New Steroidal Erythrityl Triesters from the Heat Processed Roots of Panax ginseng

Hindawi Publishing CorporationJournal of ChemistryVolume 2013 Article ID 505407 6 pageshttpdxdoiorg1011552013505407

Research ArticleNew Steroidal Erythrityl Triesters from theHeat Processed Roots of Panax ginseng

Ill-Min Chung1 Mohd Ali2 Ye-Seul Yang1 Jae-Yeon Yoon1

Youn-Pyo Hong3 and Ateeque Ahmad1

1 Department of Applied Life Science Konkuk University Seoul 143-701 Republic of Korea2 Faculty of Pharmacy Hamdard University New Delhi 110062 India3Herbal Crop Utilization Research Team NIHHIS RDA Eumseong 369-873 Republic of Korea

Correspondence should be addressed to Ateeque Ahmad ateeque97gmailcom

Received 7 May 2013 Revised 20 August 2013 Accepted 27 August 2013

Academic Editor Lian-Wen Qi

Copyright copy 2013 Ill-Min Chung et al This is an open access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

Two new compounds stigmasta-3120572-ol-3120572-(21015840R31015840S)-butane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate (1) and stigmasta-5-en-3120573-ol-3120573-(21015840R31015840S)-butane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate (2) along with 120573-sitosterol-120573-D-glucoside were isolated and identified from the heat processed roots of Panax ginsengThe structures of the new compounds were elucidated by 1D and 2D NMR (COSY HSQC and HMBC) spectroscopic techniquesaided by FAB-MS ESI FTMS and IR spectra

1 Introduction

Ginseng (Panax ginseng C AMeyer Araliaceae) is one of themost important oriental medicinal plants in Japan Korea andChina [1] Of the two kinds of ginseng white ginseng is airdried and red ginseng is produced by steaming raw ginsengat 98ndash100∘C for 2-3 h It has been reported that red ginsengis more effective in pharmacological activities than whiteginseng [2ndash5] The differences in biological activities andchemical constituents of red and white ginsengs have beenreported Anticancer properties and other pharmacologicalactivities of Panax ginseng [6ndash8] have been studied andginsenosides are recognized as active anticancer compounds[6] Compared with Asian white ginseng red ginseng hasstronger anticancer activities [9 10] Recently there was areport using a steaming process to treat American ginsengroot [5] In the study however the treatment temperaturewas 100∘C and thus chemical constituents did not changesignificantly

Anticarcinogenic and antidiabetic effects of P ginsenghave been reported [9 11] Several other compounds andbiological activities have been reported from the ginseng

roots of P ginseng [12ndash14] The most well-known chemicalconstituent of ginseng is ginsenosides which are dammaraneglycosides Dammarane glycosides were reported frommanyparts of ginseng and heat processed P ginseng roots [1516] The chemical and morphological variations of Panaxnotoginseng and their relationship were recently described[17]

In continuation of our previous work [18 19] on P ginsengroots two more new compounds were isolated as naturalproducts This paper deals with the isolation and structureelucidation of two new compounds stigmasta-3120572-ol-3120572-(21015840R31015840S)-butane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate (1) and stigmasta-5-en-3120573-ol-3120573-(21015840R31015840S)-butane-11015840 21015840 31015840 41015840-tetraolyl-21015840 31015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate (2)on the basis of 1H and 13C NMR spectroscopic studiesincluding 2D-NMR (COSY HMBC and HSQC) FAB-MSESI FTMS IR spectroscopy and chemical reactions fromthe heat processed roots of P ginseng This is the first reportof the isolated compounds (1 and 2) from the heat processedroots of P ginseng Due to the significance of ginseng rootsof P ginseng of this plant as a medicinal the work in this area

2 Journal of Chemistry

has already been done The aim of the present investigationis to report some of the new findings in the form of naturalproducts from heat processed roots of P ginseng (Korean redginseng)

2 Materials and Methods

Optical rotationwasmeasured with an instrument on anAA-10 model polarimeter (Instruments Ltd Seoul Republic ofKorea) IR spectra were recorded on an Infinity Gold FT-IR(Thermo Mattson Waltham MA USA) spectrophotometerwhichwas available at Korea Institute of Science andTechnol-ogy Seoul Republic of Korea Both 1H and 13C-NMR spectrawere obtained on a Bruker Avance 600 high-resolutionspectrometer operating at 600 and 150MHz respectivelyThisNMRmachinewas available at SeoulNationalUniversity(SNU) Seoul Republic of Korea and all NMR spectra wererecorded at SNU (Instrument Bruker Germany) NMR spec-tra were obtained in deuterated chloroform using tetram-ethylsilane (TMS) as an internal standard with chemicalshifts expressed in ppm (120575) and coupling constants (119869) inHz FABMS data were recorded on a JMS-700 (Jeol MitakaJapan) spectrometer instrument which was available at SNUSeoul Republic of Korea All chemicals used were of ana-lytical grade Hexane ethyl acetate chloroform methanolethanol water sulphuric acid and vanillin were purchasedfrom Daejung Chemicals and Metals Co Ltd Republicof Korea Precoated TLC plates (layer thickness 025mm)silica gel for column chromatography (70ndash230mesh Amer-ican Society Testing Materials) and LiChroprep RP-18 (40ndash63 120583m) were from Merck (Darmstadt Germany) Authenticstandards of chemicals were purchased from Sigma-AldrichUSA Previously isolated authentic standards of 120573-sitosterol-120573-D-glucoside were available

21 Plant Material Fresh ginseng (P ginseng) was cultivatedof ground dried roots ginseng (6 years old) in GanghwadoRepublic of Korea A voucher specimen (No PG-R-11) hasbeen deposited at the Department of Applied Life ScienceKonkuk University Korean red ginseng was prepared byusing nonpeeled fresh ginseng which was steamed at 98∘Cfor 2 h using an autoclave The steamed ginseng after dryingand powdered 2978 g was prepared for extraction

22 Extraction of Korean Red Ginseng Powder The Koreanred ginseng powder (2978 g) was immersed in methanol(3 times 1 litre) for three days at room temperature and then thesupernatant was concentrated under vacuum to yield 301 g ofthe extract which was suspended in water and extracted withhexane ethyl acetate and n-butanol successively to produce5 g 89 g and 142 g extract respectively

23 Isolation of the Compounds from Ethyl Acetate ExtractThe entire ethyl acetate extract was subjected to normalphase column chromatography over silica gel (500 g)to yield 30 fractions (each of 500mL) with the fol-lowing eluants fractions 1-2 with hexane fractions2ndash4 with hexane-chloroform (9 1) fractions 5-6 with

hexane-chloroform (8 2) fractions 7-8 with hexane-chloroform (7 3) fractions 9-10 with hexane chloroform(6 4) fractions 11-12 with hexane chloroform (1 1)fractions 13-14 with hexane chloroform (4 6) fractions15-16 with hexane chloroform (3 7) fractions 17-18with hexane chloroform (2 8) fractions 19-20 withhexane chloroform (1 9) fractions 12ndash22 with chloroformfractions 23-24 with chloroform Methanol (98 02)fractions 25-26 with chloroform Methanol (95 05)fractions 27-28 with chloroform Methanol (9 1) andfractions 29-30 with CHCl

3MeOH (85 15) All fractions

were examined by TLC Fractions 1ndash4 were not furtherseparated due to the low amount of the substance Fractions25-26 (09 g) were crystallized after the purificationby column chromatography yielding 120573-sitosterol-120573-D-glucoside (20mg) whose identity was confirmed throughthe comparison of TLC and spectroscopic data withthose of an authentic sample Fractions 23-24 (14 g) wererechromatographed over LiChroprep RP-18 (ODS silica gel40ndash63 120583m 100 g each fraction 100mL) The elution wassequentially performed with methanol and water to yield 10fractions fractions 1-2 with H

2O MeOH (1 1) fractions 3-4

with H2O MeOH (2 8) fractions 5-6 with H

2O MeOH

(1 9) and fractions 7ndash10 with MeOH Fraction 9 (11 g)after rechromatography over silica gel with chloroform andmethanol in the ratio of (95 05 and 9 1) to yield two newcompounds 1 (29mg) and 2 (23mg)

24 Stigmasta-3120572-ol-3120572-(21015840R 31015840S)-butane-11015840210158403101584041015840-tetraolyl-21015840 31015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840 121015840101584010158401015840-dienoate(1) Yellow viscous liquid 119877

119891034 CHCl

3MeOH 95 05

[120572]D22 237 (MeOH 119888 02) IR (KBr) ] (cmminus1) 2924 2854

1740 1733 1721 1645 1458 1376 1165 1073 721 1H NMR(600MHz CDCl

3) 120575ppm 538 (1H m H-910158401015840) 536 (1H m

H-1010158401015840) 534 (1HmH-9101584010158401015840) 532 (1HmH-10101584010158401015840) 531 (1HmH-91015840101584010158401015840 H-101015840101584010158401015840) 530 (1H m H-121015840101584010158401015840) 528 (1H m H-131015840101584010158401015840)507 (1H m H-21015840) 498 (1H d 119869 = 48Hz H

2-41015840a) 430 (1H

d 119869 = 54Hz H2-41015840b) 413 (1H m H-31015840) 405 (1H br m

11988212= 125Hz H-3120573) 372 (1H d 119869 = 52Hz H

2-11015840a) 370

(1H d 119869 = 66Hz H2-11015840b) 115 (3H br s Me-19) 093 (3H d

119869 = 66HzMe-21) 089 (3H d 119869 = 65HzMe-26) 087 (3Hd 119869 = 63Hz Me-27) 085 (3H t 119869 = 78Hz Me-29) 084(3H t 119869 = 66Hz Me-1810158401015840) 082 (3H t 119869 = 66Hz Me-18101584010158401015840)080 (3H t 119869 = 63Hz Me-181015840101584010158401015840) 070 (3H br s Me-18)13C-NMR (150MHz CDCl

3) see Table 1 FAB-MS (positive

ion mode) (119898119911 ) 1312 [M+H]+ (11) (C87H155

O7) 415

(162) 398 (212) 282 (116) 280 (181) 263 (545) ESIFTMS119898119911 13121776 [M+H]+ (calcd for C

87H155

O7 13121779)

25 Stigmasta-5-en-3120573-ol-3120573-(21015840R31015840S)-butane-11015840210158403101584041015840-tet-raolyl-21015840 31015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-die-noate (2) Yellow semisolid119877

119891029 CHCl

3 MeOH 95 05


1745 1732 1650 1460 1378 1239 1053 754 1H NMR(600MHz CDCl

3) 120575 572 (1H m H-131015840101584010158401015840) 540 (1H m

H-121015840101584010158401015840) 538 (1H m H-101015840101584010158401015840) 535 (1H m H-91015840101584010158401015840) 533(1H m H-6) 530 (1H m H-9101584010158401015840) 526 (1H m H-910158401015840)

Journal of Chemistry 3

Table 1 13C NMR (150 MHz) spectral data of compounds 1 and 2

Position 120575C (1) 120575C (2)1 390 3722 314 3153 708 7174 423 4045 509 14076 174 12167 319 3188 340 3619 511 50110 359 36411 225 22612 397 39713 457 45814 564 56715 248 24216 271 28217 558 56018 119 11919 208 21020 414 42221 197 19722 335 33923 255 27124 467 45325 293 29126 186 18927 186 18728 230 23029 118 11811015840 614 61421015840 720 71131015840 649 65041015840 620 620110158401015840 1738 17381101584010158401015840 1736 173211015840101584010158401015840 1733 1718910158401015840 1318 13011010158401015840 1280 12999101584010158401015840 1301 129610101584010158401015840 1278 129291015840101584010158401015840 1297 1280101015840101584010158401015840 1270 1270121015840101584010158401015840 1253 1382131015840101584010158401015840 1236 12361810158401015840 142 14018101584010158401015840 140 140

Table 1 Continued

Position 120575C (1) 120575C (2)181015840101584010158401015840 140 136

CH2 (ester units)342 341 338 337296minus290 279 259226 211 210 204

356 342 341 340314 296minus292 288

260minus243 225

514 (1H m H-1010158401015840) 508 (1H m H-10101584010158401015840) 502 (1H dd 119869 =84 90Hz H-21015840) 430 (2H m H

2-11015840) 496 (1H m H-31015840)

406 (1H d 119869 = 60Hz H2-41015840a) 372 (1H d 119869 = 54Hz

H2-41015840b) 351 (1H br m 119882

12= 156Hz H-3120572) 101 (3H br

s Me-19) 092 (3H d 119869 = 60Hz Me-21) 090 (3H d119869 = 63Hz Me-26) 088 (3H d 119869 = 61Hz Me-27) 086(3H t 119869 = 65Hz Me-1810158401015840) 084 (3H t 119869 = 62Hz Me-18101584010158401015840) 082 (3H t 119869 = 60Hz Me-181015840101584010158401015840) 080 (3H d 119869 =63Hz Me-29) 067 (3H br s Me-18) 13C NMR (150MHzCDCl

3) see Table 1 FAB-MS (positive ion mode) (mz )

1310 [M+H]+ (11) (C87H153

O7) (27) 413 (100) 398 (998)

395 (985) 381 (661) 282 (830) 280 (217) 271 (693) 255(902) 213 (921) ESIFTMS 119898119911 13101619 [M+H]+ (calcdfor C87H153

O7 13101622)

26 Alkaline Hydrolysis A solution of compounds 1 and2 (10mg each) in 5 dry KOH MeOH (2mL) was heatedunder stirring separately at temperature (40ndash50∘C) for 4 hThe reaction mixture was acidified to pH 70 and partitionedbetweenMeOHandn-hexaneThen-hexane layer containingthe fatty acids was confirmed on the basis of TLC Eachsolution after separation of the fatty acids was evaporatedto dryness and the residue was dissolved in chloroform toisolate steroids (120573-sitosterol was compared by TLC) Eachsolid residue was identified as erythritol by HPLC 119877

11990513min

[23]

3 Results and Discussion

Compound 1 showed IR absorption bands for ester functions(1740 1733 1721 cmminus1) unsaturation (1645 cmminus1) and longaliphatic chain (721 cmminus1) On the basis of FAB mass and 13CNMR spectra the molecular ion peak of 1 was determinedat 119898119911 1311 [M+H]+ consistent with the molecular formulaof a steroidal erythrityl triester C

87H155

O7 The ion peaks

arising at mz 415 [M minus erythrityl unit]+ and 398 [415 minusOH]+ suggested stigmastane unit in the molecule The ionfragments generated atmz 282 [CH

3(C16H30)COOH]+ 280

[CH3(C16H28)COOH]+ and 263 [280 minusOH]+ indicated that

oleic and linoleic acids were esterifiedwith the erythritol unitThe 1H-NMRspectrumof 1 showedmultiple signals from120575 538 to 528 assigned to eight vinylic protons oxygenatedmethine protons of the steroid unit at 120575 405 with half widthof 125Hz ascribed to H-3120573 four one-proton doublets at 120575433 (119869 = 48Hz) 430 (119869 = 54Hz) 120575 372 (119869 = 52Hz)and 370 (119869 = 66Hz) attributed to oxygenated methyleneH2-11015840 and H

2-41015840 protons and two one-proton multiplets at 120575

507 and 498 accounted to oxygenated methine H-21015840 and H-31015840 protons respectively Nine three-proton signals as broadsignals at 120575 115 and 070 as doublets at 120575 093 (119869 = 66Hz)


089 (119869 = 65Hz) and 120575 087 (119869 = 63Hz) and as tripletsbetween 120575 085 and 075 were associated with the tertiary C-19 and C-18 secondary C-21 C-26 and C-27 and primary C-29 C-1810158401015840 C-18101584010158401015840 andC-181015840101584010158401015840methyl protons respectively allattached to saturated carbons

The 13C-NMR spectrum of 1 exhibited signals for estercarbons at 120575 1738 (C-110158401015840) 1736 (C-1101584010158401015840) and 1733 (C-11015840101584010158401015840)vinylic carbons between 120575 1318 and 1236 steroidal oxy-genated methine carbon at 120575 682 (C-3) erythritol carbonsat 120575 614 (C-11015840) 720 (C-21015840) 649 (C-31015840) and 620 (C-41015840) andmethyl carbons from 120575 208 to 118The stereochemistry of thesteroids at C-3 oxygenated methine proton was establishedby coupling interaction of the 1H NMR spectral data and bycomparison of the 1H and 13C NMR values of the steroidalcarbon frameworks with the reported steroidal data [20ndash22]The poliol was detected as erythritol by comparing retentiontime by HPLC [23]

The 1H-1H COSY spectrum of 1 showed correlationsof H-3 with H

2-2 and H

2-4 H-21015840 with H-11015840 and H-31015840

H-910158401015840H-9101584010158401015840 with H-1010158401015840H-10101584010158401015840 and H2-111015840101584010158401015840 with H-91015840101584010158401015840

H-101015840101584010158401015840 H-121015840101584010158401015840 and H-131015840101584010158401015840 The HMBC spectrum of 1 thatexhibited interactions of proton carbon relations is shownin Figure 3 The HSQC spectrum of 1 showed correlationof H-3 (120575 405) H

2-11015840 (120575 370 372) H-21015840 (120575 507) H-31015840 (120575

413) and H-41015840 (120575 433 430) with the respective oxygenatedcarbons C-3 (120575 682) C-11015840 (120575 614) C-21015840 (120575 720) C-31015840(120575 649) and C-41015840 (120575 620) and vinyl and methyl protonswith their corresponding carbon signals The absence of acarbon signal between 120575 110 and 90 supported the linkageof erythritol moiety to the steroid Alkaline hydrolysis of1 yielded 3-epistigmastanol oleic and linoleic acids (TLCcomparable) and erythritol (HPLC comparable) On the basisof foregoing description the structure of 1 was elucidatedas stigmasta-3120572-ol-3120572-(21015840R31015840S)-butane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate(1 Figure 1) This is a new steroidal erythrityl trimester

Compound 2 showed distinctive IR absorption bands forester groups (1745 1732 cmminus1) unsaturation (1650 cmminus1) andaliphatic chain (754 cmminus1) It had amolecular ion peak atmz1309 [M+H]+ determined on the basis of FAB mass and 13CNMR spectra consistent with themolecular formula steroidalerythritol triester C

87H153

O7 The ion peaks arising at mz

413 [M minus erythtrityl triester]+ 398 [413 minus Me]+ 395 [413 minusOH]+ and 381 [398 minus Me]+ suggested that 120573-sitosterol waspresent as an aglyconic unit It was also supported by the ionpeaks generated at mz 271 [413 minus side chain]+ 255 [271 minusOH]+ and 213 [255 minus ring D]+ The ion fragments producedat mz 282 [CH

3(CH2)7CH=CH(CH

2)7COOH]+ and 280

[CH3(C16H28)COOH]+ indicated that oleic and linoleic acids

were esterified with erythritol unitThe 1H-NMR spectrum of 2 showed nine one-proton

multiplets between 120575 572 and 508 assigned to vinylic protonsof the steroid and fatty acid units A one-proton doubledoublet at 120575 502 (J = 84 90Hz) a two-proton multipletat 120575 430 a one-proton multiplet at 120575 496 and two one-proton doublets at 120575 406 (J = 60Hz) and 372 (J = 54Hz)were ascribed to the erythritol protons H-21015840 H

2-11015840 H-31015840

and H2-41015840 respectively A one-proton broad multiplet at 120575

21

3

4

5

67

8

9

10

1112

13

1718

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2

21

3

4

5

67

8

9

10

1112

13 17

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1

CHndashOCO(CH2)7ndashCH=CHndash(CH2)7CH3


CH2ndashOCO(CH2)7ndashCH=CHndashCH2ndashCH=CH(CH2)4CH3




Figure 1 Chemical structures of compounds 1 and 2

351 with half width of 156Hz was due to oxygenated H-3120572methine proton Nine three-proton signals as broad singletsat 120575 101 and 067 as doublets at 120575 092 (J = 60Hz) 090(J = 63Hz) and 088 (J = 61Hz) and as triplets at 120575 086(J = 65Hz) 084 (J = 62Hz) 082 (J = 60Hz) and 080(J = 63Hz) were associated with the tertiary C-18 and C-19secondary C-21 C-26 and C-27 and primary C-1810158401015840 C-18101584010158401015840C-181015840101584010158401015840 and C-29 methyl protons respectively all attachedto saturated carbons The 13C-NMR spectrum of 2 exhibitedimportant signals for ester carbons at 120575 1738 (C-110158401015840) 1732(C-1101584010158401015840) and 1718 (C-11015840101584010158401015840) vinylic carbons between 120575 1407and 1236 oxygenated steroidal methine carbon at 120575 717


21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1




mz 415

mz 795

mz 398

mz 282

21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

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1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2




mz 413

mz 795

mz 395

mz 282

mz 271

Figure 2 Mass fragmentation pattern of compounds 1 and 2

(C-3) and erythritol carbons at 120575 614 (C-11015840) 681 (C-21015840)650 (C-31015840) and 620 (C-41015840) methyl carbons from 120575 210 to118 The absence of an anomeric carbon signals from 120575 110to 90 supported erythritol unit attached to the steroid Thestereochemistry of the steroids at C-3 oxygenated methineproton was established by coupling interaction of the 1HNMR spectral data and by comparison of the 1H and 13CNMR values of the steroidal carbon frameworks with thereported steroidal data [20ndash22] The poliol was detected aserythritol by comparing retention time by HPLC [23]

O

CH2

H

HH

2

O

CH2

H

HH

H

1







1998400998400998400

Figure 3 Key HMBC correlations of new compounds 1 and 2


2-2 and H

2-4 H-6 with H

2-4 H

2-7 and

H-8 H-21015840 with H2-11015840 H-31015840 and H

2-41015840 and H

2-111015840101584010158401015840 with

H-91015840101584010158401015840 H-101015840101584010158401015840 H-12101584010158401015840 and H-131015840101584010158401015840 The key HMBCcorrelations of 2 that exhibited interactions of proton carbonrelations are shown in Figure 3 The HSQC spectrum of 2showed correlations of H-3 at 120575 351 with C-3 at 120575 7122H2-11015840 at 120575 502 with C-21015840 at 120575 6819 H

2-11015840 at 120575 430 with

C-11015840 at 120575 6136 H-31015840 at 120575 413 with C-31015840 at 120575 6501 andH2-41015840 at 120575 372 and 351 with C-41015840 at 120575 6207 Alkaline

hydrolysis of 2 yielded 120573-sitosterol oleic and linoleicacids TLC comparable These lines of evidence led to theformulation of the structure of 2 as stigmasta-5-en-3120573-ol-3120573-(21015840R31015840S)-butane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate (2 Figure 2) This is anew steroidal erythrityl triestrer


4 Conclusion

Two new compounds stigmasta-3120572-ol-3120572-(21015840R31015840S)-bu-tane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-oc-tadec-91015840101584010158401015840121015840101584010158401015840-dienoate (1) and stigmasta-5-en-3120573-ol-3120573-(21015840R31015840S)-butane-11015840210158403101584041015840-tetraolyl-2101584031015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-dienoate (2) were isolated fromthe methanolic extraction of heat processed roots of Pginseng A lot of work already studied P ginseng compoundsand biological activity Further studies on the P ginsengcompounds and bioactivity are also needed

Acknowledgment

This work was carried out with the support of CooperativeResearch Program for Agriculture Science amp TechnologyDevelopment (PJ0083022011) Rural Development Adminis-tration Republic of Korea

References

[1] M K Ang-Lee J Moss and C S Yuan ldquoHerbal medicinesand perioperative carerdquo The Journal of the American MedicalAssociation vol 286 no 2 pp 208ndash216 2001

[2] T Takaku K Kameda Y Matsuura K Sekiya and H OkudaldquoStudies on insulin-like substances in Korean red ginsengrdquoPlanta Medica vol 56 no 1 pp 27ndash30 1990

[3] J H Do H O Lee S K Lee K B Noh S D Lee and K SLee ldquoComparisons of acidic polysaccharide contents in variousginseng species and partsrdquo Korean Journal of Ginseng Sciencevol 17 no 2 pp 145ndash147 1993

[4] W Y Kim J M Kim S B Han et al ldquoSteaming of ginsengat high temperature enhances biological activityrdquo Journal ofNatural Products vol 63 no 12 pp 1702ndash1704 2000

[5] C Z Wang H H Aung M Ni et al ldquoRed American ginsengginsenoside constituents and antiproliferative activities of heat-processedPanax quinquefolius rootsrdquoPlantaMedica vol 73 no7 pp 669ndash674 2007

[6] S Helms ldquoCancer prevention and therapeutics Panax ginsengrdquoAlternative Medicine Review vol 9 no 3 pp 259ndash274 2004

[7] J T Xie S Mchendale and C S Yuan ldquoGinseng and diabetesrdquoThe Americam Journal of Chinese Medicine vol 33 no 3 pp397ndash404 2005

[8] C J Liou W C Huang and J Tseng ldquoLong-term oraladministration of ginseng extract modulates humoral immuneresponse and spleen cell functionsrdquo The American Journal ofChinese Medicine vol 33 no 4 pp 651ndash661 2005

[9] T K Yun Y S Lee Y H Lee S I Kim and H Y YunldquoAnticarcinogenic effect of Panax ginseng CA Meyer andidentification of active compoundsrdquo Journal of Korean MedicalScience vol 16 supplement pp S6ndashS18 2001

[10] H H Yoo T Yokosawa A Satoh K S Kang and H YKim ldquoEffects of ginseng on the proliferation of human lungfibroblastsrdquo The American Journal of Chinese Medicine vol 34no 1 pp 137ndash146 2006

[11] A S Attele Y P Zhou J T Xie et al ldquoAntidiabetic effects ofPanax ginseng berry extract and the identification of an effectivecomponentrdquo Diabetes vol 51 no 6 pp 1851ndash1858 2002

[12] N FukuyamaM Shibuya and Y Orihara ldquoAntimicrobial poly-acetylenes fromPanax ginseng hairy root culturerdquoChemical andPharmaceutical Bulletin vol 60 no 3 pp 377ndash380 2012

[13] M C Rho H S Lee S W Lee et al ldquoPolyacetylenic com-pounds ACAT inhibitors from the roots of Panax ginsengrdquoJournal of Agricultural and Food Chemistry vol 53 no 4 pp919ndash922 2005

[14] I H Park N Y Kim S B Han et al ldquoThree new dammaraneglycosides from heat processed ginsengrdquo Archives of PharmacalResearch vol 25 no 4 pp 428ndash432 2002

[15] N Baek D S Kim Y H Lee J D Park C B Lee and S IKim ldquoGinsenoside Rh4 a genuine dammarane glycoside fromKorean red ginsengrdquo Planta Medica vol 62 no 1 pp 86ndash871996

[16] J H Ryu J H Park J H Eun J H Jung and D HSohn ldquoA dammarane glycoside from Korean red ginsengrdquoPhytochemistry vol 44 no 5 pp 931ndash933 1997

[17] D Wang H I Koh Y Hong et al ldquoChemical and morpho-logical variations of Panax notoginseng and their relationshiprdquoPhytochemistry vol 93 no 3 pp 88ndash95 2013

[18] I M Chung M Y Kim N Praveen Y P Hong and A AhmadldquoFatty acid constituent from the heat processed roots of Panaxginsengrdquo Asian Journal of Chemistry vol 25 no 2 pp 1086ndash1088 2013

[19] I M Chung M Ali Y P Hong and A Ahmad ldquoNewcompound from the heat processed roots of Panax ginsengrdquoAsian Journal of Chemistry vol 25 no 8 pp 4667ndash4669 2013

[20] I M Chung M Ali T D Khanh M G Choung H J Parkand A Ahmad ldquoNew stigmastane steroids constituents fromrice hulls ofOryza sativa and inhibitory activity on radish seedrdquoBulletin of the Korean Chemical Society vol 27 no 1 pp 93ndash982006

[21] I M Chung M Ali A Ahmad J D Lim C Y Yu and J SKim ldquoChemical constituents of rice (Oryza sativa) hulls andtheir herbicidal activity against duckweed (Lemna paucicostataHegelm 381)rdquo Phytochemical Analysis vol 17 no 1 pp 36ndash452006

[22] I M Chung M Ali A Ahmad et al ldquoSteroidal constituents ofrice (Oryza sativa) hulls with algicidal and herbicidal activityagainst blue-green algae and duckweedrdquo Phytochemical Analy-sis vol 18 no 2 pp 133ndash145 2007

[23] T Shindou Y Sasaki H Miki T Eguchi K Hagiwara and TIchikawa ldquoIdentification of erythritol byHPLCandGC-MS andquantitative measurement in pulps of various fruitsrdquo Journal ofAgricultural and Food Chemistry vol 37 no 6 pp 1474ndash14761989

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy


Carbohydrate Chemistry

International Journal of


Journal of

Chemistry


Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of


The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of


Chromatography Research International


Applied ChemistryJournal of



Theoretical ChemistryJournal of


Journal of

Spectroscopy

Analytical ChemistryInternational Journal of


Journal of


Quantum Chemistry


Organic Chemistry International

ElectrochemistryInternational Journal of



CatalystsJournal of


has already been done The aim of the present investigationis to report some of the new findings in the form of naturalproducts from heat processed roots of P ginseng (Korean redginseng)

2 Materials and Methods

Optical rotationwasmeasured with an instrument on anAA-10 model polarimeter (Instruments Ltd Seoul Republic ofKorea) IR spectra were recorded on an Infinity Gold FT-IR(Thermo Mattson Waltham MA USA) spectrophotometerwhichwas available at Korea Institute of Science andTechnol-ogy Seoul Republic of Korea Both 1H and 13C-NMR spectrawere obtained on a Bruker Avance 600 high-resolutionspectrometer operating at 600 and 150MHz respectivelyThisNMRmachinewas available at SeoulNationalUniversity(SNU) Seoul Republic of Korea and all NMR spectra wererecorded at SNU (Instrument Bruker Germany) NMR spec-tra were obtained in deuterated chloroform using tetram-ethylsilane (TMS) as an internal standard with chemicalshifts expressed in ppm (120575) and coupling constants (119869) inHz FABMS data were recorded on a JMS-700 (Jeol MitakaJapan) spectrometer instrument which was available at SNUSeoul Republic of Korea All chemicals used were of ana-lytical grade Hexane ethyl acetate chloroform methanolethanol water sulphuric acid and vanillin were purchasedfrom Daejung Chemicals and Metals Co Ltd Republicof Korea Precoated TLC plates (layer thickness 025mm)silica gel for column chromatography (70ndash230mesh Amer-ican Society Testing Materials) and LiChroprep RP-18 (40ndash63 120583m) were from Merck (Darmstadt Germany) Authenticstandards of chemicals were purchased from Sigma-AldrichUSA Previously isolated authentic standards of 120573-sitosterol-120573-D-glucoside were available

21 Plant Material Fresh ginseng (P ginseng) was cultivatedof ground dried roots ginseng (6 years old) in GanghwadoRepublic of Korea A voucher specimen (No PG-R-11) hasbeen deposited at the Department of Applied Life ScienceKonkuk University Korean red ginseng was prepared byusing nonpeeled fresh ginseng which was steamed at 98∘Cfor 2 h using an autoclave The steamed ginseng after dryingand powdered 2978 g was prepared for extraction

22 Extraction of Korean Red Ginseng Powder The Koreanred ginseng powder (2978 g) was immersed in methanol(3 times 1 litre) for three days at room temperature and then thesupernatant was concentrated under vacuum to yield 301 g ofthe extract which was suspended in water and extracted withhexane ethyl acetate and n-butanol successively to produce5 g 89 g and 142 g extract respectively

23 Isolation of the Compounds from Ethyl Acetate ExtractThe entire ethyl acetate extract was subjected to normalphase column chromatography over silica gel (500 g)to yield 30 fractions (each of 500mL) with the fol-lowing eluants fractions 1-2 with hexane fractions2ndash4 with hexane-chloroform (9 1) fractions 5-6 with

hexane-chloroform (8 2) fractions 7-8 with hexane-chloroform (7 3) fractions 9-10 with hexane chloroform(6 4) fractions 11-12 with hexane chloroform (1 1)fractions 13-14 with hexane chloroform (4 6) fractions15-16 with hexane chloroform (3 7) fractions 17-18with hexane chloroform (2 8) fractions 19-20 withhexane chloroform (1 9) fractions 12ndash22 with chloroformfractions 23-24 with chloroform Methanol (98 02)fractions 25-26 with chloroform Methanol (95 05)fractions 27-28 with chloroform Methanol (9 1) andfractions 29-30 with CHCl

3MeOH (85 15) All fractions

were examined by TLC Fractions 1ndash4 were not furtherseparated due to the low amount of the substance Fractions25-26 (09 g) were crystallized after the purificationby column chromatography yielding 120573-sitosterol-120573-D-glucoside (20mg) whose identity was confirmed throughthe comparison of TLC and spectroscopic data withthose of an authentic sample Fractions 23-24 (14 g) wererechromatographed over LiChroprep RP-18 (ODS silica gel40ndash63 120583m 100 g each fraction 100mL) The elution wassequentially performed with methanol and water to yield 10fractions fractions 1-2 with H

2O MeOH (1 1) fractions 3-4

with H2O MeOH (2 8) fractions 5-6 with H

2O MeOH

(1 9) and fractions 7ndash10 with MeOH Fraction 9 (11 g)after rechromatography over silica gel with chloroform andmethanol in the ratio of (95 05 and 9 1) to yield two newcompounds 1 (29mg) and 2 (23mg)

24 Stigmasta-3120572-ol-3120572-(21015840R 31015840S)-butane-11015840210158403101584041015840-tetraolyl-21015840 31015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840 121015840101584010158401015840-dienoate(1) Yellow viscous liquid 119877

119891034 CHCl

3MeOH 95 05


1740 1733 1721 1645 1458 1376 1165 1073 721 1H NMR(600MHz CDCl

3) 120575ppm 538 (1H m H-910158401015840) 536 (1H m

H-1010158401015840) 534 (1HmH-9101584010158401015840) 532 (1HmH-10101584010158401015840) 531 (1HmH-91015840101584010158401015840 H-101015840101584010158401015840) 530 (1H m H-121015840101584010158401015840) 528 (1H m H-131015840101584010158401015840)507 (1H m H-21015840) 498 (1H d 119869 = 48Hz H

2-41015840a) 430 (1H

d 119869 = 54Hz H2-41015840b) 413 (1H m H-31015840) 405 (1H br m

11988212= 125Hz H-3120573) 372 (1H d 119869 = 52Hz H

2-11015840a) 370

(1H d 119869 = 66Hz H2-11015840b) 115 (3H br s Me-19) 093 (3H d

119869 = 66HzMe-21) 089 (3H d 119869 = 65HzMe-26) 087 (3Hd 119869 = 63Hz Me-27) 085 (3H t 119869 = 78Hz Me-29) 084(3H t 119869 = 66Hz Me-1810158401015840) 082 (3H t 119869 = 66Hz Me-18101584010158401015840)080 (3H t 119869 = 63Hz Me-181015840101584010158401015840) 070 (3H br s Me-18)13C-NMR (150MHz CDCl

3) see Table 1 FAB-MS (positive

ion mode) (119898119911 ) 1312 [M+H]+ (11) (C87H155

O7) 415

(162) 398 (212) 282 (116) 280 (181) 263 (545) ESIFTMS119898119911 13121776 [M+H]+ (calcd for C

87H155

O7 13121779)

25 Stigmasta-5-en-3120573-ol-3120573-(21015840R31015840S)-butane-11015840210158403101584041015840-tet-raolyl-21015840 31015840-dioctadec-9101584010158409101584010158401015840-enoyl-41015840-octadec-91015840101584010158401015840121015840101584010158401015840-die-noate (2) Yellow semisolid119877

119891029 CHCl

3 MeOH 95 05


1745 1732 1650 1460 1378 1239 1053 754 1H NMR(600MHz CDCl

3) 120575 572 (1H m H-131015840101584010158401015840) 540 (1H m

H-121015840101584010158401015840) 538 (1H m H-101015840101584010158401015840) 535 (1H m H-91015840101584010158401015840) 533(1H m H-6) 530 (1H m H-9101584010158401015840) 526 (1H m H-910158401015840)



Position 120575C (1) 120575C (2)1 390 3722 314 3153 708 7174 423 4045 509 14076 174 12167 319 3188 340 3619 511 50110 359 36411 225 22612 397 39713 457 45814 564 56715 248 24216 271 28217 558 56018 119 11919 208 21020 414 42221 197 19722 335 33923 255 27124 467 45325 293 29126 186 18927 186 18728 230 23029 118 11811015840 614 61421015840 720 71131015840 649 65041015840 620 620110158401015840 1738 17381101584010158401015840 1736 173211015840101584010158401015840 1733 1718910158401015840 1318 13011010158401015840 1280 12999101584010158401015840 1301 129610101584010158401015840 1278 129291015840101584010158401015840 1297 1280101015840101584010158401015840 1270 1270121015840101584010158401015840 1253 1382131015840101584010158401015840 1236 12361810158401015840 142 14018101584010158401015840 140 140

Table 1 Continued

Position 120575C (1) 120575C (2)181015840101584010158401015840 140 136


356 342 341 340314 296minus292 288

260minus243 225


2-11015840) 496 (1H m H-31015840)

406 (1H d 119869 = 60Hz H2-41015840a) 372 (1H d 119869 = 54Hz

H2-41015840b) 351 (1H br m 119882

12= 156Hz H-3120572) 101 (3H br



1310 [M+H]+ (11) (C87H153

O7) (27) 413 (100) 398 (998)


O7 13101622)


11990513min

[23]



87H155

O7 The ion peaks


3(C16H30)COOH]+ 280









2-2 and H

2-4 H-21015840 with H-11015840 and H-31015840



2-11015840 (120575 370 372) H-21015840 (120575 507) H-31015840 (120575



87H153



3(CH2)7CH=CH(CH

2)7COOH]+ and 280




2-11015840 H-31015840


21

3

4

5

67

8

9

10

1112

13

1718

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2

21

3

4

5

67

8

9

10

1112

13 17

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1










21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1




mz 415

mz 795

mz 398

mz 282

21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2




mz 413

mz 795

mz 395

mz 282

mz 271



O

CH2

H

HH

2

O

CH2

H

HH

H

1







1998400998400998400



2-2 and H

2-4 H-6 with H

2-4 H

2-7 and

H-8 H-21015840 with H2-11015840 H-31015840 and H

2-41015840 and H

2-111015840101584010158401015840 with


2-11015840 at 120575 430 with




4 Conclusion


Acknowledgment


References

































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of



Position 120575C (1) 120575C (2)1 390 3722 314 3153 708 7174 423 4045 509 14076 174 12167 319 3188 340 3619 511 50110 359 36411 225 22612 397 39713 457 45814 564 56715 248 24216 271 28217 558 56018 119 11919 208 21020 414 42221 197 19722 335 33923 255 27124 467 45325 293 29126 186 18927 186 18728 230 23029 118 11811015840 614 61421015840 720 71131015840 649 65041015840 620 620110158401015840 1738 17381101584010158401015840 1736 173211015840101584010158401015840 1733 1718910158401015840 1318 13011010158401015840 1280 12999101584010158401015840 1301 129610101584010158401015840 1278 129291015840101584010158401015840 1297 1280101015840101584010158401015840 1270 1270121015840101584010158401015840 1253 1382131015840101584010158401015840 1236 12361810158401015840 142 14018101584010158401015840 140 140

Table 1 Continued

Position 120575C (1) 120575C (2)181015840101584010158401015840 140 136


356 342 341 340314 296minus292 288

260minus243 225


2-11015840) 496 (1H m H-31015840)

406 (1H d 119869 = 60Hz H2-41015840a) 372 (1H d 119869 = 54Hz

H2-41015840b) 351 (1H br m 119882

12= 156Hz H-3120572) 101 (3H br



1310 [M+H]+ (11) (C87H153

O7) (27) 413 (100) 398 (998)


O7 13101622)


11990513min

[23]



87H155

O7 The ion peaks


3(C16H30)COOH]+ 280









2-2 and H

2-4 H-21015840 with H-11015840 and H-31015840



2-11015840 (120575 370 372) H-21015840 (120575 507) H-31015840 (120575



87H153



3(CH2)7CH=CH(CH

2)7COOH]+ and 280




2-11015840 H-31015840


21

3

4

5

67

8

9

10

1112

13

1718

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2

21

3

4

5

67

8

9

10

1112

13 17

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1










21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1




mz 415

mz 795

mz 398

mz 282

21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2




mz 413

mz 795

mz 395

mz 282

mz 271



O

CH2

H

HH

2

O

CH2

H

HH

H

1







1998400998400998400



2-2 and H

2-4 H-6 with H

2-4 H

2-7 and

H-8 H-21015840 with H2-11015840 H-31015840 and H

2-41015840 and H

2-111015840101584010158401015840 with


2-11015840 at 120575 430 with




4 Conclusion


Acknowledgment


References

































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of





2-2 and H

2-4 H-21015840 with H-11015840 and H-31015840



2-11015840 (120575 370 372) H-21015840 (120575 507) H-31015840 (120575



87H153



3(CH2)7CH=CH(CH

2)7COOH]+ and 280




2-11015840 H-31015840


21

3

4

5

67

8

9

10

1112

13

1718

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2

21

3

4

5

67

8

9

10

1112

13 17

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1










21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1




mz 415

mz 795

mz 398

mz 282

21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2




mz 413

mz 795

mz 395

mz 282

mz 271



O

CH2

H

HH

2

O

CH2

H

HH

H

1







1998400998400998400



2-2 and H

2-4 H-6 with H

2-4 H

2-7 and

H-8 H-21015840 with H2-11015840 H-31015840 and H

2-41015840 and H

2-111015840101584010158401015840 with


2-11015840 at 120575 430 with




4 Conclusion


Acknowledgment


References

































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

1




mz 415

mz 795

mz 398

mz 282

21

3

4

5

67

8

9

10

1112

1317

18

1619

15

20

2128

29

27

25

26

22

O

CH21998400

2998400

3998400

4998400

1998400998400

9998400998400

10998400998400

18998400998400

1998400998400998400

9998400998400998400

10998400998400998400

18998400998400998400

1998400998400998400998400

9998400998400998400998400

10998400998400998400998400

12998400998400998400998400

13998400998400998400998400

18998400998400998400998400

H

HH

2




mz 413

mz 795

mz 395

mz 282

mz 271



O

CH2

H

HH

2

O

CH2

H

HH

H

1







1998400998400998400



2-2 and H

2-4 H-6 with H

2-4 H

2-7 and

H-8 H-21015840 with H2-11015840 H-31015840 and H

2-41015840 and H

2-111015840101584010158401015840 with


2-11015840 at 120575 430 with




4 Conclusion


Acknowledgment


References

































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


4 Conclusion


Acknowledgment


References

































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of










Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

New Steroidal Erythrityl Triesters from the Heat Processed Roots of Panax ginseng

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Transcript of New Steroidal Erythrityl Triesters from the Heat Processed Roots of Panax ginseng