Isolation and Characterization of a Cyclic Hydroxamic Acid from a Pollen Extract, Which Inhibits Cancerous Cell Growth in Vitro

Abstract

One fraction, designated FV-7, in the water soluble ingredient of the pollen extract Cernilton was found to be inhibitory to the growth of a prostate cancer cell line. Characterization of FV-7 by high-resolution mass spectrometry and nuclear magnetic resonance identified the fraction as hydroxamic acid, 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA). To confirm this further, we synthesized an authentic sample of DIBOA and found subsequently that the synthetic DIBOA was structurally indistinguishable from FV-7. Furthermore, in a separate experiment we compared the in vitro effects of FV-7 and DIBOA on the growth of a prostate cancer cell line and found that in both cases the effect was inhibitory and that the inhibition curves obtained for both compounds were virtually identical.

The genetic background of benzoxazinoid biosynthesis in cereals

“…They are considered to be capable of lowering cancer risk (Zhang et al 1995;Roberts et al 1998) and insulin secretion (Landberg et al 2010). Moreover, they have antiallergic properties (Otsuka et al1988;Poupaert et al 2005), appetite suppression and weight reduction effects (Rosenfeld and Forsberg 2009).…”

Cyclic hydroxamic acid inhibitors of prostate cancer cell growth: Selectivity and structure activity relationships

“…A cyclic hydroxamic acid, 2,4-dihydroxy-2H,1,4-benzoxazin-3(4H)-one (DIBOA, 1), was reported recently to inhibit growth of the DU-145 human prostate cancer cell line [1,2]. DIBOA (1) was isolated from the water-soluble fraction of the pollen extract, cernilton, which has been shown to cause symptomatic improvement in patients with benign prostatic hyperplasia, chronic prostatitis, and prostatodynia [3,4].…”

Pólen apícola desidratado: composição físico-química, qualidade microbiologica, compostos fenólicos e flavonoides, capacidade antioxidante e origem botânica

“…Barreto et al, (2006) BUCK et al, 1990;SUZUKI et al, 1992;RUGENDORFF et al, 1993;KRELL, 1996;SHOSKES, 2002;SHOSKES e MANICKAM, 2003, SHAPLYGIN E SIVAKOV, 2007WAGENLEHENER et al, 2009), dessensibilização frente às alergias, ganho de peso em animais com alimentação suplementada de pólen apícola, efeito bacteriostático, bactericida e proteção contra efeitos adversos dos raios X nos tratamentos com uso de radiação (SCHMIDT e BUCHMANN, 1992;KRELL, 1996;EATON e LAW, 2000). Além disso, existem estudos comprovando a atividade benéfica do pólen apícola relativa à aterosclerose (WOJCICKI et al, 1986) e neoplasias (ZHANG et al, 1995 propriedades regenerativas e pelo aumento da longevidade dos consumidores deste produto (CAMPOS, CUNHA e MARKHAM, 1996;NAGAI et al, 2002;CAMPOS et al, 2003). (SIMÕES et al, 2004).…”