Azaphilones, Furanoisophthalides, and Amino Acids from the Extracts of <i>Monascus pilosus</i>-Fermented Rice (Red-Mold Rice) and Their Chemopreventive Effects

Akihisa, Toshihiro; Tokuda, Harukuni; Yasukawa, Ken; Ukiya, Motohiko; Kiyota, Ayaka; Sakamoto, Naoyuki; Suzuki, Takashi; Tanabe, Nobukazu; Nishino, Hoyoku

doi:10.1021/jf040199p

Cited by 197 publications

(156 citation statements)

References 16 publications

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“…All azaphilones showed weak to very weak antioxidant activities (Table 1) compared to the known standard, ascorbic acid. In particular, compounds (8)(9)(10) in group C were void of any activity, so the inhibition of NO production in RAW cells was not due to their free-radical scavenging activities.…”

Section: Discussionmentioning

confidence: 96%

“…2,3) Although previous publications showed that azaphilones exhibit broad activities in many biological systems, such as cholesteryl ester transfer protein, 4) monoamine oxidase inhibition, 5) endothelin receptor binding, 6) the inhibition of gp120-CD4 binding, 7) telomerase inhibition, 8) the induction of Epstein-Barr virus, 9) and antimicrobial activities, 3,10,11) there is no report about the inhibition of nitric oxide (NO) production by azaphilones.…”

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confidence: 99%

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Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Quang

Harinantenaina

Nishizawa

et al. 2006

Biological & Pharmaceutical Bulletin

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The Xylariaceae (Ascomycete) is a large family and currently comprises more than 36 genera. So far, at least one third of these genera have been chemically investigated. 1)One of these specific metabolites repeatedly isolated from this family is azaphilone, with various substitution groups linked to the main skeleton.2,3) Although previous publications showed that azaphilones exhibit broad activities in many biological systems, such as cholesteryl ester transfer protein, 4) monoamine oxidase inhibition, 5) endothelin receptor binding, 6) the inhibition of gp120-CD4 binding, 7) telomerase inhibition, 8) the induction of Epstein-Barr virus, 9) and antimicrobial activities, 3,10,11) there is no report about the inhibition of nitric oxide (NO) production by azaphilones.NO is synthesized from L-arginine by nitric oxide synthase (NOS). Currently, three distinct isoforms of NOS have been identified: Neuronal NOS (nNOS), inducible NOS (iNOS), and endothelial NOS (eNOS).12) Of these, iNOS is an important enzyme involved in the regulation of inflammation 13) and in the generation of a large amount of NO.14) Overproduction of NO by iNOS has been implicated in various pathological processes including septic shock, tissue damage following inflammation, and rheumatoid arthritis. [15][16][17][18][19] Therefore, suppression of nitric oxide (NO) production in macrophages could be a target for potential anti-inflammatory drugs.In the present study, we screened the inhibitory activity of fifteen azaphilones, which were isolated from mushrooms belonging to the Xylariaceae family, and also elucidated the mechanism of inhibition of NO production stimulated by lipopolysaccharide (LPS) in RAW 264.7 cells. MATERIALS AND METHODS Isolation of AzaphilonesFifteen azaphilones, specifically daldinins C, E and F (1-3) from Hypoxylon fuscum, 20,21) multiformin D (4) from H. multiforme, 11) sassafrins A-C (5-7) from Creospharia sassafras, 10) entonaemin A (8) and rubiginosins A-C (9-11) from H. rubiginosin, 22) cohaerins A and B (12, 13) from H. cohaerens, 23) rutilins A and B (14, 15) from H. rutilin, 24) were isolated from xylariaceous fungi and their structures characterized by a combination of NMR spectrometry and X-ray crystallographic analysis.Cell Culture RAW 264.7 cells, a mouse macrophage cell line, were grown in RPMI 1640 supplemented with 10% fetal bovine serum, kanamycin (50 mg/ml), and ampicillin (60 mg/ml) at 37°C in an atmosphere of 5% CO 2 and 95% air.Inhibition of NO Production of Fifteen Azaphilones One hundred microliters of RAW 264.7 cells (8ϫ10 5 cells/ ml) was pipetted into the wells of 96-well culture plates and then cultured. After 24 h incubation, 50 ml of medium containing various concentrations of each azaphilone derivative diluted in DMSO was added to each well. The final DMSO concentration was less than 0.1%. At this concentration, DMSO did not show any NO-induction without stimulation with LPS. Then, 50 ml of vehicle or LPS purified from Pantoea agglomerans (4 mg/ml) was added to each well. The cells were further in...

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Section: Discussionmentioning

confidence: 96%

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confidence: 99%

Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Quang

Harinantenaina

Nishizawa

et al. 2006

Biological & Pharmaceutical Bulletin

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“…RMR, a common fermented product of Monascus, has been used as a traditional cuisine and medicinal agent in Eastern Asia for several centuries. Currently, RMR is recognized as a functional food because of the proven benefits of some of its secondary metabolites, such as monacolins (cholesterollowering agents), 44 g-aminobutyric acid (hypotensive agent), 45 azaphilone pigments (anti-inflammatory agents) 46 and dimerumic acid, tannin, phenol and unsaturated fatty acids (antioxidants). 14,15 Monacolin K, also known as lovastatin, is usually the most abundant monacolin in RMR.…”

Section: Discussionmentioning

confidence: 99%

Red mold rice prevents the development of obesity, dyslipidemia and hyperinsulinemia induced by high-fat diet

Chen

Lee

et al. 2008

Int J Obes

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Objective: To investigate the influences of red mold rice (RMR) on obesity and related metabolic abnormalities. Methods and results:The 3T3-L1 cell line was used to examine the effects of RMR extracts on preadipocytes and on mature adipocytes. Both water and ethanol extracts of RMR had inhibitory effects on 3T3-L1 preadipocyte proliferation and differentiation. Water extracts of RMR enhanced the lipolysis activity in mature adipocytes, which negatively correlated with the triglyceride content within cells. RMR treatment did not affect heparin-releasable lipoprotein lipase activity in mature adipocytes. Furthermore, animal studies were carried out to explore the antiobesity effects of RMR. The control group of male Wistar rats were fed regular laboratory feed, whereas the other groups were fed the high-fat (HF) diet supplemented with lovastatin, rice or RMR (0.4 and 2%, w w À1 ). The relative caloric intakes of the control and HF groups were 3.34 and 4.85 kcal g À1 , respectively. After 6 weeks, rats treated with RMR at the 0.4 and 2% doses had lower weight gain and less fat pads mass accompanied with smaller fat cells than did the HF-diet rats. These effects probably resulted from an increase in the lipolysis activity of adipose tissue and a reduction in food/energy consumption. On the other hand, the RMR supplement significantly reduced serum total cholesterol, serum low-density lipoprotein (LDL) cholesterol, the ratio of LDL to high-density lipoprotein (HDL) cholesterol and serum insulin in the HF group. Moreover, the 2% RMR treatment significantly increased serum HDL cholesterol. Conclusion: This study reveals for the first time that RMR can prevent body fat accumulation and improve dyslipidemia. The antiobesity effects of RMR mainly derive from the lipolytic activity and mild antiappetite potency of RMR. In addition, extracts of RMR suppressed the proliferation and differentiation in 3T3-L1 preadipocytes, which might have contributed to the inhibition of new adipocyte formation or hyperplasia in adipose tissue.

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“…on health, including anti-osteoporotic (Cho et al, 2010), hypoglycemic (Lu et al, 2010), anti-tumor (Ho et al, 2010), neuro-protective , anti-atherosclerotic (Setnikar et al, 2005), anti-stress, anti-fatigue (Kim et al, 2002), and chemopreventive (Akihisa et al, 2005) activities, compared with non-fermented extracts. However, whether FRes have bifidogenic growth stimulating effects in vitro is not known.…”

Section: Fermented Rice Extracts (Fres) Have Various Beneficial Effectsmentioning

confidence: 99%

The Growth-Stimulating Effects of Fermented Rice Extract (FRe) on Lactic Acid Bacteria and Bifidobacterium spp.

Lee¹,

Cho

Kim

et al. 2014

FSTR

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Azaphilones, Furanoisophthalides, and Amino Acids from the Extracts of Monascus pilosus-Fermented Rice (Red-Mold Rice) and Their Chemopreventive Effects

Cited by 197 publications

References 16 publications

Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Red mold rice prevents the development of obesity, dyslipidemia and hyperinsulinemia induced by high-fat diet

The Growth-Stimulating Effects of Fermented Rice Extract (FRe) on Lactic Acid Bacteria and Bifidobacterium spp.

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