research people publications PDB codes protocols & software intranet
current lab members alumni

Chris Waddling

x-ray facility manager

Room S126C
Department of Biochemistry & Biophysics
University of California, San Francisco
Mission Bay, Genentech Hall
600 16th St.
San Francisco CA
94143-2140
(415) 476-8288 (Ph)
(415) 514-4142 (Fax)

"Structurally Novel Bioconversion Products of the Marine Natural Product Sarcophine Effectively Inhibit JB6 Cell Transformation," K.A. El Sayed, M.T. Hamann, C.A. Waddling, C. Jensen, S.K. Lee, C. Andersson Dunstan, and J.M. Pezzuto, J. Org. Chem., 1998, 63(21), 7449.

54 articles citing this article:

Putra, Masteria Yunovilsa; Ianaro, Angela; Panza, Elisabetta; Bavestrello, Giorgio; Cerrano, Carlo; Fattorusso, Ernesto; Taglialatela-Scafati, Orazio, Sinularioside, a triacetylated glycolipid from the Indonesian soft coral Sinularia sp., is an inhibitor of NO release, Bioorganic & Medicinal Chemistry Letters (2012), 22(8), 2723-2725.

Hegazy, Mohamed-Elamir F.; Gamal Eldeen, Amira M.; Shahat, Abdelaaty A.; Abdel-Latif, Fathy F.; Mohamed, Tarik A.; Whittlesey, Bruce R.; Pare, Paul W., Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum, Marine Drugs (2012), 10, 209-222.

Pandey, Kartikay, Potent bioactive compounds from the ocean: some interesting aspects and applications, Pharmacognosy Journal (2012), 4(27), 1-5.

Hegazy, Mohamed-Elamir F.; El-Beih, Ahmed A.; Moustafa, Alaa Y.; Hamdy, Abdelhamed A.; Alhammady, Montaser A.; Selim, Rehab M.; Abdel-Rehim, Mohamed; Pare, Paul W., Cytotoxic cembranoids from the Red Sea soft coral Sarcophyton glaucum, Natural Product Communications (2011), 6(12), 1809-1812.

Hassan, Hossam M.; Sallam, Asmaa A.; Mohammed, Rabab; Hifnawy, Mohamed S.; Youssef, Diaa T. A.; El Sayed, Khalid A., Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors. Bioorganic & Medicinal Chemistry (2011), 19(16), 4928-4934.

Baraka, Hany N.; Khanfar, Mohammad A.; Williams, John C.; El-Glar, Emad M.; El Sayed, Khalid A. Bioactive natural, biocatalytic, and semisynthetic tobacco cembranoids. Planta Medica (2011), 77(5), 467-476.

Arif, Jamal M.; Kunhi, Mohammed; Siddiqui, Yunus M.; El Sayed, Khalid A.; Orabi, Khaled Y.; Al-Hazzani, Amal; Al-Ahdal, Mohammed N.; Al-Khodairy, Fahad M. Differential modulation of benzo[a]pyrene-derived DNA adducts in MCF-7 cells by marine compounds. DNA Adducts (2010), 127-142.

Baraka, Hany Nashaat. Microbial transformation of podocarpic acid and evaluation of transformation products for antioxidant activity. Planta Medica (2010), 76(8), 815-817.

Martin, Glenroy D. A. Biotransformation reactions by Rhizopus spp. Current Organic Chemistry (2010), 14(1), 1-14.

Cheng, Shi-Yie; Wang, Shang-Kwei; Chiou, Shu-Fen; Hsu, Chi-Hsin; Dai, Chang-Feng; Chiang, Michael Y.; Duh, Chang-Yih. Cembranoids from the Octocoral Sarcophyton ehrenbergi. Journal of Natural Products (2010), 73(2), 197-203.

Kutrzeba, Lukasz M.; Karamyan, Vardan T.; Speth, Robert C.; Williamson, John S.; Zjawiony, Jordan K. In vitro studies on metabolism of salvinorin A. Pharmaceutical Biology (London, United Kingdom) (2010), Volume Date 2009, 47(11), 1078-1084.

Ferchmin, P. A.; Pagan, One R.; Ulrich, Henning; Szeto, Ada C.; Hann, Richard M.; Eterovic, Vesna A. Actions of octocoral and tobacco cembranoids on nicotinic receptors. Toxicon (2009), 54(8), 1174-1182.

Yao, Li-Gong; Liu, Hai-Li; Guo, Yue-Wei; Mollo, Ernesto. New Cembranoids from the Hainan Soft Coral Sarcophyton glaucum. Helvetica Chimica Acta (2009), 92(6), 1085-1091.

Grote, Daniela; Shaker, Kamel H.; Soliman, Hesham S. M.; Hegazi, Muhammmad M.; Seifert, Karlheinz. Cembranoid diterpenes from the soft corals Sarcophyton sp. and Sarcophyton glaucum. Natural Product Communications (2008), 3(9), 1473-1478.

Martin, Glenroy D. A.; Durrant, Marcus C.; Reese, Paul B. A predictive cytochrome P450 monooxygenase functional model for generic hydroxylation by Rhizopus oryzae ATCC 11145. Journal of Theoretical & Computational Chemistry (2008), 7(3), 421-433.

Pezzuto, John M. Resveratrol as an Inhibitor of Carcinogenesis. Pharmaceutical Biology (New York, NY, United States) (2008), 46(7-8), 443-573.

El Sayed, Khalid A.; Laphookhieo, Surat; Baraka, Hany N.; Yousaf, Muhammad; Hebert, Anne; Bagaley, Danielle; Rainey, Frederick A.; Muralidharan, A.; Thomas, Shibu; Shah, Girish V. Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol. Bioorganic & Medicinal Chemistry (2008), 16(6), 2886-2893.

Fattorusso, Ernesto; Romano, Adriana; Taglialatela-Scafati, Orazio; Achmad, M. Janib; Bavestrello, Giorgio; Cerrano, Carlo. Lobozoanthamine, a new zoanthamine-type alkaloid from the Indonesian soft coral Lobophytum sp. Tetrahedron Letters (2008), 49(14), 2189-2192.

Bilasy, Shymaa El-Shawadfy; Khalifa, Sherief I.; Saleh, Samy M.; Abou El-Ela, Soad H. HPLC method for the quantitative determination of sarcophine, a source of cembranoids with cancer chemopreventive activity. Journal of Pharmaceutical and Biomedical Analysis (2008), 46(4), 784-787.

El Sayed, Khalid A.; Laphookhieo, Surat; Yousaf, Muhammad; Prestridge, Justin A.; Shirode, Amit B.; Wali, Vikram B.; Sylvester, Paul W. Semisynthetic and Biotransformation Studies of (1S,2E,4S,6R,7E,11E)-2,7,11-Cembratriene-4,6-diol. Journal of Natural Products, (2008), 71(1), 117–122.

Jain, Sandeep; Shirode, Amit; Yacoub, Shenouda; Barbo, Ashley; Sylvester, Paul W.; Huntimer, Eric; Halaweish, Fathi; El Sayed, Khalid A. Biocatalysis of the anticancer sipholane triterpenoids. Planta Medica (2007), 73(6), 591-596.

Kamel, Haidy Nasr; Fronczek, Frank Rolf; Khalifa, Sherief Ibrahim; Slattery, Marc. Microbial transformation of 5-Episinuleptolide. Chemical & Pharmaceutical Bulletin (2007), 55(4), 537-540.

El Sayed, Khalid A.; Sylvester, Paul W. Biocatalytic and semisynthetic studies of the anticancer tobacco cembranoids. Expert Opinion on Investigational Drugs (2007), 16(6), 877-887.

Arif, Jamal M.; Sawant, Swapnali S.; El Sayed, Khalid A.; Kunhi, Muhammad; Subramanian, Manogaran P.; Siddiqui, Yunus M.; Youssef, Diaa T. A.; Al-Hussain, Khalid; Al-Ahdal, Mohammed N.; Al-Khodairy, Fahad. Antiproliferative potential of sarcophine and its semisynthetic sulfur-containing derivatives against human mammary carcinoma cell lines. Journal of Natural Medicines (2007), 61(2), 154-158.

Hamann, Mark T. The manzamines as an example of the unique structural classes available for the discovery and optimization of infectious disease controls based on marine natural products. Current Pharmaceutical Design (2007), 13(6), 653-660.

Bilasy, Shymaa E.; Khalifa, Sherief I.; Saeed, Hesham; Saleh, Samy M.; Abou El-Ela, Soad H. Morphological, chemical and protein characterization of the Red Sea soft coral Sarcophyton species, a comparative study. Asian Journal of Biochemistry (2006), 1(4), 262-275.

Sawant, Swapnali; Youssef, Diaa; Mayer, Alejandro; Sylvester, Paul; Wali, Vikram; Arant, Mark; El Sayed, Khalid. Anticancer and anti-inflammatory sulfur-containing semisynthetic derivatives of sarcophine. Chemical & Pharmaceutical Bulletin (2006), 54(8), 1119-1123.

Sawant, Swapnali S.; Youssef, Diaa T. A.; Reiland, Jane; Ferniz, Melissa; Marchetti, Dario; El Sayed, Khalid A. Biocatalytic and Antimetastatic Studies of the Marine Cembranoids Sarcophine and 2-epi-16-Deoxysarcophine. Journal of Natural Products (2006), 69(7), 1010-1013

Pezzuto, John M. Resveratrol as an inhibitor of carcinogenesis. Oxidative Stress and Disease (2006), 20(Resveratrol in Health and Disease), 233-383.

Yin, Shuai-Wen; Shi, Yan-Ping; Li, Xiao-Ming; Wang, Bin-Gui. A new cembranoid diterpene and other related metabolites from the south-china-sea soft coral Lobophytum crassum. Helvetica Chimica Acta (2006), 89(3), 567-572.

Grote, Daniela; Soliman, Hesham S. M.; Shaker, Kamel H.; Hamza, Mohamed; Seifert, Karlheinz. Cembranoid diterpenes and a briarane diterpene from corals. Natural Product Research (2006), 20(3), 285-291.

Pezzuto, John M.; Kosmeder, Jerome W., II; Park, Eun-Jung; Lee, Sang Kook; Cuendet, Muriel; Gills, Joell; Bhat, Krishna; Grubjesic, Simonida; Park, Hye-Sung; Mata-Greenwood, Eugenia; Tan, YingMeei; Yu, Rong; Lantvit, Daniel D.; Kinghorn, A. Douglas. Characterization of natural product chemopreventive agents. Cancer Chemoprevention (2005), 2 3-37.

Arif, Jamal M.; Kunhi, Mohammed; Siddiqui, Yunus M.; El Sayed, Khalid A.; Orabi, Khaled Y.; Al-Hazzani, Amal; Al-Ahdal, Mohammed N.; Al-Khodairy, Fahad M. Role of intermediary biomarkers in determining the anticancer efficacy of marine compounds. Medicinal Chemistry Research (2004), 13(6/7), 553-562.

Arif, Jamal M.; Kunhi, Mohammed; Siddiqui, Yunus M.; El Sayed, Khalid A.; Orabi, Khaled Y.; Al-Hazzani, Amal; Al-Ahdal, Mohammed N.; Al-Khodairy, Fahad M. Differential modulation of benzo[a]pyrene-derived DNA adducts in MCF-7 cells by marine compounds. International Journal of Cancer Prevention (2004), 1(4), 259-268.

Sawant, Swapnali S.; Sylvester, Paul W.; Avery, Mitchell A.; Desai, Prashant; Youssef, Diaa T. A.; El Sayed, Khalid A. Bioactive Rearranged and Halogenated Semisynthetic Derivatives of the Marine Natural Product Sarcophine. Journal of Natural Products (2004), 67(12), 2017-2023

Arif, Jamal M.; Al-Hazzani, Amal A.; Kunhi, Muhammed; Al-Khodairy, Fahad. Novel marine compounds: anticancer or genotoxic? Journal of Biomedicine & Biotechnology (2004), 2004(2), 93-98.

Kinghorn, A. Douglas; Su, Bao-Ning; Jang, Dae Sik; Chang, Leng Chee; Lee, Dongho; Gu, Jian-Qiao; Carcache-Blanco, Esperanza J.; Pawlus, Alison D.; Lee, Sang Kook; Park, Eun Jung; Cuendet, Muriel; Gills, Joell J.; Bhat, Krishna; Park, Hye-Sung; Mata-Greenwood, Eugenia; Song, Lynda L.; Jang, Meishiang; Pezzuto, John M. Natural inhibitors of carcinogenesis. Planta Medica (2004), 70(8), 691-705.

Martin, Glenroy D. A.; Reynolds, William F.; Reese, Paul B. Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145. Phytochemistry (Elsevier) (2004), 65(15), 2211-2217.

Ata, Athar; Nachtigall, Jason A. Microbial transformations of a-santonin. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2004), 59(3/4), 209-214.

Collins, Dwight O.; Reynolds, William F.; Reese, Paul B. New Cembranes from Cleome spinosa. Journal of Natural Products (2004), 67(2), 179-183.

Hamann, Mark T. Enhancing marine natural product structural diversity and bioactivity through semisynthesis and biocatalysis. Current Pharmaceutical Design (2003), 9(11), 879-889.

Peng, Jiangnan; Shen, Xiaoyu; El Sayed, Khalid A.; Dunbar, D. Charles; Perry, Tony L.; Wilkins, Scott P.; Hamann, Mark T.; Bobzin, Steve; Huesing, Joseph; Camp, Robin; Prinsen, Mike; Krupa, Dan; Wideman, Margaret A. Marine natural products as prototype agrochemical agents. Journal of Agricultural and Food Chemistry (2003), 51(8), 2246-2252.

Fahmy, Hesham; Zjawiony, Jordan K.; Khalifa, Sherief; Fronczek, Frank R. A semi-synthetic analog of the cembranoid sarcophine. Acta Crystallographica, Section C: Crystal Structure Communications (2003), C59(2), o85-o87.

Kasanah, Noer; Rao, Karumanchi V.; Yousaf, Muhammad; Wedge, David E.; Hamann, Mark T. The biocatalytic conversion of 8-hydroxymanzamine A to manzamine A. Tetrahedron Letters (2003), 44(6), 1291-1293.

Kinghorn, A. D.; Su, B.-N.; Lee, D.; Gu, J.-Q.; Pezzuto, J. M. Cancer chemopreventive agents discovered by activity-guided fractionation: an update. Current Organic Chemistry (2003), 7(3), 213-226.

Katsuyama, Isamu; Fahmy, Hesham; Zjawiony, Jordan K.; Khalifa, Sherief I.; Kilada, Raouf W.; Konoshima, Takao; Takasaki, Midori; Tokuda, Harakuni. Semisynthesis of New Sarcophine Derivatives with Chemopreventive Activity. Journal of Natural Products (2002), 65(12), 1809-1814.

Yousaf, Muhammad; El Sayed, Khalid A.; Rao, Karumanchi V.; Lim, Chi Won; Hu, Jin-Feng; Kelly, Michelle; Franzblau, Scott G.; Zhang, Fangqiu; Peraud, Olivier; Hill, Russell T.; Hamann, Mark T. 12,34-Oxamanzamines, novel biocatalytic and natural products from manzamine producing Indo-Pacific sponges. Tetrahedron (2002), 58(37), 7397-7402.

El Sayed, Khalid A.; Yousaf, Muhammad; Hamann, Mark T.; Avery, Mitchell A.; Kelly, Michelle; Wipf, Peter. Microbial and Chemical Transformation Studies of the Bioactive Marine Sesquiterpenes (S)-(+)-Curcuphenol and -Curcudiol Isolated from a Deep Reef Collection of the Jamaican Sponge Didiscus oxeata. Journal of Natural Products (2002), 65(11), 1547-1553.

El Sayed, Khalid A.; Orabi, Khaled Y.; Dunbar, D. Chuck; Hamann, Mark T.; Avery, Mitchell A.; Sabnis, Yogesh A.; Mossa, Jaber S.; El-Feraly, Farouk S. Transformation of lactone to lactam in sarcophine and antimalarial activity of the resulting N-substituted azasarcophines. Tetrahedron (2002), 58(19), 3699-3708.

Su, Bao-Ning; Misico, Rosana; Park, Eun Jung; Santarsiero, Bernard D.; Mesecar, Andrew D.; Fong, Harry H. S.; Pezzuto, John M.; Kinghorn, A. Douglas. Isolation and characterization of bioactive principles of the leaves and stems of Physalis philadelphica. Tetrahedron (2002), 58(17), 3453-3466.

Hanson, James R. Diterpenoids (1998). Natural Product Reports (2000), 17(2), 165-174.

El Sayed, Khalid A.; Mayer, Alejandro M. S.; Kelly, Michelle; Hamann, Mark T. The Biocatalytic Transformation of Furan to Amide in the Bioactive Marine Natural Product Palinurin. Journal of Organic Chemistry (1999), 64(25), 9258-9260.

El Sayed, Khalid A.; Dunbar, D. Chuck; Bartyzel, Piotr; Zjawiony, Jordan K.; Day, William; Hamann, Mark T. Marine natural products as leads to develop new drugs and insecticides. Biologically Active Natural Products (2000), 233-252.

Gao, Hongfeng; Kelly, Michelle; Hamann, Mark T. Bromotyrosine-derived metabolites from the sponge Aiolochroia crassa. Tetrahedron (1999), 55(32), 9717-9726

600 16th St, San Francisco, California, 94143-2240 | phone (415)476-2521 | fax (415) 476-1902
University of California, San Francisco || About UCSF || Search UCSF || Macromolecular Structure Group || UCSF Biochemistry