Terpenoids of the rhizomes ofRhodiola rosea

Куркин, В. А.; Zapesochnaya, G. G.; Shchavlinskii, A. N.

doi:10.1007/bf00579060

Cited by 23 publications

(32 citation statements)

References 6 publications

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“…PEP inhibitory activity was measured with a Perkin-Elmer HTS7000 bioassay reader. Column chromatography was performed over normal-phase (Fuji Silysia BW-820MH) or reversed-phase (Cosmosil 75C 18 The same numbering system as for 22 is used.…”

Section: Methodsmentioning

confidence: 99%

“…They were analyzed by the 1 H-1 H shift correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and HMBC spectra, and 22 was identified as rosiridin, previously isolated from R. rosea. 18) However, the configuration at C-4 of rosiridin was not determined, and thus we determined the absolute configuration of C-4 by applying a modified Mosher's method. 19) An excess amount of (R)-a-methoxy-a-trifluoromethylphenylacetic acid (MTPA) chlorides gave per-MTPA esters, which failed to give definitive results, perhaps due to the effect of the MTPA moieties on the glucose unit.…”

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confidence: 99%

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Prolyl Endopeptidase Inhibitors from the Underground Part of Rhodiola sachalinensis

Fan

Tezuka

Ni³

et al. 2001

Chem. Pharm. Bull.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Prolyl Endopeptidase Inhibitors from the Underground Part of Rhodiola sachalinensis

Fan

Tezuka

Ni³

et al. 2001

Chem. Pharm. Bull.

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“…Reinvestigation of the Absolute Configuration of (؊)-Rosiridol Rosiridin (2) }, 2 was identified to be rosiridin, which was isolated from R. rosea 20) and R. sachalinensis, in which the absolute stereostructure of rosiridin was reported to be 2Ј. 18 .…”

Section: )mentioning

confidence: 99%

“…The EtOAc-soluble fraction was subjected to normal-phase and reverse-phase column chromatographies, and finally HPLC to give rosiridoside C (5, 0.0013%). The n-BuOH-soluble phase was subjected to Diaion HP-20 column chromatography to afford a methanoleluted fraction (3.5%) as previously reported.1,16) The methanol-eluted fraction was separated by normal-and reversed-phase column chromatography, and finally HPLC to give rosiridosides A (3, 0.00019%) and B (4, 0.00032%) together with rosiridin (2, 0.49%).Reinvestigation of the Absolute Configuration of (؊)-Rosiridol Rosiridin (2) }, 2 was identified to be rosiridin, which was isolated from R. rosea 20) and R. sachalinensis, in which the absolute stereostructure of rosiridin was reported to be 2Ј. …”

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Reinvestigation of Absolute Stereostructure of (-)-Rosiridol: Structures of Monoterpene Glycosides, Rosiridin, Rosiridosides A, B, and C, from Rhodiola sachalinensis

Yoshikawa

Nakamura

et al. 2008

Chem. Pharm. Bull.

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In the course of our serial studies on bioactive constituents from Chinese natural medicines, [2][3][4][5][6][7][8][9][10][11] we have characterized the structures of aliphatic alcohol and monoterpene oligoglycosides and cyanogenic glycosides from the roots of Rhodiola (R) quadrifida, 12,13) R. sacra, 14) and R. crenulata. 15)Among the isolated compounds, several monoterpene oligoglycosides were found to show histamine release from rat exudate cells induced by an antigen-antibody reaction. 14) Furthermore, from the extracts of R. sachalinensis with a protective effect an D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes, we isolated monoterpene oligoglycosides, flavonol bisdesmosides, and cyanogenic glycoside named sachalosides I-VIII and reported their structures and hepatoprotective effects.1,16) As a continuing study on R. sachalinensis, we isolated three new (Ϫ)-rosiridol glycosides termed rosiridosides A (3), B (4), and C (5) together with rosiridin (2) The absolute configuration of the 4-position in (Ϫ)-rosiridol (1) was first reported to be S by the total enantioselective synthesis and chemical transformation to (Ϫ)-eldanolide. 17)However, the absolute configuration of the 4-position in (Ϫ)-rosiridol and rosiridin was recently revised to be R (1Ј, 2Ј) by the application of the modified Mosher's method. 18,19) In order to determine the absolute stereostructures of rosiridosides (3-5), we began with a reinvestigation of the absolute configuration of (Ϫ)-rosiridol. This paper deals with the application of the modifiel Mosher's method for (Ϫ)-and (ϩ)-rosiridol pivalate (6, 11), which supported the previous synthetic evidence to be S configuration (1, 2) rather than R form (1Ј, 2Ј). Furthermore, we described the isolation and structure elucidation of three new (Ϫ)-rosiridol glycosides (3, 4, 5).Isolation of Rosiridin and Rosiridosides A, B, and C The methanolic extract from the roots of R. sachalinensis was partitioned into an EtOAc-H 2 O mixture to furnish an EtOAc-soluble phase (3.5% from the roots) and aqueous layer, which was further extracted with n-BuOH to give a nBuOH-soluble phase. The EtOAc-soluble fraction was subjected to normal-phase and reverse-phase column chromatographies, and finally HPLC to give rosiridoside C (5, 0.0013%). The n-BuOH-soluble phase was subjected to Diaion HP-20 column chromatography to afford a methanoleluted fraction (3.5%) as previously reported.1,16) The methanol-eluted fraction was separated by normal-and reversed-phase column chromatography, and finally HPLC to give rosiridosides A (3, 0.00019%) and B (4, 0.00032%) together with rosiridin (2, 0.49%).Reinvestigation of the Absolute Configuration of (؊)-Rosiridol Rosiridin (2) }, 2 was identified to be rosiridin, which was isolated from R. rosea 20) and R. sachalinensis, in which the absolute stereostructure of rosiridin was reported to be 2Ј.

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“…[1][2][3][4][5] Although several monoterpenoids have been reported in other Rhodiola species, 6,7) only one monoterpenoid, rosiridol and its glucoside, rosiridin have been isolated from R. rosea. 3,8) Our continuing phytochemical investigations on Chinese medicinal plants [9][10][11][12] have resulted in the isolation of five new monoterpene glycosides, rhodiolosides A-E (1-5) from the roots of R. rosea. This paper deals with the isolation and structure elucidation of these new compounds.…”

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Rhodiolosides A-E, Monoterpene Glycosides from Rhodiola rosea

Wei

Dou

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Rhodiola rosea L. (Crassulaceae), also known as golden root or rose root, is a perennial herbaceous plant widely distributed at high altitudes in the arctic and mountainous regions throughout Europe and Asia. The roots of R. rosea are traditionally used as a tonic and adaptpgen in Russia, and also as a hemostatic in Tibetan folk medicine. Various pharmacological effects of the roots of R. rosea have been reported, such as improvement of the memory and learning abilities, anti-stress and anticancer effects, etc.1,2) Previous chemical investigation on R. rosea has demonstrated the occurrence of over thirty compounds, belonging to the phenylethanoids, phenylpropanoides, flavonoids, phenolic acids, cyanoglycosides, monoterpenoids, and triterpenes. [1][2][3][4][5] Although several monoterpenoids have been reported in other Rhodiola species, 6,7) only one monoterpenoid, rosiridol and its glucoside, rosiridin have been isolated from R. rosea. 3,8) Our continuing phytochemical investigations on Chinese medicinal plants [9][10][11][12] have resulted in the isolation of five new monoterpene glycosides, rhodiolosides A-E (1-5) from the roots of R. rosea. This paper deals with the isolation and structure elucidation of these new compounds. Results and DiscussionThe air-dried roots of R. rosea were extracted with 80% aqueous EtOH. The extract was concentrated, suspended in H 2 O and then partitioned successively with CHCl 3 , EtOAc and n-BuOH. The n-BuOH-soluble fraction was evaporated under reduced pressure and fractionated using silica gel and ODS columns. Further purification by repeated reversedphase HPLC afforded five new monoterpene glycosides, rhodiolosides A-E (1-5).Rhodioloside A (1) was isolated as a colorless viscous oil. The molecular formula was established as C 16 H 28 O 8 by highresolution (HR)-FAB-MS. On acidic hydrolysis, 1 afforded D-glucose, which was identified by gas-liquid chromatography (GLC) analysis of its trimethylsilyl thiazolidine derivative. 13 The

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Terpenoids of the rhizomes ofRhodiola rosea

Cited by 23 publications

References 6 publications

Prolyl Endopeptidase Inhibitors from the Underground Part of Rhodiola sachalinensis

Prolyl Endopeptidase Inhibitors from the Underground Part of Rhodiola sachalinensis

Reinvestigation of Absolute Stereostructure of (-)-Rosiridol: Structures of Monoterpene Glycosides, Rosiridin, Rosiridosides A, B, and C, from Rhodiola sachalinensis

Rhodiolosides A-E, Monoterpene Glycosides from Rhodiola rosea

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