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Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius.
J Nat Prod. 2004 May; 67(5):823-8.JN

Abstract

Three unique pyrano[4,3-c][2]benzopyran-1,6-dione derivatives and a new furo[3,2-c]pyran-4-one, named phelligridins C-F (2-5), together with hispolon (8), (E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one (9), 4-hydroxybenzaldehyde, protocatechualdehyde, syringic acid, protocatechuic acid, caffeic acid, isoergosterone, and octadecyl ferulate were isolated and identified from the ethanolic extract of Phellinus igniarius. Their structures were determined by spectroscopic methods including IR, MS, and 1D and 2D NMR experiments. The structures of the new compounds were characterized as 3-(4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (2), 3-(3,4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (3), 8,9-dihydroxy-3-[5',6'-dihydroxy-5' '-methyl-3' '-oxo-spiro[fural-2' '(3' 'H),1'-indene]-2'-yl]-1H,6H-pyrano[4,3-c][2]benzopyran-1,6-dione (4), and (3Z)-3-(3,4-dihydroxybenzylidene)-6-(3,4-dihydroxystyryl)-2,3-dihydro-2-methoxy-2-(2-oxo-propyl)furo[3,2-c]pyran-4-one (5), respectively. Some compounds including 2 and 3 showed in vitro selective cytotoxicity against a human lung cancer cell line (A549) and a liver cancer cell line (Bel7402). Possible biogenetic sequences to the formation of 1-9 are postulated.

Authors+Show Affiliations

Mo S
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
Wang S
No affiliation info available
Zhou G
No affiliation info available
Yang Y
No affiliation info available
Li Y
No affiliation info available
Chen X
No affiliation info available
Shi J
No affiliation info available

MeSH

Antineoplastic AgentsBenzofuransBenzopyransChinaDrug Screening Assays, AntitumorHumansMolecular ConformationMolecular StructurePolyporaceaeStereoisomerismTumor Cells, Cultured

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15165144

Citation

Mo, Shunyan, et al. "Phelligridins C-F: Cytotoxic Pyrano[4,3-c][2]benzopyran-1,6-dione and Furo[3,2-c]pyran-4-one Derivatives From the Fungus Phellinus Igniarius." Journal of Natural Products, vol. 67, no. 5, 2004, pp. 823-8.
Mo S, Wang S, Zhou G, et al. Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. J Nat Prod. 2004;67(5):823-8.
Mo, S., Wang, S., Zhou, G., Yang, Y., Li, Y., Chen, X., & Shi, J. (2004). Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. Journal of Natural Products, 67(5), 823-8.
Mo S, et al. Phelligridins C-F: Cytotoxic Pyrano[4,3-c][2]benzopyran-1,6-dione and Furo[3,2-c]pyran-4-one Derivatives From the Fungus Phellinus Igniarius. J Nat Prod. 2004;67(5):823-8. PubMed PMID: 15165144.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. AU - Mo,Shunyan, AU - Wang,Sujuan, AU - Zhou,Guangxiong, AU - Yang,Yongchun, AU - Li,Yan, AU - Chen,Xiaoguang, AU - Shi,Jiangong, PY - 2004/5/29/pubmed PY - 2004/6/25/medline PY - 2004/5/29/entrez SP - 823 EP - 8 JF - Journal of natural products JO - J Nat Prod VL - 67 IS - 5 N2 - Three unique pyrano[4,3-c][2]benzopyran-1,6-dione derivatives and a new furo[3,2-c]pyran-4-one, named phelligridins C-F (2-5), together with hispolon (8), (E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one (9), 4-hydroxybenzaldehyde, protocatechualdehyde, syringic acid, protocatechuic acid, caffeic acid, isoergosterone, and octadecyl ferulate were isolated and identified from the ethanolic extract of Phellinus igniarius. Their structures were determined by spectroscopic methods including IR, MS, and 1D and 2D NMR experiments. The structures of the new compounds were characterized as 3-(4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (2), 3-(3,4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (3), 8,9-dihydroxy-3-[5',6'-dihydroxy-5' '-methyl-3' '-oxo-spiro[fural-2' '(3' 'H),1'-indene]-2'-yl]-1H,6H-pyrano[4,3-c][2]benzopyran-1,6-dione (4), and (3Z)-3-(3,4-dihydroxybenzylidene)-6-(3,4-dihydroxystyryl)-2,3-dihydro-2-methoxy-2-(2-oxo-propyl)furo[3,2-c]pyran-4-one (5), respectively. Some compounds including 2 and 3 showed in vitro selective cytotoxicity against a human lung cancer cell line (A549) and a liver cancer cell line (Bel7402). Possible biogenetic sequences to the formation of 1-9 are postulated. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/15165144/Phelligridins_C_F:_cytotoxic_pyrano[43_c][2]benzopyran_16_dione_and_furo[32_c]pyran_4_one_derivatives_from_the_fungus_Phellinus_igniarius_ DB - PRIME DP - Unbound Medicine ER -