Four new and other 4α-methylsterols in the seeds of Solanaceae

Itoh, Toshihiro; Ishii, Teruhisa; Tamura, Toshitake; Matsumoto, Tarô

doi:10.1016/s0031-9422(00)88659-8

Cited by 90 publications

(22 citation statements)

References 53 publications

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“…The deshielding of the cyclopropane protons suggested the presence of a carbonyl group at C-3, which was further confirmed by the presence of a two protons multiplet at d 2.79 for the ketomethylene protons (Jian Xin et al, 1993). The double doublets at d 5.09 (7.5, 5.0 Hz) and 5.12 (J = 7.5, 9.0 Hz) were assigned to H-22 and H-23 double bond (Goswamy et al, 1996;Itoh et al, 1978). A triplet at d 5.16 (J = 6.0 Hz) confirmed the position of double bond in ring B at H-7 (Rao and Suseela, 1982).…”

Section: Resultsmentioning

confidence: 94%

Isolation and characterization of new compounds from seeds of Nigella sativa

et al. 2008

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Two new triterpenoids were isolated from the n-hexane extract of seeds of Nigella sativa Linn. and identified as cycloart-23-methyl-7,20,22-triene-3b, 30-diol (1) and cycloart-3-one-7,22-diene-24-ol (2). In addition, two aliphatic compounds and two known sugars were isolated from alcohol extract, and identified as 4-hydroxy undecyl nonanoate (3), 14,20-dimethyl heptacosanol (4), maltose (5), and sucrose (6). They were characterized on the basis of spectral analysis and by comparing literature data. Extraction and transportation study of sugars were also investigated, which evaluated biological phenomena.

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Section: Resultsmentioning

confidence: 94%

Isolation and characterization of new compounds from seeds of Nigella sativa

et al. 2008

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“…Sterols bearing a 14␣-methyl group and one methyl group at C-4 have actually been identified in some algae and higher plants but they are generally minor or trace components [12][13][14][15][16][17][18]. Only some echinoderms (Holuthurians) contain significant amounts of these sterols [19,20].…”

Section: Origins Of 414-dimethylcholestanementioning

confidence: 99%

Combination of gas chromatography–mass spectrometry and mass spectral deconvolution for structural elucidation of an unusual C29-steroid detected in a complex sedimentary matrix

Finck

Aydin

Pellaton

et al. 2004

Journal of Chromatography A

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A complex sedimentary sample from the Monterey Formation (CA, USA) has been submitted to GC-MS analysis followed by mass spectral deconvolution using Automated Mass Spectral Deconvolution and Identification System (AMDIS). Adjusting the parameters of the software allowed for the extraction of the spectrum of an unusual steroidal hydrocarbon coeluting with the major compound of the chromatogram. Following a careful interpretation of the "extracted" mass spectrum, the structure of the unknown has been postulated to be the 4,14-dimethylcholestane (DMC). Possible origins of this rare steroid are briefly discussed. Thus, application of AMDIS appears to be particularly suitable for the GC-MS analysis of natural complex mixtures characterized by a high number of analytes present in low amounts.

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“…The second components of the NLs q-antitatively were fatty acid esters with cyclic and aliphatic alcohols (FAEs) and, in the flesh, free fatty acids (FFAs). We must mention the presence of monoacylglycerols and diacylglycerols in the lipids of both samples, their proportion in the lipids of the flesh being higher than in the seeds and the tuberous roots [1].The level of polar lipids in the seeds of M. turcomanica was the same as in the tuberous roots [ 1] but far smaller than in the fruit flesh. Of the two groups of polar lipids, the GLs predominated in the flesh, and the PhLs in the seeds.…”

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confidence: 99%

“…In the alcohols olxained from the FAEs, GLC [1] showed the presence of (%): C20H41OH (4.5), C.~H45OH (9.6), C23H47OH (4.8), CuH49OH (20.4), C~HstOH (7.3), C~H53OH (14.8), C~Hs~3H (2.0), C2sHs~OH (5.1), C30H61OH (0.1), cholesterol together with an unidentified component (2.8), campesterol and lophenol (13.2), stigmasterol (0. I), ~-sitosterol (10.8) and cycloartsnol (4.5).…”

mentioning

confidence: 99%

“…We have identified the above-mentioned sterols and triterpenols, including lophenol, in the flee form and as esters in the tuberous roots ofM. turcomanica previously [1]. The lipids were extracted from the air-dry seeds and flesh by Folch's method, while ballast substances were eliminated and the fatty acids were isolated from the acyl-containing lipids according to [11].…”

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confidence: 99%

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Lipids of the seeds and flesh of the fruit ofMandragora turcomanica

Asilbekova¹,

Glushenkova²

1998

Chem Nat Compd

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The lipid compositions of the seeds and the flesh of the fruit of Mandragora turcomanica have been investigcaed The qualitative identity of the lipid compositions of the two parts of the fruit has been shown and it has been found that the degrees of saturation of the fatty acids of the trlacylglycerides and phospholipids and of the free fatty acids of the fruit flesh are higher than those of the lipid classes of the seeds.We have previously investigated the composition of the lipids [1] and the structure of the triacylglycerides [2] of the tuberous roots of the mandrake Mandragora turcomo~ca Mizger. (faro. Solanaceae). Continuing the study of the lipids of this plant, we have made a comparative analysis of the lipids of the seeds (I) and of the flesh with peel (II) of the ripe fruit. The seeds made up 13% of the crude weight of the ~xfit.The neutral lipids (NLs) of (I) and (11) were extracted repeatedly with hexane, after which the total polar lipids (PLs) were isolated with chloroform--methanol (2:1, v/v) according to Folch. The PLs, contaminated with a small amount of NLs, were separated with the aid of CC into NLs, glyco-GLs, and phospholipids (PhLs). The NLs eluted from the column were combined with the hexane extract. The components of the NLs and the GLs were obtained by the use of CC in combination with preparative TLC on silica gel, and were estimated gravimetrically. The PhLs were identified qualitatively. The assignment of the comlxments of the three groups was made on the basis of their chromatographic and spectral characteristics in comparison with known substances and with the aid of qualitative reactions and chemical transformations. The composition of the fatty acids (FAs) of the main acyl-containing lipids and that of the free fatty acids were established by the GLC of their methyl esters. Alkaloids were present among the nonlipid components of the PLs of the fruit. The amounts and compositions of the NLs, GLs, and PhLs of (I) and (1I) are shown in Table 1, and the fatty acid compositions of lipids (I) and (11) in Tables 2 and 3. The yields of total lipids from the seeds and flesh of the fruit amounted to 221.02 and 19.95 mg/g a.d.w, respectively. In spite of the large difference in their amounts, the main components of both samples were NLs with a predominance of triacylglycerides. The second components of the NLs q-antitatively were fatty acid esters with cyclic and aliphatic alcohols (FAEs) and, in the flesh, free fatty acids (FFAs). We must mention the presence of monoacylglycerols and diacylglycerols in the lipids of both samples, their proportion in the lipids of the flesh being higher than in the seeds and the tuberous roots [1].The level of polar lipids in the seeds of M. turcomanica was the same as in the tuberous roots [ 1] but far smaller than in the fruit flesh. Of the two groups of polar lipids, the GLs predominated in the flesh, and the PhLs in the seeds. The qualitative compositions of the GLs in the samples studied and in the tuberous roots were the same, but substantial difference...

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Four new and other 4α-methylsterols in the seeds of Solanaceae

Cited by 90 publications

References 53 publications

Isolation and characterization of new compounds from seeds of Nigella sativa

Isolation and characterization of new compounds from seeds of Nigella sativa

Combination of gas chromatography–mass spectrometry and mass spectral deconvolution for structural elucidation of an unusual C29-steroid detected in a complex sedimentary matrix

Lipids of the seeds and flesh of the fruit ofMandragora turcomanica

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