Biflavone and a Plant Sterol Isolated from Antidesma bunius

Biflavone and a Plant Sterol Isolated from Antidesma bunius A Biflavone and a Plant Sterol Isolated from Antidesma bunius (Linn.) Spreng. Ivan L. Lawagai,* Suad Naheedb, Mohammed Mosihuzzamanc, Allan, Patrick G. Macabeoadeg, Erickson Paragasefk, Peter Prokschh, Alicia M. Aguinaldoaeg Keywords: Antidesma, Antidesma bunius, Amentoflavone, Betasitosterol, biflavone, sterols 1. Subject and source Antidesma bunius (Linn.) Spreng. (Euphrbiaceae) ‘‘bignay† is a common plant found throughout the Philippines. The bark is poisonous as it contains an alkaloid thus, is used medicinally. The leaves are acidic and diaphoretic, and, when young, these are boiled with pot-herbs, and employed by the natives in syphilitic infections (Quisumbing, 1978). The leaves are sudorific and are employed in treating snakebite in Asia (Morton, 1987). The leaves of Antidesma bunius, commonly known as â€Å"bignay†, are traditionally used by native Filipinos to control diabetes (Lawag et al., 2012). Fresh leaves were collected from the hills of Brgy. Agustin Navarra, Ivisan, Capiz Province in January 2009. The plant was identified by Asst. Prof. Rosie A. Madulid and a voucher specimen (USTH 5357) is deposited at the UST Herbarium, Botany Laboratory, Research Center for the Natural and Applied Sciences, University of Santo Tomas (UST), Manila, Philippines. 2. Previous work Dammara-20, 24-dien-3ÃŽ ²-ol and friedelin were isolated from the stem and leaves of A. bunius (Hui and Sung, 1968). In 2008, Samappito and Butkhup identified the flavonoids catechin, Procyanidin B1 and Procyanidin B2 from the fruits and Gallic acid, quercetin, catechin and epicatechin were also detected from the fruits of A. bunius (Santiago et al., 2005). 3. Present study 3.1. Extraction and isolation Dried and ground leaves Antidesma bunius (1610 g) were extracted with 80% ethanol to give a green syrupy extract (240.0 g) which was subjected to vacuum liquid chromatography (VLC) using solvents of increasing polarity starting with hexane, hexane-dichloromethane (1:1), dichloromethane, dichloromethane -ethyl acetate (1:1), ethyl acetate, ethyl acetate-methanol (1:1), and methanol to give seven fractions. The fifth fraction (4.04 g) was further fractionated twice on silica gel packed on VLC using solvents of increasing polarity starting from hexane and ending with methanol giving five fractions each, respectively. Fraction three which was purified twice on silica gel using hexane-dichloromethane (1:1) and hexane-dichloromethane (95:5) furnished 1 (16.13 mg). Isolation of 2: the fourth fraction (12.34 g) after VLC was chromatographed on silica gel using 5-10% gradients of methanol in dichloromethane to give ten fractions. Fraction three (42.3 mg) was further purified using Sephadex LH20 using 20% gradients of methanol in DCM to give 2 (5.9 mg). (1)(2) 3.2. Identification of purified compounds The compounds were identified as Stigmast-5-en-3ÃŽ ²-ol or ÃŽ ²-sitosterol, a plant sterol, (1) (Balamurugan et al., 2012) and (Sosinska, et al., 2013) and 3,8-biapigenin (Amentoflavone), a biflavone (2) (Chari et al., 1977) and (Ryu et al., 2010) on the basis of their IR, LR-EIMS, LR-ESIMS and NMR (1H NMR, 13C NMR, 1H-1H COSY, HMBC and HSQC) spectral data and by comparison of spectra reports with the literature. 4. Chemotaxonomic significance Other Antidesma species like A. menasu (Risvi et al., 1980a), (Risvi et al., 1980b) and A. pentandrum (Chen et al., 2004), (Kikuchi, 1983) are known to contain plant sterols. A. puncticulatum is known to contain flavonoids (Nuengchamnong and Ingkaninan, 2009), while A. laciniatum was reported to contain both plant sterols and flavonoids (Tchinda et al., 2006). The isolation process that was presently preformed on the ethanolic leaf extract of A. bunius afforded compounds 1 and 2 which were coherent to the compounds that were previously isolated or reported from the other Antidesma species. Although the said compounds were reported for the very first time in A. bunius, compound 1 was also reported to be present in A. pentandrum (Chen et al., 2004) and in A. laciniatum (Tchinda et al., 2006), while compound 2 was reported to be present in A. laciniatum (Tchinda et al., 2006). This further establishes the chemotaxonomic relationship of A. bunius towards the other species of the genus Antidesma. Although plant sterols (Hui and Sung, 1968) and biflavones (Samappito and Butkhup, 2008), (Santiago et al., 2005) were previously reported in the leaf and bark extracts A. bunius, this is the first report that indicated the presence of ÃŽ ²-sitosterol (1) and Amentoflavone (2). Compounds 1 and 2 therefore add up to the list of isolated and identified compounds from the leaves of A. bunius. References Quisumbing, E., 1978. Medicinal Plants of the Philippines. Katha Publishing Inc., Quezon City, Philippines. Balamurugan, R., Stalin, A. and Ignacimuthu, S., 2012. European Journal of Medicinal Chemistry 47, 38 – 43. Chari, V. M., Ilyas, M., Wagner, H., Neszmelyi, A., Chen, F., Chen, L., Lin, Y., Lin, Y., 1977. Phytochemistry 16, 1273 – 1278. Chen, Y.C.; Cheng, M.J.; Lee, S.J.; Dixit, A.K., Ishikawa, T., Tsai, I.L.; Chen, I.S., 2004. Helvetica Chimica Acta 87 (11), 2805 – 2811. Hui, W. H.; Sung, M. L., 1968. Australian Journal of Chemistry 21(8), 2137-40. Kikuchi, H., Tensho, A., Shimizu, I., Shiokawa, H., Kuno, A., Yamada, S., Fujiwara, T., Tomita, K., 1983. Chemistry Letters (4), 603 –606. Lawag, I., Aguinaldo, A., Naheed, S., Mossihuzzaman, M., 2012. Journal of Ethnopharmacology 144(1), 217 – 219. Morton, J., 1987. Bignay. p. 210–212. Fruits of Warm Climates. Julia F. Morton, Miami, FL. Nuengchamnong, N., and Ingkaninan, K., 2010. Food Chemistry 118, 147 – 152. Samappito, S.; Butkhup, L., 2008. Pakistan Journal of Biological Sciences 11 (13), 1654 – 1661. Santiago, D.M.O., 2005. MS Thesis University of the Philippines, Los Banos. Sosinska, E., Przybylski, R., Hazendonk, P., Zhao, Y. Y., Curtis, J., 2013. Food Chemistry 139, 464 – 474. Rizvi, S. H. Shoeb, A. Kapil, R. S. Popli, S. P., 1980. Experientia 36. Birkhauser Verlag, Basel (Schweiz). Rizvi, S., Shoeb, A., Kapil, R., Popli, S., 1980. Phytochemistry 19 (11), 2409 – 10. Ryu, Y. B., Jeong, H. J., Kima, J. H., Kima, Y. M., Park, J., Kim, D., Naguyen, T.T.H., Park, S., Chang, J. S., Park, K. H., Rho, M., Lee, W. S., 2010. Bioorganic Medicinal Chemistry 18, 7940 – 7947. Tchinda, A..; Teshome, A.; Dagne, E.; Arnold, N.; Wessjohann, L., 2006. Bulletin of the Chemical Society of Ethiopia 20 (2), 325 – 328. Current Affiliations: iChemistry Department, Adamson University, Ermita, Manila, Philippines. jJinnah University for Women, Nazimabad, Karachi, Pakistan kDepartment of Chemistry, Washington State University, Pullman, WA, 99164, USA * Corresponding author. E-mail address:*[emailprotected] (I.L. Lawag)

Alicia Moore (Pink) Essay -- Biography Singer Pink Essays

Alicia Moore (Pink) Alicia Moore, or Pink as she is better known, has become a music sensation around the United States. My reason for choosing her as a topic is the fact that she was born and raised in Doylestown, Pennsylvania my hometown. Doylestown is about an hour northeast of Philadelphia, and it’s easy to take note of anyone famous who comes out of D-Town, as it is called, because it is not the largest of areas. Pink went to the rival high school of mine, Central Bucks High School West, and I actually know a few people who knew her as Alicia Moore through various activities. Pink had a very rough childhood. She wanted to leave her house and envisioned a better life for herself when she was growing up. "I was screwed up, lost and unhappy," she said of her childhood. Her parents were fighting all the time and eventually divorced when Pink was only eight years old. She had little interest in school, got kicked of the house by her mother when she was 15, and went to live with her father and then dropped out of C.B. West her junior year. She claims she never even had any friends her own age. "My best friend was an 85-year-old woman who lived across the street," she said. Despite a difficult childhood, she always felt music was going to be her life. "I always knew I wanted to sing. I would tell my first grade teachers, 'Homework? What? I'm a rock star!' Seriously, I had it in my mind and that's why I fought with my parents so much because I was 30 by the time I was 10. I was ready to go, like, 'Come on. Put me onstage. Where's Star Search? What's going on?' An d it couldn't happen fast enough." After dropping out, Pink worked in places like Pizza Hut, McDonalds and Wendy's, but she was never on time and basically, hated tak... ...t happened all over again." Pink’s individuality is really shown throughout her life, from the desire to be a musician from a young age, to her comments on the other music icons of her age and gender. Pink’s music is unique and no two songs seem to sound the same. She’s a girl that knows what she wants and I think this will aid in her staying atop the charts for a long time. It’s seems very impressive and almost a claim to fame for my hometown, that Alicia Moore, Pink, a Doylestown native, has made such a large impact on the world of music. Works Cited: MSN Web Page, http://ninemsn.com.au/entertainment/music/pink.asp The Billboard Music Web Page, http://www.billboard.com The Detroit Free Press Web Page, http://www.freep.com/entertainment/music/pink30_20011130.htm The MTV Web Page, http://www.mtv.com/bands/p/pink/news_feature_112101/index2.jhtml

Jackie Robinson Assessment

1. Many people agree that Robinson was not the best player in the Negro League in the mid 1940s. If so why did Rickey choose him? Because he wasn’t looking for the best baseball player, he was looking for a player who was talented, with a background beyond criticism, with an unshakable self-control and with a good winner attitude. He thought that Robinson would be ideal to break the color line of the Major League Baseball teams, plus he was a very good player.2. Do you think professional sports would be the same today if it had not been for Robinson? I think Robinson played a very big role in the history of sports in America because today some of the most watched sports in the country like baseball (MLB) or basketball (NBA) are mostly formed by African-American players. If it had not been for Robinson I think sports in America wouldn’t be the same as they are now.3. Do you think Robinson’s success with the Dodgers had any impact beyond sports? I think Robinsonâ⠂¬â„¢s success with the Brooklyn Dodgers had a very big impact beyond sports because since he made it to an all white league and be actually successful in it, it motivated to other players of all negro leagues to became better and try to make it to this new opportunity that they had. I think Robinson played a big role in the history of sports of America and that’s why now he’s one of the biggest names in history of baseball. ï » ¿Jackie Robinson Assessment 1. Many people agree that Robinson was not the best player in the Negro League in the mid 1940s. If so why did Rickey choose him? Because he wasn’t looking for the best baseball player, he was looking for a player who was talented, with a background beyond criticism, with an unshakable self-control and with a good winner attitude. He thought that Robinson would be ideal to break the color line of the Major League Baseball teams, plus he was a very good player.2. Do you think professional sports would be the same today if it had not been for Robinson? I think Robinson played a very big role in the history of sports in America because today some of the most watched sports in the country like baseball (MLB) or basketball (NBA) are mostly formed by African-American players. If it had not been for Robinson I think sports in America wouldn’t be the same as they are now.3. Do you think Robinson’s success with the Dodgers had any impact beyond sports? I think Robinsonâ⠂¬â„¢s success with the Brooklyn Dodgers had a very big impact beyond sports because since he made it to an all white league and be actually successful in it, it motivated to other players of all negro leagues to became better and try to make it to this new opportunity that they had. I think Robinson played a big role in the history of sports of America and that’s why now he’s one of the biggest names in history of baseball.

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