NOVEL MICROBIAL METABOLITES OF THE PHOSLACTOMYCINS FAMILY INDUCE PRODUCTION OF COLONY-STIMULATING FACTORS BY BONE MARROW STROMAL CELLS II. ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION
Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641:...
Saved in:
| Published in | Journal of antibiotics Vol. 46; no. 10; pp. 1512 - 1519 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
1993
Japan Antibiotics Research Association |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C32H52O10NP, 669: C34H56O10NP and 669: C34H56O10NP, respectively. The structure elucidation revealed that they belong to the phoslactomycin group antibiotics, and their structures contain an α, β-unsaturated δ-lactone, an amino group, a phosphate ester and a cyclohexane ring moiety. The structures differ only at the substituent bound to the cyclohexane ring. |
|---|---|
| AbstractList | Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C32H52O10NP, 669: C34H56O10NP and 669: C34H56O10NP, respectively. The structure elucidation revealed that they belong to the phoslactomycin group antibiotics, and their structures contain an alpha,beta-unsaturated delta-lactone, an amino group, a phosphate ester and a cyclohexane ring moiety. The structures differ only at the substituent bound to the cyclohexane ring. Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C32H52O10NP, 669: C34H56O10NP and 669: C34H56O10NP, respectively. The structure elucidation revealed that they belong to the phoslactomycin group antibiotics, and their structures contain an α, β-unsaturated δ-lactone, an amino group, a phosphate ester and a cyclohexane ring moiety. The structures differ only at the substituent bound to the cyclohexane ring. Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C sub(32)H sub(52)O sub(10)NP, 669: C sub(34)H sub(56)O sub(10)NP and 669: C sub(34)H sub(56)O sub(10)NP, respectively. The structure elucidation revealed that they belong to the phoslactomycin group antibiotics, and their structures contain an alpha , beta -unsaturated delta -lactone, an amino group, a phosphate ester and a cyclohexane ring moiety. The structures differ only at the substituent bound to the cyclohexane ring. |
| Author | KANEKO, ISAO NAKAMURA, TAKEMICHI SHIRAISHI, AKIO KINOSHITA, TAKESHI KOHAMA, TAKAFUMI |
| Author_xml | – sequence: 1 fullname: KOHAMA, TAKAFUMI organization: Bioscience Research Laboratories, Sankyo Co., Ltd – sequence: 2 fullname: NAKAMURA, TAKEMICHI organization: Analytical and Metabolic Research Laboratories, Sankyo Co., Ltd – sequence: 3 fullname: KINOSHITA, TAKESHI organization: Analytical and Metabolic Research Laboratories, Sankyo Co., Ltd – sequence: 4 fullname: KANEKO, ISAO organization: Bioscience Research Laboratories, Sankyo Co., Ltd – sequence: 5 fullname: SHIRAISHI, AKIO organization: Bioscience Research Laboratories, Sankyo Co., Ltd |
| BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3830498$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/7503976$$D View this record in MEDLINE/PubMed |
| BookMark | eNqFkcGOmzAURa1qqmlm2i-oKrGouiO1MdhmSSiZIBlcAWmVFXKMaRkRmOJk0R-Y7x6nQdHsuvGzdM9990n3DtwM46AB-IjgkiLif5XDsdt347FTZumTJQqQ9wYsEGPIRT4Jb8ACQg-5jHnwHbgz5hFCTDFlt-CWBhCHlCzAcy5-JNzJ0rgQqzSyv6SKVoKnVVI6Yu1Um8T5vhElj-JKZLs4zUtnHWUp3zlp_m0bW7UQdlapyM98LLjId25ZpdmWR1WaP1jcWovSWe2clcgTJ4uKQvx0yqoQmQ2ME87L9-BtK3ujP8zzHmzXSRVvXC4e0jjirsIh8twWQ40JlaxRCGJGlSYKU6o9FmBPN1R5jQr2DQkR0QFRkrZQSUVwGDSN9miI78GXy96nafxz0uZYHzqjdN_LQY8nU1MCaUCh918QkdD3KMMWxBdQTaMxk27rp6k7yOlvjWB9rql-VVPtk_pck3V9mtef9gfdXD1zL1b_POvSKNm3kxxUZ64YZhj6IbNYfsEezVH-0lddTjat16-jUUjYv3g4v-c7rqD6LadaD_gFYUuxMg |
| CODEN | JANTAJ |
| CitedBy_id | crossref_primary_10_1021_ol8004672 crossref_primary_10_1021_ol101340n crossref_primary_10_1002_1521_3757_20020517_114_10_1819__AID_ANGE1819_3_0_CO_2_T crossref_primary_10_1002_ejoc_201700379 crossref_primary_10_1021_ol101659y crossref_primary_10_1021_acs_orglett_2c02791 crossref_primary_10_1002_ange_200600458 crossref_primary_10_1002_chem_201000104 crossref_primary_10_1016_j_tet_2008_05_012 crossref_primary_10_1016_j_tetlet_2007_03_152 crossref_primary_10_1021_jo1010203 crossref_primary_10_1021_np400232j crossref_primary_10_1002_ange_201200559 crossref_primary_10_1021_ol900757k crossref_primary_10_1271_bbb_60516 crossref_primary_10_1016_j_tet_2021_132573 crossref_primary_10_1021_ol8029142 crossref_primary_10_1021_ja2090993 crossref_primary_10_1002_ejoc_201701336 crossref_primary_10_1016_j_tetlet_2014_10_152 crossref_primary_10_1002_tcr_202000086 crossref_primary_10_1111_j_1348_0421_1994_tb01850_x crossref_primary_10_1089_107999002753675776 crossref_primary_10_1016_j_abb_2011_01_008 crossref_primary_10_1021_ja0340679 crossref_primary_10_1021_ja9097252 crossref_primary_10_1074_jbc_M305082200 crossref_primary_10_3390_md16020070 crossref_primary_10_4274_cjms_2020_2779 crossref_primary_10_3762_bjoc_18_143 crossref_primary_10_1002_anie_201200559 crossref_primary_10_1021_jo300184h crossref_primary_10_1007_s10295_006_0116_1 crossref_primary_10_1016_S0040_4020_03_01205_5 crossref_primary_10_1089_jir_1998_18_863 crossref_primary_10_1002_hlca_201500038 crossref_primary_10_1021_ol2011192 crossref_primary_10_1002_ijch_202100022 crossref_primary_10_1016_j_tet_2010_05_050 crossref_primary_10_1021_jacs_5b07438 crossref_primary_10_1016_j_tetlet_2007_06_058 crossref_primary_10_1021_jo8005599 crossref_primary_10_1039_D1NP00078K crossref_primary_10_1038_ja_2005_78 crossref_primary_10_1128_AEM_02590_08 crossref_primary_10_1002_1521_3773_20020517_41_10_1748__AID_ANIE1748_3_0_CO_2_X crossref_primary_10_1021_acs_chemrev_6b00488 crossref_primary_10_1021_jo962402o crossref_primary_10_1016_S0040_4020_02_00528_8 crossref_primary_10_1002_anie_200600458 crossref_primary_10_1021_ja108848d crossref_primary_10_1016_0040_4020_95_00759_2 crossref_primary_10_1016_j_chembiol_2012_10_018 |
| ContentType | Journal Article |
| Copyright | Japan Antibiotics Research Association 1994 INIST-CNRS |
| Copyright_xml | – notice: Japan Antibiotics Research Association – notice: 1994 INIST-CNRS |
| DBID | IQODW CGR CUY CVF ECM EIF NPM AAYXX CITATION 7QO 8FD FR3 P64 7X8 |
| DOI | 10.7164/antibiotics.46.1512 |
| DatabaseName | Pascal-Francis Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef Biotechnology Research Abstracts Technology Research Database Engineering Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef Engineering Research Database Biotechnology Research Abstracts Technology Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic |
| DatabaseTitleList | MEDLINE MEDLINE - Academic Engineering Research Database |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Pharmacy, Therapeutics, & Pharmacology |
| EISSN | 1881-1469 |
| EndPage | 1519 |
| ExternalDocumentID | 10_7164_antibiotics_46_1512 7503976 3830498 article_antibiotics1968_46_10_46_10_1512_article_char_en |
| Genre | Journal Article Comparative Study |
| GroupedDBID | --- -~X .55 .GJ 2WC 3O- 53G 5GY AAUGY ABAWZ ACGFS AENEX AHMBA ALMA_UNASSIGNED_HOLDINGS DU5 F5P JSF JSH KQ8 OK1 RJT RNT RZJ TKC UPT W2D X7M YQT ZGI ZXP -Q- 0R~ 29J 39C 3V. 4.4 406 41~ 70F 7X7 88E 88I 8FI 8FJ AABQG AADWK AANZL AATNV AAWBL AAYFA AAYJO AAZLF ABUWG ACBMV ACBRV ACBYP ACIGE ACKTT ACRQY ACTTH ACVWB ADBBV ADHDB ADMDM ADQMX ADYYL AEDAW AEFTE AEJRE AEVLU AEXYK AFKRA AFNRJ AFSHS AGAYW AGEZK AGGBP AGHAI AHSBF AILAN AJCLW AJDOV AJRNO ALFFA AMRJV AMYLF AXYYD AZQEC BAWUL BBNVY BENPR BHPHI BKKNO BPHCQ BVXVI CCPQU DIK DNIVK DPUIP DWQXO EBLON EBS EE. EIOEI EJD EMB EMOBN FDQFY FERAY FIZPM FSGXE FYUFA GNUQQ HCIFZ HZ~ IQODW IWAJR JSO JZLTJ M1P M2P M7P NAO NQJWS NYICJ O9- P6G PQQKQ PROAC PSQYO RNTTT SNX SNYQT SOHCF SRMVM SV3 SWTZT TAOOD TBHMF TDRGL TR2 TSG UKHRP X7J AACDK AASML ABAKF ABJNI ABZZP ACAOD ACZOJ AEFQL AEMSY AFBBN AGQEE AIGIU ALIPV CGR CUY CVF ECM EIF FIGPU HMCUK NPM AAYXX CITATION 7QO 8FD FR3 P64 7X8 |
| ID | FETCH-LOGICAL-c3912-f30e367a8dc10387ce6c377e28532ed7c2dc5bd6916e56ca7f0cac6395dde2793 |
| ISSN | 0021-8820 |
| IngestDate | Sat Aug 17 02:25:52 EDT 2024 Fri Aug 16 10:35:40 EDT 2024 Fri Aug 23 00:43:19 EDT 2024 Sat Sep 28 08:40:27 EDT 2024 Sun Oct 29 17:06:03 EDT 2023 Thu Aug 17 20:29:34 EDT 2023 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 10 |
| Keywords | Streptomycetaceae Secretion Cytokine Colony stimulating factor Inductor Actinomycetales Microbial origin Hematopoiesis Bacteria Isolation Actinomycetes Physicochemical properties Streptomyces platensis Structural analysis Growth factor |
| Language | English |
| License | CC BY 4.0 |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c3912-f30e367a8dc10387ce6c377e28532ed7c2dc5bd6916e56ca7f0cac6395dde2793 |
| Notes | ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 ObjectType-Article-1 ObjectType-Feature-2 |
| OpenAccessLink | https://www.jstage.jst.go.jp/article/antibiotics1968/46/10/46_10_1512/_article/-char/en |
| PMID | 7503976 |
| PQID | 16942783 |
| PQPubID | 23462 |
| PageCount | 8 |
| ParticipantIDs | proquest_miscellaneous_76075702 proquest_miscellaneous_16942783 crossref_primary_10_7164_antibiotics_46_1512 pubmed_primary_7503976 pascalfrancis_primary_3830498 jstage_primary_article_antibiotics1968_46_10_46_10_1512_article_char_en |
| PublicationCentury | 1900 |
| PublicationDate | 1993-00-00 |
| PublicationDateYYYYMMDD | 1993-01-01 |
| PublicationDate_xml | – year: 1993 text: 1993-00-00 |
| PublicationDecade | 1990 |
| PublicationPlace | Tokyo |
| PublicationPlace_xml | – name: Tokyo – name: Japan |
| PublicationTitle | Journal of antibiotics |
| PublicationTitleAlternate | J. Antibiot. |
| PublicationYear | 1993 |
| Publisher | JAPAN ANTIBIOTICS RESEARCH ASSOCIATION Japan Antibiotics Research Association |
| Publisher_xml | – name: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION – name: Japan Antibiotics Research Association |
| References | 11) KITAOKA, M.; H. NAGAKI, T. KINOSHITA, M. KURABAYASHI, T. KOYAMA & K. OGURA: Negative ion fast atom bombardment-tandem mass spectrometry for structural analysis of isoprenoid diphosphates. Anal. Biochem. 185: 182-186, 1990 2) KOHAMA, T.; R. ENOKITA, T. OKAZAKI, H. MIYAOKA, A. TORIKATA, M. INUKAI, I. KANEKO, T. KAGASAKI, Y. SAKAIDA, A. SATOH & A. SHIRAISHI: Novel microbial metabolites of phoslactomycins family induce production of colony-stimulating factors by bone marrow stromal cells. I. Taxonomy, fermentation and biological properties. J. Antibiotics 46: 1503-1511, 1993 10) NAKAMURA, T.; T. TAKAZAWA, Y. MARUYAMA-OHKI, H. NAGAKI & T. KINOSHITA: Location of double bonds in unsaturated fatty alcohols by microderivatization and liquid secondary ion tandem mass spectrometer. Anal. Chem. 65: 837-840, 1993 9) TOMIYA, T.; M. URAMOTO & K. ISONO: Isolation and structure of phosphazomycin C. J. Antibiotics 43: 118-121, 1990 3) FUSHIMI, S.; K. FURIHATA & H. SETO: Studies on new phosphate ester antifungal antibiotics phoslactomycins. II. Structure elucidation of phoslactomycins A to F. J. Antibiotics 42: 1026-1036, 1989 8) OZASA, T.; K. SUZUKI, M. SASAMATA, K. TANAKA, M. KOBORI, S. KADOTA, K. NAGAI, T. SAITO, S. WATANABE & M. IWANAMI: Novel antitumor antibiotic phospholine. I. Production, isolation and characterization. J Antibiotics 42: 1331-1338, 1989 6) RICHARD, W. B.; J. C. LUCILLE & H. SEBASTIAN: Antifungal substances and process for their production. U. S. Pat. Appl. 593,448, Mar. 26, 1984 12) JENSEN, N. J.; K. B. TOMER & M. L. GROSS: Gas-phase ion decompositions occurring remote to a charge site. J. Am. Chem. Soc. 107: 1863-1868, 1985 1) KOHAMA, T.; H. MIYAOKA, A. TORIKATA, M. INUKAI, I. KANEKO & A. SfflRAiSHi: Screening method for colonystimulating factor inducers using a human bone marrow stromal cell line, KM-102. J. Antibibiotics 46: 1494-1502, 1993 4) FUSHIMI, S.; S. NISHIKAWA, A. SHIMAZU & H. SETO: Studies on new phosphate ester antifungal antibiotics phoslactomycins. I. Taxonomy, fermentation, purification and biological activities. J. Antibiotics 42: 1019-1025, 1989 5) MAEDA, M.; T. KODAMA & S. ASAMI: 2-Pyranone derivatives Jpn. Kokai 304893 ('89), Dec. 8, 1989 7) OZASA, T.; K. TANAKA, M. SASAMATA,, H. KANIWA, M. SHIMIZU, H. MATSUMOTO & M. IWANAMI: Novel antitumor antibiotic phospholine. II. Structure determination. J. Antibiotics 42: 1339-1343, 1989 |
| References_xml | |
| SSID | ssj0037378 |
| Score | 1.6144695 |
| Snippet | Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191... |
| SourceID | proquest crossref pubmed pascalfrancis jstage |
| SourceType | Aggregation Database Index Database Publisher |
| StartPage | 1512 |
| SubjectTerms | Biological and medical sciences Blood. Blood coagulation. Reticuloendothelial system Bone Marrow - drug effects Chromatography, High Pressure Liquid Granulocyte Colony-Stimulating Factor - biosynthesis Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Medical sciences Organophosphorus Compounds - chemistry Organophosphorus Compounds - isolation & purification Organophosphorus Compounds - pharmacology Pharmacology. Drug treatments Pyrones Streptomyces - chemistry Streptomyces platensis |
| Subtitle | II. ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION |
| Title | NOVEL MICROBIAL METABOLITES OF THE PHOSLACTOMYCINS FAMILY INDUCE PRODUCTION OF COLONY-STIMULATING FACTORS BY BONE MARROW STROMAL CELLS |
| URI | https://www.jstage.jst.go.jp/article/antibiotics1968/46/10/46_10_1512/_article/-char/en https://www.ncbi.nlm.nih.gov/pubmed/7503976 https://search.proquest.com/docview/16942783 https://search.proquest.com/docview/76075702 |
| Volume | 46 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| ispartofPNX | The Journal of Antibiotics, 1993/10/25, Vol.46(10), pp.1512-1519 |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3db9owELfabg-bpmlf1djW7R6mvpSwkA87PKKpHQwB3QCpb1HiJBoTEDToJPZH7m_aXZw4gdJp3QMRwY4V8_PvfOc7nxl7n8Sm58hQGJY0Q8MRJi00WcIIJWrzlggCx6X9zv0B70ycz1fu1cHhw0rU0vU6bMhfe_eV_A-q-BviSrtk74CsbhR_wO-IL14RYbz-E8aD9Gc8O5tPs2RK2TaQNWJKu4pXhe9_-S1F0OU6nW8kRcPkCxpoiSOmFJ0VqfSxKrx8li42BpJ-nh3qRTGW-XE8qKSG6YKCXSlnI-0wSeeUWSSezVaNs24XP9hVFSmCoKn1ktSQRTqCJa35_6DkrZm3QmWtJd9FVITj6AFyU1NG8KfhNF1XAvN7ww75BrKow177YtLXi78DvO9PvhZlNMw6urDXHQxHne5Yl44qZe3BeW-YycxRe1iuhlDsYVW2W00D7QXl5YmVOPe8poFzQasq7_Mlz3xcmxXpTdpPRRPA29a-WYZMzCy9su58w-GN8uFqTu-duVZHQKLtRc34lUZ8h_vUyCG7Z6HUpPjU3hftErOFnasVeTdVCi1q5MOeN9lSs-5_R0uDUkg8WgYrBD1RZ7bcblRlytX4CXucYw1tNcSfsoN48YydXqq06ps6jMtdgqs6nMJlmXB985z9zngAmgdQ4QGkCSAPYIcHoHgAigdQ8oDq3-QB5DyAcAPEA1A8gJwHoHgAyAPQPKjDLgugZAEgC0CzALZY8IJNLs7HHztGfk6JIe1W0zIS24xtLgIvknTcgJAxl7YQsYWqsBVHQlqRdMOIoyUWu1wGIjFlINE0cFG3IKiP2dEC3_0lgyDBCT_iJveatiMdO7Ck47QkTqrk73d5jdULWP2lSkfj_2Uo1dgnBb2unMuqamWcg73sATO_0pO6Im3-RFlbYydbY0c3aHvkqPdq7F0xlnycoOhvDxZxer3ym7yVHedzew3B0W4RJr7tsRqEunEKskB76dXdev2aPVBhybRQ-oYdIZjxCZoO6_BtRqk_F2UoMw |
| link.rule.ids | 315,783,787,4031,27935,27936,27937 |
| linkProvider | Colorado Alliance of Research Libraries |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Novel+microbial+metabolites+of+the+phoslactomycins+family+induce+production+of+colony-stimulating+factors+by+bone+marrow+stromal+cells.+II.+Isolation%2C+physico-chemical+properties+and+structure+determination&rft.jtitle=Journal+of+antibiotics&rft.au=KOHAMA%2C+TAKAFUMI&rft.au=NAKAMURA%2C+TAKEMICHI&rft.au=KINOSHITA%2C+TAKESHI&rft.au=KANEKO%2C+ISAO&rft.date=1993&rft.issn=0021-8820&rft.eissn=1881-1469&rft.volume=46&rft.issue=10&rft.spage=1512&rft.epage=1519&rft_id=info:doi/10.7164%2Fantibiotics.46.1512&rft.externalDBID=n%2Fa&rft.externalDocID=10_7164_antibiotics_46_1512 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0021-8820&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0021-8820&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0021-8820&client=summon |