A new flavane acid from the fruits of Illicium verum

Abstract A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (1H NMR, 13C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC50 values of 4.63 μM and 9.17 μM, respectively. The structure of a new compound isolated from the fruits of Illiciumverum has been determined by detailed spectroscopic analyses. Thecytotoxicity activities of four compounds were determined againstP-388, NUGC, HT-29 and A549 cancer cell lines. Illiciumflavane acid (1)and (E)-1,2-bis(4-methoxyphenyl)ethene (5) showed activites againstthe four cell lines that were comparable to cisplatin.

[1]  Chao Liu,et al.  A new triterpenoid saponin from Gleditsia sinensis and its antiproliferative activity , 2016, Natural product research.

[2]  Lijia Yang,et al.  Two new sesquiterpene lactones from the fruits of Illicium jiadifengpi , 2016, Natural product research.

[3]  Wansheng Chen,et al.  A new aromatic glucoside from stem bark of Illicium difengpi K.I.B. et K.I.M. , 2015, Natural product research.

[4]  Tin-yin Liu,et al.  A new illicinolide from leaves of Illicium micranthum Dunn , 2014, Natural product research.

[5]  M. Zheng,et al.  (−)-Catechin glycosides from Ulmus davidiana , 2014, Archives of pharmacal research.

[6]  Jie Liang,et al.  Chemical composition, antinociceptive and anti-inflammatory properties of essential oil from the roots of Illicium lanceolatum , 2012, Natural product research.

[7]  Qun Sun,et al.  Antibacterial activity of water-soluble extract from pine needles of Cedrus deodara. , 2012, International journal of food microbiology.

[8]  S. Alqasoumi,et al.  Novel flavonoids with antioxidant activity from a Chenopodiaceous plant , 2012, Pharmaceutical biology.

[9]  A. Tiwari,et al.  New advanced glycation end-products inhibitors from Dichrostachys cinerea Wight & Arn. , 2011, Journal of Natural Medicines.

[10]  F. Echeverri,et al.  O-Methylation of phenylphenalenone phytoalexins in Musaacuminata and Wachendorfia thyrsiflora. , 2010, Phytochemistry.

[11]  A. Raal,et al.  Essential oil composition of Pimpinella anisum L. fruits from various European countries , 2008, Natural product research.

[12]  T. Ohta,et al.  Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus. , 2008, Phytochemistry.

[13]  A. Slawin,et al.  Stereoselective synthesis of olefins by a reductive coupling reaction. , 2007, Dalton transactions.

[14]  D. Ferreira,et al.  Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. , 2005, Phytochemistry.

[15]  M. Jahangir,et al.  Three p-cymene derivatives from Zataria multiflora , 1999 .

[16]  D. Ferreira,et al.  Circular Dichroic Properties of Flavan-3-ols , 1999 .

[17]  G. Brown,et al.  Novel phenylpropanoids and lignans from Illicium verum. , 1998, Journal of natural products.

[18]  E. Okuyama,et al.  Neurotropic components from star anise (Illicium verum Hook. fil.) , 1996, Chemical & pharmaceutical bulletin.

[19]  M. Kaouadji.  Two new C-prenylated derivatives of 2,4-dihydroxy benzoic acid from Lonchocarpus nicou roots , 1988 .

[20]  K. Scott.  Carbon-13 nuclear magnetic resonance of biologically important aromatic acids. I. Chemical shifts of benzoic acid and derivatives. , 1972, Journal of the American Chemical Society.