Structures of New Limonoid Glycosides in Lemon (<i>Citrus limon</i>Burm.<i>f</i>.) Peelings

Matsubara, Yoshiharu; Sawabe, Akiyoshi; Iizuka, Yoshitomi

doi:10.1080/00021369.1990.10870087

Cited by 28 publications

(16 citation statements)

References 3 publications

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“…19) Acidic sterols in the feces were measured by GLC according to the method of Grundy et al 20) Part of the cecal content was taken out into desalted water in a vial without exposure to air and suspended. The suspension of cecal content was deproteinised with perchloric acid to form Na salts of SCFAs.…”

Section: Methodsmentioning

confidence: 99%

Effect of White Wheat Bread Containing Sugar Beet Fiber on Serum Lipids and Hepatic mRNA in Rats Fed on a Cholesterol-Free Diet

Nakamura

Kanazawa

Liyanage

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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Section: Methodsmentioning

confidence: 99%

Effect of White Wheat Bread Containing Sugar Beet Fiber on Serum Lipids and Hepatic mRNA in Rats Fed on a Cholesterol-Free Diet

Nakamura

Kanazawa

Liyanage

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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“…Further analysis by 1D-and 2D-NMR spectra, compared to data reported for limonoid ichangin 4, [12][13][14][15] H correlation spectroscopy (COSY) key correlations led to assigning the planar structure of 1, as shown in Fig. 2.…”

Section: )mentioning

confidence: 99%

“…Further analysis by 1D-and 2D-NMR spectra, compared to data reported for limonoid ichangin 4, [12][13][14][15] led to determining that 1 also contained a furan ring [d H 7.46 (1H, s, H-23) AA 14490, Cra 30 45-03, Ciudad Universitaria, Bogotá D.C., Colombia. Received January 21, 2011; accepted April 16, 2011; published online April 25, 2011 A novel seco-limonoid, rel- (1S,5R,9S,7R,8S,9R,10S,11R,13S,14R,15R,17R)-11,19-dihydroxy-7-acetoxy-7-deoxoichangin (raputiolide) (1), and two novel quinolone alkaloids N-methyl-2-phenoxyquinolin-4(1H)-one (heptaphyllone A) (2) and 6-methylbenzofuro[2,3-b]quinolin-4(1H)-one (heptaphyllone B) (3), along with the known seco-limonoid ichangin (4), were isolated from Raputia heptaphylla PITTIER (Rutaceae) stem bark.…”

Section: )mentioning

confidence: 99%

seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

Barrera

Coy-Barrera

Granados-Falla

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleThe Rutaceae family, consisting of ca. 150 genera and 1600 species, is mostly distributed throughout tropical regions. Species from this family have important uses in industry such as in food, pharmaceuticals and ornamental purposes, as well as having a wide variety of ethnobotanical uses 1) ; they are studied in terms of obtaining alkaloids and limonoids as bioactive principles.2) Among important plants from Rutaceae, those from the Raputia genus have attracted special attention because of their use in South-America due to their trypanocidal and leishmanicidal properties. 3)Leishmaniasis is an endemic disease which affects nearly 12 million people worldwide in tropical and subtropical regions.4) Clinically, the disease compromises skin, mucosa, and/or visceral organs and its specific action depends on both the species involved and the host's immunological system. Cutaneous and mucocutaneous varieties are often disabling, having high morbidity rates, whereas the visceral type affects a smaller number of people.5) More than 98% cases in Colombia are caused by cutaneous Leishmaniasis, being mostly transmitted by Leishmania (Viannia) panamensis (L. (V.) panamensis) species. 6) At clinical level, 20% of cases are neither reported nor treated; furthermore, nearly 80% of infections are spontaneously resolved due to the host's immunological response against parasites.7) Clinical cases which cannot be immunologically resolved are often treated by first-line drugs (e.g. pentavalent antimonial salts) which have shown higher toxicity and parasite-induced resistance. This had consequently led to the search and development of novel therapeutic agents for controlling this disease. Hence, studying the active principles obtained from traditional medicinal plants still has special importance.8) As part of our research into bioactive compounds from Rutaceae plants, this article thus describes the isolation, elucidation and antileishmanial activity of a novel seco-limonoid (1) and two novel alkaloids (2-3), along with other six known compounds [a seco-limonoid (4) and five alkaloids (5-9)] obtained from Raputia heptaphylla stem bark and leaves. The antileishmanial effect of isolated compounds was evaluated on L. (V.) panamensis (promastigotes and amastigotes). Compounds 1 and 5 revealed important antileishmanial activity at different levels. Results and DiscussionEthanol extract from R. heptaphylla (20 g) stem bark was subjected to an ultrasound-assisted acid-base extraction for alkaloids 9,10) affording an alkaloid extract (1.2 g). Chloroform-soluble extract was purified by repeated CC on silica gel to give compounds 1-4. Alkaloids 5-9 were also isolated using an identical procedure on ethanol extract from R. heptaphylla leaves (50 g). Structures were established on the basis of full spectroscopic data analysis compared to data from the pertinent literature (Fig. 1).Compound 1 was obtained as colorless crystals (mp 220-222°C, MeOH). Its high resolution-electrospray ionization mass spectra (HR-ESI-MS) showed a pseud...

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“…Total cholesterol and HDL cholesterol concentrations in the serum were determined enzymatically using commercially available reagent kits (assay kits for the TDx system; Abbott Laboratory Co., Irving, TX Total lipids were extracted from liver and feces by using a mixture of chloroform/methanol (2:1, vol/vol) (16). The neutral sterol portion in each total lipid sample obtained by saponification was acetylated (17) and analyzed by GLC using a Shimadzu 14A chromatograph (Kyoto, Japan) with a DB17 capillary column (0.25 mm × 30 m; J&W Scientific, Folsom, CA) with nitrogen as the carrier gas. Acidic sterols in feces were measured by GLC following the method of Grundy et al (18).…”

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confidence: 99%

Enzyme‐resistant fractions of beans lowered serum cholesterol and increased sterol excretions and hepatic mRNA levels in rats

Han

Fukushima

Kato

et al. 2003

Lipids

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Feeding rats beans with resistant starch reduces their serum cholesterol concentration; however, the mechanism by which this occurs is not fully understood. We examined the effects of enzyme-resistant fractions of adzuki (Vigna angularis) and tebou (Phaseolus vulgaris, var.) beans on serum cholesterol and hepatic mRNA in rats. Rats were fed a cholesterol-free diet with 50 g of cellulose powder (CP)/kg, 50 g of an enzyme-resistant fraction of adzuki starch (AS)/kg, or 50 g of an enzyme-resistant fraction of tebou starch (TS)/kg diet for 4 wk. There were no significant differences in body weight, liver weight, and cecum contents among the groups, nor was there a significant difference in food intake among the groups. The levels of serum total cholesterol, VLDL + intermediate density lipoprotein + LDL-cholesterol, and HDL cholesterol in the AS and TS groups were significantly (P < 0.05) lower than in the CP group throughout the feeding period. Total hepatic cholesterol in the CP group was significantly (P < 0.05) lower than in the AS and TS groups, fecal cholesterol excretion in the TS group was significantly (P < 0.05) greater than in the CP and AS groups, and the fecal total bile acid concentrations in the AS and TS groups were significantly (P < 0.05) higher than in the CP group. Cecal acetate, propionate, and n-butyrate concentrations in the AS and TS groups were significantly (P < 0.05) higher than in the CP group. The level of hepatic scavenger receptor class B1 (SR-B1) mRNA in the TS group was significantly (P < 0.05) higher than in the CP group, and the levels of hepatic cholesterol 7alpha-hydroxylase mRNA in the AS and TS groups were significantly (P < 0.05) higher than in the CP group. These results suggest that AS and TS have a serum cholesterol-lowering function due to the enhanced levels of hepatic SR-B1 and cholesterol 7alpha-hydroxylase mRNA.

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Structures of New Limonoid Glycosides in Lemon (Citrus limonBurm.f.) Peelings

Cited by 28 publications

References 3 publications

Effect of White Wheat Bread Containing Sugar Beet Fiber on Serum Lipids and Hepatic mRNA in Rats Fed on a Cholesterol-Free Diet

Effect of White Wheat Bread Containing Sugar Beet Fiber on Serum Lipids and Hepatic mRNA in Rats Fed on a Cholesterol-Free Diet

seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

Enzyme‐resistant fractions of beans lowered serum cholesterol and increased sterol excretions and hepatic mRNA levels in rats

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