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Sterol Compositions in Some Cucurbitaceae Vegetable Oils

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Sterol Compositions in Some Cucurbitaceae Vegetable Oils DAEHAN HWAHAK HWOEJEE (Journal of the Korean Chemical Society) Vol. 21, So. 3, 1977 Printed in Republic of Korea 몇가지 박과 식물 종자유중의 Sterol 조성 鄭泰明 •梁敏錫 •松本太郞 * 경상대학 농화학과 *일본대학 이공학부 공업 화학과 (1977. 1. 25 접수 ) Sterol Compositions in Some Cucurbitaceae Vegetable Oils Tae Myoung Jeong, Min Suk Yang and Taro Matsumoto* Department of Agricultural Chemistry, Gyeongsang University, Jinjut Korea ^College of Science & Technology, Nihon University, Tokyo, Japan (Received Jan. 25, 1977) 요 약 . 오이 , 수박 , 수세 미 , 박 , 하늘수박의 다섯 가지 박과식물 종자유에 서 세 가지 스테 롤 플랙 숀을 박층 크로마토그래 피 로 나누고 각 플랙숀의 조성 을 가스크로와 가스크로에 연결된 질 량분석 법으로 밝혔다 . 이 중 4-데 스메 틸 스테 롤 플랙 숀에 서 a-spinasterol, J7-22- 25-stigmastatrienol 및 J7- 25-stigmastadienol 를 단리 (單離 )하여 IR, NMR 및 질량분석법으로 동정 (同定 )하였다 ABSTRACT. Three sterol fractions ； 4-desmethyl-, 4-monomethyl-, and 4,4-dimethylsterol, separated by thin layer chromatography from the unsaponifiables of five Cucurbitaceae (cucumber, watermelon, sponge cucumber, gourd and snake gourd) seed oils were analyzed by gas liquid chro­ matography and combined gas liquid chromatography-mass spectrometry. a-Spinasterol, J7- 22> 25-stig- mastatrienol and J7,25-stigmastadienol isolated from the 4-desmethylsterol fraction were identified by IR, NMR and mass spectrometry. sitosterol, campesterol, stigmasterol and J5-av- INTRODUCTION enasterol of 4-desmethylsterol fraction were Recently some sterol compositions of 4-des- found to be the major component of most of methylsterol, 4-monomethylsterol, and 4,4-dime- vegetable oils investigated and some other ve­ thylsterol fractions have been identified from the getable oils were composed of mostly J7~sterol various vegetable oils'우 . The J5-sterols such as such as a-spinasterol, J7-stigmastenol and J7- 一 193 — 194 鄭泰明 •梁敏錫 •松本太郞 avenasterol. -ol Sucrow6 reported previously that three kinds 24- methykiholegt-7 - enol = 24-methylcholest-7- of J7-sterol were isolated from the 4-desme- en-3/S-ol thylsterol fractions of some Cucurbitaceae vege­ sitosterol = 24-methylcholest~5-en-3j9-ol table oils and these oils were considered to a-spinasterol=24-ethylcholesta-7,22-dien contain mainly 匕 卩— 아 eroL Among twenty kinds of vegetable oils from 』7,22,25_stigmastatrienol = 24-ethyl 사 ］ 시 esta- 7, which 4-desmethylsterol fraction was separated 22, 25-trien-3/3-ol in the previous report5, only the seed oil of J7- 25-stigmastadienol= 24-ethylcliolesta-7) 25~ pumpkin, which belongs to Cucurbitaceae fami­ dien-3/3-ol ly, was made of mai니 y a-spinasterol, J7-stig- J7-stigmastenol=24-ethylcholest-7-en-3jS-ol mastenol and J7-avenasterol, and characterized J7-avenasterol = 24-ethylidenecholest-7~en-3/3 by a J7-sterol type. The miscellaneous minor -ol sterol components detected from 4 -desmethyl - lophenol=4a-methyl-5a-cholest-7-en-3/3-ol sterol fraction of pumpkin seed oil were identifi­ obtusif oliol=4a~, 14a—dimethyl—24- methyl- ed as 24-methylcholest-7-enol, campesterol and ene-5a-cholest-8-en-3jS-ol stigmastenol. Furthermore two unidentified gas cycloeucalenol=4a-, 14a-dimethyl-9^, 19- liquid chromatographic peaks were found in the cyclo-24-methylene~5a-cholestan-3jS-ol 4~desmetliylsterol fraction of pumpkin seed oil. gramisterol=4a-methyl-24-methylene-5a- This study was designed for the further cholest-7-en-3/3-ol analysis of 4-desmethylsterol fraction, the iden­ citrostadienol=4a-methyl-24-ethylidene-5a- tification of sterol components or 4-monoire- cholest-7-en-3^S-ol thylsterol and 4,4-dimethylsterol fraction, lanostenol=5a-lanost-8~en-3j3-ol hitherto little investigated, and the contribution lanosterol=5a-lanosta-8, 24-dien-3/3-cl to estimation of biosynthesis pathway in the cycloartenol=9& 19-cyclo-5a-lanost-24~en- above plants. 30项 The unsaponifiables from five kinds of seed 24-methylenecycloartanol=24-methylene-9j6, oils such as cucumber, watermelon, sponge 19-cyclo-5a-lanostan-3^3-ol cucumber, gourd and snake gourd were separa­ butyrospermol= 5a-eupha-7, 24-dien-3/3-ol ted into five to six fractions by thin layer j8-amyrin= 5aDleanT2-en-36~시 chromatography (TLC). Among these fractions Iupeol= 5a-lup-20 (29) -en-3/9-ol 4-desmethylsterol, 4-monomethylsterol and 4,4- EXPERIMENTAL dimethylsterol fractions were further analyzed by gas liquid chromatography (GLC) and combined Materials. The seed oil of cucumber, water­ GLC-mass spectrometry (GLC-MS). The a- melon, sponge cucumber, gourd and snake gourd- spinasterol, J7-25-stigmastadienol arid J7,22,25- were prepared from the respective dried seeds stigmastatrienol isolated from the oils were by soxhlet extraction with methylene chloride. identified by mass spectrometry, IR and NMR. The oil contents, saponification and iodine val­ The trivial names are used in this paper ： ues, and the unsaponifiable contents of these oils campesterol = 24-metliylcliolest-5-en-3J6-ol are indicated in Table 1. Authentic specimens stigmasterol^ 24-methylcholesta-5, 22-dien-3g of a 4-desmethylsterol fraction consisting of Journal of the Korean Chemical Society 몇 가지 박과식물 종자유중의 Sterol 조성 195 campesterol, stigmasterol, and sitosterol were combined, washed 5 times with 700 mZ portion supplied by Riken Vitamin Oil Co., Tokyo, of distilled water and dried over anhydrous Japan. Specimens of a-spinasterol and 24-me- sodium sulfate, and the IPE was removed by thylcholest-7-enol, and lanosterol were prepared evaporation. The content of unsaponifiables in from tea seed oil3 and yeast7, respectively. Thir­ oil was expressed by wt percentage. teen Xerols reported in the previous work5 such Thin Layer Chromatography. Unsaponifiables as lophenol, obutusifoliol, cycloeucalenol, gra- were fractionated on 20 X 20 cm plates coated misterol, citrostadienol, lanostenol, cycloartanol, with a 0. 5 mm layer of Wakogel B-10 (Wako cycloartenol, 24-methylene-cycloartanol, buty- Pure Chemical Industries Ltd., Osaka, Japan). rospermol,伊 amyrin and lupeol were used as A sample of 30 mg was applied uniformly along the authentic specimens for GLC and combined a line 1. 5 cm from one edge of the plate and GLC-MS. The J7,22,25-stigmastatrienol as an developed with hexane-ether (7:3) for 60 min authentic specimen was supplied by Sucrow. using a Toyo continuous flow development pre­ Relative retention times (RRT) of these auth­ parative TLC. The plate was sprayed with entic specimens were presented in Table 2 and 0. 01 % rhodamine-6G solution in ethanol and all the sterols except lanostenol and lano마 erol observed under UVTight (3,600A). Separated were identified in this work. zones (5 zones) of less polar compounds, 4,4~ Saponification. The oil (100g) in 1,000 ral dimethylsterols (triterpene alcohols), 4-mono- alcoholic LON potassium hydroxide was reflux­ methylsterols, 4一 desm아 hylsterols and nonde­ ed for lhr under nitrogen. The reaction mix­ veloped matters were cut off respectively and ture was diluted with 2,000 mZ of distilled water quantitatively extracted with ether. The ether and the unsaponifiables were extracted with one extracts from the zones of 4,4-dimethylsterol, 1, 000 mZ portion and three 800 mZ portion of 4-monomethylsterol and 4-desmeth}dsterol were isopropyl ether (IPE). The IPE extracts were desicated for the subsequent GLC. Table 1. Content of oils in dried seeds, content of unsapcnifiables in oils, and yields of each fraction from unsaponifiales by thin layer chromatography. Content of oil Total yield Yield of each fraction』(%)e Oil In seed USM。 SVb IVC (%)。 (%)e by TLC 1 2 2f 3 4 5 Cucumber (Cucumis Sativus L.) 30.5 0.7 226.7 121.9 92.3 9.0 — 7.2 6-4 60.6 16.8 Watermelon (Citrullus battich F.) 15.7 0.5 218.0 118.1 95-1 34.7 11.8 6-6 2.0 28.7 16.2 Sponge cucumber (Luffa cylindrica R.) 27.5 0.3 202.2 89.0 90.6 4.7 — 27.0 7-0 39.2 22.1 Gourd (La흥 enaria siceraria S.、) 18.5 0.8 206.3 125.7 93.6 17.5 15-7 5.7 3.5 36.2 21.4 Snake gourd (Trichosanthes kirilowii M.) 5.3 0.5 173.5 143.2 94.2 15-2 7-8 18.3 5-0 34.0 19.7 "Unsaponifi천 ble matter； ^Saponification value； cIodine value (Wijs' method): ^Fraction l=less polar com pounds (hydrocarbons, etc. ), fraction 2=unknown sterol, fraction 2’= 4. 4-dimethyl ster시 s (triterpene ale사 gls), fraction 3=4-monomethylsterols, fraction 4=4-desmethylsterols and fraction 5—nondevelopped matters ； 'Based on weight. Vol. 21, No. 3, 1977 196 鄭泰明 •梁敏錫 •松本太郞 Table 2. Relative retention time of the authentic specimens of sterol on OV-17 c시 umn. r-__ Position of Other structural t기 yr Compounds | double bond characteristics 4-Desmethylsterols (Cholestane series) Campesterol 5 24R-CH3 0. 81 Stigmasterol 5, 22 24S-C2H5 0.88 24-Methylcholest-7-enol 7 24-CHg 0.95 Sitosterol 5 24R-C2H5 1. 00 a-Spinasterol 7, 22 24S-C2H5 1.03 j7,22,25_Stigmastatrienol 7, 22, 25 24-C2H5 1- 09 J7>25-StigmastadienoF 7, 25 24-C2H5 1.18 J7-Stigmastenol 7 24R-C2H5 1.18 J7-Avenasterol 7,24(28) 24Z-C2H4 1. 31 4-Monomethylsterols (4a-Methylcholestane series) Lophenol 7 一 0. 83 Obtusifoliol 8, 24(28) 14<y—CH3, 24—CH2 0.95 Cycloeucalenol 24(28) 14a-CH3, 24CH2, 9:19cyclofi 1.11 Gramisterol 7,24(28) 24-CH2 1.13 Citrostadienol 7,24(28) 24Z-C2H4 1. 52 4,4-DimethylsteroIs (Lanostane series) Lanostenol 8 I4CZ-CH3 0- 89 Cycloartanol 一 9：19-cyclo 1. 02 Lanosterol 8, 24 14a-CH3 1. 07 Cydoartenol 24 9： 19 - cyclo 1. 24 24-Methylenecycloartanol 24(28) 9:19-cyclo, 24-CH2 1.
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