87888-40-2Relevant academic research and scientific papers
Total synthesis and structure activity relationship studies of phelligridins C and D, and phellifuropyranone A
Ohyoshi, Takayuki,Mitsugi, Keisuke,Ichimura, Fumitaka,Higuma, Tatsuya,Yoshida, Masahito,Kigoshi, Hideo
, p. 1540 - 1551 (2020/12/29)
α-Pyrone polyphenols, phelligridins C and D (meshimakobnols B and A), and phellifuropyranone A, isolated from a Japanese mushroom, are growth inhibitors of cancer cells. Herein, we report full details of the total synthesis of phelligridins C and D. The key reactions of the synthetic pathways were Pd catalyzed cross-coupling and aldol-type condensation. This strategy also enabled the total synthesis of phellifuropyranone A and artificial analogs of phelligridins. Subsequent biological evaluation of these compounds clarified that the whole skeleton of phelligridin C and the catechol group of the left hand side are essential for the cytotoxicity.
Easy and green synthesis of 6-(arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones in aqueous potassium hydroxide
Benferrah,Hammadi,Berthiol
, p. 2881 - 2886 (2017/03/22)
A convenient green procedure have been proposed for the synthesis of 6-(2-arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones by condensation of 6-(arylvinyl)-4-hydroxy-2H-pyran-2-ones with S-phenyl benzenesulfonothioate in aqueous potassium hydroxide at room temperature.
The Chemical Basis of Fungal Bioluminescence
Purtov, Konstantin V.,Petushkov, Valentin N.,Baranov, Mikhail S.,Mineev, Konstantin S.,Rodionova, Natalja S.,Kaskova, Zinaida M.,Tsarkova, Aleksandra S.,Petunin, Alexei I.,Bondar, Vladimir S.,Rodicheva, Emma K.,Medvedeva, Svetlana E.,Oba, Yuichi,Oba, Yumiko,Arseniev, Alexander S.,Lukyanov, Sergey,Gitelson, Josef I.,Yampolsky, Ilia V.
supporting information, p. 8124 - 8128 (2015/07/07)
Many species of fungi naturally produce light, a phenomenon known as bioluminescence, however, the fungal substrates used in the chemical reactions that produce light have not been reported. We identified the fungal compound luciferin 3-hydroxyhispidin, which is biosynthesized by oxidation of the precursor hispidin, a known fungal and plant secondary metabolite. The fungal luciferin does not share structural similarity with the other eight known luciferins. Furthermore, it was shown that 3-hydroxyhispidin leads to bioluminescence in extracts from four diverse genera of luminous fungi, thus suggesting a common biochemical mechanism for fungal bioluminescence.
Anti-obesity effects of hispidin and alpinia zerumbet bioactives in 3t3-l1 adipocytes
Tu, Pham Thi Be,Tawata, Shinkichi
, p. 16656 - 16671 (2015/02/19)
Obesity and its related disorders have become leading metabolic diseases. In the present study, we used 3T3-L1 adipocytes to investigate the anti-obesity activity of hispidin and two related compounds that were isolated from Alpinia zerumbet (alpinia) rhizomes. The results showed that hispidin, dihydro-5,6-dehydrokawain (DDK), and 5,6-dehydrokawain (DK) have promising anti-obesity properties. In particular, all three compounds significantly increased intracellular cyclic adenosine monophosphate (cAMP) concentrations by 81.2% ± 0.06%, 67.0% ± 1.62%, and 56.9% ± 0.19%, respectively. Hispidin also stimulated glycerol release by 276.4% ± 0.8% and inhibited lipid accumulation by 47.8% ± 0.16%. Hispidin and DDK decreased intracellular triglyceride content by 79.5% ± 1.37% and 70.2% ± 1.4%, respectively, and all three compounds inhibited glycerol-3-phosphate dehydrogenase (GPDH) and pancreatic lipase, with hispidin and DDK being the most potent inhibitors. Finally, none of the three compounds reduced 3T3-L1 adipocyte viability. These results highlight the potential for developing hispidin and its derivatives as anti-obesity compounds.
A β-secretase (BACE1) inhibitor hispidin from the mycelial cultures of Phellinus linteus
Park, In-Hye,Jeon, So-Young,Lee, Hee-Ju,Kim, Sang-In,Song, Kyung-Sik
, p. 143 - 146 (2007/10/03)
In the course of screening for anti-dementia agents from natural products, a β-secretase (BACE1) inhibitor was isolated from the culture broth of Phellinus linteus and identified as hispidin. It showed an IC50 value of 4.9 × 10-6 M and a Ki value of 8.4 × 10 -6 M. The compound was a non-competitive inhibitor. Hispidin also inhibited a prolyl endopeptidase (IC50 = 1.6 × 10-5 M, Ki = 2.4 × 10-5 M), but it was less inhibitory to α-secretase (TACE) and other serine proteases such as chymotrypsin, trypsin, and elastase.
A convenient synthesis of hispidin from piperonal
Adam,Saha-Moller,Veit,Welke
, p. 1133 - 1134 (2007/10/02)
An improved synthesis of hispidin (overall yield 24%) starting from the commercially available piperonal is reported. This three-step method is more effective and advantageous compared to the known six-step preparation.
