The first 6′- O-sulfated phenylanthraquinones: isolation from Bulbine frutescens, structural elucidation, enantiomeric purity, and partial synthesis
From the roots of Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures were elucidated by spectroscopic and chiroptical methods, by acid hydrolysis or by partial synthesis. The new compounds have the usual stereo-...
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| Published in | Tetrahedron Vol. 61; no. 35; pp. 8475 - 8484 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
29.08.2005
Elsevier |
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| Abstract | From the roots of
Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures were elucidated by spectroscopic and chiroptical methods, by acid hydrolysis or by partial synthesis. The new compounds have the usual stereo-orientation at the biaryl axis (i.e., with the acetyl portion above the anthraquinone plane) except for sodium
ent-knipholone 6′-
O-sulfate (and thus, also its hydrolysis product,
ent-knipholone), which exhibit an opposite axial configuration. We also describe the first stereoanalysis of natural phenylanthraquinones, some of which were found to be not enantiomerically pure, some even near-racemic. We furthermore, report on the first X-ray structure analysis of a phenylanthraquinone, viz. 4′-
O-demethylknipholone.
Graphical Abstract |
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| AbstractList | From the roots of Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures were elucidated by spectroscopic and chiroptical methods, by acid hydrolysis or by partial synthesis. The new compounds have the usual stereo-orientation at the biaryl axis (i.e.. with the acetyl portion above the anthraquirione plane) except for sodium ent-knipholone 6 '-O-sulfate (and thus, also its hydrolysis product, ent-knipholone), which exhibit an opposite axial configuration. We also describe the first stereoanalysis of natural phenylanthraquinones, some of which were found to be not enantiomerically pure, some even near-racemic. We furthermore. report on the first X-ray structure analysis of a phenylanthraquinone, viz. 4 '-O-deniethylknipholone. (c) 2005 Elsevier Ltd. All rights reserved. From the roots of Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures were elucidated by spectroscopic and chiroptical methods, by acid hydrolysis or by partial synthesis. The new compounds have the usual stereo-orientation at the biaryl axis (i.e., with the acetyl portion above the anthraquinone plane) except for sodium ent-knipholone 6′- O-sulfate (and thus, also its hydrolysis product, ent-knipholone), which exhibit an opposite axial configuration. We also describe the first stereoanalysis of natural phenylanthraquinones, some of which were found to be not enantiomerically pure, some even near-racemic. We furthermore, report on the first X-ray structure analysis of a phenylanthraquinone, viz. 4′- O-demethylknipholone. Graphical Abstract |
| Author | Bezabih, Merhatibeb Brun, Reto Kocher, Nikolaus Mutanyatta, Joan Abegaz, Berhanu M. Dreyer, Michael Bringmann, Gerhard |
| Author_xml | – sequence: 1 givenname: Joan surname: Mutanyatta fullname: Mutanyatta, Joan organization: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany – sequence: 2 givenname: Merhatibeb surname: Bezabih fullname: Bezabih, Merhatibeb organization: Department of Chemistry, University of Botswana, Private Bag 0022, Gaborone, Botswana – sequence: 3 givenname: Berhanu M. surname: Abegaz fullname: Abegaz, Berhanu M. email: abegazb@mopipi.ub.bw organization: Department of Chemistry, University of Botswana, Private Bag 0022, Gaborone, Botswana – sequence: 4 givenname: Michael surname: Dreyer fullname: Dreyer, Michael organization: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany – sequence: 5 givenname: Reto surname: Brun fullname: Brun, Reto organization: Swiss Tropical Institute, Socinstrasse 57, CH-4002 Basel, Switzerland – sequence: 6 givenname: Nikolaus surname: Kocher fullname: Kocher, Nikolaus organization: Institute of Inorganic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany – sequence: 7 givenname: Gerhard surname: Bringmann fullname: Bringmann, Gerhard email: bringmann@chemie.uni-wuerzburg.de organization: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany |
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| CitedBy_id | crossref_primary_10_1002_chem_200701328 crossref_primary_10_1002_med_21282 crossref_primary_10_1016_j_chroma_2007_06_034 crossref_primary_10_1021_ol063013b crossref_primary_10_1515_ncrs_2020_0177 crossref_primary_10_1039_b803784c crossref_primary_10_1021_acs_joc_6b01678 crossref_primary_10_1093_jaoacint_qsab075 crossref_primary_10_1016_j_jep_2020_112986 crossref_primary_10_1002_ange_200462661 crossref_primary_10_1371_journal_pone_0090655 crossref_primary_10_1007_s11101_008_9090_8 crossref_primary_10_1016_j_tet_2007_07_001 crossref_primary_10_1211_jpp_61_11_0001 crossref_primary_10_1016_j_bmc_2009_02_022 crossref_primary_10_1016_j_phytochem_2016_11_014 crossref_primary_10_1016_j_phytol_2014_04_004 crossref_primary_10_1155_2018_4089541 crossref_primary_10_1021_ja905628h crossref_primary_10_1021_acs_orglett_9b00706 crossref_primary_10_1002_anie_200462661 crossref_primary_10_1021_jo062566x crossref_primary_10_3390_d14121014 |
| Cites_doi | 10.1021/np0301442 10.1021/np030061l 10.1021/np000247+ 10.1021/np0201218 10.1021/jo020189s 10.1016/S0031-9422(00)81907-X 10.1016/S0031-9422(98)80097-6 10.1071/CH9931245 10.1016/S0031-9422(97)00402-0 10.1016/S0031-9422(00)83479-2 10.1016/S0031-9422(98)00502-0 10.1016/S0031-9422(00)90587-9 10.1016/S0031-9422(97)01053-4 10.1016/S0031-9422(00)90377-7 10.1016/S0031-9422(99)00487-2 10.1002/1099-0690(200203)2002:6<1107::AID-EJOC1107>3.0.CO;2-4 10.1039/a827171z 10.1055/s-2006-960859 10.1016/0031-9422(88)80720-9 10.1016/S0031-9422(00)98585-6 10.1016/0031-9422(77)80079-4 10.1016/0031-9422(88)83161-3 10.1016/0031-9422(79)83027-7 10.1016/S0031-9422(00)81848-8 10.1016/S0031-9422(00)84701-9 10.1016/0031-9422(88)87003-1 10.1016/0031-9422(81)83026-9 10.1016/S0031-9422(01)00345-4 10.1016/S0031-9422(00)94392-9 10.1016/S0040-4020(01)87695-X 10.1039/p19870001821 10.1016/S0031-9422(01)00066-8 10.1016/S0031-9422(00)82374-2 |
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| Keywords | Enantiomeric resolution Bulbine frutescens LC–CD coupling Sulfated phenylanthraquinones Axial chirality Crystal structure DIRECTED BIARYL SYNTHESIS ANTIPLASMODIAL ACTIVITY FLAVERIA-BIDENTIS sulfated phenylanthraquinones KNIPHOLONE enantiomeric resolution FLAVONOID SULFATES axial chirality QUERCETIN CENTAUREA-BRACTEATA LC-CD coupling AERIAL PARTS crystal structure ROOTS DERIVATIVES |
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| References | Toki, Saito, Ueda, Chibana, Shigihara, Honda (bib16) 1994; 37 Ibrahim (bib27) 2000; 53 Bringmann, Menche, Brun, Msuta, Abegaz (bib6) 2002 Thomson, Sharma, Khanna, Rohatgi, Thomson, Khanna, Sharma, Thomson, Capon, Groves, Urban, Watson (bib29) 1997; 27 Cabrera, Juliani (bib24) 1977; 16 Harborne (bib23) 1977 Mues, Timmermann, Ohno, Mabry (bib10) 1979; 18 Barron, Ibrahim (bib30) 1987; 43 Hutchings (bib1) 1996 Bringmann, Menche, Bezabih, Abegaz, Kaminsky (bib3) 1999; 65 Bezabih, Motlhagodi, Abegaz (bib4) 1997; 46 Abegaz, Bezabih, Msuta, Brun, Menche, Mühlbacher, Bringmann (bib2) 2002; 65 Barron, Ibrahim (bib26) 1987; 26 bib28 Cabrera, Juliani (bib25) 1979; 18 Dagne, Steglich (bib8) 1984; 23 Stalke (bib33) 1998; 27 Sheldrick (bib36) 1990; 46 Mann, Tofern, Kaloga, Eich (bib18) 1999; 50 Kuroda, Mimaki, Sakagami, Sashida (bib7) 2003; 66 Barron, Varin, Ibrahim, Harborne, Williams (bib14) 1988; 27 Tomás-Barberán, Harborne, Self (bib13) 1987; 26 Bezabih, Abegaz (bib5) 1998; 48 Sheldrick, G.M. Flamini, Antognoli, Morelli (bib19) 2001; 57 Harborne, Mokhatari (bib21) 1977; 16 Krenn, Presser, Pradhan, Bahr, Paper, Mayer, Kopp (bib22) 2003; 66 Op de Beck, Dijoux, Cartier, Mariotte (bib17) 1998; 47 Ahmed, Mabry (bib12) 1987; 26 Sheldrick, G. M. University of Göttingen, 1997. Harborne (bib9) 1975; 14 Gurni, König, Kubitzki (bib11) 1981; 20 Bringmann, Menche, Kraus, Mühlbacher, Peters, Peters, Brun, Bezabih, Abegaz (bib31) 2002; 67 Seabra, Alves (bib15) 1988; 27 Bringmann, Hamm, Günther, Michel, Brun, Mudogo (bib32) 2000; 63 Bruker-AXS Inc., SAINT-NT; Madison WI, 2000. Bringmann, Günther, Ochse, Schupp, Tasler (bib38) 2001; Vol. 82 van Staden, Drewes (bib39) 1994; 35 Flamini, Pardini, Morelli (bib20) 2001; 58 : University of Göttingen, 2001. BARRON, D (WOS:A1987G630300065) 1987; 26 Bringmann, G (CCC:000173312100001) 2001; 82 BARRON, D (WOS:A1987L130600004) 1987; 43 de Beck, PO (WOS:000073016200046) 1998; 47 Bringmann, G (WOS:000165548000002) 2000; 63 Bezabih, M (WOS:000074694800028) 1998; 48 TOKI, K (WOS:A1994PQ58500052) 1994; 37 Flamini, G (WOS:000172949900016) 2001; 58 Krenn, L (WOS:000184942300016) 2003; 66 THOMSON RH (WOS:000231211800020.38) 1997; 4 HARBORNE, JB (WOS:A1977DL47000046) 1977; 16 GURNI, AA (WOS:A1981LS90300026) 1981; 20 Flamini, G (WOS:000168881100011) 2001; 57 SEABRA, RM (WOS:A1988P894600071) 1988; 27 SHARMA, PK (WOS:A1988M104100074) 1988; 27 BRUK AXS INC (WOS:000231211800020.1) 2000 HUTCHINGS A (WOS:000231211800020.25) 1996 CABRERA, JL (WOS:A1977DB80100029) 1977; 16 VANSTADEN, LF (WOS:A1994MY39400028) 1994; 35 Mann, P (WOS:000078216500013) 1999; 50 HARBORNE JB (WOS:000231211800020.22) 1977 SHELDRICK, GM (WOS:A1990DJ92700008) 1990; 46 Bringmann, G (WOS:000177318300017) 2002; 67 CABRERA, JL (WOS:A1979GN24900038) 1979; 18 BARRON, D (WOS:A1988P401400002) 1988; 27 Stalke, D (WOS:000074059200001) 1998; 27 SHELDRICK GM (WOS:000231211800020.34) 2001 SHELDRICK GM (WOS:000231211800020.36) 1997 CAPON, RJ (WOS:A1993LN84100011) 1993; 46 AHMED, AA (WOS:A1987H639600059) 1987; 26 Bezabih, M (WOS:A1997YH45900016) 1997; 46 Ibrahim, ARS (WOS:000085178000006) 2000; 53 Bringmann, G (WOS:000174531400017) 2002; 2002 Kuroda, M (WOS:000183814600036) 2003; 66 Abegaz, BM (WOS:000177703000006) 2002; 65 DAGNE, E (WOS:A1984TE04600049) 1984; 23 TOMASBARBERAN, FA (WOS:A1987J488900027) 1987; 26 HARBORNE, JB (WOS:A1975AJ88500002) 1975; 14 Bringmann, G (WOS:000084478700022) 1999; 65 MUES, R (WOS:A1979HG72700024) 1979; 18 KHANNA, RN (WOS:A1987J657300029) 1987 Flamini (10.1016/j.tet.2005.06.055_bib20) 2001; 58 10.1016/j.tet.2005.06.055_bib35 Sheldrick (10.1016/j.tet.2005.06.055_bib36) 1990; 46 Seabra (10.1016/j.tet.2005.06.055_bib15) 1988; 27 10.1016/j.tet.2005.06.055_bib34 Harborne (10.1016/j.tet.2005.06.055_bib21) 1977; 16 Tomás-Barberán (10.1016/j.tet.2005.06.055_bib13) 1987; 26 Barron (10.1016/j.tet.2005.06.055_bib14) 1988; 27 Bringmann (10.1016/j.tet.2005.06.055_bib31) 2002; 67 Kuroda (10.1016/j.tet.2005.06.055_bib7) 2003; 66 10.1016/j.tet.2005.06.055_bib37 Krenn (10.1016/j.tet.2005.06.055_bib22) 2003; 66 Ibrahim (10.1016/j.tet.2005.06.055_bib27) 2000; 53 Bringmann (10.1016/j.tet.2005.06.055_bib3) 1999; 65 Capon (10.1016/j.tet.2005.06.055_bib29_4) 1993; 46 Toki (10.1016/j.tet.2005.06.055_bib16) 1994; 37 Op de Beck (10.1016/j.tet.2005.06.055_bib17) 1998; 47 Barron (10.1016/j.tet.2005.06.055_bib26) 1987; 26 Bringmann (10.1016/j.tet.2005.06.055_bib38) 2001; Vol. 82 Hutchings (10.1016/j.tet.2005.06.055_bib1) 1996 Harborne (10.1016/j.tet.2005.06.055_bib9) 1975; 14 van Staden (10.1016/j.tet.2005.06.055_bib39) 1994; 35 Bringmann (10.1016/j.tet.2005.06.055_bib6) 2002 Bringmann (10.1016/j.tet.2005.06.055_bib32) 2000; 63 Thomson (10.1016/j.tet.2005.06.055_bib29_1) 1997 Mann (10.1016/j.tet.2005.06.055_bib18) 1999; 50 Sharma (10.1016/j.tet.2005.06.055_bib29_2) 1988; 27 Harborne (10.1016/j.tet.2005.06.055_bib23) 1977 Gurni (10.1016/j.tet.2005.06.055_bib11) 1981; 20 Flamini (10.1016/j.tet.2005.06.055_bib19) 2001; 57 Dagne (10.1016/j.tet.2005.06.055_bib8) 1984; 23 Mues (10.1016/j.tet.2005.06.055_bib10) 1979; 18 Barron (10.1016/j.tet.2005.06.055_bib30) 1987; 43 Stalke (10.1016/j.tet.2005.06.055_bib33) 1998; 27 Bezabih (10.1016/j.tet.2005.06.055_bib5) 1998; 48 Cabrera (10.1016/j.tet.2005.06.055_bib25) 1979; 18 Abegaz (10.1016/j.tet.2005.06.055_bib2) 2002; 65 Khanna (10.1016/j.tet.2005.06.055_bib29_3) 1987 Ahmed (10.1016/j.tet.2005.06.055_bib12) 1987; 26 Bezabih (10.1016/j.tet.2005.06.055_bib4) 1997; 46 Cabrera (10.1016/j.tet.2005.06.055_bib24) 1977; 16 |
| References_xml | – volume: 27 start-page: 3019 year: 1988 end-page: 3020 ident: bib15 publication-title: Phytochemistry contributor: fullname: Alves – volume: 58 start-page: 1229 year: 2001 end-page: 1233 ident: bib20 publication-title: Phytochemistry contributor: fullname: Morelli – volume: 66 start-page: 1107 year: 2003 end-page: 1109 ident: bib22 publication-title: J. Nat. Prod. contributor: fullname: Kopp – volume: 48 start-page: 1071 year: 1998 end-page: 1073 ident: bib5 publication-title: Phytochemistry contributor: fullname: Abegaz – start-page: 1107 year: 2002 end-page: 1111 ident: bib6 publication-title: Eur. J. Org. Chem. contributor: fullname: Abegaz – year: 1977 ident: bib23 publication-title: Biology and Chemistry of the Compositae contributor: fullname: Harborne – volume: 53 start-page: 209 year: 2000 end-page: 212 ident: bib27 publication-title: Phytochemistry contributor: fullname: Ibrahim – volume: 47 start-page: 1171 year: 1998 end-page: 1173 ident: bib17 publication-title: Phytochemistry contributor: fullname: Mariotte – volume: 16 start-page: 400 year: 1977 ident: bib24 publication-title: Phytochemistry contributor: fullname: Juliani – volume: 14 start-page: 1147 year: 1975 end-page: 1155 ident: bib9 publication-title: Phytochemistry contributor: fullname: Harborne – ident: bib28 – volume: 43 start-page: 5197 year: 1987 end-page: 5202 ident: bib30 publication-title: Tetrahedron contributor: fullname: Ibrahim – volume: 23 start-page: 1729 year: 1984 end-page: 1731 ident: bib8 publication-title: Phytochemistry contributor: fullname: Steglich – volume: 18 start-page: 510 year: 1979 end-page: 511 ident: bib25 publication-title: Phytochemistry contributor: fullname: Juliani – volume: 26 start-page: 1517 year: 1987 end-page: 1518 ident: bib12 publication-title: Phytochemistry contributor: fullname: Mabry – volume: 37 start-page: 885 year: 1994 end-page: 887 ident: bib16 publication-title: Phytochemistry contributor: fullname: Honda – volume: 50 start-page: 267 year: 1999 end-page: 271 ident: bib18 publication-title: Phytochemistry contributor: fullname: Eich – volume: 63 start-page: 1465 year: 2000 end-page: 1470 ident: bib32 publication-title: J. Nat. Prod. contributor: fullname: Mudogo – volume: 26 start-page: 2281 year: 1987 end-page: 2284 ident: bib13 publication-title: Phytochemistry contributor: fullname: Self – volume: Vol. 82 start-page: 1 year: 2001 end-page: 249 ident: bib38 publication-title: Progress in the Chemistry of Organic Natural Products contributor: fullname: Tasler – volume: 67 start-page: 5595 year: 2002 end-page: 5610 ident: bib31 publication-title: J. Org. Chem. contributor: fullname: Abegaz – volume: 35 start-page: 685 year: 1994 end-page: 686 ident: bib39 publication-title: Phytochemistry contributor: fullname: Drewes – volume: 46 start-page: 1063 year: 1997 end-page: 1067 ident: bib4 publication-title: Phytochemistry contributor: fullname: Abegaz – volume: 16 start-page: 1314 year: 1977 end-page: 1315 ident: bib21 publication-title: Phytochemistry contributor: fullname: Mokhatari – year: 1996 ident: bib1 article-title: Zulu Medicinal Plants: An Inventory contributor: fullname: Hutchings – volume: 65 start-page: 757 year: 1999 end-page: 758 ident: bib3 publication-title: Planta Med. contributor: fullname: Kaminsky – volume: 65 start-page: 1117 year: 2002 end-page: 1121 ident: bib2 publication-title: J. Nat. Prod. contributor: fullname: Bringmann – volume: 20 start-page: 1057 year: 1981 end-page: 1059 ident: bib11 publication-title: Phytochemistry contributor: fullname: Kubitzki – volume: 57 start-page: 559 year: 2001 end-page: 564 ident: bib19 publication-title: Phytochemistry contributor: fullname: Morelli – volume: 18 start-page: 1379 year: 1979 end-page: 1383 ident: bib10 publication-title: Phytochemistry contributor: fullname: Mabry – volume: 27 start-page: 2375 year: 1988 end-page: 2395 ident: bib14 publication-title: Phytochemistry contributor: fullname: Williams – volume: 66 start-page: 894 year: 2003 end-page: 897 ident: bib7 publication-title: J. Nat. Prod. contributor: fullname: Sashida – volume: 26 start-page: 1181 year: 1987 end-page: 1184 ident: bib26 publication-title: Phytochemistry contributor: fullname: Ibrahim – volume: 27 start-page: 632 year: 1997 end-page: 633 ident: bib29 article-title: Naturally Occurring Quinones IV Recent Advances publication-title: Phytochemistry contributor: fullname: Watson – volume: 46 start-page: 467 year: 1990 end-page: 473 ident: bib36 article-title: Acta Crystallogr., Sect. A publication-title: Sect. A contributor: fullname: Sheldrick – volume: 27 start-page: 171 year: 1998 end-page: 178 ident: bib33 publication-title: Chem. Soc. Rev. contributor: fullname: Stalke – volume: 58 start-page: 1229 year: 2001 ident: WOS:000172949900016 article-title: A flavonoid sulphate and other compounds from the roots of Centaurea bracteata publication-title: PHYTOCHEMISTRY contributor: fullname: Flamini, G – volume: 43 start-page: 5197 year: 1987 ident: WOS:A1987L130600004 article-title: SYNTHESIS OF FLAVONOID SULFATES .1. STEPWISE SULFATION OF POSITION-3, POSITION-7, AND POSITION-4' USING N,N'-DICYCLOHEXYLCARBODIIMIDE AND TETRABUTYLAMMONIUM HYDROGEN SULFATE publication-title: TETRAHEDRON contributor: fullname: BARRON, D – volume: 66 start-page: 1107 year: 2003 ident: WOS:000184942300016 article-title: Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np0301442 contributor: fullname: Krenn, L – volume: 18 start-page: 510 year: 1979 ident: WOS:A1979GN24900038 article-title: 2 NEW QUERCETIN SULFATES FROM LEAVES OF FLAVERIA-BIDENTIS publication-title: PHYTOCHEMISTRY contributor: fullname: CABRERA, JL – volume: 20 start-page: 1057 year: 1981 ident: WOS:A1981LS90300026 article-title: FLAVONOID GLYCOSIDES AND SULFATES FROM THE DILLENIACEAE publication-title: PHYTOCHEMISTRY contributor: fullname: GURNI, AA – volume: 66 start-page: 894 year: 2003 ident: WOS:000183814600036 article-title: Bulbinelonesides A-E, phenylanthraquinone glycosides from the roots of Bulbinella floribunda publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np030061l contributor: fullname: Kuroda, M – volume: 35 start-page: 685 year: 1994 ident: WOS:A1994MY39400028 article-title: KNIPHOLONE FROM BULBINE LATIFOLIA AND BULBINE FRUTESCENS publication-title: PHYTOCHEMISTRY contributor: fullname: VANSTADEN, LF – volume: 47 start-page: 1171 year: 1998 ident: WOS:000073016200046 article-title: Quercitrin 3 '-sulphate from leaves of Leea guinensis publication-title: PHYTOCHEMISTRY contributor: fullname: de Beck, PO – volume: 2002 start-page: 1107 year: 2002 ident: WOS:000174531400017 article-title: Novel concepts in directed biaryl synthesis. Part 98. Bulbine-knipholone, a new, axially chiral phenylanthraquinone from Bulbine abyssinica (Asphodelaceae): Isolation, structural elucidation, synthesis, and antiplasmodial activity publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Bringmann, G – start-page: 137 year: 1996 ident: WOS:000231211800020.25 publication-title: ZULU MED PLANTS INVE contributor: fullname: HUTCHINGS A – volume: 27 start-page: 2375 year: 1988 ident: WOS:A1988P401400002 article-title: SULFATED FLAVONOIDS - AN UPDATE publication-title: PHYTOCHEMISTRY contributor: fullname: BARRON, D – volume: 63 start-page: 1465 year: 2000 ident: WOS:000165548000002 article-title: Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np000247+ contributor: fullname: Bringmann, G – start-page: 1821 year: 1987 ident: WOS:A1987J657300029 article-title: A REVISED STRUCTURE FOR DEHYDROTECTOL AND TECOMAQUINONE-I publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: KHANNA, RN – volume: 53 start-page: 209 year: 2000 ident: WOS:000085178000006 article-title: Sulfation of naringenin by Cunninghamella elegans publication-title: PHYTOCHEMISTRY contributor: fullname: Ibrahim, ARS – volume: 50 start-page: 267 year: 1999 ident: WOS:000078216500013 article-title: Flavonoid sulfates from the Convolvulaceae publication-title: PHYTOCHEMISTRY contributor: fullname: Mann, P – volume: 27 start-page: 632 year: 1988 ident: WOS:A1988M104100074 article-title: TECOMAQUINONE-III - A NEW QUINONE FROM TABEBUIA-PENTAPHYLLA publication-title: PHYTOCHEMISTRY contributor: fullname: SHARMA, PK – volume: 37 start-page: 885 year: 1994 ident: WOS:A1994PQ58500052 article-title: MALVIDIN 3-GLUCOSIDE-5-GLUCOSIDE SULFATES FROM BABIANA-STRICTA publication-title: PHYTOCHEMISTRY contributor: fullname: TOKI, K – year: 1977 ident: WOS:000231211800020.22 publication-title: BIOL CHEM COMPOSITAE contributor: fullname: HARBORNE JB – volume: 26 start-page: 2281 year: 1987 ident: WOS:A1987J488900027 article-title: 12 6-OXYGENATED FLAVONE SULFATES FROM LIPPIA-NODIFLORA AND LIPPIA-CANESCENS publication-title: PHYTOCHEMISTRY contributor: fullname: TOMASBARBERAN, FA – volume: 27 start-page: 3019 year: 1988 ident: WOS:A1988P894600071 article-title: QUERCETIN 3-GLUCURONIDE-3'-SULPHATE FROM HYPERICUM-ELODES publication-title: PHYTOCHEMISTRY contributor: fullname: SEABRA, RM – year: 1997 ident: WOS:000231211800020.36 publication-title: SHELXL 97 PROGRAM CR contributor: fullname: SHELDRICK GM – volume: 57 start-page: 559 year: 2001 ident: WOS:000168881100011 article-title: Two flavonoids and other compounds from the aerial parts of Centaurea bracteata from Italy publication-title: PHYTOCHEMISTRY contributor: fullname: Flamini, G – volume: 82 start-page: 1 year: 2001 ident: CCC:000173312100001 article-title: Biaryls in nature: A multi-facetted class of stereochemically, biosynthetically, and pharmacologically intriguing secondary metabolites publication-title: PROGRESS IN THE CHEMISTRY OF ORGANIC NATURAL PRODUCTS, VOL 82 contributor: fullname: Bringmann, G – volume: 46 start-page: 1245 year: 1993 ident: WOS:A1993LN84100011 article-title: SPONGIAQUINONE REVISITED - STRUCTURAL AND STEREOCHEMICAL STUDIES ON MARINE SESQUITERPENE QUINONES FROM A SOUTHERN AUSTRALIAN MARINE SPONGE, SPONGIA SP publication-title: AUSTRALIAN JOURNAL OF CHEMISTRY contributor: fullname: CAPON, RJ – volume: 23 start-page: 1729 year: 1984 ident: WOS:A1984TE04600049 article-title: KNIPHOLONE - A UNIQUE ANTHRAQUINONE DERIVATIVE FROM KNIPHOFIA-FOLIOSA publication-title: PHYTOCHEMISTRY contributor: fullname: DAGNE, E – year: 2001 ident: WOS:000231211800020.34 publication-title: SADABS 2 03 contributor: fullname: SHELDRICK GM – volume: 48 start-page: 1071 year: 1998 ident: WOS:000074694800028 article-title: 4 '-demethylknipholone from aerial parts of Bulbine capitata publication-title: PHYTOCHEMISTRY contributor: fullname: Bezabih, M – volume: 16 start-page: 400 year: 1977 ident: WOS:A1977DB80100029 article-title: ISORHAMNETIN 3,7-DISULFATE FROM FLAVERIA-BIDENTIS publication-title: PHYTOCHEMISTRY contributor: fullname: CABRERA, JL – volume: 14 start-page: 1147 year: 1975 ident: WOS:A1975AJ88500002 article-title: FLAVONOID SULFATES - NEW CLASS OF SULFUR-COMPOUNDS IN HIGHER-PLANTS publication-title: PHYTOCHEMISTRY contributor: fullname: HARBORNE, JB – volume: 46 start-page: 1063 year: 1997 ident: WOS:A1997YH45900016 article-title: Isofuranonaphthoquinones and phenolic and knipholone derivatives from the roots of Bulbine capitata publication-title: PHYTOCHEMISTRY contributor: fullname: Bezabih, M – year: 2000 ident: WOS:000231211800020.1 publication-title: SAINT NT contributor: fullname: BRUK AXS INC – volume: 65 start-page: 1117 year: 2002 ident: WOS:000177703000006 article-title: Gaboroquinones A and B and 4 '-O-demethylknipholone-4 '-O-,8-D-glucopyranoside, phenylanthraquinones from the roots of Bulbine frutescens publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np0201218 contributor: fullname: Abegaz, BM – volume: 26 start-page: 1517 year: 1987 ident: WOS:A1987H639600059 article-title: FLAVONOIDS OF IPHIONA-SCABRA publication-title: PHYTOCHEMISTRY contributor: fullname: AHMED, AA – volume: 26 start-page: 1181 year: 1987 ident: WOS:A1987G630300065 article-title: QUERCETIN AND PATULETIN 3,3'-DISULFATES FROM FLAVERIA-CHLORAEFOLIA publication-title: PHYTOCHEMISTRY contributor: fullname: BARRON, D – volume: 4 start-page: 134 year: 1997 ident: WOS:000231211800020.38 publication-title: NATURALLY OCCURING Q contributor: fullname: THOMSON RH – volume: 67 start-page: 5595 year: 2002 ident: WOS:000177318300017 article-title: Novel concepts in directed biaryl synthesis, part 100 - Atropo-enantioselective total synthesis of knipholone and related antiplasmodial phenylanthraquinones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo020189s contributor: fullname: Bringmann, G – volume: 27 start-page: 171 year: 1998 ident: WOS:000074059200001 article-title: Cryo crystal structure determination and application to intermediates publication-title: CHEMICAL SOCIETY REVIEWS contributor: fullname: Stalke, D – volume: 46 start-page: 467 year: 1990 ident: WOS:A1990DJ92700008 article-title: PHASE ANNEALING IN SHELX-90 - DIRECT METHODS FOR LARGER STRUCTURES publication-title: ACTA CRYSTALLOGRAPHICA SECTION A contributor: fullname: SHELDRICK, GM – volume: 16 start-page: 1314 year: 1977 ident: WOS:A1977DL47000046 article-title: 2 SULFATED ANTHRAQUINONE DERIVATIVES IN RUMEX-PULCHER publication-title: PHYTOCHEMISTRY contributor: fullname: HARBORNE, JB – volume: 18 start-page: 1379 year: 1979 ident: WOS:A1979HG72700024 article-title: 6-METHOXYFLAVONOIDS FROM BRICKELLIA-CALIFORNICA publication-title: PHYTOCHEMISTRY contributor: fullname: MUES, R – volume: 65 start-page: 757 year: 1999 ident: WOS:000084478700022 article-title: Antiplasmodial activity of knipholone and related natural phenylanthraquinones publication-title: PLANTA MEDICA contributor: fullname: Bringmann, G – year: 1977 ident: 10.1016/j.tet.2005.06.055_bib23 contributor: fullname: Harborne – ident: 10.1016/j.tet.2005.06.055_bib35 – ident: 10.1016/j.tet.2005.06.055_bib37 – volume: 66 start-page: 1107 year: 2003 ident: 10.1016/j.tet.2005.06.055_bib22 publication-title: J. Nat. Prod. doi: 10.1021/np0301442 contributor: fullname: Krenn – volume: 67 start-page: 5595 year: 2002 ident: 10.1016/j.tet.2005.06.055_bib31 publication-title: J. Org. Chem. doi: 10.1021/jo020189s contributor: fullname: Bringmann – volume: 18 start-page: 510 year: 1979 ident: 10.1016/j.tet.2005.06.055_bib25 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)81907-X contributor: fullname: Cabrera – volume: 65 start-page: 1117 year: 2002 ident: 10.1016/j.tet.2005.06.055_bib2 publication-title: J. Nat. Prod. doi: 10.1021/np0201218 contributor: fullname: Abegaz – volume: 47 start-page: 1171 year: 1998 ident: 10.1016/j.tet.2005.06.055_bib17 publication-title: Phytochemistry doi: 10.1016/S0031-9422(98)80097-6 contributor: fullname: Op de Beck – volume: 46 start-page: 1245 year: 1993 ident: 10.1016/j.tet.2005.06.055_bib29_4 publication-title: Aust. J. Chem. doi: 10.1071/CH9931245 contributor: fullname: Capon – volume: 46 start-page: 1063 year: 1997 ident: 10.1016/j.tet.2005.06.055_bib4 publication-title: Phytochemistry doi: 10.1016/S0031-9422(97)00402-0 contributor: fullname: Bezabih – volume: 23 start-page: 1729 year: 1984 ident: 10.1016/j.tet.2005.06.055_bib8 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)83479-2 contributor: fullname: Dagne – volume: 66 start-page: 894 year: 2003 ident: 10.1016/j.tet.2005.06.055_bib7 publication-title: J. Nat. Prod. doi: 10.1021/np030061l contributor: fullname: Kuroda – volume: 50 start-page: 267 year: 1999 ident: 10.1016/j.tet.2005.06.055_bib18 publication-title: Phytochemistry doi: 10.1016/S0031-9422(98)00502-0 contributor: fullname: Mann – volume: 35 start-page: 685 year: 1994 ident: 10.1016/j.tet.2005.06.055_bib39 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)90587-9 contributor: fullname: van Staden – volume: 48 start-page: 1071 year: 1998 ident: 10.1016/j.tet.2005.06.055_bib5 publication-title: Phytochemistry doi: 10.1016/S0031-9422(97)01053-4 contributor: fullname: Bezabih – volume: 37 start-page: 885 year: 1994 ident: 10.1016/j.tet.2005.06.055_bib16 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)90377-7 contributor: fullname: Toki – volume: Vol. 82 start-page: 1 year: 2001 ident: 10.1016/j.tet.2005.06.055_bib38 contributor: fullname: Bringmann – volume: 53 start-page: 209 year: 2000 ident: 10.1016/j.tet.2005.06.055_bib27 publication-title: Phytochemistry doi: 10.1016/S0031-9422(99)00487-2 contributor: fullname: Ibrahim – start-page: 1107 year: 2002 ident: 10.1016/j.tet.2005.06.055_bib6 publication-title: Eur. J. Org. Chem. doi: 10.1002/1099-0690(200203)2002:6<1107::AID-EJOC1107>3.0.CO;2-4 contributor: fullname: Bringmann – volume: 27 start-page: 171 year: 1998 ident: 10.1016/j.tet.2005.06.055_bib33 publication-title: Chem. Soc. Rev. doi: 10.1039/a827171z contributor: fullname: Stalke – volume: 65 start-page: 757 year: 1999 ident: 10.1016/j.tet.2005.06.055_bib3 publication-title: Planta Med. doi: 10.1055/s-2006-960859 contributor: fullname: Bringmann – volume: 27 start-page: 3019 year: 1988 ident: 10.1016/j.tet.2005.06.055_bib15 publication-title: Phytochemistry doi: 10.1016/0031-9422(88)80720-9 contributor: fullname: Seabra – volume: 14 start-page: 1147 year: 1975 ident: 10.1016/j.tet.2005.06.055_bib9 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)98585-6 contributor: fullname: Harborne – volume: 46 start-page: 467 year: 1990 ident: 10.1016/j.tet.2005.06.055_bib36 article-title: Acta Crystallogr., Sect. A publication-title: Sect. A contributor: fullname: Sheldrick – year: 1996 ident: 10.1016/j.tet.2005.06.055_bib1 contributor: fullname: Hutchings – volume: 16 start-page: 400 year: 1977 ident: 10.1016/j.tet.2005.06.055_bib24 publication-title: Phytochemistry doi: 10.1016/0031-9422(77)80079-4 contributor: fullname: Cabrera – volume: 27 start-page: 632 year: 1988 ident: 10.1016/j.tet.2005.06.055_bib29_2 publication-title: Phytochemistry doi: 10.1016/0031-9422(88)83161-3 contributor: fullname: Sharma – volume: 18 start-page: 1379 year: 1979 ident: 10.1016/j.tet.2005.06.055_bib10 publication-title: Phytochemistry doi: 10.1016/0031-9422(79)83027-7 contributor: fullname: Mues – volume: 26 start-page: 1517 year: 1987 ident: 10.1016/j.tet.2005.06.055_bib12 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)81848-8 contributor: fullname: Ahmed – volume: 26 start-page: 2281 year: 1987 ident: 10.1016/j.tet.2005.06.055_bib13 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)84701-9 contributor: fullname: Tomás-Barberán – volume: 27 start-page: 2375 year: 1988 ident: 10.1016/j.tet.2005.06.055_bib14 publication-title: Phytochemistry doi: 10.1016/0031-9422(88)87003-1 contributor: fullname: Barron – volume: 20 start-page: 1057 year: 1981 ident: 10.1016/j.tet.2005.06.055_bib11 publication-title: Phytochemistry doi: 10.1016/0031-9422(81)83026-9 contributor: fullname: Gurni – volume: 58 start-page: 1229 year: 2001 ident: 10.1016/j.tet.2005.06.055_bib20 publication-title: Phytochemistry doi: 10.1016/S0031-9422(01)00345-4 contributor: fullname: Flamini – volume: 16 start-page: 1314 year: 1977 ident: 10.1016/j.tet.2005.06.055_bib21 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)94392-9 contributor: fullname: Harborne – volume: 43 start-page: 5197 year: 1987 ident: 10.1016/j.tet.2005.06.055_bib30 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)87695-X contributor: fullname: Barron – start-page: 1821 year: 1987 ident: 10.1016/j.tet.2005.06.055_bib29_3 publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/p19870001821 contributor: fullname: Khanna – volume: 57 start-page: 559 year: 2001 ident: 10.1016/j.tet.2005.06.055_bib19 publication-title: Phytochemistry doi: 10.1016/S0031-9422(01)00066-8 contributor: fullname: Flamini – year: 1997 ident: 10.1016/j.tet.2005.06.055_bib29_1 contributor: fullname: Thomson – volume: 63 start-page: 1465 year: 2000 ident: 10.1016/j.tet.2005.06.055_bib32 publication-title: J. Nat. Prod. doi: 10.1021/np000247+ contributor: fullname: Bringmann – volume: 26 start-page: 1181 year: 1987 ident: 10.1016/j.tet.2005.06.055_bib26 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)82374-2 contributor: fullname: Barron – ident: 10.1016/j.tet.2005.06.055_bib34 |
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Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures... From the roots of Bulbine frutescens, the first sulfated phenylanthraquinones were isolated, together with their known sulfate-free analogs. Their structures... |
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| SubjectTerms | Axial chirality Bulbine frutescens Chemistry Chemistry, Organic Crystal structure Enantiomeric resolution LC–CD coupling Physical Sciences Science & Technology Sulfated phenylanthraquinones |
| Title | The first 6′- O-sulfated phenylanthraquinones: isolation from Bulbine frutescens, structural elucidation, enantiomeric purity, and partial synthesis |
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