-6,7-methylenedioxyisoflavone [4] (irilone), 5,3'-dihydroxy-4',5'-dimethoxy-6,7methylenedioxyisoflavone [5], acetovanillone, ferulic acid, ß-sitosterol and sucrose. The new structures were established by spectroscopic and chemical methods.Iris nigricans Dinsmore (Iridaceae) is a perennial herb with a stout and compact rhizome. It is endemic in the fallow fields and steppe habitats of Jordan and is known by the common name "sawsan aswad," which refers to the dark brown-purple color of the flower (1,2). There have been no reports on the chemical constituents of this species. The genus, however, is rich in isoflavonoid compounds (3-6). Isoflavonoids have drawn considerable attention, because they have anti-mutagenic activity (7), and inhibitory effects on protein tyrosine kinase (8) and on pulmonary tumor promotion (9). In addition, cytotoxic compounds have been isolated from I. missouriensis (3,4). This paper deals with the isolation and characterization of two new isoflavones, 1 and 3• RESULTS AND DISCUSSIONCompound 1, C17H1206 from hrms, was obtained as yellow needles and showed significant eims ion peaks at miz 194 and 118 arising from the A and B rings by retro-Diels-Alder fission (10), and the number of carbons was confirmed from its 13C-nmr spectrum. The uv spectrum exhibited absorption maxima at 2 68 and 344 (sh) nm which are characteristic for a trioxygenated A-ring of an isoflavone derivative (11). The absorption maxima showed no shifts on addition of A1C13, indicating the absence of a free OH group at C-5 (11); this was also confirmed by the lack of a low-field singlet signal in the 'H-nmr spectrum (10-13 ppm) (10,11). Ir absorption bands were found at 3220 (free OH), 1668 (C=0), and 940 cm"1 (OCH20) (5,6).

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“…Several Iris species, including Iris tectorum, Iris germanica and Iris missouriensis, have attracted the attention of researchers in the oncology field (Wong et al, 1986;Tan et al, 2001;Wollenweber et al, 2003;Rui et al, 2008). However, there are no studies on the anticancer activities of Iris nertschinskia, traditionally used in East Asian medicine for the treatment of inflammation-related diseases.…”

Section: Introductionmentioning

confidence: 99%

Iris Nertschinskia Ethanol Extract Differentially Induces Cytotoxicity in Human Breast Cancer Cells Depending on AKT1/2 Activity

Shin

Maeng

Hong

et al. 2012

Asian Pacific Journal of Cancer Prevention

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Recently, we reported that an ethanol extract of Iris nertschinskia induces p53-dependent apoptosis in the MCF7 human breast cancer cell line. However, the detailed mechanisms were not fully explored. Here, we demonstrate another aspect of the activity of I. nertschinskia in breast cancer cells. We compared the response to an ethanol extract of I. nertschinskia in two different human breast cancer cell lines, Hs578Tand MDA-MB231, respectively with relatively low and high AKT1/2 activity by trypan blue exclusion assay and FACS analysis. Knockdown of endogenous AKT1 or AKT2 in breast cancer cells by RNA interference determined the sensitivity to I. nertschinskia ethanol extract compared to control cells. The I. nertschinskia ethanol extract induced cell death in a manner that depended on the level of phosphorylated AKT1/2 protein and was associated with a significant increase in the sub-G1 cell population, indicative of apoptosis. Our results indicate that an ethanol extract of I. nertschinskia differentially induces cell death in breast cancer cells depending on their level of phosphorylated AKT1/2.

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Isolation and Characterization of a New Triterpene from Iris missouriensis

Cited by 13 publications

References 8 publications

Hexane Extract of Echinops spinosissimus Turra subsp. spinosus from Tunisia: A Potential Source of Acetylated Sterols – Investigation of its Biological Activities

Hexane Extract of Echinops spinosissimus Turra subsp. spinosus from Tunisia: A Potential Source of Acetylated Sterols – Investigation of its Biological Activities

New Isoflavones from Iris nigricans

Iris Nertschinskia Ethanol Extract Differentially Induces Cytotoxicity in Human Breast Cancer Cells Depending on AKT1/2 Activity

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