Structures and Cytotoxic Evaluation of New and Known Acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge

Four new compounds, (−)-petrosynoic acids A–D (1–4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structure...

Full description

Saved in:
Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 76; no. 3; pp. 425 - 432
Main Authors Mejia, Eric J, Magranet, Lindsay B, De Voogd, Nicole J, TenDyke, Karen, Qiu, Dayong, Shen, Young Yongchun, Zhou, Zhongrui, Crews, Phillip
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 22.03.2013
Amer Chemical Soc
Subjects
American Samoa
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Chemistry, Medicinal
Drug Screening Assays, Antitumor
Humans
Life Sciences & Biomedicine
Marine Biology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Petrosia - chemistry
Pharmacology & Pharmacy
Plant Sciences
Polyynes - chemistry
Polyynes - isolation & purification
Polyynes - pharmacology
Science & Technology
METABOLITES
POLYACETYLENE
ACID
ACETYLENIC ALCOHOLS
Online AccessGet full text

Cover

Abstract Four new compounds, (−)-petrosynoic acids A–D (1–4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C31–C33 polyacetylenes (1–9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1–9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.
AbstractList Four new compounds, (-)-petrosynoic acids A-D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C31-C33 polyacetylenes (1-9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1-9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.
Four new compounds, (-)-petrosynoic acids A D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C-31-C-33 polyacetylenes (1-9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1-9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.
Four new compounds, (−)-petrosynoic acids A–D (1–4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C31–C33 polyacetylenes (1–9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1–9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.
Four new compounds, (−)-petrosynoic acids A–D ( 1–4 ), and five known congeners, pellynols A ( 5 ), C ( 6 ), D ( 7 ), F ( 8 ), and I ( 9 ) were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C 31 -C 33 polyacetylenes ( 1–9 ) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1–9 were found to be broadly cytotoxic with limited selectivity for cancer cells as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.
Author Mejia, Eric J
Zhou, Zhongrui
Shen, Young Yongchun
De Voogd, Nicole J
Crews, Phillip
Magranet, Lindsay B
TenDyke, Karen
Qiu, Dayong
AuthorAffiliation University of California, Berkeley
Eisai Inc
University of California, Santa Cruz
The National Museum of Natural History
AuthorAffiliation_xml – name: The National Museum of Natural History
– name: Eisai Inc
– name: University of California, Santa Cruz
– name: University of California, Berkeley
– name: QB3/Chemistry Mass Spectrometry Facility, University of California, Berkeley, CA 94720
– name: Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064
– name: The National Museum of Natural History, 2300 RA Leiden, The Netherlands
– name: Eisai Inc., 4 Corporate Drive, Andover, Massachussetts 01810
Author_xml – sequence: 1
  givenname: Eric J
  surname: Mejia
  fullname: Mejia, Eric J
– sequence: 2
  givenname: Lindsay B
  surname: Magranet
  fullname: Magranet, Lindsay B
– sequence: 3
  givenname: Nicole J
  surname: De Voogd
  fullname: De Voogd, Nicole J
– sequence: 4
  givenname: Karen
  surname: TenDyke
  fullname: TenDyke, Karen
– sequence: 5
  givenname: Dayong
  surname: Qiu
  fullname: Qiu, Dayong
– sequence: 6
  givenname: Young Yongchun
  surname: Shen
  fullname: Shen, Young Yongchun
– sequence: 7
  givenname: Zhongrui
  surname: Zhou
  fullname: Zhou, Zhongrui
– sequence: 8
  givenname: Phillip
  surname: Crews
  fullname: Crews, Phillip
  email: pcrews@ucsc.edu
BackLink https://www.ncbi.nlm.nih.gov/pubmed/23368996$$D View this record in MEDLINE/PubMed
BookMark eNqNkV9rFDEUxYNU7Lb64BeQvAiKTE0m_2ZehGVoVSwqrD74FLKZO3XKTDJNMl332zfbrYuCDz7lwP2dk3s5J-jIeQcIPafkjJKSvnUTI6TiXD5CCypKUkhSiiO0IFSyglWSH6OTGK8JIYzU4gk6LhmTVV3LBZpWKcw2zQEiNq7FzTb55H_1Fp_fmmE2qfcO-w5_hs39_JPzG4eXdmuHHeOg-OGytQt-zHO8HCH0NouVGb3BXyEFH3uD43SGV5N3V_AUPe7MEOHZw3uKvl-cf2s-FJdf3n9slpeF4YqmQggLVK2FqYThlFFFQVEmakk5oUK1sjSVZVlQXvOOqLJUtlVScgFMtIyyU_RunzvN6xFaCy4FM-gp9KMJW-1Nr_-euP6nvvK3mikuGFE54NVDQPA3M8Skxz5aGAbjwM9R56VqWilRiYy-3qM2XxsDdIdvKNG7hvShocy--HOvA_m7kgy82QMbWPsu2h6chQO265BKpVidFa0yXf0_3fTpvtDGzy5l68u91dior_0cXO7jHxvfAdpAuS4
CitedBy_id crossref_primary_10_3390_md19030122
crossref_primary_10_1007_s11418_019_01377_6
crossref_primary_10_1021_cr4006507
crossref_primary_10_31857_S0044460X23100049
crossref_primary_10_1016_j_bmcl_2016_04_060
crossref_primary_10_3390_md22030101
crossref_primary_10_1002_cbdv_202200159
crossref_primary_10_1134_S1070363219030289
crossref_primary_10_1016_j_tet_2018_05_041
crossref_primary_10_1016_j_tetlet_2017_07_094
crossref_primary_10_1134_S1070428019060253
crossref_primary_10_1002_cmdc_201800284
crossref_primary_10_1021_acs_jnatprod_1c00798
crossref_primary_10_1134_S1070363218100274
crossref_primary_10_1134_S1070428017110173
crossref_primary_10_1007_s42995_022_00132_3
crossref_primary_10_1016_j_cclet_2018_09_011
crossref_primary_10_1080_14786419_2023_2175359
crossref_primary_10_1016_j_fitote_2020_104511
crossref_primary_10_1039_C4NP00144C
crossref_primary_10_3390_ijms150916511
crossref_primary_10_1039_C9RA08119D
crossref_primary_10_1134_S1070363223100043
Cites_doi 10.1021/np900465e
10.1021/jm8008585
10.1158/1535-7163.MCT-08-1026
10.1016/j.tetlet.2011.05.059
10.1021/np900565a
10.1007/s10886-012-0124-8
10.1021/np900326a
10.1021/np060633c
10.1007/s11745-008-3249-3
10.1021/np300231f
10.1016/j.bcp.2009.09.027
10.1021/np020080f
10.1016/S0040-4039(01)93008-4
10.1021/np50082a019
10.1021/np990167+
10.1021/np9803427
10.1021/ja00061a065
10.1016/S0040-4020(99)01093-5
10.1080/10575630008043772
10.1016/S0040-4039(00)87828-4
10.1016/S0040-4039(00)88018-1
10.1016/S0040-4020(96)01037-X
10.2174/187152008783497073
10.3390/md101046
10.1021/np50126a001
10.1021/np960366i
ContentType Journal Article
Copyright Copyright © 2013 American Chemical Society and American Society of Pharmacognosy
Copyright_xml – notice: Copyright © 2013 American Chemical Society and American Society of Pharmacognosy
DBID 1KM
BLEPL
DTL
GKMDS
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
5PM
DOI 10.1021/np3008446
DatabaseName Index Chemicus
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2013
Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
CrossRef
MEDLINE - Academic
PubMed Central (Full Participant titles)
DatabaseTitle Web of Science
MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
CrossRef
MEDLINE - Academic
DatabaseTitleList MEDLINE
MEDLINE - Academic
Web of Science
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: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
Biology
Pharmacy, Therapeutics, & Pharmacology
EISSN 1520-6025
EndPage 432
ExternalDocumentID 10_1021_np3008446
23368996
000316773900018
a519954392
Genre Research Support, U.S. Gov't, Non-P.H.S
Journal Article
Research Support, N.I.H., Extramural
GrantInformation_xml – fundername: NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA
  grantid: R01 CA 047135
– fundername: NATIONAL CANCER INSTITUTE; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI)
  grantid: R01CA047135
– fundername: NMR equipment grants
  grantid: NSF CHE 0342912; NIH S10-RR19918
– fundername: NATIONAL CENTER FOR RESEARCH RESOURCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Center for Research Resources (NCRR)
  grantid: S10RR019918
– fundername: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS)
  grantid: R25GM058903
– fundername: IMSD (MBRS) program (NIH/NIGMS)
  grantid: R25GM058903
– fundername: NCI NIH HHS
  grantid: R01 CA047135
– fundername: NIGMS NIH HHS
  grantid: R25GM058903
– fundername: NCI NIH HHS
  grantid: R01 CA 047135
– fundername: NCRR NIH HHS
  grantid: S10-RR19918
– fundername: National Cancer Institute : NCI
  grantid: R01 CA047135 || CA
GroupedDBID -
4.4
53G
55A
5GY
7~N
AABXI
AAWTL
ABFLS
ABFSI
ABMVS
ABOCM
ABUCX
ACGFS
ACJ
ACNCT
ACS
AEESW
AENEX
AFEFF
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
CS3
DU5
EBS
ED
ED~
EJD
F5P
GNL
IH9
IHE
JG
JG~
LG6
P2P
ROL
TN5
UI2
VF5
VG9
W1F
X
XKZ
YZZ
---
-~X
1KM
5VS
AAHBH
ABJNI
ABQRX
ADHLV
AGXLV
AHGAQ
BAANH
BLEPL
CUPRZ
DTL
GGK
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
5PM
ID FETCH-LOGICAL-a471t-55ce17b5a85a413171e713596140157d62a8c357d1494f07227cd76645e35d313
IEDL.DBID ACS
ISICitedReferencesCount 25
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000316773900018
ISSN 0163-3864
IngestDate Tue Sep 17 21:19:16 EDT 2024
Sat Oct 26 05:04:14 EDT 2024
Fri Aug 23 02:08:00 EDT 2024
Sat Nov 02 12:31:08 EDT 2024
Fri Nov 08 20:05:40 EST 2024
Wed Sep 18 06:11:40 EDT 2024
Thu Aug 27 13:42:51 EDT 2020
IsDoiOpenAccess false
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 3
Keywords METABOLITES
POLYACETYLENE
ACID
ACETYLENIC ALCOHOLS
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-a471t-55ce17b5a85a413171e713596140157d62a8c357d1494f07227cd76645e35d313
Notes NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
DEDICATION
Dedicated to Dr. Lester A Mitscher, of the University of Kansas, for his pioneering work on the discovery of bioactive natural products and their derivatives.
OpenAccessLink https://europepmc.org/articles/pmc3745307?pdf=render
PMID 23368996
PQID 1319187585
PQPubID 23479
PageCount 8
ParticipantIDs webofscience_primary_000316773900018
pubmedcentral_primary_oai_pubmedcentral_nih_gov_3745307
proquest_miscellaneous_1319187585
acs_journals_10_1021_np3008446
crossref_primary_10_1021_np3008446
webofscience_primary_000316773900018CitationCount
pubmed_primary_23368996
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
XKZ
7~N
ACJ
VG9
W1F
ACS
AEESW
AFEFF
ABMVS
ABUCX
IH9
AQSVZ
ED~
UI2
PublicationCentury 2000
PublicationDate 2013-03-22
PublicationDateYYYYMMDD 2013-03-22
PublicationDate_xml – month: 03
  year: 2013
  text: 2013-03-22
  day: 22
PublicationDecade 2010
PublicationPlace WASHINGTON
PublicationPlace_xml – name: WASHINGTON
– name: United States
PublicationTitle Journal of natural products (Washington, D.C.)
PublicationTitleAbbrev J NAT PROD
PublicationTitleAlternate J. Nat. Prod
PublicationYear 2013
Publisher American Chemical Society and American Society of Pharmacognosy
Amer Chemical Soc
Publisher_xml – name: American Chemical Society and American Society of Pharmacognosy
– name: Amer Chemical Soc
References Schumacher, M (WOS:000273624600009) 2010; 79
Kamel, HN (WOS:000269485100024) 2009; 72
Fu, X (WOS:000082910800032) 1999; 62
El Sayed, KA (WOS:000085305800002) 2000; 56
GULAVITA, NK (WOS:A1992HM44700019) 1992; 55
Dai, JR (WOS:A1996VK42900008) 1996; 59
Lansdell, TA (WOS:000304385800019) 2012; 75
Crews, P. (000316773900018.4) 2010
QUINOA, E (WOS:A1988N309300009) 1988; 29
Fu, X (WOS:A1997WA54000001) 1997; 53
CIMINO, G (WOS:A1977DB09000012) 1977
Kuznetsov, G (WOS:000266189900029) 2009; 8
Rubio, BK (WOS:000246007200025) 2007; 70
Molinski, T. F. (000316773900018.30) 2003; 1
Kim, JS (WOS:000079959300004) 1999; 62
Mooberry, SL (WOS:000078390900027) 1999; 59
FUSETANI, N (WOS:A1983QW58000018) 1983; 24
Johnson, TA (WOS:000275885000012) 2010; 73
Amagata, T (WOS:000261056600023) 2008; 51
Robinson, SJ (WOS:000271950400021) 2009; 72
Jung, JH (CCC:000239870600012) 2006
Siddiq, A (WOS:000255810200003) 2008; 8
Hallock, YF (WOS:A1995TW33600001) 1995; 58
Rashid, MA (WOS:000089742200010) 2000; 14
KINNEL, RB (WOS:A1993KY50600065) 1993; 115
Lee, HS (WOS:000261790800009) 2009; 44
DeFelice, R. C. (000316773900018.3) 2003
Rohde, S (WOS:000304208300004) 2012; 38
Utkina, NK (WOS:000292472400018) 2011; 52
Nishimura, S (WOS:000178274700029) 2002; 65
Rubio B. K. (ref14/cit14) 2007; 70
Utkina N. K. (ref4/cit4) 2011; 52
Crews P. (ref16/cit16) 2010
Mooberry S. L. (ref7/cit7) 1999; 59
Kuznetsov G. (ref29/cit29) 2009; 8
Fu X. (ref22/cit22) 1999; 62
Fu X. (ref18/cit18) 1997; 53
Zhou G.-X. (ref28/cit28) 2003; 1
Robinson S. J. (ref9/cit9) 2009; 72
Kamel H. N. (ref3/cit3) 2009; 72
Amagata T. (ref6/cit6) 2008; 51
Lansdell T. A. (ref12/cit12) 2012; 75
Rashid M. A. (ref23/cit23) 2000; 14
Quinoa E. (ref17/cit17) 1988; 29
El Sayed K. A. (ref8/cit8) 2000; 56
Jung J. H. (ref13/cit13) 2006
Johnson T. A. (ref15/cit15) 2010; 73
Cimino G. (ref30/cit30) 1977; 15
Gulavita N. K. (ref2/cit2) 1992; 55
Kinnel R. B. (ref11/cit11) 1993; 115
Siddiq A. (ref25/cit25) 2008; 8
Rohde S. (ref5/cit5) 2012; 38
Dai J.-R. (ref19/cit19) 1996; 59
Kim J. S. (ref21/cit21) 1999; 62
Hallock Y. F. (ref26/cit26) 1995; 58
Nishimura S. (ref24/cit24) 2002; 65
Lee H.-S. (ref27/cit27) 2009; 44
Fusetani N. (ref20/cit20) 1983; 24
Schumacher M. (ref10/cit10) 2010; 79
ref1/cit1
References_xml – volume: 72
  start-page: 1857
  year: 2009
  ident: WOS:000271950400021
  article-title: Using Enzyme Assays to Evaluate the Structure and Bioactivity of Sponge-Derived Meroterpenes
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np900465e
  contributor:
    fullname: Robinson, SJ
– volume: 29
  start-page: 2037
  year: 1988
  ident: WOS:A1988N309300009
  article-title: MELYNES, POLYACETYLENE CONSTITUENTS FROM A VANUATU MARINE SPONGE
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: QUINOA, E
– volume: 51
  start-page: 7234
  year: 2008
  ident: WOS:000261056600023
  article-title: Interrogating the Bioactive Pharmacophore of the Latrunculin Chemotype by Investigating the Metabolites of Two Taxonomically Unrelated Sponges
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm8008585
  contributor:
    fullname: Amagata, T
– volume: 24
  start-page: 2771
  year: 1983
  ident: WOS:A1983QW58000018
  article-title: BIOACTIVE MARINE METABOLITES .3. A NOVEL POLYACETYLENE ALCOHOL, INHIBITOR OF CELL-DIVISION IN FERTILIZED SEA-URCHIN EGGS, FROM THE MARINE SPONGE TETROSIA SP
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: FUSETANI, N
– volume: 8
  start-page: 1250
  year: 2009
  ident: WOS:000266189900029
  article-title: Potent in vitro and in vivo anticancer activities of des-methyl, des-amino pateamine A, a synthetic analogue of marine natural product pateamine A
  publication-title: MOLECULAR CANCER THERAPEUTICS
  doi: 10.1158/1535-7163.MCT-08-1026
  contributor:
    fullname: Kuznetsov, G
– volume: 52
  start-page: 3765
  year: 2011
  ident: WOS:000292472400018
  article-title: Diplopuupehenone, a new unsymmetrical puupehenone-related dimer from the marine sponge Dysidea sp.
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2011.05.059
  contributor:
    fullname: Utkina, NK
– volume: 73
  start-page: 359
  year: 2010
  ident: WOS:000275885000012
  article-title: Assessing Pressurized Liquid Extraction for the High-Throughput Extraction of Marine-Sponge-Derived Natural Products
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np900565a
  contributor:
    fullname: Johnson, TA
– volume: 1
  start-page: 46
  year: 2003
  ident: 000316773900018.30
  publication-title: Mar. Drugs
  contributor:
    fullname: Molinski, T. F.
– volume: 59
  start-page: 653
  year: 1999
  ident: WOS:000078390900027
  article-title: Laulimalide and isolaulimalide, new paclitaxel-like microtubule stabilizing agents
  publication-title: CANCER RESEARCH
  contributor:
    fullname: Mooberry, SL
– volume: 62
  start-page: 554
  year: 1999
  ident: WOS:000079959300004
  article-title: Cytotoxic polyacetylenes from the marine sponge Petrosia sp.
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: Kim, JS
– volume: 38
  start-page: 463
  year: 2012
  ident: WOS:000304208300004
  article-title: Spatial Variability in Secondary Metabolites of the Indo-Pacific Sponge Stylissa massa
  publication-title: JOURNAL OF CHEMICAL ECOLOGY
  doi: 10.1007/s10886-012-0124-8
  contributor:
    fullname: Rohde, S
– volume: 59
  start-page: 860
  year: 1996
  ident: WOS:A1996VK42900008
  article-title: Triangulynes A-H and triangulynic acid, new cytotoxic polyacetylenes from the marine sponge Pellina triangulata
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: Dai, JR
– volume: 62
  start-page: 1336
  year: 1999
  ident: WOS:000082910800032
  article-title: Swinholides and new acetylenic compounds from an undescribed species of Theonella sponge
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: Fu, X
– volume: 56
  start-page: 949
  year: 2000
  ident: WOS:000085305800002
  article-title: Marine natural products as antituberculosis agents
  publication-title: TETRAHEDRON
  contributor:
    fullname: El Sayed, KA
– volume: 72
  start-page: 1492
  year: 2009
  ident: WOS:000269485100024
  article-title: Scalarane Sesterterpenoids: Semisynthesis and Biological Activity
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np900326a
  contributor:
    fullname: Kamel, HN
– volume: 8
  start-page: 132
  year: 2008
  ident: WOS:000255810200003
  article-title: Acetylenic anticancer agents
  publication-title: ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
  contributor:
    fullname: Siddiq, A
– year: 2010
  ident: 000316773900018.4
  publication-title: Organic Structure Analysis
  contributor:
    fullname: Crews, P.
– volume: 53
  start-page: 799
  year: 1997
  ident: WOS:A1997WA54000001
  article-title: New acetylenic metabolites from the marine sponge Pellina triangculata
  publication-title: TETRAHEDRON
  contributor:
    fullname: Fu, X
– volume: 70
  start-page: 628
  year: 2007
  ident: WOS:000246007200025
  article-title: Extending the record of meroditerpenes from Cacospongia marine sponges
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np060633c
  contributor:
    fullname: Rubio, BK
– volume: 58
  start-page: 1801
  year: 1995
  ident: WOS:A1995TW33600001
  article-title: Antitumor activity and stereochemistry of acetylenic alcohols from the sponge Cribrochalina vasculum
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: Hallock, YF
– volume: 115
  start-page: 3376
  year: 1993
  ident: WOS:A1993KY50600065
  article-title: PALAUAMINE - A CYTOTOXIC AND IMMUNOSUPPRESSIVE HEXACYCLIC BISGUANIDINE ANTIBIOTIC FROM THE SPONGE STYLOTELLA-AGMINATA
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: KINNEL, RB
– start-page: 182
  year: 2003
  ident: 000316773900018.3
  article-title: Introduced Marine Species in Pago Pago Harbor, Fagatele Bay and the National Park Coast, American Samoa
  publication-title: Bishop Museum Technical Report No. 26
  contributor:
    fullname: DeFelice, R. C.
– volume: 44
  start-page: 71
  year: 2009
  ident: WOS:000261790800009
  article-title: Identification of Novel Acetylenic Alcohols and a New Dihydrothiopyranone from the Tropical Sponge Reniochalina sp.
  publication-title: LIPIDS
  doi: 10.1007/s11745-008-3249-3
  contributor:
    fullname: Lee, HS
– start-page: 451
  year: 2006
  ident: CCC:000239870600012
  article-title: Bioactive polyacetylenic compounds from marine sponges
  publication-title: BIOMATERIALS FROM AQUATIC AND TERRESTRIAL ORGANISMS
  contributor:
    fullname: Jung, JH
– volume: 55
  start-page: 506
  year: 1992
  ident: WOS:A1992HM44700019
  article-title: ISOLATION OF LATRUNCULIN-A, 6,7-EPOXYLATRUNCULIN-A, FIJIANOLIDE-A, AND EURYFURAN FROM A NEW GENUS OF THE FAMILY THORECTIDAE
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: GULAVITA, NK
– volume: 75
  start-page: 980
  year: 2012
  ident: WOS:000304385800019
  article-title: Palau'amine and Related Oroidin Alkaloids Dibromophakellin and Dibromophakellstatin Inhibit the Human 20S Proteasome
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np300231f
  contributor:
    fullname: Lansdell, TA
– volume: 14
  start-page: 387
  year: 2000
  ident: WOS:000089742200010
  article-title: Pellynol I, a new cytotoxic polyacetylene from the sponge Pellina sp.
  publication-title: NATURAL PRODUCT LETTERS
  contributor:
    fullname: Rashid, MA
– volume: 79
  start-page: 610
  year: 2010
  ident: WOS:000273624600009
  article-title: Heteronemin, a spongean sesterterpene, inhibits TNF alpha-induced NF-kappa B activation through proteasome inhibition and induces apoptotic cell death
  publication-title: BIOCHEMICAL PHARMACOLOGY
  doi: 10.1016/j.bcp.2009.09.027
  contributor:
    fullname: Schumacher, M
– volume: 65
  start-page: 1353
  year: 2002
  ident: WOS:000178274700029
  article-title: Corticatic acids D and E, polyacetylenic geranylgeranyltransferase type I inhibitors, from the marine sponge Petrosia corticata
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np020080f
  contributor:
    fullname: Nishimura, S
– start-page: 1325
  year: 1977
  ident: WOS:A1977DB09000012
  article-title: NEW ACETYLENIC-COMPOUNDS FROM SPONGE RENIERA-FULVA
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: CIMINO, G
– volume: 79
  start-page: 610
  year: 2010
  ident: ref10/cit10
  publication-title: Biochem. Pharmacol.
  doi: 10.1016/j.bcp.2009.09.027
  contributor:
    fullname: Schumacher M.
– volume: 15
  start-page: 1325
  year: 1977
  ident: ref30/cit30
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(01)93008-4
  contributor:
    fullname: Cimino G.
– volume: 55
  start-page: 506
  year: 1992
  ident: ref2/cit2
  publication-title: J. Nat. Prod.
  doi: 10.1021/np50082a019
  contributor:
    fullname: Gulavita N. K.
– volume: 62
  start-page: 1336
  year: 1999
  ident: ref22/cit22
  publication-title: J. Nat. Prod.
  doi: 10.1021/np990167+
  contributor:
    fullname: Fu X.
– volume: 62
  start-page: 554
  year: 1999
  ident: ref21/cit21
  publication-title: J. Nat. Prod.
  doi: 10.1021/np9803427
  contributor:
    fullname: Kim J. S.
– volume: 38
  start-page: 463
  year: 2012
  ident: ref5/cit5
  publication-title: J. Chem. Ecol.
  doi: 10.1007/s10886-012-0124-8
  contributor:
    fullname: Rohde S.
– volume: 44
  start-page: 71
  year: 2009
  ident: ref27/cit27
  publication-title: Lipids
  doi: 10.1007/s11745-008-3249-3
  contributor:
    fullname: Lee H.-S.
– volume: 52
  start-page: 3765
  year: 2011
  ident: ref4/cit4
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2011.05.059
  contributor:
    fullname: Utkina N. K.
– volume: 73
  start-page: 359
  year: 2010
  ident: ref15/cit15
  publication-title: J. Nat. Prod.
  doi: 10.1021/np900565a
  contributor:
    fullname: Johnson T. A.
– volume: 72
  start-page: 1492
  year: 2009
  ident: ref3/cit3
  publication-title: J. Nat. Prod.
  doi: 10.1021/np900326a
  contributor:
    fullname: Kamel H. N.
– volume: 51
  start-page: 7234
  year: 2008
  ident: ref6/cit6
  publication-title: J. Med. Chem.
  doi: 10.1021/jm8008585
  contributor:
    fullname: Amagata T.
– volume: 115
  start-page: 3376
  year: 1993
  ident: ref11/cit11
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00061a065
  contributor:
    fullname: Kinnel R. B.
– volume: 56
  start-page: 949
  year: 2000
  ident: ref8/cit8
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(99)01093-5
  contributor:
    fullname: El Sayed K. A.
– volume: 14
  start-page: 387
  year: 2000
  ident: ref23/cit23
  publication-title: Nat. Prod. Lett.
  doi: 10.1080/10575630008043772
  contributor:
    fullname: Rashid M. A.
– volume: 29
  start-page: 2037
  year: 1988
  ident: ref17/cit17
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)87828-4
  contributor:
    fullname: Quinoa E.
– volume: 75
  start-page: 980
  year: 2012
  ident: ref12/cit12
  publication-title: J. Nat. Prod.
  doi: 10.1021/np300231f
  contributor:
    fullname: Lansdell T. A.
– volume: 24
  start-page: 2771
  year: 1983
  ident: ref20/cit20
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)88018-1
  contributor:
    fullname: Fusetani N.
– volume: 72
  start-page: 1857
  year: 2009
  ident: ref9/cit9
  publication-title: J. Nat. Prod.
  doi: 10.1021/np900465e
  contributor:
    fullname: Robinson S. J.
– ident: ref1/cit1
– volume-title: Organic Structure Analysis
  year: 2010
  ident: ref16/cit16
  contributor:
    fullname: Crews P.
– volume: 53
  start-page: 799
  year: 1997
  ident: ref18/cit18
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(96)01037-X
  contributor:
    fullname: Fu X.
– volume: 8
  start-page: 132
  year: 2008
  ident: ref25/cit25
  publication-title: Anti-Cancer Agents Med. Chem.
  doi: 10.2174/187152008783497073
  contributor:
    fullname: Siddiq A.
– volume: 65
  start-page: 1353
  year: 2002
  ident: ref24/cit24
  publication-title: J. Nat. Prod.
  doi: 10.1021/np020080f
  contributor:
    fullname: Nishimura S.
– volume: 8
  start-page: 1250
  year: 2009
  ident: ref29/cit29
  publication-title: Mol. Cancer Ther.
  doi: 10.1158/1535-7163.MCT-08-1026
  contributor:
    fullname: Kuznetsov G.
– volume: 1
  start-page: 46
  year: 2003
  ident: ref28/cit28
  publication-title: Mar. Drugs
  doi: 10.3390/md101046
  contributor:
    fullname: Zhou G.-X.
– start-page: 451
  volume-title: Biomaterials from Aquatic and Terrestrial Organisms
  year: 2006
  ident: ref13/cit13
  contributor:
    fullname: Jung J. H.
– volume: 58
  start-page: 1801
  year: 1995
  ident: ref26/cit26
  publication-title: J. Nat. Prod.
  doi: 10.1021/np50126a001
  contributor:
    fullname: Hallock Y. F.
– volume: 59
  start-page: 860
  year: 1996
  ident: ref19/cit19
  publication-title: J. Nat. Prod.
  doi: 10.1021/np960366i
  contributor:
    fullname: Dai J.-R.
– volume: 59
  start-page: 653
  year: 1999
  ident: ref7/cit7
  publication-title: Cancer Res.
  contributor:
    fullname: Mooberry S. L.
– volume: 70
  start-page: 628
  year: 2007
  ident: ref14/cit14
  publication-title: J. Nat. Prod.
  doi: 10.1021/np060633c
  contributor:
    fullname: Rubio B. K.
SSID ssj0003095
Score 2.2345946
Snippet Four new compounds, (−)-petrosynoic acids A–D (1–4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia...
Four new compounds, (-)-petrosynoic acids A D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia...
Four new compounds, (-)-petrosynoic acids A-D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia...
Four new compounds, (−)-petrosynoic acids A–D ( 1–4 ), and five known congeners, pellynols A ( 5 ), C ( 6 ), D ( 7 ), F ( 8 ), and I ( 9 ) were isolated from a...
Source Web of Science
SourceID pubmedcentral
proquest
crossref
pubmed
webofscience
acs
SourceType Open Access Repository
Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 425
SubjectTerms American Samoa
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Chemistry, Medicinal
Drug Screening Assays, Antitumor
Humans
Life Sciences & Biomedicine
Marine Biology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Petrosia - chemistry
Pharmacology & Pharmacy
Plant Sciences
Polyynes - chemistry
Polyynes - isolation & purification
Polyynes - pharmacology
Science & Technology
Title Structures and Cytotoxic Evaluation of New and Known Acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge
URI http://dx.doi.org/10.1021/np3008446
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000316773900018
https://www.ncbi.nlm.nih.gov/pubmed/23368996
https://www.proquest.com/docview/1319187585
https://pubmed.ncbi.nlm.nih.gov/PMC3745307
Volume 76
WOS 000316773900018
WOSCitedRecordID wos000316773900018
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Ja9wwFH6kKaW9dJlu7hLUNuQUT6PdPgY3IRRaApNAejKyrWmHpLLBHqj76_tkj51Mky43g54Elj69BUnfB7DNmYklUyzE2JCFghkaRiZmYebTXcsljzue7U-f1dGp-Hgmzzbg3R9O8Bl97yruSd-FugW3mcZN4fOfZDa6W74X9_cUFQ95pMRAH3S1qw89eb0eeq7lkzdfi_wtFHVh5_ABfBge7_S3Tc6nyyab5j-vczn-7Y8ewv1V2kn2e5w8gg3rJnCnF6JsJ3A3GXTfJrBz3LNZt7vk5PJxVr1LdsjxJc91-xiqWcc9u8SCnRhXkKRtyqb8scjJwUghTso5QT_atXuFbUf28za_8DbOhl_QzxL_wAXbyXB2RGbme2mIl_oq64UhdTUls6p0X-0TOD08OEmOwpWAQ2gw5jWhlLmlOpMmkgaDJdXUekXAWPmqTupCMRPlHD-wTBPzPc2YzgutlJCIkoJT_hQ2XenscyA6i6O5VVzk3u0ogWk2pVhdC8sZfhUBbOEKp6sNWKfd2Tqj6TjXAbwdFj-teiKPm4zeDLBIcdb92YlxtlzieOiqaOSLqwCe9TAZh2GcKyxbsbdeA9Bo4Cm811vc4ltH5c21kOhlA9i-CrWxo4c3VVpzL-1KowDo_5glK3Z3z2rQvPjXxLyEe6yT-OAhY69gE6FjX2Oi1WRb3Ub7Ba25HX0
link.rule.ids 230,315,783,787,888,2772,27088,27936,27937,57066,57116
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Ja9wwGBVtSkkvXaabu6RqCTlF00iyJPsYhoRpm4TATCA9GdnWtENb2WAP1P31_SQvk0kDzc2gBfnj6VuQ9B5Cu5zpWDDJCMSGlIRMUxLpmJHUpbuGCx57nu3TMzm9CD9fisuOJse9hYFFVDBT5Q_x1-wC9KMtueN-D-VddE8oCJQuDZrMBq_LD-L2uqLkhEcy7FmErg51ESirNiPQP2nlzbcjr0UkH32OH7UyRn7d_tLJj_GqTsfZn2uUjrf7scfoYZeE4sMWNU_QHWNH6H4rS9mM0PakV4Ebob3zltu62cfz9VOtah_v4fM163XzFJUzz0S7gvIda5vjSVMXdfF7meGjgVAcFwsMXtW3O71tiw-zJvvp-lhDvoLXxe65C7Tj_iQJz_SvQmMn_FVUS42rcoxnZWG_mWfo4vhoPpmSTs6BaIiANREiM1SlQkdCQ-ikihqnDxhLV-MJlUumo4zDBxRt4eJAMaayXEkZCsBMzil_jrZsYc1LhFUaRwsjeZg5JyRDSLophVo7NJzBVx6gHTB10m3HKvEn7Ywmg60D9KHHQFK2tB43dXrfoyMBq7uTFG1NsYL5wHHRyJVaAXrRomWYhnEuoYiF0WoDR0MHR-i92WKX3z2xN1ehAJ8boN2riBsGOpRTqRR3Qq80ChC9TbdJx_XuOA7qV_8zzDu0PZ2fniQnn86-vEYPmBf_4ISxN2gLYGTeQgpWpzt-7_0FPIwl4g
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Zb9QwEB5BEccLx3KFoxhU9alZaju2k8dV6KpcZaVtpfIUOYkXVkASKVmJ5dczdo52SyX6Fsljyxl9nkNjfwOww5mOBJPMR9-Q-gHT1A91xPzUhruGCx45nu3PR_LwJPhwKk67RNG-hcFN1LhS7Yr49lRX-aJjGKBvi4pb_vdAXocbQlFXlp3E88Hy8v2ovbIouc9DGfRMQuenWi-U1Zte6J_Q8vIbkhe8kvNA03vwZdi7u3jyY7xq0nH25wKt49V_7j7c7YJRMmnR8wCumWIEN9v2lOsR3I77bnAj2J21HNfrPXJ89mSr3iO7ZHbGfr1-CNXcMdKuMI0nushJvG7Kpvy9zMjBQCxOygVB6-rGbd_tgkyydfbTyhTG_4rWl9hnLzhO-ooSmetfpSa2AVhZLzWpqzGZV2XxzTyCk-nBcXzod20dfI2esPGFyAxVqdCh0OhCqaLG9gmMpM31hMol02HG8QOTt2CxrxhTWa6kDARiJ-eUP4atoizMUyAqjcKFkTzIrDGSAQbflGLOHRjO8Cv3YBvVnXTHsk5cxZ3RZNC1B296HCRVS-9xmdDrHiEJat1WVHRhyhWuhwaMhjbl8uBJi5hhGca5xGQWZ6sNLA0Clth7c6RYfncE31wFAm2vBzvnUTdMtEinUiluG77S0AN6FbG443y3XAfNs_8p5hXcmr2bJp_eH318DneY6wHCfcZewBaiyLzESKxJt93x-wutzyhc
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=Structures+and+Cytotoxic+Evaluation+of+New+and+Known+Acyclic+Ene-Ynes+from+an+American+Samoa+Petrosia+sp.+Sponge&rft.jtitle=Journal+of+natural+products+%28Washington%2C+D.C.%29&rft.au=Mejia%2C+Eric+J.&rft.au=Magranet%2C+Lindsay+B.&rft.au=De+Voogd%2C+Nicole+J.&rft.au=TenDyke%2C+Karen&rft.date=2013-03-22&rft.issn=0163-3864&rft.eissn=1520-6025&rft.volume=76&rft.issue=3&rft.spage=425&rft.epage=432&rft_id=info:doi/10.1021%2Fnp3008446&rft_id=info%3Apmid%2F23368996&rft.externalDBID=PMC3745307
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0163-3864&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0163-3864&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0163-3864&client=summon