Isolation of new lucilactaene derivatives from P450 monooxygenase and aldehyde dehydrogenase knockout Fusarium sp. RK97-94 strains and their biological activities Islam A. Abdelhakim, Takayuki Motoyama, Toshihiko Nogawa, Fauze Bin Mahmud, Yushi Futamura, Shunji Takahashi, Hiroyuki Osada* J Antibiot.75 :361-374 (2022) doi: 10.1021/acschembio.2c00163
Identification and Characterization of Bifunctional Drimenol Synthases of Marine Bacterial Origin Nhu Ngoc Quynh Vo*, Yuhta Nomura, Kiyomi Kinugasa, Hiroshi Takagi, and Shunji Takahashi* ACS Chem. Biol.17, 5 :1226-1238 (2022) doi: 10.1021/acschembio.2c00163
Crystal structures of a 6-dimethylallyltryptophan synthase, IptA: Insights into substrate tolerance and enhancement of prenyltransferase activity Hironori Suemune, Doukan Nisnimura, Kenjirou Mizutani, Yusuke Sato, Tomoya Hino, Hiroshi Takagi, Yumi Shiozaki-Sato, Shunji Takahashi, Shingo Nagano* Biochem Biophys Res Commun.19; 593 : 144-150 (2022) doi: 10.1016/j.bbrc.2022.01.018.
Dihydrolucilactaene, a Potent Antimalarial Compound from Fusarium sp. RK97-94 Islam A. Abdelhakim, Fauze Bin Mahmud, Takayuki Motoyama, Yushi Futamura, Shunji Takahashi, and Hiroyuki Osada* J. Nat. Prod.85, 1 : 63–69 (2022) doi: org/10.1021/acs.jnatprod.1c00677
6,9-Dihydroxytetrangulol, a novel angucyclinone antibiotic accumulated in kiqO gene disruptant in the biosynthesis of kinanthraquinone. Sakai K., Takao R., Koshino H., Futamura Y., Osada H., and Takahashi S.* J. Antibiot.74 : 593-595 (2021) doi: 10.1038/s41429-021-00442-1
Molecular basis for two stereoselective Diels-Alderases that produce decalin skeletons. Fujiyama K., Kato N.*, Re S., Kinugasa K., Watanabe K., Takita R., Nogawa T., Hino T., Osada H., Sugita Y., Takahashi S.*, and Nagano S.* Angew Chem. Int. Ed.2021, 60: 22401-22410 doi: 10.1002/anie.202106186
The conserved Colletotrichum spp. effector candidate CEC3 induces nuclear expansion and cell death in plants. Tsushima A., Narusaka M., Gan P., Kumakura N., Hiroyama R., Kato N., Takahashi S., Takano Y., Narusaka Y., and Shirasu K. Front. Microbiol.12: 682155 (2021) doi: 10.3389/fmicb.2021.682155
Identification of the kinanthraquinone biosynthetic gene cluster by expression of an atypical response regulator. Risa Takao, Katsuyuki Sakai, Hiroyuki Koshino, Hiroyuki Osada, and Shunji Takahashi Biosci. Biotechnol. Biochem.85 (3): 714-721 (2021) doi: 10.1093/bbb/zbaa082
Heterologous expression of the biosynthetic gene cluster for verticilactam and identification of new analogues. Toshihiko Nogawa, Atsutaka Terai, Keita Amagai, Junko Hashimoto, Yushi Futamura, Akiko Okano, Manabu Fujie, Noriyuki Satoh, Haruo Ikeda, Kazuo Shin-ya, Hiroyuki Osada, Shunji Takahashi J. Nat. Prod.83: 3598–3605 (2020) doi: 10.1021/acs.jnatprod.0c00755
Developing Aspergillus niger as a cell factory for food enzyme production. Cen Li, Jingwen Zhou, Guocheng Du, Jian Chen, Shunji Takahashi, Song Liu Biotechnol. Adv.44: 107630 (2020) doi: 10.1016/j.biotechadv.2020.107630
β-carboline chemical signals induce reveromycin production through a LuxR family regulator in Streptomyces sp. SN-593.
Suresh Panthee, Naoko Kito, Teruo Hayashi, Takeshi Shimizu, Jun Ishikawa, Hiroshi Hamamoto, Hiroyuki Osada & Shunji Takahashi Scientific Reports, 10: 10230 (2020) doi:10.038/s41598-020-66974-y Press released on September 11,2020
An integrated screening system for the selection of exemplary substrates for natural and engineered cytochrome P450s
Naoki Kanoh, Ayano Kawamata-Asano, Kana Suzuki, Yusuke Takahashi, Takeshi Miyazawa, Takemichi Nakamura, Takashi Moriya, Hiroyuki Hirano, Hiroyuki Osada, Yoshiharu Iwabuchi, Shunji Takahashi Sci Rep, 9: 18023 (2019) doi: 10.1038/s41598-019-54473-8
Structure and biological activity of metarhizin C, a stereoisomer of BR-050 from Tolypocladium album RK17-F0007
Toshihiko Nogawa, Makoto Kawatani, Akiko Okano, Yushi Futamura, Harumi Aono, Takeshi Shimizu, Naoki Kato, Haruhisa Kikuchi, Hiroyuki Osada J Antibiot, 72: 996-1000 (2019) doi: 10.1038/s41429-019-0229-1
β-carboline biomediators induce reveromycin production in Streptomyces sp. SN-593
Suresh Panthee, Shunji Takahashi, Teruo Hayashi, Takeshi Shimizu, Hiroyuki Osada Sci Rep, 9: 5802 (2019) doi: 10.1038/s41598-019-42268-w
Biosynthesis of quinolidomicin, the largest known macrolide of terrestrial origin: identification and heterologous expression of a biosynthetic gene cluster over 200 kb.
Takuya Hashimoto, Junko Hashimoto, Ikuko Kozone, Keita Amagai, Teppei Kawahara, Shunji Takahashi, Haruo Ikeda, Kazuo Shin-ya Org Lett, 20: 7996-7999 (2018) doi: 10.1021/acs.orglett.8b03570
Catenulisporolides, glycosylated triene macrolides from the chemically underexploited actinomycete Catenulispora species.
Sangkeun Son, Young-Soo Hong, Yushi Futamura, Mina Jang, Jae Kyoung Lee, Kyung Taek Heo, Sung-Kyun Ko, Jung Sook Lee, Shunji Takahashi, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn Org Lett, 20: 7234-7238 (2018) doi: 10.1021/acs.orglett.8b03160
Control of the stereochemical course of [4+2] cycloaddition during trans-decalin formation by Fsa2-family enzymes.
Naoki Kato, Toshihiko Nogawa, Ryo Takita, Kiyomi Kinugasa, Misae Kanai, Masanobu Uchiyama, Hiroyuki Osada, Shunji Takahashi Angew Chem Int Ed Engl, 57: 9754-9758 (2018) doi: 10.1002/anie.201805050 Press released on July 5, 2018
Pentaminomycins A and B, hydroxyarginine-containing cyclic pentapeptides from Streptomyces sp. RK88-1441.
Jun-Pil Jang, Gwi Ja Hwang, Min Cheol Kwon, In-Ja Ryoo, Mina Jang, Shunji Takahashi, Sung-Kyun Ko, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn J Nat Prod, 81: 806-810 (2018) doi: 10.1021/acs.jnatprod.7b00882
Kinanthraquinone, a new anthraquinone carboxamide isolated from Streptomycesreveromyceticus SN-593-44.
Hiroshi Takagi, Toshihiko Nogawa, Yushi Futamura, Shunji Takahashi, Hiroyuki Osada J Antibiot, 71: 480–482 (2018) doi: 10.1038/s41429-017-0020-0
Biosynthesis and structure-activity relationship studies of okaramines that target insect glutamate-gated chloride channels.
Naoki Kato, Shogo Furutani, Junnosuke Otaka, Akira Noguchi, Kiyomi Kinugasa, Kenji Kai, Hideo Hayashi, Makoto Ihara, Shunji Takahashi, Kazuhiko Matsuda, Hiroyuki Osada ACS Chem Biol, 13: 561-566 (2018) doi: 10.1021/acschembio.7b00878 Press released on May 25, 2018
Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058.
Toshihiko Nogawa, Naoki Kato, Takeshi Shimizu, Akiko Okano, Yushi Futamura, Shunji Takahashi, Hiroyuki Osada J Antibiot, 71: 123–128 (2018) doi: 10.1038/ja.2017.103
Identification of a gene cluster for telomestatin biosynthesis and heterologous expression using a specific promoter in a clean host.
Keita Amagai, Haruo Ikeda, Junko Hashimoto, Ikuko Kozone, Miho Izumikawa, Fumitaka Kudo, Tadashi Eguchi, Takemichi Nakamura, Hiroyuki Osada, Shunji Takahashi, Kazuo Shin-ya Sci Rep, 7: 3382 (2017) doi: 10.1038/s41598-017-03308-5
Temperature during conidiation affects stress tolerance, pigmentation, and trypacidin accumulation in the conidia of the airborne pathogen Aspergillus fumigatus.
Daisuke Hagiwara, Kanae Sakai, Satoshi Suzuki, Myco Umemura, Toshihiko Nogawa, Naoki Kato, Hiroyuki Osada, Akira Watanabe, Susumu Kawamoto, Tohru Gonoi, Katsuhiko Kamei PLoS One12, e0177050 (2017) doi: 10.1371/journal.pone.0177050
Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum.
Jun-Pil Jang, Toshihiko Nogawa, Yushi Futamura, Takeshi Shimizu, Daisuke Hashizume, Shunji Takahashi, Jae-Hyuk Jang, Jong Seog Ahn, Hiroyuki Osada J Nat Prod, 80: 134-140 (2017) doi: 10.1021/acs.jnatprod.6b00758
Characterization of giant modular PKSs provides insight into genetic mechanism for structural diversification of aminopolyol polyketides.
Lihan Zhang, Takuya Hashimoto, Bin Qin, Junko Hashimoto, Ikuko Kozone, Teppei Kawahara, Masahiro Okada, Takayoshi Awakawa, Takuya Ito, Yoshinori Asakawa, Masashi Ueki, Shunji Takahashi, Hiroyuki Osada, Toshiyuki Wakimoto, Haruo Ikeda, Kazuo Shin-ya, Ikuro Abe Angew Chem Int Ed Engl, 56: 1740-1745 (2017) doi: 10.1002/anie.201611371
RK-144171, a new benadrostin derivative produced by Streptomyces sp. RK88-1441.
Jun-Pil Jang, Shunji Takahashi, Yushi Futamura, Toshihiko Nogawa, Jae-Hyuk Jang, Jong Seog Ahn, Hiroyuki Osada J Antibiot, 70: 102-104 (2017) doi: 10.1038/ja.2016.65
Opantimycin A, a new metabolite isolated from Streptomyces sp. RK88-1355.
Toshihiko Nogawa, Akiko Okano, Chung Liang Lim, Yushi Futamura, Takeshi Shimizu, Shunji Takahashi, Darah Ibrahim, Hiroyuki Osada J Antibiot, 70: 222-225 (2017) doi: 10.1038/ja.2016.113
A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units.
Lauren Ray, Timothy R. Valentic, Takeshi Miyazawa, David M. Withall, Lijiang Song, Jacob C. Milligan, Hiroyuki Osada, Shunji Takahashi, Shiou-Chuan Tsai, Gregory L. Challis Nat Commun, 7: 13609 (2016) doi: 10.1038/ncomms13609 Press released on January 17, 2017
Stachybotrysin, an osteoclast differentiation inhibitor from the marine-derived fungus Stachybotrys sp. KCB13F013
Jong Won Kim, Sung-Kyun Ko, Hye-Min Kim, Gun-Hee Kim, Sangkeun Son, Gil Soo Kim, Gwi Ja Hwang, Eun Soo Jeon, Kee-Sun Shin, In-Ja Ryoo, Young-Soo Hong, Hyuncheol Oh, Kyung Ho Lee, Nak-Kyun Soung, Daisuke Hashizume, Toshihiko Nogawa, Shunji Takahashi, Bo Yeon Kim, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn J Nat Prod, 79: 2703-2708 (2016) doi: 10.1021/acs.jnatprod.6b00641
Identification of a novel sesquiterpene biosynthetic machinery involved in astellolide biosynthesis.
Yasutomo Shinohara, Shunji Takahashi, Hiroyuki Osada, Yasuji Koyama Sci Rep, 6: 32865 (2016) doi: 10.1038/srep32865 Press released on September 26, 2016
New cyclic lipopeptides of the iturin class produced by saltern-derived Bacillus sp. KCB14S006.
Sangkeun Son, Sung-Kyun Ko, Mina Jang, Jong Won Kim, Gil Soo Kim, Jae Kyoung Lee, Eun Soo Jeon, Yushi Futamura, In-Ja Ryoo, Jung-Sook Lee, Hyuncheol Oh, Young-Soo Hong, Bo Yeon Kim, Shunji Takahashi, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn Mar Drugs, 14: 72 (2016) doi: 10.3390/md14040072
Unantimycin A, a new neoantimycin analog isolated from a microbial metabolite fraction library.
Chung Liang Lim, Toshihiko Nogawa, Akiko Okano, Yushi Futamura, Makoto Kawatani, Shunji Takahashi, Darah Ibrahim, Hiroyuki Osada J Antibiot, 69: 456-458 (2016) doi: 10.1038/ja.2015.124
Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field.
Sangkeun Son, Sung-Kyun Ko, Jong Won Kim, Jae Kyoung Lee, Mina Jang, In-Ja Ryoo, Gwi Ja Hwang, Min Cheol Kwon, Kee-Sun Shin, Yushi Futamura, Young-Soo Hong, Hyuncheol Oh, Bo Yeon Kim, Masashi Ueki, Shunji Takahashi, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn Phytochemistry, 122: 154-164 (2016) doi: 10.1016/j.phytochem.2015.12.008
Identification of middle chain fatty acyl-CoA ligase responsible for the biosynthesis of 2-alkylmalonyl-CoAs for polyketide extender unit.
Takeshi Miyazawa, Shunji Takahashi, Akihiro Kawata, Suresh Panthee, Teruo Hayashi, Takeshi Shimizu, Toshihiko Nogawa, Hiroyuki Osada J Biol Chem, 290: 26994-27011 (2015) doi: 10.1074/jbc.M115.677195 Press released on November 12, 2015
Haenamindole, an unusual diketopiperazine derivative from a marine-derived Penicillium sp. KCB12F005.
Jong Won Kim, Sung-Kyun Ko, Sangkeun Son, Kee-Sun Shin, In-Ja Ryoo, Young-Soo Hong, Hyuncheol, Oh, Bang Yeon Hwang, Hiroshi Hirota, Shunji Takahashi, Bo Yeon Kim, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn Bioorg Med Chem Lett, 25: 5398-5401 (2015) doi: 10.1016/j.bmcl.2015.09.026
RK-270A−C, new oxindole derivatives isolated from a microbial metabolites fraction library of Streptomyces sp. RK85-270.
Jun-Pil Jang, Toshihiko Nogawa, Masakazu Uramoto, Akiko Okano, Yushi Futamura, Takeshi Shimizu, Shunji Takahashi, Jae-Hyuk Jang, Jong Seog Ahn, Hiroyuki Osada J Antibiot, 68: 293-295 (2015) doi: 10.1038/ja.2014.141
A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis
Naoki Kato, Toshihiko Nogawa, Hiroshi Hirota, Jae-Hyuk Jang, Shunji Takahashi, Jong Seog Ahn, Hiroyuki Osada Biochem Biophys Res Commun, 460: 210-215 (2015) doi: 10.1016/j.bbrc.2015.03.011 Press released on April 28, 2015
Structure-function analyses of cytochrome P450revI involved in reveromycin A biosynthesis and evaluation of the biological activity of its substrate, reveromycin T.
Shunji Takahashi, Shingo Nagano, Toshihiko Nogawa, Naoki Kanoh, Masakazu Uramoto, Makoto Kawatani, Takeshi Shimizu, Takeshi Miyazawa, Yoshitsugu Shiro, Hiroyuki Osada J Biol Chem, 289: 32446-32458 (2014), doi: 10.1074/jbc.M114.598391
RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening.
Chung Liang Lim, Toshihiko Nogawa, Masakazu Uramoto, Akiko Okano, Yayoi Hongo, Takemichi Nakamura, Hiroyuki Koshino, Shunji Takahashi, Darah Ibrahim, Hiroyuki Osada J Antibiot, 67: 323-329 (2014) doi: 10.1038/ja.2013.144
Pyrrolizilactone, a new pyrrolizidinone metabolite produced by a fungus
Toshihiko Nogawa, Makoto Kawatani, Masakazu Uramoto, Akiko Okano, Harumi Aono, Yushi Futamura, Hiroyuki Koshino, Shunji Takahashi, Hiroyuki Osada J Antibiot, 66: 621-623 (2013) doi: 10.1038/ja.2013.55
A point mutation in ftmD blocks the fumitremorgin biosynthetic pathway in Aspergillusfumigatus strain Af293.
Naoki Kato, Hirokazu Suzuki, Hideo Okumura, Shunji Takahashi, Hiroyuki Osada
Biosci Biotechnol Biochem, 77: 1061-1067 (2013) doi: 10.1271/bbb.130026
Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library.
Toshihiko Nogawa, Shunji Takahashi, Akiko Okano, Makoto Kawatani, Masakazu Uramoto, Tamio Saito, Hiroyuki Osada J Antibiot, 65: 123-128 (2012) doi: 10.1038/ja.2011.121
Detection of cytochrome P450 substrates by using a small molecule droplet array on an NADH-immobilized solid surface
Hiroshi Takayama, Shunji Takahashi, Takashi Moriya, Hiroyuki Osada, Yoshiharu Iwabuchi, Naoki Kanoh Chembiochem, 12: 2748-2752 (2011) doi: 10.1002/cbic.201100541
Improvement of transformation efficiency by strategic circumvention of restriction barriers in Streptomyces griseus.
Hirokazu Suzuki, Shunji Takahashi, Hiroyuki Osada, Ken-ichi Yoshida J Microbiol Biotechnol, 21: 675-678 (2011)
Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation.
Shunji Takahashi, Atsushi Toyoda, Yasuyo Sekiyama, Hiroshi Takagi, Toshihiko Nogawa, Masakazu Uramoto, Ryuichiro Suzuki, Hiroyuki Koshino, Takuto Kumano, Suresh Panthee, Tohru Dairi, Jun Ishikawa, Haruo Ikeda, Yoshiyuki Sakaki, Hiroyuki Osada Nat Chem Biol, 7: 461-468 (2011) doi: 10.1038/nchembio.583 Press released on June 6, 2011
Furaquinocins I and J: novel polyketide isoprenoid hybrid compounds from Streptomycesreveromyceticus SN-593.
Suresh Panthee, Shunji Takahashi, Hiroshi Takagi, Toshihiko Nogawa, Eri Oowada, Masakazu Uramoto, Hiroyuki Osada J Antibiot, 64: 509-513 (2011) doi: 10.1038/ja.2011.41
Genetic safeguard against mycotoxin cyclopiazonic acid production in Aspergillus oryzae.
Naoki Kato, Masafumi Tokuoka, Yasutomo Shinohara, Makoto Kawatani, Masakazu Uramoto, Yasuyo Seshime, Isao Fujii, Katsuhiko Kitamoto, Tadashi Takahashi, Shunji Takahashi, Yasuji Koyama, Hiroyuki Osada Chembiochem, 12: 1376-1382 (2011) doi: 10.1002/cbic.201000672
Gene disruption and biochemical characterization of verruculogen synthase of Aspergillus fumigatus.
Naoki Kato, Hirokazu Suzuki, Hiroshi Takagi, Masakazu Uramoto, Shunji Takahashi, Hiroyuki Osada Chembiochem, 12: 711-714, (2011) doi: 10.1002/cbic.201000562
Verticilactam, a new macrolactam isolated from a microbial metabolite fraction library.
Toshihiko Nogawa, Akiko Okano, Shunji Takahashi, Masakazu Uramoto, Hideaki Konno, Tamio Saito, Hiroyuki Osada Org Lett, 12: 4564-4567 (2010) doi: 10.1021/ol1018618
Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-593
Shunji Takahashi, Hiroshi Takagi, Atsushi Toyoda, Masakazu Uramoto, Toshihiko Nogawa, Masashi Ueki, Yoshiyuki Sakaki, Hiroyuki Osada J Bacteriol, 192: 2839-2851 (2010) doi: 10.1128/JB.01557-09
Molecular cloning and characterization of a broad substrate terpenoid oxidoreductase from Artemisia annua.
Anna-Margareta Rydén, Carolien Ruyter-Spira, Ralph Litjens, Shunji Takahashi, Wim Quax, Hiroyuki Osada, Harro Bouwmeester, Oliver Kayser Plant Cell Physiol, 51: 1219-1228 (2010) doi: 10.1093/pcp/pcq073
Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis
Makoto Hashimoto, Yusuke Higuchi, Shunji Takahashi, Hiroyuki Osada, Toshiyuki Sakaki, Tomonobu Toyomasu, Takeshi Sassa, Nobuo Kato, TohruDairi Bioorg Med Chem Lett, 19: 5640-5643 (2009) doi: 10.1016/j.bmcl.2009.08.026
Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus.
Naoki Kato, Hirokazu Suzuki, Hiroshi Takagi, Yukihiro Asami, Hideaki Kakeya, Masakazu Uramoto, Takeo Usui, Shunji Takahashi, Yoshikazu Sugimoto, Hiroyuki Osada Chembiochem, 10: 920-928 (2009) doi: 10.1002/cbic.200800787
Reviews
Meeting report of the 8th Korea-Japan Chemical Biology Symposium -Chemical Biology Notes from a small island-.
Tilman Schneider-Poetsch, Shunji Takahashi, Jae-Hyuk Jang, Jong Seog Ahn, Hiroyuki Osada J Antibiot, 69: 885-888 (2016) doi: 10.1038/ja.2016.58
Construction of a microbial natural product library for chemical biology studies.
Naoki Kato, Shunji Takahashi, Toshihiko Nogawa, Tamio Saito, Hiroyuki Osada Curr Opin Chem Biol,16: 101-108 (2012) doi: 10.1016/j.cbpa.2012.02.016
Mevalonate Pathway in Bacteria and Archaea
Tomohisa Kuzuyama, Hisashi Hemmi, Shunji Takahashi
In Comprehensive Natural Products II (Eds.; Lewis Mander & Hung-Wei Lui, Elsevier), 493-516 (2010)
