(−)-3β-Acetoxydrimenin from the leaves of Drimys winteri

Sierra, Jorge; López, Javier Sánchez; Cortés, Manuel

doi:10.1016/s0031-9422(00)94542-4

Cited by 30 publications

(34 citation statements)

References 6 publications

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“…1,103.1, 104.3,106.6, 116.4(weak), 117.4(weak), 122.2,122.9, 206.4 (weak), 206.7 (weak) (CH, CH,); 22.8,24.9,25.8,26.1,26. 7,30.3,36.9,37.7,44.6,46.0,71.6,72.6,134.0,136.9 (C,CH2); hreims (probe 160°C), m/z calcd. for Cl5HZ2O4 (M'): 266.1518; found: 266.1514 (6), 248 ( M f -H20, 36), 220 (57), 202 (29), 201 (25), 174 (20), 173 (loo), 172 (63), 159 ( 3 3 , 132 (26), 131 (43), 124 (27), 119(44), 117 (27), 107 (28), 105 (go), 104 (28), 93 (28), 91 (71), 81 (24), 79 (46), 69 (58), 67 (29), 57 (30), 55 (49), 53 (27).…”

Section: Growth Of Marasmius Oreades On Potato Dextrose Yeast Broth Amentioning

confidence: 99%

“…2 H~, H -1 2 ) , 4 . 4 9 ( 1 H , d d (CDCI,(6)(7)(8)(9)(10)(11)(12)(13)(14) 160.8 (C-15), 210.9 (C-1) (s,'Hnmr (CDCl,) 6: 1.13 (3H,s,CH3),1.14 (3H,s,CH,),m ,2.45 ( l H ,dd,J 10.0,lO.OHz,2.47 ( l H ,dd,J 14.9,3.4 Hz,2.81 ( l H ,m ,2.89 (lH,ddd , J 1 5 . 0 , 3 .…”

Section: -Hydroxymarasmen-3-one ( L L a ) Was Obtained As A Clear Omentioning

confidence: 99%

“…Fractions 8-10 (6.0 mg) were combined and chromatographed on a column of silica gel (ethyl acetate -Skellysolve B, 1:lO) to give marasmene (7). were combined and chromatographed on a column of silica gel (ethyl acetate -dichloromethane, 1 :2) and then the fractions rich in 19a were combined and subjected to preparative tlc (methanol-dichloromethane, 1:40, several developments) to give 13-hydroqmarasmene (19a, 3.1 mg).…”

Section: Marasmenmentioning

confidence: 99%

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Metabolites of the fairy ring fungus, Marasmiusoreades. Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin

Ayer¹,

Craw²

1989

Can. J. Chem.

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The fungus Marasmius oreades has previously been reported to produce the sesquiterpenes marasmone ( I ) , anhydromarasmone ( 2 ) , isomarasmone (3), and dihydromarasmone (4) when grown in liquid culture. We report herein several other sesquiterpene metabolites of the same skeleton but with differing oxidation patterns. The norsesquiterpenes 0-formyloreadone (lSa), 3a-hydroxyoreadone (15c), and dehydrooreadone (17b) are also reported. It is suggested that the formyl group in 15a is derived biogenetically from C-15 of a precursor sesquiterpene. Oxidation of l a , 15-dihydroxymarasmene (13a), one of the new sesquiterpenes reported, with one equivalent of pyridinium dichromate gives 0-formyloreadone (15a) as one of the products. Agrocybin (5), a plyacetylene amide previously isolated from the fungus Agrocybe dura, has also been isolated from the cultures of M. oreades. It is suggested that agrocybin (5) is the phytotoxic compound responsible for the killing of grass caused by the f a j r ring mushroom fungus. On a dCj8 rapport6 que le champignon Marasmius oreades, en croissance dans une culture liquide, produit les sesquiterpknes marasmone ( I ) , l'anhydromarasmone (2), l'isomarasmone (3) et la dihydromarasmone (4). On rapporte dans cet article plusieurs autres mktabolites sesquiterp6niques ayant le m&me squelette mais avec des modkles d'oxydation diffkrents. Nous dCcrivons Cgalement les norsesquiterpknes : la 0-formylorCadone (15a), l'hydroxy-3a-ortadone (15c) et la dChydroorCadone (17b). On suggkre que le groupe formyle du terpkne (15a) dCrive biogCnCtiquement du carbone C15 d'un sesquiterpkne prCcurseur. L'oxydation du dihydro-la, 15-marasmkne (13a), un des nouveaux sesquiterpknes rapportCs, avec un Cquivalent de dichromate de pyridinium donne entre produits la 0-formylorCadone (15a). On a tgalement is016 l'agocybine (5), un amide polyacCtylCnique is016 antkrieurement du champignon Agrocybe dura a partir des cultures de M. oreades. On suggkre que I'agrocybine (5) est le compsC phytotoxique responsable de la destruction du gazon provoquCe par le mousseron du champignon. --

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Section: Growth Of Marasmius Oreades On Potato Dextrose Yeast Broth Amentioning

confidence: 99%

Section: -Hydroxymarasmen-3-one ( L L a ) Was Obtained As A Clear Omentioning

confidence: 99%

Section: Marasmenmentioning

confidence: 99%

See 1 more Smart Citation

Metabolites of the fairy ring fungus, Marasmiusoreades. Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin

Ayer¹,

Craw²

1989

Can. J. Chem.

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“…Chemical studies has shown the presence of a variety of sesquiterpenes with drimano skeleton 2 and flavonoids. Some of these structures have shown significant antibacterial, antifungi, antitumor and insecticide properties 3,4 . The extract of Drimys winteri leaves afforded Cinnamolide and Drimenin two lactones with drimano skeleton.…”

Section: Introductionmentioning

confidence: 99%

X-Ray Crystallographic Structural Study on a Cinnamolide-Class Sesquiterpene Lactone From Drimys Winteriforst. Var. Chilensis

Brito

Cárdenas

Zárraga³

et al. 2008

J. Chil. Chem. Soc.

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“…Reduction of 10 with sodium borohydride in methanol at room temperature produced diol 9 in an excellent yield (Scheme 2). 24,25 It was previously reported that treatment of diol 9 with one equivalent of tert-butyl dimethyl chlorosilane monoprotected specifically the C-12 hydroxy position. 24 In our case, protection of diol 9 with one equivalent of tert-butyl, diphenylsilyl chloride in DMF, in the presence of imidazole, produced silyl ether 11, with identical specificity towards the allylic alcohol, and excellent yield.…”

Section: Scheme 1 Oxidation Of Drimenol (8)mentioning

confidence: 99%

Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives

Cuéllar¹,

Moreno²,

Preite³

2003

Arkivoc

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(−)-3β-Acetoxydrimenin from the leaves of Drimys winteri

Cited by 30 publications

References 6 publications

Metabolites of the fairy ring fungus, Marasmiusoreades. Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin

Metabolites of the fairy ring fungus, Marasmiusoreades. Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin

X-Ray Crystallographic Structural Study on a Cinnamolide-Class Sesquiterpene Lactone From Drimys Winteriforst. Var. Chilensis

Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives

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