Fingerprint analysis of organic acids chromones and triterpenoid saponins in five Cimicifuga species by thin layer chromatography
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1 Chin J Pharm Anal G nm nm ChemPattern 6 QTofMS 365 nm nm 16 3 R917 A Fingerprint analysis of organic acids chromones and triterpenoid saponins in five Cimicifuga species by thin layer chromatography XIAO Hong - hua 1 SUN Lei 2 JIN Hong - yu 2 MA Shuang - cheng 2 1. Beijing Chaoyang Institute for Drug Control Beijing China 2. National Institutes for Food and Drug Control Beijing China Abstract Objective To establish a method for fingerprint analysis and chemometric analysis of five Cimicifuga species by thin - layer chromatography TLC. Methods The samples were extracted by ultrasonic with methanol sample spotting for chromatography was performed on the silica gel 60 TLC plate using the lower layer of a mixture of chloroform - methanol - water stored below 10 as the developing solvent. The samples were examined and their chromatograms were recorded in UV light at 365 nm then in UV light at 365 nm after derivatization with anisaldehyde test solution heated at 105. The images were converted to a digital profile with grayscale intensity and then the common pattern of TLC fingerprint was generated with ChemPattern software and authentication and quality assessment were conducted by similarity analysis 2D cluster analysis and principal component a- nalysis. The compounds released by the bands were identified by six reference substances and QT of MS. Results In the chromatogram of authentic Cimicifuga nine light blue bands were visualized by UV light at 365 nm sixteen characteristic bands with difference colors were visualized by UV light at 365 nm after derivatization with anisaldehyde test solution. These bands could be easily distinguished from authentic Cimicifuga and the other species by comparison with the TLC chromatogram. The fingerprints of the three authentic Cimicifuga samples were generally i- dentical. Conclusion The TLC fingerprint analysis method can be used for rapid identification and quality control of Cimicifuga. Key words Cimicifuga thin layer chromatography TLC fingerprint quadrupole time of flight mass spectrometry QTofMS chromone triterpenoid saponins digital profile graph TCM rapid identification 2D cluster analysis Cimicifuga heracleifolia Kom. 1 C. dahurica Turcz. Maxim. C. foetida L. 1 Tel E - mail dasunlei@ sina. com Tel E - mail xhh98@ sina. com
2 548 Chin J Pharm Anal C. racemosa L. Nutt. 2 1 HPLC Linomat 5 Digistore TLC Camag Acquity UPLC/Xevo QTofMS Waters ChemPattern TLC H actein deoxyactein Chromodex TLC Limit RO H G60 Merck 16 TLC 1 Tab 1 1 Information of Cimicifuga species No. original plant type source 1 C. racemosa L. Nutt. extract 2 C. simplex Wormsk 3 C. foetida L. 4 C. heracleifolia Kom. 5 C. dahurica Turcz. Maxim. 6 Cimicifuga sample 7 Cimicifuga sample 8 Cimicifuga sample 9 Cimicifuga sample 10 Cimicifuga sample 11 Cimicifuga sample 12 Cimicifuga sample 13 Cimicifuga sample 14 Cimicifuga sample 15 Cimicifuga sample 16 Cimicifuga sample Germany North Korea Gansu North Korea reference substance of crude drug Heilongjiang Jilin Ningxia Qinghai Gansu μl ml 0. 1 mg g 10 ml 250 W 40 khz 20 min 2. 3 TLC 2 μl nm nm 2. 4
3 Chin J Pharm Anal ChemPattern TLC 1 - A 2. 5 UPLC - QTofMS 1 - B nm 3 % Rf 0. 5 ml 1 min μm j k 2. 6 UPLC - QTofMS Acquity UPLC BEH C mm 50 mm 1. 7 μmx ~ A B 0 ~ 6. 5 min 20% A 70% A 0. 3 ml min μl ESI kv V MS E 15 ~ 45 V L h L h - 1 m /z 100 ~ ~ m n o ~ s t u v w r Rf y u Rf y Rf u t 2 1 Fig 1 TLC A 365 nm B 365 nm TLC chromatograms A 365 nm B 365 nm after derivatization S1. cimifugin S2. ferulic acid S3. isoferulic acid actein S deoxyactein 1 ~ 16 samples S4. prim - O - glucosylcimifugin S TLC ~ 3 ~ TLC ~ a ~ i 9 j ~ y
4 550 Chin J Pharm Anal Tab 2 Information of bands code compound colour Rf Rf value detection condition a b c d e f g h i j k l prim - O - glucosylcimifugin isoferulic acid ferulic acid cimifugin light blue without derivatization light blue without derivatization light blue without derivatization light blue without derivatization light blue without derivatization light blue without derivatization light blue without derivatization light blue without derivatization light blue without derivatization yellow or orange derivatization yellow or orange derivatization pink derivatization m C 39 H 60 O 1 1 pink derivatization n C 40 H 58 O 13 and C 40 H 60 O 13 pink derivatization o p q pink derivatization pink derivatization pink derivatization r C 38 H 58 O 11 pink derivatization s C 35 H 54 O 9 pink derivatization t C 37 H 56 O 10 and C 37 H 58 O 10 pink derivatization u C 37 H 56 O 10 and C 37 H 58 O 10 pink derivatization v w x pink derivatization pink derivatization yellow or orange derivatization y actein 27 - yellow or orange derivatization 27 - deoxyactein triterpenoid saponins see below for details of relevant structure analysis 3. 3 TLC a c b 2 - B A 3 t u k n f e i g h d
5 Chin J Pharm Anal Fig 2 A 365 nm B 365 nm Cluster analysis results A 365 nm B 365 nm after derivatization 3 Fig 3 A 365 nm B 365 nm Results of principal component analysis A 365 nm B 365 nm after derivatization 6 ~ m/z 673 M + H M + H M + H M + H r u s m n TLC 1 u min u 1 C 37 H 58 O 10 m /z 645 M + H M + H M + H M + H M + H M + H M + H C 37 H 56 O O O - β - D A 27 - O O - β - D - 2 UPLC min m /z 661 M + H M + Na M + K + m /z 601 M + H M + H M + H r min 4 - B M + H M + H M + H M + H C. acerina u min u 2 C 37 H 56 O 10 u 2 3' - O - m/z 691 M + H M + Na + MassLynx O - C 38 H 58 O O O O O - β - D α - L - 11 O O - β - D -
6 552 Chin J Pharm Anal r Fig 4 QTofMS spectra of reference substance and the band r A deoxyactein B. r band r s min C 35 H 54 O O TLC 13 3 O - α - L - A TLC m /z 601 M + 14 H M + H m / z 487 M + H M + H % 451 M + H % 2 n min n 1 C 40 H 58 O 13 m /z 729 M + H M + H M + H M + H M + H O O - 2' - O β - D min n 2 C 40 H 60 O O O - 2' - O - - β - D - 11 n 1 2 H m min C 39 H 60 O 11 m /z 687 M + H M + H M + H C Rf Rf 0. 2 ~ ~ ' - O - B ~ 15 TLC 2
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