Abstract
A new dihydroflavonol, songaricol (1 ) and seven known flavonoids, ayamenin A (2 ), irisflavone A (3 ), 5,7-dihydroxy-2′,6-dimethoxyisoflavone (4 ), irilin B (5 ), 5,3′-dihydroxy-7,8,2′-trimethoxyisoflavone (6 ) and irisoid A (7 ) were isolated from rhizome and roots of Iris songarica . Structure elucidation of 1 was achieved through extensive NMR and circular dichroism techniques. Compounds 1 , 5 and 7 showed antioxidant activity in HL-60 cells (IC50 values of 21, 11 and 3.8 μg/mL), whereas 2 , 5 and the previously isolated irisone B were able to show estrogenic response (EC50 values of 305.5, 159.7 and 322.0 μg/mL) in yeast cells expressing human estrogen
receptor (ER-alpha).
Key words
Iris songarica
- Iridaceae - songaricol - flavonoids - antioxidant - estrogenic
References
1 Mazhari N. Flora of Iran, Vol. 31: Iridaceae. Tehran; Research Institute of Forest
and Ranglands Press 2000.
2 Ali S I, Mathew B. Flora of Pakistan, Vol. 202: Iridaceae. St. Louis; Missouri Botanical
Garden Press 2000.
3
Atta-ur-Rahman , Naism S, Baig I, Jalil S, Orhan I, Sener B. et al .
Anti-inflammatory isoflavonoids from the rhizomes of Iris germanica .
J Ethnopharmacol.
2003;
86
177-80
4
Wollenweber E, Stevens J F, Kilmo K, Kanuft K, Frank F, Gerhauser C.
Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica .
Planta Med.
2003;
69
15-20
5
Ayatollahi S M, Moein M R, Kobarfarcd F, Choudhary M I.
Two isoflavones from Iris songarica Schrenk.
DARU.
2004;
12
54-7
6
Slade D, Ferreira D, Marais J PJ.
Circular dichroism, a powerful tool for the assessment of absolute configuration of
flavonoids.
Phytochemistry.
2005;
66
2177-215
7
Kojima K, Gombosurengyin P, Ondognyi P, Begzsurengyin D, Zevgeegyin O, Hatano K. et
al .
Flavanones from Iris tenuifolia .
Phytochemistry.
1997;
44
711-4
8
Hanawa F, Tahara S, Mizutani J.
Isoflavonoids produced by Iris pseudacorus leaves treated with cupric chloride.
Phytochemistry.
1991;
30
157-63
9
Choudhary M I, Nur-E-Alam M, Baig I, Akhtar F, Khan A M, Ndögnii P Ö. et al .
Four new flavones and a new isoflavone from Iris bungei.
.
J Nat Prod.
2001;
64
857-60
10
Shawl A S, Vishwapaul , Zaman A, Kalla A K.
Isoflavones of Iris spuria.
.
Phytochemistry.
1984;
23
2405-6
11
Woldu Y, Abegaz B.
Isoflavonoids from Salsola somalensis .
Phytochemistry.
1990;
29
2013-5
12
Choudhary M I, Nur-E-Alam M, Akhtar F, Ahmad S, Baig I, Öndögnii P. et al .
Five new peltogynoids from underground parts of Iris bungei : a Mongolian medicinal plant.
Chem Pharm Bull.
2001;
49
1295-8
13
Ma G, Khan S I, Benavides G, Schühly W, Fischer N H, Khan I A. et al .
Inhibition of NF-kB mediated transcription and induction of apoptosis by melampolides
and repandolides.
Cancer Chemother Pharmacol.
2007;
60
35-43
14
Reddy M K, Gupta S K, Jacob M R, Khan S I, Ferreira D.
Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins
and phenolic acids from Punica granatum.
.
Planta Med.
2007;
73
461-7
15
Basly J -P, Lavier M -CC.
Dietary phytoestrogens: potential selective estrogen enzyme modulators?.
Planta Med.
2005;
71
287-94
16
Scudiero D A, Shoemaker R H, Paull K D, Monks A, Tierney S, Nofziger T H.
Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity
in culture using human and other cell lines.
Cancer Res.
1988;
48
4827-33
17
Tabanca N, Khan S I, Bedir E, Annavarapu S, Willett K, Khan I A. et al .
Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen.
Planta Med.
2004;
70
728-35
18
Mustafa J, Khan S I, Ma G, Walker L A, Khan I A.
Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin.
Lipids.
2004;
39
167-72
Ikhlas A. Khan
National Center for Natural Products Research
University of Mississippi
Oxford
MS 38677
USA
Telefon: +1-662-915-7821
Fax: +1-662-915-7989
eMail: ikhan@olemiss.edu