New Bioactive Orange Pigments with Yellow Fluorescence from Monascus-Fermented Dioscorea

Abstract

Red mold dioscorea (RMD) is a fermented product of Monascus purpureus NTU 568 using dioscorea as culture substrate. To investigate the bioactive components of RMD, six orange pigments including four new azaphilones with yellow fluorescence, monapilol A-D (1-4), and known monascorubrin (5) and rubropunctatin (6) were isolated and characterized. Structural elucidation of new isolates was based on nuclear magnetic resonance ((1)H NMR, (13)C NMR, COSY, HMQC, and HMBC) and other spectroscopic analyses. The structures of monapilols (1-4) were similar to those of monascorubrin (5) and rubropunctatin (6); however, the hydroxyl group (8-OH) in compounds 1-4 substituted for the C-8 carbonyl in compounds 5 and 6. Biological evaluation indicated that compounds 1-4 inhibited nitric oxide (NO) production on lipopolysaccharide-stimulated RAW 264.7 cells. Compounds 1-4 also exhibited antiproliferative activities against human laryngeal carcinoma (HEp-2) and human colon adenocarinoma (WiDr).

Fungal Pigments and Their Prospects in Different Industries

“…Monascin (yellow), monascorubrin (orange), monascorubramine (red), monapurone A-C (yellow), monasphilone A and B (yellow), ankaflavin (yellow), rubropunctamine (purple-red), rubropunctatin (orange), monopilol A-D (yellow), citrinin (yellow), 9-(1-hydroxyhexyl)-3-(2-hydroxypropyl)-6a-methyl-9,9a-dihydrofuro [2,3-h] isoquinoline-6,8(2H,6aH)-dione (red), uncharacterized (red) [56][57][58][59][60][61] Monascus ruber…”

“…Several studies have revealed the fungal pigments as a potential anticancer drug. Pigments of Monascus species (M. purpureus and M. pilosus) such as monascin, ankaflavin, monaphilone A-B, monasphilone A-B, monapilol A-D, and monapurone A-C have been proved to possess anticancer/antitumor potential against different types of cancers, such as mouse skin carcinoma, human laryngeal carcinoma, human colon adenocarcinoma, human hepatocellular carcinoma, and pulmonary adenocarcinoma (Figure 12) [32,[56][57][58]204,205]. Besides Monascus, pigments from other fungi such as norsolorinic acid from A. nidulans, shiraiarin from Shiraia bambusicola, alterporriol K, alterporriol L, and alterporriol M from Alternaria spp., benzoquinone from Pigments from different taxonomic groups of fungi having promising anticancer or antitumor potential, re-drawn from [32,[56][57][58]62,68,88,89,113,204,205].…”

Edible Filamentous Fungi from the Species Monascus: Early Traditional Fermentations, Modern Molecular Biology, and Future Genomics

“…Currently, 9 Monascus species have been internationally recognized in the genus; these are M. argentinensis , M. eremophilus , M. floridanus , M. lunisporas , M. pallens , M. pilosus , M. purpureus , M. ruber , and M. sanguineus (Shao and others ). Among them, M. pilosus , M. purpureus , and M. ruber are the most common species used in industrial applications (Hsu and others ; Cheng and others ; Lian and others ).…”

Skp2 is a Promising Therapeutic Target in Breast Cancer

“…Consistent with this notion, overexpression of Skp2 promotes resistance to ATRA and prevents p27 accumulation in breast cancer cells (Dow et al, 2001). Hsu et al (2011) found that gallic acid markedly reduced cell growth of human breast cancer cells and induced cell cycle arrest by inhibition of Skp2 and attenuation of Skp2–p27 association as well as reduction of p27 ubiquitination. Huang et al (2008) reported that EGCG (Epigallocatechin-3-gallate), the main constituent of green tea, inhibited human breast cancer cell growth in part through down-regulation of Skp2 expression and accumulation of p27.…”