Antitubercular chromones and flavonoids from Pisonia aculeata.

Three new chromones, pisonins A (1), B (2), and D (4), two new flavonoids, pisonivanone [(2S)-5,7,2'-trihydroxy-8-methylflavanone] (7) and pisonivanol [(2R,3R)-3,7-dihydroxy-5,6-dimethoxyflavanone] (8), one new isoflavonoid, pisonianone (5,7,2'-trihydroxy-6-methoxy-8-methylisoflavone) (9), and five compounds first isolated from nature, namely, pisonins C (3), E (5), and F (6), pisoniamide (10), and pisonolic acid (11), together with 18 known compounds have been isolated from the methanol extract of the combined stem and root of Pisonia aculeata. Among these isolates, 2, 7, 14, 16, and 19 exhibited antitubercular activities (MICs≤50.0 μg/mL) against Mycobacterium tuberculosis H37Rv in vitro.

[1]  P. Bagchi,et al.  Studies on the Ultraviolet Absorption Spectra of Coumarins and Chromones. II. Hydroxy Derivatives1 , 1959 .

[2]  Y. Kuo,et al.  Separation and Determination of Chemical Constituents in the Roots of Rhus Javanica L. Var. Roxburghiana , 2005 .

[3]  K. Kavitha,et al.  Hepatoprotective and Antioxidant Effect of Pisonia aculeata L. against CCl4-Induced Hepatic Damage in Rats , 2008 .

[4]  B. K. Ganguly,et al.  Studies on the Ultraviolet Absorption Spectra of Coumarins and Chromones.1 Part I , 1956 .

[5]  P. Hergenrother,et al.  Identification from a combinatorial library of a small molecule that selectively induces apoptosis in cancer cells. , 2003, Journal of the American Chemical Society.

[6]  W. König,et al.  Constituents of the fungi Daedalea quercina and Daedaleopsis confragosa var. tricolor. , 2000, Phytochemistry.

[7]  H. Wulff,et al.  4-Phenoxybutoxy-substituted heterocycles--a structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3. , 2009, European journal of medicinal chemistry.

[8]  M. Nógrádi,et al.  Synthesis of homoisoflavanones—II , 1971 .

[9]  S. Fry,et al.  In vitro peroxidase-catalysed oxidation of ferulic acid esters , 1995 .

[10]  L. Calhoun,et al.  Characterization of cross-linked hydroxycinnamic acid amides isolated from potato common scab lesions. , 2005, Phytochemistry.

[11]  B. S. Joshi,et al.  Isolation and identification of two phenolic ketones and a chromone from Dysophylla stellata Benth. , 1977 .

[12]  E. Giorgio,et al.  Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power. , 2004, Organic & biomolecular chemistry.

[13]  K. Hahm,et al.  Anti-fungal effects of phenolic amides isolated from the root bark of Lycium chinense , 2004, Biotechnology Letters.

[14]  J. Simpson,et al.  A C -methylflavone from Trianthema portulacastrum , 1997 .

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

[16]  T. Miyase,et al.  Chemical Studies on the Constituents of Polygonum nodosum , 1982 .

[17]  Kazuo Itô,et al.  A phenolic amide from Actinodaphne longifolia , 1989 .

[18]  N. Ohkura,et al.  Stereochemistry and putative origins of flavanones found in post-administration urine of the traditional Chinese remedies shosaiko-to and daisaiko-to. , 1998, Chemical and pharmaceutical bulletin.

[19]  D. T. Coxon,et al.  Abnormal metabolites produced by Daucus carota roots stored under conditions of stress , 1973 .

[20]  I. Chen,et al.  Secondary Metabolites and Antimycobacterial Activities from the Roots of Ficus nervosa , 2010, Chemistry & biodiversity.

[21]  H. Ogura,et al.  Sterol glucosides from Prunella vulgaris , 1990 .

[22]  M. Iinuma,et al.  ^ C-Nuclear Magnetic Resonance (NMR) Spectral Studies on Polysubstituted Flavonoids. I. 13C-NMR Spectra of Flavones , 1980 .

[23]  F. Chang,et al.  Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. , 2001, Journal of natural products.

[24]  C. D. Hufford,et al.  New flavonoid and coumarin derivatives of Uvaria afzelii , 1981 .

[25]  I. Abe,et al.  A plant type III polyketide synthase that produces pentaketide chromone. , 2005, Journal of the American Chemical Society.