Aurovertin E, a New Polyene Pyrone from the Basidiomycete Albatrellus confluens

Wang, Fei; Luo, Du‐Qiang; Liu, Ji‐Kai

doi:10.1038/ja.2005.53

Cited by 44 publications

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“…[5][6][7] China is extraordinarily rich in higher fungi, with over 6000 species reported to belong to about 1200 genera. In our on-going research to explore the biologically active natural products of the higher fungi of China, [8][9][10][11][12] the chemical constituents of the fruiting bodies of Lactarius vellereus were investigated. This report describes the isolation and structure elucidation of an unusual highly functionalized lactarane sesquiterpene, named velleratretraol (1), and its anti-HIV activity.…”

Section: Introductionmentioning

confidence: 99%

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

et al. 2009

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An unusual highly functionalized lactarane sesquiterpene, named velleratretraol (1), was isolated from the ethanol extract of the fruiting body of the mushroom Lactarius vellereus. Its structure was determined through spectroscopic analysis and singlecrystal X-ray diffraction studies. The proposed assignment of the absolute configuration is based on computational results. It showed weak activity against HIV-1 cells with an effective concentration of 68.0 mg ml À1 and a selectivity index of 2.0. The Journal of Antibiotics (2009) 62, 129-132; doi:10.1038/ja.2008; published online 23 January 2009Keywords: lactarane sesquiterpene; Lactarius vellereus; velleratretraol; X-ray INTRODUCTIONThe Russulaceae family is one of the largest in the subdivision Basidiomycotina in Whittaker's Kingdom of Fungi and comprises hundreds of species. 1 Sesquiterpenes play an important biological role in a majority of the Lactarius species. They are responsible for the pungent and bitter taste of the milky juice, the color change in the latex upon air exposure, 2 and they constitute a chemical defense system against intruders such as bacteria, fungi, animals and insects. 3 The fungal subdivision Basidiomycotina produces many toxic sesquiterpenes derived from the protoilludane skeleton. This skeleton is transformed and rearranged into a multitude of compounds. Fungal sesquiterpenes formed via the humulane-protoilludane biosynthetic pathway are characteristic for the subdivision Basidiomycotina. The largest group of sesquiterpenes, belonging to the classes of lactaranes, secolactaranes, marasmanes, isolactaranes, norlactaranes and caryophyllanes, are believed to be biosynthesized from humulane. 4 Fungi of the genus Lactarius have been shown to be a good source of bioactive secondary metabolites. [5][6][7] China is extraordinarily rich in higher fungi, with over 6000 species reported to belong to about 1200 genera. In our on-going research to explore the biologically active natural products of the higher fungi of China, [8][9][10][11][12] the chemical constituents of the fruiting bodies of Lactarius vellereus were investigated. This report describes the isolation and structure elucidation of an unusual highly functionalized lactarane sesquiterpene, named velleratretraol (1), and its anti-HIV activity. (d, 35.9) by analysis of the DEPT spectra. An analysis of the 1 H-NMR spectrum indicated the presence of three methyl groups at d¼1.03 (s), 1.12 (s) and 1.27 (s). The first two resonances were ascribed to geminal methyl groups, and the third one was ascribed to the methyl group on the carbon atom bearing the tetramethylene oxide carbocycle group. In particular, a doublet occurring at d¼3.73 (d, 11.8) was attributed to the C-4 bearing a secondary OH group, and two resonances at d¼5.55 (s) and 5.35 (s) were assigned at C-14 and C-15, respectively. Its formula indicated a sesquiterpene skeleton containing 4 degrees of unsaturation. The structure was suggested to be a tetracyclic sesquiterpene. RESULTS AND DISCUSSIONThe key connectivity of the pr...

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Section: Introductionmentioning

confidence: 99%

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

et al. 2009

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“…The molecular formula C 23 H 32 O 8 was determined by HREIMS at m/z 436.2097 [M] + . The 1D and 2D NMR data suggested that the structure of 5 was related to that of aurovertin E (13), 8 except that the double bond between C-9 and C-10 in 14 was opened to form a hydroxymethine at C-10 (δ C 69.8), as implied by the HMBC correlations from δ H 4.53 (1H, br. s, H-10) to δ C 75.9 (d, C-8), 39.6 (t, C-9), and 141.5 (d, C-11).…”

Section: Resultsmentioning

confidence: 99%

“…The structures of the known compounds 11-14 isolated were identified as aurovertin B, 5 aurovertin C, 22 aurovertin E, 8 and aurovertin I, 10 respectively, by comparison of their spectroscopic data with literature values. All aurovertins obtained from cultures of the basidiomycete A. confluens were yellow syrup, and could not obtain as crystals in diverse solution systems.…”

Section: Resultsmentioning

confidence: 99%

“…They have attracted considerable attention of chemists because of their actitivities as potent inhibitors of ATP synthesis and antitumor agents. [2][3][4][5][6][7] There have been nine aurovertins (A-I) structurally elucidated to date, 1,[8][9][10] while the relative and absolute configurations of aurovertin B were determined by spectroscopic analysis and total synthesis, respectively. 11,12 The absolute configuration of aurovertin F was determined by analysis of the CD spectrum recently.…”

Section: Introductionmentioning

confidence: 99%

“…9 It is deduced that aurovertin-type of compounds obtained in literature probably share the same absolute configuration on biosynthetic grounds. 10,13 During our continuing investigation of bioactive microbial secondary metabolites from the fungus, 8,[14][15][16][17][18][19][20][21][22][23] ten new aurovertin derivatives, named as aurovertins J-S (1-10), along with four previously reported aurovertins B, C, E and I (11)(12)(13)(14), were isolated from cultures of the basidiomycete Albatrellus confluens (Alb. et Schw.…”

Section: Introductionmentioning

confidence: 99%

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Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Guo

Feng

et al. 2013

Nat. Prod. Bioprospect.

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A New Meroterpenoid Pigment from the Basidiomycete Albatrellus confluens

Yang

Qin

Wang

et al. 2008

Chemistry & Biodiversity

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A new farnesyl phenol named (+)-(R)-grifolinone C (1) has been isolated from the fruiting bodies of the basidiomycete Albatrellus confluens. (+)-(R)-Grifolinone C (1), a dimeric meroterpenoid, is accompanied by albatrellin (2), grifolinone B (3), grifolin (4), and grifolinone A (5). Albatrellin (2) exhibited cytotoxic activity against HepG2 human lung carcinoma cells with IC(50) value of 1.55 mug ml(-1). The structures were established on the basis of spectral evidence (IR, 1D- and 2D-NMR, and MS analyses).

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Aurovertin E, a New Polyene Pyrone from the Basidiomycete Albatrellus confluens

Cited by 44 publications

References 14 publications

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

A New Meroterpenoid Pigment from the Basidiomycete Albatrellus confluens

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