Constituents of Berchemia racemosa SIEB. et ZUCC.

Kikuchi, Masao; Sato, Kenichi; Shiraishi, Yoshihisa; Nakayama, Ryoichi; Watanabe, Reiko; Sugiyama, Masataka

doi:10.1248/yakushi1947.110.5_354

Cited by 7 publications

(6 citation statements)

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“…The unmetabolized arachidonic acid was separated from the prostaglandin products by CC and eluted with nhexane-dioxane-glacial acetic acid (70: 30: 1). The prostaglandin products were then eluted with EtOAc-MeOH The spectral data of 6 corresponded with literature 1H-NMR data (22,23) and 13C-NMR data (24). However, the 13C-NMR data reported for the aglycone, mearnsetin (25), and its 3,7dirhamnoside (26) did not agree with our data concerning assignments of C-3',5' and C-4'.…”

Section: Cox-i and Cox-2 Catalysed Prostaglandin Biosynthesis Assaycontrasting

confidence: 48%

Flavan-3-ols Isolated from Some Medicinal Plants Inhibiting COX-1 and COX-2 Catalysed Prostaglandin Biosynthesis

Noreen

Serrano²,

Perera³

et al. 1998

Planta Med

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Extracts from the four plant species Atuna racemosa Raf. ssp. racemosa, Syzygium corynocarpum (A. Gray) C. Muell., Syzygium malaccense (L.) Merr. & Perry and Vantanea peruviana Macbr., traditionally used for inflammatory conditions, were fractionated using a cyclooxygenase-1 catalysed prostaglandin biosynthesis in vitro assay. The flavan-3-ol derivatives (+)-catechin, (+)-gallocatechin, 4'-O-Me-ent-gallocatechin, ouratea-catechin and ouratea-proanthocynidin A were isolated as active principles. The IC50 values ranged from 3.3 microM to 138 microM whilst indomethacin under the same test conditions had an IC50 value of 1.1 microM. The flavonol rhamnosides mearnsitrin, myricitrin and quercitrin were also isolated. When further tested for inhibitory effect on cyclooxygenase-2 catalysed prostaglandin biosynthesis, the five flavan-3-ol derivatives exhibited from equal to weaker inhibitory potencies, as compared to their cyclooxygenase-1 inhibitory effects. The flavonol rhamnosides were inactive towards both enzymes.

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Section: Cox-i and Cox-2 Catalysed Prostaglandin Biosynthesis Assaycontrasting

confidence: 48%

Flavan-3-ols Isolated from Some Medicinal Plants Inhibiting COX-1 and COX-2 Catalysed Prostaglandin Biosynthesis

Noreen

Serrano²,

Perera³

et al. 1998

Planta Med

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“…The largest class of DAMs was flavonoid including 7 flavanones, 24 flavones, 9 flavonoid, 10 flavonols, and 1 isoflavone. In previous works, the biggest group of medicinal metabolites reported in Berchemia plant were flavonoid containing 1 flavone, 8 flavonols, 2 flavanones and 2 flavonoid (Bekker et al., 1996; Kikuchi et al., 1990; Lee et al, 1995; Shen, Teng, Yang, et al, 2010; Wang et al., 2006; Yang, Duan, et al, 2006). Among them, the accumulation of 4, 2′, 4′, 6′‐Tetrahydroxychalcone, kaempferol, dihydroquercetin, aromadendrin, naringenin, eriodictyol and 5, 7‐Dihydroxychromone in Berchemia fruits were up‐regulated from break stage to full‐mature stage (Table 3).…”

Section: Resultsmentioning

confidence: 98%

“… a Reference 3 (Inoshiri et al., 1988), 5 (Inoue et al., 1990) & 6 (Sakurai et al, 1992): B. racemosa SIEB. et ZUCC, stem; Reference 4 (Kikuchi et al, 1990): B. racemosa SIEB. et ZUCC, leaves & wood; Reference 7 (Lee et al, 1995): B. formosana : Stem & root; Reference 8 (Bekker et al., 1996), 14 (Shen, Teng, Yang, et al, 2010) & 15 (Shen et al., 2010): B. lineata (L.) DC.…”

Section: Resultsmentioning

confidence: 99%

Widely targeted metabolic analysis revealed the changed pigmentation and bioactive compounds in the ripening Berchemia floribunda (Wall.) Brongn. fruit

Shuai

Liu²,

Liao

et al. 2021

Food Science & Nutrition

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Berchemia plants were important materials for Chinese traditional medicines due to their special secondary metabolites. Unlike the root, stem and leaf tissues, Berchemia floribunda (Wall.) Brongn. fruit was lacked of systematic metabolic investigation. Biochemical analysis found that the total flavonoid and total phenolic content of Berchemia fruit pulp showed a peak value at red ripe stage, and then decreased, but the total anthocyanin content sharply increased along with the coloration. By widely targeted metabolomic analysis, 644 metabolites were identified and categorized into 23 groups mainly including flavonoid, organic acids, amino acids, lipids, phenylpropanoid, nucleotides, alkaloids, carbohydrates, alcohols, anthocyanins & proanthocyanidins, vitamins, terpenes, polyphenols, phenolamides, quinones, indole derivatives, and sterides. Among them, 111 metabolites and 123 metabolites respectively showed up‐ and down‐regulation from break stage to full mature. KEGG enrichment analysis indicated that active secondary metabolism such as biosynthesis of phenylpropanoids, flavonoid, and alkaloids happened during Berchemia fruit ripening. More importantly, Cyanidin‐3‐O‐galactoside and other 3 cyanidins were found to be the predominant pigments in mature Berchemia fruit and increased cyanidins and pelargonidins but decreased anthocyanins might be contributed to the purple pigmentation of Berchemia fruit. Interestingly, 29 pharmaceutical compounds previously reported in other Berchemia tissues were also detected in ripening Berchemia fruit pulp: 8 flavonoid, 2 quinones & sucrose showed up‐regulated accumulation while 6 polyphenols, 5 flavonoid, 3 phenylpropanoid, 2 organic acids, 1 quinones and β‐sitosterol showed down‐regulated accumulation In conclusion, our first comprehensive metabolic fingerprint will promote the further study of B. floribunda fruit and its medical and food application.

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“…Yield 0.660 g (96%), mp 209.5–210.5°C (Lit. 210–211°C). 1 H NMR (DMSO‐ d 6 ) δ (ppm): 6.82 (d, J = 8.6 Hz, 2H), 7.78 (d, J = 8.6 Hz, 2H), 10.2 (brs, 1H, OH), 12.4 (brs, 1H, COOH).…”

Section: Methodsmentioning

confidence: 99%

Hydrolysis of Diazonium Salts Using a Two‐Phase System (CPME and Water)

Taniguchi

Imoto

Takeda

et al. 2015

Heteroatom Chemistry

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A new method for the hydrolysis of diazonium salts, without the formation of tar, was developed. A two‐phase system consisting of cyclopentyl methyl ether (CPME) and water is very effective for the hydrolysis of diazonium salts. Using this solvent system, the diazonium salt prepared from 3‐(4‐nitrophenoxy)aniline gave 3‐(4‐nitrophenoxy)phenol in high yield (96%) within 20 min. The synthesized phenol is an industrially important raw material in polymer syntheses. Furthermore, the use of the present two‐phase system of CPME and water successfully brought about the efficient conversions of several m‐substituted anilines into the corresponding m‐substituted phenols. This is the first example of hydrolysis of diazonium salts using the two‐phase system (CPME and water).

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Constituents of Berchemia racemosa SIEB. et ZUCC.

Cited by 7 publications

References 0 publications

Flavan-3-ols Isolated from Some Medicinal Plants Inhibiting COX-1 and COX-2 Catalysed Prostaglandin Biosynthesis

Flavan-3-ols Isolated from Some Medicinal Plants Inhibiting COX-1 and COX-2 Catalysed Prostaglandin Biosynthesis

Widely targeted metabolic analysis revealed the changed pigmentation and bioactive compounds in the ripening Berchemia floribunda (Wall.) Brongn. fruit

Hydrolysis of Diazonium Salts Using a Two‐Phase System (CPME and Water)

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