Agariblazeispirol C from the cultured mycelia of the fungus, Agaricus blazei, and the chemical conversion of blazeispirol A

Hirotani, Masao; Masuda, Miyuki; Sukemori, Aya; Hirotani, Seiko; Sato, Noriko; Yoshikawa, Takafumi

doi:10.1016/j.tet.2004.10.051

Cited by 12 publications

(12 citation statements)

References 15 publications

(20 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Unlike blazeispirane derivatives, the occurrence of the 18-methyl group at C-14 is these novel des-A-ergostane type compounds is unprecedented. The experimental results supported that agariblazeispirols A-C should be biosynthesized from blazeispirol A (32,33). It has also been shown that 2.4 and 4.7 µg/mL of agariblazeispirols A and B, respectively, inhibited the growth of P388/VCR mouse leukemia cells with multidrug resistance cells in the presence of 13 ng/ mL of vincristine, which alone did not possess the growth inhibitory activity on P388/VCR cells (32,34).…”

Section: Discussionmentioning

confidence: 54%

Black Soybean Promotes the Formation of Active Components with Antihepatoma Activity in the Fermentation Product of Agaricus blazei

Hwang

Kuo

et al. 2008

J. Agric. Food Chem.

View full text Add to dashboard Cite

The antihepatoma activity and related active components in the fermentation products of Agaricus blazei (AB) cultured in the medium containing soybean (S) or black soybean (BS) were investigated. AB(BS)-pE and AB(S)-pE were the ethanolic extracts from the fermentation products of AB(BS) and AB(S), respectively. According to the IC 50 values, AB(BS)-pE (161.1 and 24.0 microg/mL for Hep 3B and Hep G2 cells, respectively) exhibited stronger cytotoxicities against hepatoma cells than AB(S)-pE (>200 and 99.9 microg/mL for Hep 3B and Hep G2 cells, respectively). AB(BS)-pE was separated by silica gel column chromatography and eluted with n-hexane/ethyl acetate/methanol gradient solvent system into 21 fractions. Fraction 3 [AB(BS)-pE-F3], eluted with n-hexane/ethyl acetate (97:3 and 19:1, v/v), was the most active fraction having inhibitory activity on the proliferation of Hep 3B and Hep G2 cells (IC 50 of 3.6 and 1.9 microg/mL, respectively). Three major compounds, compounds 1- 3, were further isolated from the AB(BS)-pE-F3 fraction by reversed-phase semipreparative high-performance liquid chromatography. Compounds 2 and 3 gave better antihepatoma activity than that of compound 1. The IC 50 values of compounds 2 and 3 were 2.8 and 4.5 microg/mL for Hep 3B cells and 1.4 and 2.0 microg/mL for Hep G2 cells, respectively. The structures of compounds 2 and 3 were identified by UV, IR, electron impact mass spectrometry, and (1)H and (13)C NMR to be blazeispirols A and C, respectively. Blazeispirols A and C existed in the mycelia but not in the broth and were more in AB(BS)-pE (49.9 +/- 8.9 and 14.2 +/- 2.4 mg/g, respectively) than AB(S)-pE (15.9 +/- 1.7 and 3.9 +/- 0.6 mg/g, respectively). Additionally, the result shows that the production of blazeispirols A and C was increased after cultivation in the medium containing black soybean on day 6 and reached the maximum on day 12, and the contents of blazeispirols A and C were negatively correlated with Hep 3B and Hep G2 cell viabilities ( r = -0.84 to -0.93, P < 0.01). It suggests that blazeispirols A and C could be used as biomarkers to produce the fermentation product of A. blazei with antihepatoma activity.

show abstract

Section: Discussionmentioning

confidence: 54%

Black Soybean Promotes the Formation of Active Components with Antihepatoma Activity in the Fermentation Product of Agaricus blazei

Hwang

Kuo

et al. 2008

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…Several elegant strategies reported5 for such ring systems are based on a tandem radical cyclization. Hence, a systematic study was undertaken to synthesize the angular tricyclic skeletons 1 – 3 of the natural products agariblazeispirol C,6 dankasterone7 and laurenene8 following the α‐carbonyl radical cyclization approach established by Sha and co‐workers 4…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Angularly Fused Carbocycles via Tandem Radical Cyclization of α‐Carbonyl Radicals

Prakash

Mohanakrishnan

2008

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…In this regard, a selection of these techniques have found direct application within the arena of natural product synthesis (Crawford et al, 2006;Caldwell et al, 2005;Kerr et al, 2001). More recently, these studies have targeted the total synthesis of Agariblazeispirol C, (I), which was isolated from the cultured mycelia of Agaricus blazei (Hirotani et al, 2005). Our specific approach towards the synthesis of this target includes the development of an intramolecular Pauson-Khand cyclization to expediently construct the tetracyclic core of the natural product.…”

Section: Commentmentioning

confidence: 99%

A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

et al. 2010

View full text Add to dashboard Cite

Towards the synthesis of the novel natural product Agariblazeispirol C, (5aR*,11bR*)-9-methoxy-3,8,11b-trimethyl-5,6,7,11b-tetrahydro-1H-pentaleno[1,6a-a]naphthalen-4(2H)-one, C(20)H(24)O(2), has been prepared at a key stage of the preparative programme. The structure shows the desired stereochemical outcome of the central cyclization protocol, viz. a syn-relationship between the aliphatic methyl group on the 11b-position and the methylene group on the 5a-position [C-C-C-C = -34.57 (18) degrees ].

show abstract

Agariblazeispirol C from the cultured mycelia of the fungus, Agaricus blazei, and the chemical conversion of blazeispirol A

Cited by 12 publications

References 15 publications

Black Soybean Promotes the Formation of Active Components with Antihepatoma Activity in the Fermentation Product of Agaricus blazei

Black Soybean Promotes the Formation of Active Components with Antihepatoma Activity in the Fermentation Product of Agaricus blazei

Synthesis of Angularly Fused Carbocycles via Tandem Radical Cyclization of α‐Carbonyl Radicals

A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

Contact Info

Product

Resources

About