Spirocyclic Acylphloroglucinol Derivatives from Hypericum pyramidatum

Five spirocyclic acylphloroglucinol derivatives (1–5) have been isolated from a hexanes extract of the leaves of Hypericum pyramidatum. Pyramidatones A-D (1–3, 5) are new, and chipericumin C (4) has been previously reported. The acylphloroglucinols were characterized based on spectroscopic (NMR, IR,...

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Published inNatural product communications Vol. 9; no. 7; pp. 961 - 964
Main Authors Force, Rebecca, Chen, Shui Ling, Fortier, Emily, Rowlands, Emily, Heneks, Jean, Rovnyak, David, Henry, Geneive E.
Format Journal Article
LanguageEnglish
Published Los Angeles, CA SAGE Publications 01.07.2014
Subjects
Hypericum - chemistry
Molecular Structure
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemistry
Acylphloroglucinol
Spirocyclic
Clusiaceae
Pyramidatone
Hypericum pyramidatum
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Abstract Five spirocyclic acylphloroglucinol derivatives (1–5) have been isolated from a hexanes extract of the leaves of Hypericum pyramidatum. Pyramidatones A-D (1–3, 5) are new, and chipericumin C (4) has been previously reported. The acylphloroglucinols were characterized based on spectroscopic (NMR, IR, UV-VIS) and mass spectrometric data.
AbstractList Five spirocyclic acylphloroglucinol derivatives (1-5) have been isolated from a hexanes extract of the leaves of Hypericum pyramidatum. Pyramidatones A-D (1-3, 5) are new, and chipericumin C (4) has been previously reported. The acylphloroglucinols were characterized based on spectroscopic (NMR, IR, UV-VIS) and mass spectrometric data.
Author Henry, Geneive E.
Chen, Shui Ling
Force, Rebecca
Fortier, Emily
Rowlands, Emily
Heneks, Jean
Rovnyak, David
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Cites_doi 10.1248/cpb.59.1250
10.2174/156802609789909830
10.1021/np200741x
10.1021/np060356+
10.1002/ptr.2845
10.1002/hlca.19890720820
10.1016/S1572-5995(05)80043-2
10.1016/j.phytochem.2011.01.032
10.1016/j.tet.2008.11.068
10.1021/np8001145
10.1177/1934578X0900400412
10.1016/j.phytochem.2008.04.026
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Keywords Acylphloroglucinol
Spirocyclic
Clusiaceae
Pyramidatone
Hypericum pyramidatum
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References Manning, Petrunak, Lebo, González-Sarrías, Seeram, Henry 2011; 72
Hashidi, Tanaka, Kashiwada, Sekiya, Ikeshiro 2008; 69
Chen, Li, Li, Peng, He, Wang, Pan, Cheng, Li, Zhao, Xu 2011; 59
Henry, Raithore, Zhang, Jayaprakasam, Nair, Heber, Seeram 2006; 69
Petrunak, Kester, Liu, Bowen-Forbes, Nair, Henry 2009; 4
Yin, Chen, Su, Yang, Fan, Ding, Yue 2009; 65
Crockett, Robson 2011; 5
Acuña, Jancovski, Kennelly 2009; 9
Wu, Yen, Yang, Lin 2008; 71
Decosterd, Stoeckli-Evans, Chapuis, Sordat, Hostettmann 1989; 72
Abe, Tanaka, Kobayashi 2012; 75
Henry, Campbell, Zelinsky, Liu, Bowen-Forbes, Li, Nair, Rowley, Seeram 2009; 23
Avato 2005; 30
Robson 2001; 31
bibr11-1934578X1400900720
Crockett S.L. (bibr1-1934578X1400900720) 2011; 5
Robson N.K.B. (bibr8-1934578X1400900720) 2001; 31
bibr9-1934578X1400900720
bibr3-1934578X1400900720
bibr2-1934578X1400900720
bibr4-1934578X1400900720
bibr7-1934578X1400900720
bibr5-1934578X1400900720
bibr6-1934578X1400900720
bibr13-1934578X1400900720
bibr14-1934578X1400900720
bibr12-1934578X1400900720
bibr10-1934578X1400900720
References_xml – volume: 23
  start-page: 1759
  year: 2009
  end-page: 1762
  article-title: Bioactive acylphloroglucinols from
  publication-title: Phytotherapy Research
  contributor:
    fullname: Seeram
– volume: 72
  start-page: 662
  year: 2011
  end-page: 667
  article-title: Acylphloroglucinol and xanthones from
  publication-title: Phytochemistry
  contributor:
    fullname: Henry
– volume: 65
  start-page: 1147
  year: 2009
  end-page: 1152
  article-title: Harrisotones A-E, five novel prenylated polyketides with a rare spirocyclic skeleton from
  publication-title: Tetrahedron
  contributor:
    fullname: Yue
– volume: 71
  start-page: 1027
  year: 2008
  end-page: 1031
  article-title: Phloroglucinols with antioxidant activity and xanthonolignoids from the heartwood of
  publication-title: Journal of Natural Products
  contributor:
    fullname: Lin
– volume: 4
  start-page: 507
  year: 2009
  end-page: 510
  article-title: New benzophenone -glucoside from
  publication-title: Natural Product Communications
  contributor:
    fullname: Henry
– volume: 30
  start-page: 603
  year: 2005
  end-page: 634
  article-title: A survey of the genus: secondary metabolites and bioactivity
  publication-title: Studies in Natural Product Chemistry
  contributor:
    fullname: Avato
– volume: 31
  start-page: 37
  year: 2001
  end-page: 88
  article-title: Studies in the genus L. (Guttiferae) 4(1). Sections 7. Roscyna to 9. Hypericum sensu lato (part 1)
  publication-title: Bulletin of the Natural History Museum of London (Botany)
  contributor:
    fullname: Robson
– volume: 59
  start-page: 1250
  year: 2011
  end-page: 1253
  article-title: Spirocyclic acylphloroglucinol derivatives from
  publication-title: Chemical and Pharmaceutical Bulletin
  contributor:
    fullname: Xu
– volume: 5
  start-page: 1
  year: 2011
  end-page: 13
  article-title: Taxonomy and chemotaxonomy of the genus
  publication-title: Medicinal and Aromatic Plant Science and Biotechnology
  contributor:
    fullname: Robson
– volume: 9
  start-page: 1560
  year: 2009
  end-page: 1580
  article-title: Polyisoprenylated benzophenones from Clusiaceae: potential drugs and lead compounds
  publication-title: Current Topics in Medicinal Chemistry
  contributor:
    fullname: Kennelly
– volume: 69
  start-page: 1645
  year: 2006
  end-page: 1648
  article-title: Acylphloroglucinols from
  publication-title: Journal of Natural Products
  contributor:
    fullname: Seeram
– volume: 75
  start-page: 484
  year: 2012
  end-page: 488
  article-title: Prenylated acylphloroglucinols, chipericumins A-D, from
  publication-title: Journal of Natural Products
  contributor:
    fullname: Kobayashi
– volume: 69
  start-page: 2225
  year: 2008
  end-page: 2230
  article-title: Tomoeones A-H, cytotoxic phloroglucinol derivatives from
  publication-title: ascyron. Phytochemistry
  contributor:
    fullname: Ikeshiro
– volume: 72
  start-page: 1833
  year: 1989
  end-page: 1845
  article-title: New cell growth-inhibitory cyclohexadienone derivatives from
  publication-title: Helvetica Chimica Acta
  contributor:
    fullname: Hostettmann
– ident: bibr13-1934578X1400900720
  doi: 10.1248/cpb.59.1250
– volume: 31
  start-page: 37
  year: 2001
  ident: bibr8-1934578X1400900720
  publication-title: Bulletin of the Natural History Museum of London (Botany)
  contributor:
    fullname: Robson N.K.B.
– ident: bibr3-1934578X1400900720
  doi: 10.2174/156802609789909830
– ident: bibr11-1934578X1400900720
  doi: 10.1021/np200741x
– ident: bibr4-1934578X1400900720
  doi: 10.1021/np060356+
– ident: bibr5-1934578X1400900720
  doi: 10.1002/ptr.2845
– ident: bibr10-1934578X1400900720
  doi: 10.1002/hlca.19890720820
– ident: bibr2-1934578X1400900720
  doi: 10.1016/S1572-5995(05)80043-2
– ident: bibr7-1934578X1400900720
  doi: 10.1016/j.phytochem.2011.01.032
– ident: bibr12-1934578X1400900720
  doi: 10.1016/j.tet.2008.11.068
– volume: 5
  start-page: 1
  year: 2011
  ident: bibr1-1934578X1400900720
  publication-title: Medicinal and Aromatic Plant Science and Biotechnology
  contributor:
    fullname: Crockett S.L.
– ident: bibr14-1934578X1400900720
  doi: 10.1021/np8001145
– ident: bibr6-1934578X1400900720
  doi: 10.1177/1934578X0900400412
– ident: bibr9-1934578X1400900720
  doi: 10.1016/j.phytochem.2008.04.026
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Snippet Five spirocyclic acylphloroglucinol derivatives (1–5) have been isolated from a hexanes extract of the leaves of Hypericum pyramidatum. Pyramidatones A-D (1–3,...
Five spirocyclic acylphloroglucinol derivatives (1-5) have been isolated from a hexanes extract of the leaves of Hypericum pyramidatum. Pyramidatones A-D (1-3,...
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SubjectTerms Hypericum - chemistry
Molecular Structure
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemistry
Title Spirocyclic Acylphloroglucinol Derivatives from Hypericum pyramidatum
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