Benzophenones and biflavonoids from Rheedia edulis.

Two new polyisoprenylated benzophenones, 32-hydroxy-ent-guttiferone M (1) and 6-epi-guttiferone J (2), along with seven known compounds, 6-epi-clusianone (3), guttiferone A (4), xanthochymol (5), guttiferone E (6), isoxanthochymol (7), (+)-volkensiflavone (8), and (+)-morelloflavone (9), were identified from the seeds and rinds of Rheedia edulis. Compounds 1-3 and 5-9 have been isolated and identified from this species for the first time. The structures of the new compounds were elucidated mainly by analysis of their 1D and 2D NMR spectroscopic data, and their absolute configurations were determined by comparison of their experimental optical rotation and electronic circular dichroism measurements with those values predicted by DFT calculations.

Benzophenones and biflavonoids from Garcinia livingstonei fruits.

A series of 13 known compounds, including seven benzophenones [guttiferone A (1), guttiferone K (2), xanthochymol (3), guttiferone E (4), cycloxanthochymol (5), isoxanthochymol (6), and gambogenone (7)], five biflavonoids [amentoflavone (8), 3,8''-biapigenin (9), (+)-volkensiflavone (10), (+)-morelloflavone (11), and (+)-fukugiside (12)], and the xanthone derivative alloathyriol (13), were identified from the fruits of Garcinia livingstonei (Clusiaceae). This is the first time that compounds 2-7, 9, 12, and 13 have been reported in this species. The cytotoxicity of benzophenones 1 and 2 was assessed for their effect on HCT-116, HT-29, and SW-480 human colon cancer cell lines.

Quantitative analysis of antiradical phenolic constituents from fourteen edible Myrtaceae fruits.

Many species of Myrtaceae are cultivated in home gardens throughout the tropics for their edible fruit, and have been used in traditional medicine to treat several inflammatory conditions. Fruit phenolics are important dietary antioxidant and anti-inflammatory constituents. We have investigated the antiradical activity, total phenolic content (TPC), and total anthocyanin content (TAC) of 14 underutilized Myrtaceae fruits, namely Eugenia aggregata, E.

Cytotoxic chalcones and antioxidants from the fruits of a Syzygium samarangense (Wax Jambu).

Bioassay-guided fractionation of the methanolic extracts of the pulp and seeds of the fruits of Syzygium samarangense Merr. & Perry (Blume) led to the identification of four cytotoxic compounds and eight antioxidants on the basis of HPLC-PDA analysis, MS, and various NMR spectroscopic techniques. Three C-methylated chalcones, 2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone (1), 2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (stercurensin, 2), and 2',4'-dihydroxy-6'-methoxychalcone (cardamonin, 3), were isolated and displayed cytotoxic activity (IC(50) = 10, 35, and 35 μM, respectively) against the SW-480 human colon cancer cell line.

Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora).

A new depside, jaboticabin (1), together with 17 known compounds were isolated from the fruit of jaboticaba (Myrciaria cauliflora). The structure of 1 was elucidated by spectroscopic data interpretation. Known compounds were identified by comparison of their spectroscopic data with literature values or by comparison to authentic standards.

Comparative analyses of bioactive Mammea coumarins from seven parts of Mammea americana by HPLC-PDA with LC-MS.

Mammea americana L. is tropical plant in the Clusiaceae family that bears edible fruit. Mammea coumarins are isoprenylated derivatives of the lactones of the 2-hydroxy-Z-cinnamic acids that are bioactive and have limited distribution in three Clusiaceae genera.

Antioxidant and cytotoxic isoprenylated coumarins from Mammea americana.

Antioxidant-guided fractionation of Mammea americana L. seeds resulted in the identification of three new isoprenylated coumarins, mammea B/BA hydroxycyclo F (1), mammea E/BC (2), and mammea E/BD (3). In addition, twelve known isoprenylated coumarins, mammea A/AA (4), mammea A/AA cyclo D (5), mammea A/AA cyclo F (6), mammea A/AC cyclo D (7), mammea A/AD cyclo D (8), mammea B/BA (9), mammea B/BA cyclo F (10), mammea B/BB (11), mammea B/BC (12), mammea B/BD (13), mammea E/BA (14), and mammea E/BB (15), as well as two known flavanols, (+)-catechin (16) and (-)-epicatechin (17) were identified.

Bioactive benzophenones from Garcinia xanthochymus fruits.

A MeOH extract of Garcinia xanthochymus fruits was subjected to activity-guided fractionation, yielding two new benzophenones, guttiferone H (1) and gambogenone (2). Compound 1 contains a seven-membered ring attached to the bicyclo[3.3.

Analysis of polyphenolic antioxidants from the fruits of three pouteria species by selected ion monitoring liquid chromatography-mass spectrometry.

Pouteria campechiana, Pouteria sapota, and Pouteria viridis are tropical plants in the Sapotaceae family that bear edible fruits. The fresh fruits of these three Pouteria species were each extracted, and activity-guided fractionations were performed to identify the antioxidant constituents. Seven polyphenolic antioxidants, gallic acid (1), (+)-gallocatechin (2), (+)-catechin (3), (-)-epicatechin (4), dihydromyricetin (5), (+)-catechin-3-O-gallate (6), and myricitrin (7), were isolated and identified.

Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).

Activity-guided fractionation of a methanol extract from the fruit of Manilkara zapota cv. Tikal resulted in the isolation of two new antioxidants, methyl 4-O-galloylchlorogenate (1) and 4-O-galloylchlorogenic acid (2), along with eight known polyphenolic antioxidants, namely, methyl chlorogenate (3), dihydromyricetin (4), quercitrin (5), myricitrin (6), (+)-catechin (7), (-)-epicatechin (8), (+)-gallocatechin (9), and gallic acid (10). Of the 10 polyphenols, 1 showed the highest antioxidant activity (IC(50) = 12.

Polyphenolic antioxidants from the fruits of Chrysophyllum cainito L. (Star Apple).

Chrysophyllum cainito L. (Sapotaceae), known commonly as star apple or caimito, is a tropical tree that bears edible fruits. The fruits are grown commercially in certain tropical and subtropical areas, such as southern Florida.