CCXXVI.—The constituents of the seeds of Casimiroa edulis

Power, Frederick B.; Callan, Thomas

doi:10.1039/ct9119901993

Cited by 20 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Pharmacopeia of Mexico once recognized both the fruit and seed of C. edulis, with the former used as an anthelmintic and the latter as a vulnerary (Power and Callan, 1911). In previous work, the seeds of C. edulis have afforded alkaloids (Power and Callan, 1911;Aebi, 1956;Djerassi et al, 1956Djerassi et al, , 1958Kincl et al, 1956;Meisels and Sondheimer, 1957;Sondheimer and Meisels, 1958;Randolph and Friedrich, 1958;Mechoulam et al, 1961;Raman et al, 1962;Toube et al, 1967;Romero et al, 1983;Rizvi et al, 1985), coumarins (Dreyer, 1968;Enrı ´quez et al, 1984), flavonoids (Kincl et al, 1956;Dreyer and Bertelli, 1967;Garratt et al, 1967;Dreyer, 1968;Romero et al, 1983), and limonoids (Sondheimer et al, 1959;Dreyer, 1968;Murphy et al, 1968). From the bark of C. edulis, alkaloids and flavonoids were also reported as constituents (Iriarte et al, 1956;Sondheimer and Meisels, 1960).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Ito

Shamon

et al. 1998

J. Agric. Food Chem.

View full text Add to dashboard Cite

An ethyl acetate extract derived from the seeds of the medicinal and food plant Casimiroa edulis inhibited mutagenicity induced by 7,12-dimethylbenz[a]anthracene (DMBA) with Salmonella typhimurium strain TM677. It also showed complete inhibition of DMBA-induced preneoplastic lesions with an in vitro mouse mammary gland organ culture system at a concentration of 10 μg/mL. Bioassay-guided phytochemical investigation of this extract using antimutagenicity as a monitor led to the isolation of four furocoumarins, constituted by the known compounds phellopterin (1) and isopimpinellin (2) and the novel compounds (R,S)-5-methoxy-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (3) and (R,S)-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (4). Four known alkaloids, casimiroin (5), 4-methoxy-1-methyl-2(1H)-quinolinone (6), 5-hydroxy-1-methyl-2-phenyl-4-quinolone (7), and γ-fagarine (8), and two known flavonoids, zapotin (9) and 5,6,2‘-trimethoxyflavone (10), were also isolated. Of these isolates, compounds 3 and 5 showed the most potent antimutagenic effects in the forward mutagen assay utilizing S. typhimurium strain TM677, whereas casimiroin (5) and 5,6,2‘-trimethoxyflavone (10) significantly inhibited the formation of DMBA-induced preneoplastic lesions in mouse mammary gland organ culture. Keywords: Casimiroa edulis; Rutaceae; furocoumarins; (R,S)-5-methoxy-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen; (R,S)-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen; alkaloids; flavonoids; antimutagens; mouse mammary organ culture assay; cancer chemoprevention

show abstract

Section: Introductionmentioning

confidence: 99%

“…In early pharmacological work, the seeds of C. edulis were shown to be devoid of hypnotic effects when an alcoholic extract was administered to dogs (Power and Callan, 1911). There have been a number of reports on the hypotensive, hypnotic, and sedative activities of the seeds of C. edulis.…”

Section: Introductionmentioning

confidence: 99%

Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Ito

Shamon

et al. 1998

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The first reports on the chemical composition of C. edulis seeds are attributed to José Sanchez and date to 1893. At that time, the presence of alkaloids, resin, essential oil, gums, and sugars was also evaluated [18]. The chemotaxonomic importance of zapotin in Casimiroa plants is evidenced by the presence of this compound in large amounts in C. tetrameria.…”

Section: Natural Occurrence Of Zapotinmentioning

confidence: 99%

“…3 : 259sh, 324; IR (neat) 2939, 2840, 1650, 1592, 1475, 1417, 1357, 1281, 1255, 1111 cm −1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 7.35 (t, J = 8.7 Hz, 1 H), 7.25 (d, J = 9.3 Hz, 1 H), 7.16 (d, J = 9.3 Hz, 1 H), 6.59 (d, J = 8.4 Hz, 2 H), 6.26 (s, 1 H), 3.94 (s, 3 H), 3.88 (s, 3 H), 3.75 (s, 6 H); 13 C NMR (75 MHz, CDCl 3 ) δ 177.9, 158.7, 158.2, 152.2, 149.3, 147.4, 131.8, 119.0, 118.5, 114.9, 113.5, 110.9, 103.6, 61.5, 56.8, 55.7; EIMS (m/z, relative intensity) 342 (M+, 50), 327(100), 311(7), 283(5), 253(8), 237 (3), 197 (3), 182(5), 165(37), 137 (83), 109(26), 91(18), 69 (19), 53 (14); HRMS m/z calcd for (C 19 H 18 O 6 ) 342.1103, found 342.1107. Anal.…”

mentioning

confidence: 99%

Zapotin, a Polymethoxyflavone, with Potential Therapeutic Attributes

Strawa

Jakimiuk

2021

IJMS

View full text Add to dashboard Cite

The use of plants as traditional medicines is common and has prevailed in many different cultures over time. Polymethoxyflavones (PMFs) are natural polyphenols from the group of flavonoids. Zapotin, a member of the PMFs, is found mainly in citrus plants and is almost exclusively limited to their peels. The chemical structure of zapotin has been questioned from the very beginning, since the structure of flavonoids with a single oxygen atom in the C2′ position is extremely rare in the plant kingdom. To clarify this, the structural determination and bio-inspired synthesis of zapotin are discussed in detail in this review. Due to the broad biological potential of PMFs, the complication in the isolation process and characterization of PMFs, as well as their purification, have been estimated by adapting various chromatographic methods. According to available data from the literature, zapotin may be a promising curative agent with extensive biological activities, especially as a chemopreventive factor. Apart from that, zapotin acts as an antidepressant-like, anticancer, antifungal, and antioxidant agent. Finally, accessible studies about zapotin metabolism (absorption, distribution, metabolism, excretion, and toxicity) underline its potential in use as a therapeutic substance.

show abstract

“…chim. Belg., [4] The azo compounds were prepared by the modified oxidation procedure used for 2,2'-azo-bis-2,4-dimethylvaleronitrile (56-57°isomer). Because of the abnormally slow rate of oxidation, the reaction mixture was allowed to stand for 72 hours at 0-5°before the product was isolated.…”

Section: Experimental6mentioning

confidence: 99%

Azo-bis-nitriles. III.¹ The Preparation and Decomposition of Azo-nitriles. Steric Factors

Overberger¹,

Berenbaum²

1951

J. Am. Chem. Soc.

View full text Add to dashboard Cite

CCXXVI.—The constituents of the seeds of Casimiroa edulis

Cited by 20 publications

References 0 publications

Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Zapotin, a Polymethoxyflavone, with Potential Therapeutic Attributes

Azo-bis-nitriles. III.¹ The Preparation and Decomposition of Azo-nitriles. Steric Factors

Contact Info

Product

Resources

About

CCXXVI.—The constituents of the seeds of Casimiroa edulis

Cited by 20 publications

References 0 publications

Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Zapotin, a Polymethoxyflavone, with Potential Therapeutic Attributes

Azo-bis-nitriles. III.1 The Preparation and Decomposition of Azo-nitriles. Steric Factors

Contact Info

Product

Resources

About

Azo-bis-nitriles. III.¹ The Preparation and Decomposition of Azo-nitriles. Steric Factors