Sesquiterpenes from Russula sardonia

Andina, Daniela; Bernardi, Maria De; Vecchio, A. Del; Fronza, Giovanni; Mellerio, G.; Vidari, Giovanni; Finzi, Paola Vita

doi:10.1016/0031-9422(80)85020-5

Cited by 26 publications

(18 citation statements)

References 20 publications

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“…that usually the configuration of C-12 is syiz to the ring junction protons (H-2 and H-9) vhen C-12 is geminal to an hydrogen and atzti nhen it is geminal to an hydroxy group. An exception not yet explained by this "rule" is furanether B. LICT.IR.LL (1) (14).-Lactaral 1260 nig) gave a blue spot on tlc, and was identical with an authentic sample isolated from Ritssitln serdoiiia (16).…”

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confidence: 76%

“…furanether -4 (3) (16), furanether B (3,s-enantiofuranether A) (4), furoscrobiculin B (5), furoscrobiculin C (6), furoscrobiculin D (7), lactaro~crobiculide B (8) and furandiol (9a) (21). The progressive numbering of the compounds corre-ponds both to the decreasing Ri in tlc and to the elution order in the cc (see Experimental section).…”

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confidence: 80%

“…About the stereochemistry of these compounds, it seemed again, as noticed in the Russula sardoizia metaboIites (16). that usually the configuration of C-12 is syiz to the ring junction protons (H-2 and H-9) vhen C-12 is geminal to an hydrogen and atzti nhen it is geminal to an hydroxy group.…”

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confidence: 96%

“…n-as an isomer of 3 and showed l-erj-similar spectral data (16). The most important features n hich indicated tlie structure to be 4 were the follon ing : tlie ir spectrum showed no OH absorption and the pmr spectrum indicated the presence of three tertiary methyl groups, one of which was geminal to an oxygen atom (6 1.38), and next to the furan ring \\as both a -CHO-group (6 4.78, br, q, IH), and an isolated methylene (6 2.54 and 6 2.80.…”

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confidence: 96%

“…From the combined a and b extracts after column chromatography and subsequent preparative thin layer chromatography, ethyl linoleate and cerevisterol (16,20) were isolated in addition to nine lactarane sesquiterpenes, six of which were neIv compounds. The nine sesquiterpenes n-ere lactaral (1) (14,16), furo-…”

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confidence: 99%

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Fungal Metabolites. VIII: Structures of New Sesquiterpenes From Lactarius Scrobiculatus

Battaglia¹,

Bernardi²,

Mellerio³

et al. 1980

J. Nat. Prod.

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GIORGIO MELLERIO', GIOI-ASSI T-IDARI* and P.io~.i I-ITA-FISSI~ * ?Isfituto di Chiniica Organicci--ni;,ersita degli Studi-lCale W r a n i e l l i 10-27100 PaLmia (Italy) 3Centro del C-TR p e r lo Studio delle Sostanre Organiche .\htiirali-Politecnico-Piarra L e o m r d o do Ti'nci 32-20133 X i l a n o (Italjj ;iBsTR.icT.-From lots of Lncfarrzts scrobzciilnfus extracted in different B-ays, in addition to ethyl linoleate and cerevisterol, nine lactarane sesquiterpenes have been isolated. The main compounds are furanosesquiterpenes, namely: furoscrobiculins -4-D (2, S-i), furanethers 13 and 4) and the already known lactaral (l), and furandiol 19a). Furthermore a new sesquiterpene lactone with the CO group in 13, lactaroscrobiculide B (8), has been isolated. The structures were elucidated mainly by spectroscopic methods and by some chemical transformations. Stereochemistry of most sesquiterpenes has been determined.Recently (1-3) we isolated from Lactariids scrobiciilatzks some sesquiterpenes 11-ith the lactarane skeleton which is peculiar to most of the knon-n Russulaceae metabolites (4-1i). At present the only mushrooms of this family containing sesquiterpenes with a completely different skeleton are L. deliciosus (1s) (guaianes) and L. uzidzis (19) (drimanes).Sou-11-e report the structures of ne!\ lactarane sesquiterpenes which were isolated from a nen-lot of L. scrobiciilatus extracted in a different way than in the previous \I ork (2. 3). DISCCSSIOSL. scrobiczilatus is easily distinguished not only by the morphological aspects (yellow color, big size. wrobiculated stem, pungent taste, etc.), but also by the secreted milky juice, n-hich, for some reason not yet understood, turns quickly from n hite to yelloJv when it appears at the surface of the fruit-body. This color change could indicate enzymatic degradation reactions : therefore, in order to prevent and to check possible alterations in the sesquiterpene composition. n-e carried out extraction in three different nays:The frozen material \vas then minced under its solvent and. after being removed by filtration. it was homogenized in ethanol and ice to extract the more polar compounds.b) The freshly collected mushrooms nere cut and put in acetone. The material \vas norked up in a dry-box under a S? stream as in a). In this case, the color change in the juice seemed to be slon-er but n-as still noticeable.a) The fruit-bodies nere frozen in drj ice and acetone.c) The fruit-bodiei n ere cut without any precaution.

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confidence: 76%

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confidence: 80%

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confidence: 96%

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confidence: 96%

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confidence: 99%

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