Three New Monoterpenoids from the Fruit of Genipa americana

Three new monoterpenoids, called genipacetal, genipamide, and genipaol, were isolated from the fruit of Genipa americana L. (Rubiaceae), along with the four known iridoids genipin, gardendiol, deacetyl asperulosidic acid methyl ester, and shanzhiside. Their chemical structures were determined on the...

Full description

Saved in:

Bibliographic Details
Published in:	Chemical & Pharmaceutical Bulletin Vol. 55; no. 4; pp. 632 - 634
Main Authors:	Ono, Masateru, Ishimatsu, Naoki, Masuoka, Chikako, Yoshimitsu, Hitoshi, Tsuchihashi, Ryota, Okawa, Masafumi, Kinjo, Junei, Ikeda, Tsuyoshi, Nohara, Toshihiro
Format:	Journal Article
Language:	English
Published:	Japan The Pharmaceutical Society of Japan 01-04-2007 Pharmaceutical Society of Japan Japan Science and Technology Agency
Subjects:	alkaloid Genipa americana iridoid Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure monoterpenoid Rubiaceae Rubiaceae - chemistry Spectrometry, Mass, Fast Atom Bombardment Terpenes - isolation & purification
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Abstract	Three new monoterpenoids, called genipacetal, genipamide, and genipaol, were isolated from the fruit of Genipa americana L. (Rubiaceae), along with the four known iridoids genipin, gardendiol, deacetyl asperulosidic acid methyl ester, and shanzhiside. Their chemical structures were determined on the basis of spectroscopic data.
AbstractList	Three new monoterpenoids, called genipacetal, genipamide, and genipaol, were isolated from the fruit of Genipa americana L. (Rubiaceae), along with the four known iridoids genipin, gardendiol, deacetyl asperulosidic acid methyl ester, and shanzhiside. Their chemical structures were determined on the basis of spectroscopic data.
Author	Okawa, Masafumi Ono, Masateru Masuoka, Chikako Kinjo, Junei Yoshimitsu, Hitoshi Nohara, Toshihiro Ishimatsu, Naoki Tsuchihashi, Ryota Ikeda, Tsuyoshi
Author_xml	– sequence: 1 fullname: Ono, Masateru organization: Kyushu Tokai University School of Agriculture – sequence: 2 fullname: Ishimatsu, Naoki organization: Kyushu Tokai University School of Agriculture – sequence: 3 fullname: Masuoka, Chikako organization: Kyushu Tokai University School of Agriculture – sequence: 4 fullname: Yoshimitsu, Hitoshi organization: Faculty of Pharmaceutical Sciences, Sojo University – sequence: 5 fullname: Tsuchihashi, Ryota organization: Faculty of Pharmaceutical Sciences, Fukuoka University – sequence: 6 fullname: Okawa, Masafumi organization: Faculty of Pharmaceutical Sciences, Fukuoka University – sequence: 7 fullname: Kinjo, Junei organization: Faculty of Pharmaceutical Sciences, Fukuoka University – sequence: 8 fullname: Ikeda, Tsuyoshi organization: Faculty of Medical and Pharmaceutical Sciences, Kumamoto University – sequence: 9 fullname: Nohara, Toshihiro organization: Faculty of Medical and Pharmaceutical Sciences, Kumamoto University
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/17409560$$D View this record in MEDLINE/PubMed
BookMark	eNqFkE1v1DAQhi1URLeFCz8ARULigJRl_J2IQ4WqbkEqcClny3EmbFaJHexEiH9fr7K0EhcOHh_m8Tvj54Kc-eCRkNcUtpSJ6oObmq2UW8XZM7KhXOhSMsbPyAYA6pJxxc_JRUoHACZB8xfknGoBtVSwIR_v9xGx-Ia_i6_BhxnjhD70bSq6GMZi3mOxi0s_F6ErbtH3ky3siLF31tuX5Hlnh4SvTvcl-bG7ub_-XN59v_1y_emudKqmc9nStpKguGiEVsx1yvKqQuwsOsGorpyoO9ZY4LLhbaudoECFZYJ2tLOAml-Sd2vuFMOvBdNsxj45HAbrMSzJ6PxUSFb_F6S11kxRmcG3_4CHsESfP2GoUJD3y6Yy9X6lXAwpRezMFPvRxj-GgjmaN9m8kdJk8xl-c4pcmhHbJ_SkOgO7FcjdrG8Ifug9Pg12Sbs9jr1hANoASAnCAMsnxx-L0EzXTOWgqzXokGb7Ex8n2Tj3bsC_S4m1HB8_dvY2GvT8AdsRqvI
CitedBy_id	crossref_primary_10_1007_s10600_022_03663_4 crossref_primary_10_1016_j_fitote_2013_08_025 crossref_primary_10_1007_s10600_013_0477_4 crossref_primary_10_1016_j_jep_2011_10_024 crossref_primary_10_1016_j_bjp_2017_03_006 crossref_primary_10_1002_chin_200741161 crossref_primary_10_1016_j_jpba_2017_06_021 crossref_primary_10_1016_S1875_5364_19_30035_4 crossref_primary_10_1007_s11947_018_2185_3 crossref_primary_10_1515_znc_2019_0113 crossref_primary_10_1016_j_jpba_2015_09_007 crossref_primary_10_3390_ijms161023760 crossref_primary_10_1016_j_msec_2016_02_029 crossref_primary_10_1039_D3SU00303E crossref_primary_10_3390_nu10091155 crossref_primary_10_1590_S1516_05722013000500010 crossref_primary_10_1016_j_foodres_2012_07_010 crossref_primary_10_1016_j_bjp_2017_05_002 crossref_primary_10_1021_jf503378k crossref_primary_10_5059_yukigoseikyokaishi_75_349 crossref_primary_10_3390_molecules23102521 crossref_primary_10_1002_jcb_23077 crossref_primary_10_1177_1934578X0800300202 crossref_primary_10_1016_j_bse_2014_06_011 crossref_primary_10_1089_jmf_2009_0279 crossref_primary_10_3390_molecules25010180 crossref_primary_10_1002_cbdv_201200030 crossref_primary_10_1016_j_jpba_2008_05_013 crossref_primary_10_1021_acs_orglett_6b03057 crossref_primary_10_1007_s11101_014_9383_z
Cites_doi	10.1248/cpb.48.746 10.1021/ja00467a001 10.1248/cpb.53.1342 10.1016/S0031-9422(00)80266-6 10.1248/yakushi1947.94.5_577 10.1063/1.1729860 10.1016/S0040-4039(01)96747-4 10.1021/np50078a032 10.1016/S0031-9422(00)89532-1 10.1016/S0040-4039(00)91618-6 10.1248/cpb.46.1295
ContentType	Journal Article
Copyright	2007 The Pharmaceutical Society of Japan Copyright Japan Science and Technology Agency 2007
Copyright_xml	– notice: 2007 The Pharmaceutical Society of Japan – notice: Copyright Japan Science and Technology Agency 2007
CorporateAuthor	aKyushu Tokai University School of Agriculture dFaculty of Medical and Pharmaceutical Sciences Fukuoka University bFaculty of Pharmaceutical Sciences Sojo University cFaculty of Pharmaceutical Sciences Kumamoto University
CorporateAuthor_xml	– name: aKyushu Tokai University School of Agriculture – name: bFaculty of Pharmaceutical Sciences – name: cFaculty of Pharmaceutical Sciences – name: Kumamoto University – name: dFaculty of Medical and Pharmaceutical Sciences – name: Sojo University – name: Fukuoka University
DBID	CGR CUY CVF ECM EIF NPM AAYXX CITATION 7TK 7TM 7U9 H94 7QO 8FD FR3 P64 7X8
DOI	10.1248/cpb.55.632
DatabaseName	Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef Neurosciences Abstracts Nucleic Acids Abstracts Virology and AIDS Abstracts AIDS and Cancer Research Abstracts 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 AIDS and Cancer Research Abstracts Virology and AIDS Abstracts Neurosciences Abstracts Nucleic Acids Abstracts Engineering Research Database Biotechnology Research Abstracts Technology Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic
DatabaseTitleList	MEDLINE - Academic MEDLINE Engineering Research Database AIDS and Cancer Research Abstracts
Database_xml	– sequence: 1 dbid: ECM name: MEDLINE url: https://search.ebscohost.com/login.aspx?direct=true&db=cmedm&site=ehost-live sourceTypes: Index Database
DeliveryMethod	fulltext_linktorsrc
Discipline	Pharmacy, Therapeutics, & Pharmacology
EISSN	1347-5223
EndPage	634
ExternalDocumentID	3133612591 10_1248_cpb_55_632 17409560 cs7chemi_2007_005504_024_0632_0634727926 article_cpb_55_4_55_4_632_article_char_en
Genre	Journal Article
GroupedDBID	--- .55 .GJ 29B 2WC 3O- 53G 5GY 6J9 AABQG AAUGY ABTAH ACGFO ACIWK ACPRK ADBBV AENEX AFRAH AI. ALMA_UNASSIGNED_HOLDINGS BAWUL BKOMP CS3 DIK DU5 E3Z EBS EJD F5P GX1 HH5 JMI JSF JSH KQ8 L7B MOJWN OK1 P2P RJT RZJ TKC TR2 VH1 X7J X7M XSB ZE2 ZGI ZY4 CGR CUY CVF ECM EIF NPM AAYXX CITATION 7TK 7TM 7U9 H94 7QO 8FD FR3 P64 7X8
ID	FETCH-LOGICAL-c691t-d1d850634b4762cf6a388eefaec42178c49f2ba035b3dd7c41014a241f1fa0e73
ISSN	0009-2363
IngestDate	Fri Aug 16 14:30:22 EDT 2024 Fri Aug 16 23:29:53 EDT 2024 Thu Oct 10 17:03:18 EDT 2024 Fri Aug 23 01:40:42 EDT 2024 Sat Sep 28 08:39:17 EDT 2024 Fri Nov 08 06:52:40 EST 2024 Thu Aug 17 20:29:00 EDT 2023
IsDoiOpenAccess	true
IsOpenAccess	true
IsPeerReviewed	true
IsScholarly	true
Issue	4
Language	English
LinkModel	OpenURL
MergedId	FETCHMERGED-LOGICAL-c691t-d1d850634b4762cf6a388eefaec42178c49f2ba035b3dd7c41014a241f1fa0e73
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/cpb/55/4/55_4_632/_article/-char/en
PMID	17409560
PQID	1460388250
PQPubID	1996362
PageCount	3
ParticipantIDs	proquest_miscellaneous_70354529 proquest_miscellaneous_19772615 proquest_journals_1460388250 crossref_primary_10_1248_cpb_55_632 pubmed_primary_17409560 medicalonline_journals_cs7chemi_2007_005504_024_0632_0634727926 jstage_primary_article_cpb_55_4_55_4_632_article_char_en
PublicationCentury	2000
PublicationDate	2007-04-01
PublicationDateYYYYMMDD	2007-04-01
PublicationDate_xml	– month: 04 year: 2007 text: 2007-04-01 day: 01
PublicationDecade	2000
PublicationPlace	Japan
PublicationPlace_xml	– name: Japan – name: Tokyo
PublicationTitle	Chemical & Pharmaceutical Bulletin
PublicationTitleAlternate	Chem. Pharm. Bull.
PublicationYear	2007
Publisher	The Pharmaceutical Society of Japan Pharmaceutical Society of Japan Japan Science and Technology Agency
Publisher_xml	– name: The Pharmaceutical Society of Japan – name: Pharmaceutical Society of Japan – name: Japan Science and Technology Agency
References	6) Goto H., Osawa E., Tetrahedron Lett., 33, 1343—1346 (1992). 8) Machida K., Onodera R., Furuta K., Kikuchi M., Chem. Pharm. Bull., 46, 1295—1300 (1998). 9) Machida K., Kazumi O., Ishii M., Kakuda R., Yaoita Y., Kikuchi M., Chem. Pharm. Bull., 48, 746—748 (2000). 1) Ueda S., Iwahashi Y., Tokuda Y., J. Nat. Prod., 54, 1677—1680 (1991). 2) Ono M., Ueno M., Masuoka C., Ikeda T., Nohara T., Chem. Pharm. Bull., 53, 1342—1344 (2005). 7) Karplus M., J. Chem. Phys., 30, 11—15 (1959). 11) Ono M., Nishida Y., Masuoka C., Li J.-C., Okawa M., Ikeda T., Nohara T., J. Nat. Prod., 67, 2073—2075 (2005). 3) Jensen S. R., Phytochemistry, 22, 1761—1765 (1983). 10) Horeau A., Nouaille A., Tetrahedron Lett., 22, 1939—1942 (1971). 5) Inouye H., Takeda Y., Saito S., Nishimura H., Sakuragi R., Yakugaku Zasshi, 94, 577—586 (1974). 12) Allinger N. L., J. Am. Chem. Soc., 99, 8127—8134 (1977). 4) Zhao W. M., Xu J. P., Qin G. W., Phytochemistry, 37, 1079—1082 (1994). 1 12 2 3 4 Horeau A., Nouaille A. (10) 1971; 22 6 MACHIDA K (8) 1998; 46 7 MACHIDA K (9) 2000; 48 Ono M., Nishida Y., Masuoka C., Li J.-C., Okawa M., Ikeda T., Nohara T. (11) 2005; 67 Inouye H., Takeda Y., Saito S., Nishimura H., Sakuragi R. (5) 1974; 94
References_xml	– volume: 48 start-page: 746 issn: 0009-2363 issue: 5 year: 2000 ident: 9 publication-title: Chem. Pharm. Bull. doi: 10.1248/cpb.48.746 contributor: fullname: MACHIDA K – ident: 12 doi: 10.1021/ja00467a001 – ident: 2 doi: 10.1248/cpb.53.1342 – volume: 67 start-page: 2073 issn: 0163-3864 year: 2005 ident: 11 publication-title: J. Nat. Prod. contributor: fullname: Ono M., Nishida Y., Masuoka C., Li J.-C., Okawa M., Ikeda T., Nohara T. – ident: 3 doi: 10.1016/S0031-9422(00)80266-6 – volume: 94 start-page: 577 issn: 0031-6903 year: 1974 ident: 5 publication-title: Yakugaku Zasshi doi: 10.1248/yakushi1947.94.5_577 contributor: fullname: Inouye H., Takeda Y., Saito S., Nishimura H., Sakuragi R. – ident: 7 doi: 10.1063/1.1729860 – volume: 22 start-page: 1939 issn: 0040-4039 year: 1971 ident: 10 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)96747-4 contributor: fullname: Horeau A., Nouaille A. – ident: 1 doi: 10.1021/np50078a032 – ident: 4 doi: 10.1016/S0031-9422(00)89532-1 – ident: 6 doi: 10.1016/S0040-4039(00)91618-6 – volume: 46 start-page: 1295 issn: 0009-2363 issue: 8 year: 1998 ident: 8 publication-title: Chem. Pharm. Bull. doi: 10.1248/cpb.46.1295 contributor: fullname: MACHIDA K
SSID	ssj0025073 ssib023156984 ssib014648066 ssib002822113 ssib017383858
Score	2.0060148
Snippet	Three new monoterpenoids, called genipacetal, genipamide, and genipaol, were isolated from the fruit of Genipa americana L. (Rubiaceae), along with the four...
SourceID	proquest crossref pubmed medicalonline jstage
SourceType	Aggregation Database Index Database Publisher
StartPage	632
SubjectTerms	alkaloid Genipa americana iridoid Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure monoterpenoid Rubiaceae Rubiaceae - chemistry Spectrometry, Mass, Fast Atom Bombardment Terpenes - isolation & purification
Title	Three New Monoterpenoids from the Fruit of Genipa americana
URI	https://www.jstage.jst.go.jp/article/cpb/55/4/55_4_632/_article/-char/en http://mol.medicalonline.jp/en/journal/download?GoodsID=cs7chemi/2007/005504/024&name=0632-0634e https://www.ncbi.nlm.nih.gov/pubmed/17409560 https://www.proquest.com/docview/1460388250 https://search.proquest.com/docview/19772615 https://search.proquest.com/docview/70354529
Volume	55
hasFullText	1
inHoldings	1
isFullTextHit
isPrint
ispartofPNX	Chemical and Pharmaceutical Bulletin, 2007, Vol.55(4), pp.632-634
link	http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV3Nb9MwFLfK4ICEEN8EBlgC7dJlpIkTO-KAJmgpYoxJdNJukeM4WlYtqZrlsP-e9-I0boSG4MAlahMnUd77-X342T8T8i71BJdMT1zua99lsVBuHGa-m-aZUkyESni4Gnn-kx-fic9TNh2NNjtU2XP_VdNwDnSNK2f_Qdv9Q-EE_AadwxG0Dse_1Ptam2mL0F0rnFGoy6rIaruQZLZuirb-_0WXxUqOZVe0kduBak8kgNBYnQ8GvtNtym4coG237x5_lzUEruvGou28gHi4bowVr5aFHf6um2opTbm_WMplZY0P3lR0N83B3MD_wcgE35rQ0noN8PbWRGEZwFYLxoftytKBZY5dP-iMnTbGOGAcEmWzHnljrQ2pb4dKtmV6IzNO-ptL8Bkuc1Cr9CAMD7pGQ97t4x_J7PToKFlMzxbDq8bPQxqPcSByJNz2wZ61mfvXb31eDyF1v2EffkLHggsvfm9fO4h77lxA6I-cDvcuTTnO0KLcnOW00c7iAbnfpSn00ODrIRnp8hHZOzE4uN6nC7tsr96ne_TEMqBfPyYfWhBSACEdgpAiCCmAkLYgpFVODQhpD8In5HQ2XXyau90uHa6K4smVm00yZD0MWMrAsao8koEQWudSKwb5rlAszv1UekGYBlnGFcPdoSUEjvkkl57mwVOyU1alfk6oSMHdxaGfpdxjTERSZzxTXiAUSD_ytEPebmSYrAwZS4JJLEg6AUknYZiApB0ijHj7Nl1n3LRh5gBN7RWQElgPh3wcKCTpOnadqJor7Hi4bSvO2IDEniUQ3yYePgY_nyMVZ-SQ3Y0K7c0QjSDpEgDFIW_6y2DHsTgnS1010AYSMR_Si5tbgG8OcZqEQ54ZaFgZcIZ8ot6LP7_8Jblru-ku2blaN_oVuVVnzesW0L8A14jOfw
link.rule.ids	315,782,786,27933,27934
linkProvider	Flying Publisher
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=Three+New+Monoterpenoids+from+the+Fruit+of+Genipa+americana&rft.jtitle=Chemical+%26+pharmaceutical+bulletin&rft.au=Ono%2C+Masateru&rft.au=Ishimatsu%2C+Naoki&rft.au=Masuoka%2C+Chikako&rft.au=Yoshimitsu%2C+Hitoshi&rft.date=2007-04-01&rft.pub=Japan+Science+and+Technology+Agency&rft.issn=0009-2363&rft.eissn=1347-5223&rft.volume=55&rft.issue=4&rft.spage=632&rft_id=info:doi/10.1248%2Fcpb.55.632&rft.externalDBID=NO_FULL_TEXT&rft.externalDocID=3133612591
thumbnail_l	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0009-2363&client=summon
thumbnail_m	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0009-2363&client=summon
thumbnail_s	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0009-2363&client=summon