Studies on the Plant Sterols and Triterpenes. II. Separation of Stigmasterol, β-Sitosterol and Campesterol, and about So-called "γ-Sitosterol."

Nishioka, Itsuo; Ikekawa, Nobuo; Yagi, Akira; Kawasaki, Toshio; Tsukamoto, Takeo

doi:10.1248/cpb.13.379

Cited by 22 publications

(6 citation statements)

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“…We then compared the melting points of PS and TA esters with those of free PSs and TAs. Melting points of free PSs and TAs range from 114 to 160 °C [12][13][14][15][16][17][18]; however, we found that the melting points fell considerably to 7.0-42 °C after esterification with oleic acid. From these results, esterification caused a decrease in the melting points of PSs and TAs by more than 100 °C.…”

Section: Differential Scanning Calorimetric Analysis Of the Esterscontrasting

confidence: 54%

Lipase‐Catalyzed Esterification of Triterpene Alcohols and Phytosterols with Oleic Acid

Kobayashi

Ogino

Miyake

et al. 2014

J Americ Oil Chem Soc

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Oleic acid esters of phytosterols (PSs) and triterpene alcohols (TAs), derived from rice bran, were synthesized using lipases under mild conditions. Some lipases, especially from Candida rugosa, type VII, showed very high substrate specificity towards both PSs and TAs, when a mixture of PS and TA (PS/TA mixture) was used as the substrate source. The maximum yield of PS esters was ca. 80 % in each case; however, the maximum yield of TA esters was much lower when the reaction was continued for 7 days. Due to the difficulty in purifying the esters obtained when the PS/TA mixture was used as source of substrate, free PSs and TAs were separated from the PS/TA mixture by silica‐gel and reverse‐phase chromatography prior to esterification. The pure PSs or TAs were esterified with oleic acid to obtain the corresponding esters with high purity. Differential scanning calorimetric analysis of the resulting esters revealed that their melting points ranged from 7.0 to 42 °C. These values were at least 100 °C lower than those of the free PSs and TAs.

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Section: Differential Scanning Calorimetric Analysis Of the Esterscontrasting

confidence: 54%

Lipase‐Catalyzed Esterification of Triterpene Alcohols and Phytosterols with Oleic Acid

Kobayashi

Ogino

Miyake

et al. 2014

J Americ Oil Chem Soc

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“…platanifolium, although no studies were conducted to identify its location in the berry (Puri et al, 1976). These ratios differ from those of campesterol and p-sitosterol found in dehulled soybean oil (Thompson et al, 1963;Nishioka et al, 1965). Thompson et al, (1963) reported 50/50 to 75/25 mixtures of campesterol and p-sitosterol in soybean oils.…”

Section: Resultsmentioning

confidence: 81%

“…Sterols occur in plant materials (Fenner et al, 1986;Mattson et al, 1977;Nishioka et al, 1965;Puri and Bhatnager, 1978;Thompson et al, 1963) and vegetable oils (Toshi et al, 1973). Puri and Bhatnager (1978) found sitosterol, stigmasterol and campesterol in the stems and leaves of S. plutunifolium, a highaltitude Indian plant.…”

Section: Introductionmentioning

confidence: 99%

Plant Sterols in Soybean Hulls

Ibrahim

Puri

Kapila

et al. 1990

Journal of Food Science

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Using gas chromatography techniques after lipid extraction, soybean hulls were analyzed for their plant sterol components. Soybean hulls contained 7.46% and 2.02% moisture and lipid components, respectively. Three plant sterols, campestrol, stigmasterol, and p-sitosterol, were quantified in the ratios of 1 : 1.5 : 2. The use of soybean hulls as food ingredients was discussed for their potential serum cholesterol reducing effects.

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“…11) However, the assignment of some carbon signals (C-2, 3,6,8,12,14,17,18,19) 11) have been revised on the basis of our detailed NMR analysis (COSY, HMQC and HMBC). Compounds 4 and 5 were separated from the mixture of both components by preparative TLC using hexane/EtOAc 4 : 1, affording colorless amorphous solids.…”

Section: Resultsmentioning

confidence: 99%