Tetrahydroanthraquinone And Anthraquinone Gentiobiosides From Dermocybe Splendida; The First Anthraquinonoid Disaccharides From Basidiomycetes

References

• Gill , M. and Kiefel , M. J. 1992 . “ Ravenelone, A Novel Butenolide, And Rare Pulvinic Acid Derivatives From Pulveroboletus Ravenelii (Berk. & Curt.) Murr ” . In Lift Science Advances In Press, Part 30 In The Series Pigments Of Fungi': For Part 29
   Google Scholar
• Gill , M. and Steglich , W. 1987 . “ Pigments Of Fungi (Macromycetes) ” . In Progress In The Chemistry Of Organic Natural Products , Edited by: Here , W. , Grisebach , H. , Kirby , G. W. and Tamm , Ch. 1 – 317 . Wein And New York : Springer .
   Google Scholar
• Steglich , W. , Lösel , W. and Austel , V. 1969 . Anthrachinon-Pigmente Aus Dermocybe Sanguinea (Wulf. Ex Fr.) Wünsche Und D. Semisanguinea . Chemische Berichte , 102 : 4104 – 4118 .
   Google Scholar
• Steglich , W. and Reininger , W. 1972 . Anthrachinon-Pigmente Aus Dermocybe Cinnabarina (Fr.) Wünsche . Chemische Berichte , 105 : 2922 – 2927 .
   PubMedGoogle Scholar
• Several Anthraquinone-8-O-Glycosides Are Known From Higher Plants: E.G., Physcion [1; R1=Me,R=H] Occurs As Its 8-O-β-D-Gentiobioside In Ripe Seeds Of Cassia Torosa [S. Kitanaka And M. Takido (1984) Torosachrysone And Physcion Gentiobiosides From The Seeds Of Cassia Torosa. Chemical And Pharmaceutical Bulletin, 32, 3436–3440] And In Rhubarb Roots [L. Holzschuh, B. Kopp And W. Kubelka (1982) Physcion-8-O-β-D-Gentiobioside, A New Anthraquinone Glycoside From Rhubarb Roots. Planta Medica, 46, 159–161]
   Google Scholar
• Ethanolic Extraction Of The Fresh Basidiomes Of D. Splendida Has Previously Afforded The Aglycones 8,10,14,18 And 22; For Full Details See Refs. 7 And 12
   Google Scholar
• Gill , M. , Smrdel , A. F. , Strauch , R. J. and Begley , M. J. 1990 . Pigments Of Fungi. Part 12. Structure And Absolute Stereochemistry Of Antibiotic Tetrahydroanthraquinones From The Fungus Dermocybe Splendida Horak. X-Ray Structure Determination Of Austrocortirubin Phenylboronate And Austrocortilutein Acetonide . Journal Of The Chemical Society, Perkin Transactions , 1 : 1583 – 1592 .
   Google Scholar
• Smrdel , A. F. Ph.D. Thesis University Of Melbourne . In Preparation; Details Will Be Given In The Full Paper
   Google Scholar
• Arcamone , F. and Penco , S. 1988 . “ Synthesis Of New Doxorubitin Analogs ” . In Anthracycline And Anthacenedione-Based Anticancer Agents , Edited by: Lown , J. W. 1 – 53 . Amsterdam And New York : Elsevier .
   Google Scholar
• Selected Spectroscopic Data For 5: δH (400 Mhz, Cdcl3) 13.06 (1h, S, Peri-Oh), 7.11 (1h, S, 7-H), 6.21 (1h, M, 1-H), 5.24–5.32 (2h, M, 2′-H And 3′-H), 5.12 (1h, Dd, J 9.5 And 9.5 Hz, 3″-H), 5.01 (1h, Dd, J 9.5 And 9.5 Hz, 4′-H), 5.00 (1h, Dd, J 9.9 And 9.5 Hz, 4″-H), 4.97 (1h, D, J 7.7 Hz, 1′-H), 4.88 (1h, Dd, J 9.5 And 8.1 Hz, 2″-H), 4.52 (1h, D, J 8.1 Hz, 1″-H), 4.19 (1h, Dd, J 12.5 And 5.1 Hz, 6″-HA), 4.08 (1h, Dd, J 12.5 And 2.2 Hz, 6″-HB), 4.00 (3h, S, 6-Ome), 3.85 (1h, Dd, J 10.6 And 1.1 Hz, 6′-HB), 3.73–3.79 (1h, M, 5′-H), 3.71 (1h, Dd, J 10.6 And 6.4 Hz, 6′-HA), 3.66 (1h, Ddd, J 9.9, 5.1 And 2.2 Hz, 5″-H), 3.10 (1h, Dd, J 19.8 And 1.5 Hz, 4-HEq), 2.53 (1h, S, 3-Oh), 2.45 (1h, Dd, J 19.8 And 1.1 Hz, 4-HAx), 2.21 (1h, Dm, J 15.4 Hz, 2-HEq), 2.13 (3h, S, Oac), 2.08 (6h, S, 2 X Oac), 2.05, 2.04, 2.03, 1.99, 1.94 (Each 3h, All S, Oac), 1.87 (1h, Dd, J 15.4 And 5.1 Hz, 2-HAx), 1.42 (3h, S, 3-Me); δC (100 Mhz) 190.0 (S, C-10), 179.1 (S, C-9), 170.4, 170.2, 170.1, 169.8, 169.4, 169.3, 169.2, 169.0 (All Q, J 7.3 Hz, Ch3 CO2), 154.2 (M, C-6), 151.0 (Dd, J 4.4 And 4.4 Hz, C-8), 150.5 (Dd, J 7.4 And 4.4 Hz, C-5), 143.5 (M, C-4a), 141.1 (M, C-9a), 114.1 (D, J 4.4 Hz, C-10a), 113.0 (D, J 5.9 Hz, C-8a), 112.1 (D, J 164.3 Hz, C-7), 101.0 (D, J 162.8 Hz, C-1″), 100.9 (D, J 161.3 Hz, C-1′), 73.2 (D, J 143.8 Hz, C-5′), 72.6 (D, J 149.6 Hz, C-3″), 72.3 (D, J 151.1 Hz, C-3′), 72.1 (D, J 143.7 Hz, C-5″), 70.8 (D, J 153.4 Hz, C-2′), 70.7 (D, J 150.5 Hz, C-2″), 68.7 (D, J 152.6 Hz, C-4′), 68.2 (T, J 145.3 Hz, C-6′), 68.1 (D, J 154.1 Hz, C-4″), 67.0 (M, C-3), 63.9 (Dd, J 154.0 And 5.9 Hz, C-1), 61.8 (T, J 148.9 Hz, C-6″), 56.6 (Q, J 146.7 Hz, 6-Ome), 39.2 (Tm, J 128.4 Hz, C-2), 36.5 (Tm, J 126.1 Hz, C-4), 29.5 (Q, J 126.1 Hz, 3-Me), 21.1, 20.8, 20.7 (All Q, J 130.6 Hz, CH3Co2), 20.6, 20.5 (Both Q, J 130.6 Hz, Each 2 X CH3Co2), 20.4 (Q, J 130.6 Hz, CH3Co2)
   Google Scholar
• Kelly , T. R. , Saha , J. K. and Whittle , R. R. 1985 . Bostrycin: Structure Correction And Synthesis . Journal Of Organic Chemistry , 50 : 3679 – 3685 .
   Web of Science ®Google Scholar
• Archard , M. A. , Gill , M. and Strauch , R. J. 1985 . Anthraquinones From The Genus Cortinarius . Phytochemistry , 24 : 2755 – 2758 .
   Web of Science ®Google Scholar
• Keller , G. and Steglich , W. Unpublished Work Cited In Ref. 2
   Google Scholar
• Saubern , S. Ph.D. Thesis University Of Melbourne . In Preparation; Details Will Be Given In The Full Paper
   Google Scholar
• Gill , M. , Giménez , A. , Jhingran , A. G. and Smrdel , A. F. 1989 . Dihydroanthracenones From Dermocybe Splendida And Related Fungi . Phytochemistry , 28 : 2647 – 2650 .
   Web of Science ®Google Scholar
• Kitanaka , S. and Takido , M. In Ref. 5
   Google Scholar