- Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence
-
A bioinspired acid-triggered hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade process was disclosed, diastereoselectively furnishing furo[2,3-b]chromene skeleton under mild conditions. The viability of this approach was demonstrated by syntheses of a series of furo[2,3-b]chromene and pyrano[2,3-b]chromene derivatives. The successful total syntheses of two lignan-phloroglucinol hybrids, hyperaspidinols A and B, exemplified the synthetic utility of our biomimetic methodology.
- Chen, Huiyu,Lu, Xiuxiang,Tan, Haibo,Wang, Sasa,Zhang, Wenge,Zheng, Anquan,Zhou, Tingting
-
supporting information
(2021/09/03)
-
- Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment
-
Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.
- Cheng, Xi-Chuang,Guo, Xin-Ran,Liu, Hua-Min,Liu, Yu-Lan,Qin, Zhao,Wang, Xue-De
-
p. 4348 - 4358
(2020/09/22)
-
- Structural elucidation, total synthesis, and cytotoxic activity of effphenol A
-
A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed. This journal is
- Chen, Shanchong,Chen, Yuchan,Dong, Chunmao,Liu, Hongxin,Liu, Zhaoming,Tan, Haibo,Zhang, Weimin,Zhang, Xiao
-
supporting information
p. 9035 - 9038
(2020/11/27)
-
- Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo
-
Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.
- Hofmann, Julian,Fayez, Shaimaa,Scheiner, Matthias,Hoffmann, Matthias,Oerter, Sabrina,Appelt-Menzel, Antje,Maher, Pamela,Maurice, Tangui,Bringmann, Gerhard,Decker, Michael
-
supporting information
p. 7299 - 7308
(2020/05/18)
-
- Process for preparing flavonoid derivatives and the intermediate thereof
-
The present invention provides: a method for manufacturing a flavonoid derivative using a reaction for synthesizing a chalcone derivative by a protection/deprotection reaction of a hydroxyl group and an aldol condensation reaction; and an intermediate thereof. By the method for manufacturing the flavonoid derivative of the present invention can manufacture the flavonoid derivative such as velutin and homoeriodictyol, the present invention can be usefully used in industrial fields such as cosmetics requiring mass production of flavonoid derivatives.
- -
-
Paragraph 0087-0090
(2020/10/03)
-
- Compound for treating or preventing hepatopathy (by machine translation)
-
The invention discloses a compound, an optical isomer or a pharmaceutically acceptable salt, an optical isomer or a pharmaceutically acceptable salt thereof for treating or preventing hepatopathy, and the compound, optical isomer or pharmaceutically acceptable salt thereof can be applied to the preparation of a medicine for treating or preventing liver diseases. (by machine translation)
- -
-
Paragraph 0178-0179; 0183
(2019/10/01)
-
- Synthesis method and uses of natural product Xanthohumol D and analogue thereof
-
The invention discloses a synthesis method and uses of a natural product Xanthohumol D (I) and an analogue (II) thereof, wherein the structural formula is defined the specification, the novel isopentenyl chalcone compound is obtained, and Xanthohumol D has good inhibitory activity on bacillus subtilis. According to the invention, the preparation method has advantages of few process steps and easily available raw materials, and is suitable for industrial production.
- -
-
Paragraph 0021; 0037
(2019/12/31)
-
- Mallotojaponins B and C: Total Synthesis, Antiparasitic Evaluation, and Preliminary SAR Studies
-
(Chemical Equation Presented). The first total syntheses of mallotojaponin B and C as well as several analogues have been achieved. Biological evaluation of the synthesized compounds against Plasmodium falciparum and Trypanosoma brucei have also been carried out.
- Grayfer, Tatyana D.,Grellier, Philippe,Mouray, Elisabeth,Dodd, Robert H.,Dubois, Jo?lle,Cariou, Kevin
-
supporting information
p. 708 - 711
(2016/03/01)
-
- Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
-
Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
- Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
-
supporting information
p. 11799 - 11804
(2014/10/16)
-
- DESIGN, SYNTHESIS AND FUNCTIONAL CHARACTERIZATION OF ROTTLERIN ANALOGS
-
A method of synthesizing rottlerin analogs is described. The synthesis methods described are the first known method of synthesizing rottlerin analogs from commercially-available materials to produce cost effective analogs. Rottlerin analog structures made by the synthesis methods and methods of use for treating a neurological or inflammatory response mediated by protein kinase C (PKC) are further described.
- -
-
Page/Page column 14
(2011/05/16)
-
- Prenylflavonoids and prenyl/alkyl-phloroacetophenones: Synthesis and antitumour biological evaluation
-
Several prenylflavonoids have been synthesised and tested against human tumour cell lines. The prenyl unit has been geranyl or a labdane diterpene. These labdane-flavonoids have been synthesised for the first time. The antitumour activity increase with the prenylation at C-8 position. Twenty-three C and O-prenylated acylphloroglucinols have been synthesised as well. In this case the C-alkylation products have resulted, in general, more active.
- Basabe,De Román,Marcos,Diez,Blanco,Bodero,Mollinedo,Sierra,Urones
-
experimental part
p. 4258 - 4269
(2010/10/01)
-
- Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity
-
A general strategy for the synthesis of 3′-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2′,3,4′,5-tetrahydroxy-6′-methoxy-3′-prenylchalcone (9, IC50 3.2 ± 0.4 μM) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 ± 0.5 μM), were more active in comparison to 1 (IC50 9.4 ± 1.4 μM). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 ± 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 ± 2.1) showed that the prenyl side chain at C-3′ has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4′-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 ± 0.6, 3.8 ± 0.4, and 3.8 ± 0.5 Trolox equivalents, respectively.
- Vogel, Susanne,Ohmayer, Susanne,Brunner, Gabi,Heilmann, Joerg
-
p. 4286 - 4293
(2008/12/20)
-
- Chromone studies. Part 13.1 Synthesis and electron-impact mass spectrometric studies of 5-hydroxy-2-isopropyl-7-methoxychromone, a constituent of the medicinal plant Baeckea frutescens, and side-chain analogues
-
5-Hydroxy-2-isopropyl-7-methoxychromone (1d), a chromone constituent isolated from the aerial parts of Baeckea frutescens, and four analogues (1a-c and 1e), all of which exhibit toxicity to the brine shrimp Artemia salina, have been prepared from 2′,4′,6′-trihydroxyacetophenone. High-resolution mass spectrometric analysis has permitted elucidation of the fragmentation patterns exhibited by these systems following electron-impact ionization.
- Gray, Christopher A.,Kaye, Perry T.,Nchinda, Aloysius T.
-
p. 1144 - 1146
(2007/10/03)
-
- Bulbine-knipholone, a new, axially chiral phenylanthraquinone from Bulbine abyssinica (Asphodelaceae): Isolation, structural elucidation, synthesis, and antiplasmodial activity
-
A new natural phenylanthraquinone, bulbine-knipholone (6), has been isolated from the African plant species Bulbine abyssinica (Asphodelaceae). Its structure was determined by spectroscopic and degradative methods. With the aid of the "lactone concept", an atropo-enantioselective total synthesis has been elaborated, confirming the full absolute structure. Bulbine-knipholone exhibits antiplasmodial activity. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Bringmann, Gerhard,Menche, Dirk,Brun, Reto,Msuta, Thomas,Abegaz, Berhanu
-
p. 1107 - 1111
(2007/10/03)
-
- Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents. 4. Synthesis and pharmacological properties of 4'- dehydroxyphlorizin derivatives substituted on the B ring
-
In our studies of Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents, a series of novel 4'- dehydroxyphlorizin derivatives substituted on the B ring was prepared and their effects on urinary glucose excretion were evaluated in rats. Introduction of only a small alkyl group at the 4'-position increased the activity, and 3-(benzo[b]furan-5- yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D- glucopyranoside (4) showed the most potent effect. To overcome hydrolysis of compound 4 by β-glucosidase in the digestive tract, the OH groups on the glucose moiety of compound 4 were modified. Three prodrugs (5, 42, and 55) were more potent than the parent compound 4 by oral administration, and finally 3- (benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O- (6-O-methoxycarbonyl-β-D-glucopyranoside) (5) was selected as a new promising candidate. Compound 5 was metabolized mainly by liver esterase to the active form (4), which was about 10 times more potent than 5 in inhibiting SGLT. In oral glucose tolerance test in db/db mice, compound 5 dose-dependently suppressed the elevation of glucose levels. Single administration of 5 reduced hyperglycemia concurrently with increase of glucose excretion into urine in diabetic KK-A(y) mice. Furthermore, compound 5 suppressed the elevation of blood glucose levels but did not lower it below the normal level even in fasted conditions in KK- A(y) mice. Additionally, long-term treatment with 5 dose- dependently reduced hyperglycemia and HbA1c in KK-A(y) mice. These pharmacological data strongly suggest that compound 5 has a therapeutic potential in the treatment of NIDDM.
- Tsujihara, Kenji,Hongu, Mitsuya,Saito, Kunio,Kawanishi, Hiroyuki,Kuriyama, Kayoko,Matsumoto, Mamoru,Akira, Oku,Ueta, Kiichiro,Tsuda, Minoru,Saito, Akira
-
p. 5311 - 5324
(2007/10/03)
-
- Syntheses of knerachlin A and knerachlin B
-
The first total syntheses of knerachlin A and knerachlin B are described, starting from 2,4,6-trihydroxyacetophenone and 2,6- dihydroxyacetophenone, respectively. The key step in the synthesis is the condensation of ketone 5 with cinnamaldehyde.
- Huang, Chusheng,Da, Shijun,Li, Ying,Li, Yulin
-
p. 277 - 278
(2007/10/03)
-
- Variable-Temperature NMR Studies of 2,6-Dihydroxy Acylaromatic Compounds. Deuterium Isotope Effects on Chemical Shifts, Isotopic Perturbation of Equilibrium and Barriers to Rotation
-
A series of 2,6-dihydroxy acylaromatic compounds were investigated to characterize the rotational and hydrogen bonding properties of the carbonyl group.Deuterium isotope effects on 1H and 13C chemical shifts due to deuteriation of OH groups were determined at both ambient and low temperature.In the latter case isotope effects on chemical shifts of the individual rotamers can be determined.Deuteriation of one of the OH groups may lead to isotopic perturbation of the tautomeric equilibrium of the carbonyl group and the two hydroxyl groups.The perturbation was found to be larger in ketones than in esters.Complete band shape analysis of the OH resonance of the esters and ketones in a temperature interval above and below the coalescence temperature led to ΔG(excit.), ΔH(excit.) and ΔS(excit.) values for various concentrations of added THF-d8. ΔS(excit.) was found to be strongly negative.Temperature coefficients for the shift of the OH resonances showed large variations for esters and ketones owing to the different hydrogen bond patterns.The esters have two intramolecular hydrogen bonds, one strong and an additional weaker one between the OH and OR groups.The second OH group of the ketones was shown to point primarily towards C-5.Increasing amounts of THF-d8 increased the amount of this rotamer.The anisotropy of the XC=O group at C-2, C-6 was shown to lead to a low-field shift of C-2, very different from that found for C=O groups without hydrogen bonds.The anisotropy caused by OH groups can also be estimated.On the basis of the thermodynamic parameters, a model for the rotation of the ester group is suggested.The rate-determining step involves both intramolecular hydrogen bonds, which are twisted out of the ring plane to form hydrogen bonds to the solvent or other hydrogen bond acceptors.
- Hansen, Poul Erik,Christoffersen, Morten,Bolvig, Simon
-
p. 893 - 902
(2007/10/02)
-
- Synthesis of a New Flavone
-
The structure of the naturally occuring flavone 5-O-methylacacetin (I) has been confirmed by its synthesis. 5,7-Di-O-methylacacetin has been synthesised.
- Srivastava, Savitri D.,Srivastava, Santosh K.
-
-
- SYNTHESIS OF UVARETIN, AN ANTITUMOUR AND ANTIMICROBIAL FLAVONOID
-
The flavonoid uvaretin (1-(2,4-dihydroxy-6-methoxy-3-((2-hydroxyphenyl)-methyl)-phenyl)-3-phenyl-1-propanone), known to be active against some tumours and several bacteria, has been synthesized in six steps from 2',4',6'-trimethoxyacetophenone, 2-hydroxybenzaldehyde and benzaldehyde.
- Malterud, Karl Egil,Undheim, Jorunn,Erdal, John Erik
-
p. 4807 - 4810
(2007/10/02)
-
- SYNTHESIS OF HELICHROMANOCHALKONE AND ISOXANTHOHUMOL
-
Synthesis of helichromanochalkone (1) and isoxanthohumol (2), the constituents of Helichrysum cymosum ssp. calvum and Helychrysum tenuiculum, respectively, have been achieved to provide confirmation for the structures proposed for the two new natural products.
- Sharma, V. K.,Gupta, S. R.
-
-