Search results for "Oleanolic Acid"
showing 10 items of 63 documents
Two new triterpenoid saponins fromPittosporum senaciaPutterlick (Pittosporaceae)
2012
From the branches of Pittosporum senacia Putterlick (Pittosporaceae), two new triterpenoid saponins, senaciapittosides A and B (1, 2), were isolated. Their structures were elucidated by extensive analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and chemical evidence as 3-O-[β-d-glucopyranosyl-(1 2)]-[α-l-arabinopyranosyl-(1 3)]-[α-l-arabinofuranosyl-(1 4)]-β-d-glucuronopyranosyl oleanolic acid 28-O-β-d-glucopyranosyl ester (1) and 3-O-[β-d-glucopyranosyl-(1 2)]-[α-l-arabinopyranosyl-(1 3)]-[α-l-arabinofuranosyl-(1 4)]-β-d-glucuronopyranosyl-22-O-α-l-arabinopyranosyl-21-acetoxy R1-barrigen…
Oleanolic acid and hederagenin glycosides from Weigela stelzneri
2015
Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-…
Two new biologically active triterpene saponins from Acanthophyllum squarrosum.
2000
Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect …
Acylated triterpene saponins from Silene jenisseensis
1995
Abstract From the roots of Silene jenisseensis a new trans-p-methoxycinnamoyl triterpene saponin has been isolated along with its cis-p-methoxycinnamoyl isomer as an inseparable mixture. Their structures were established by chemical means and spectroscopic methods including 1D- and 2D-homonuclear and heteronuclear correlation NMR spectroscopy as 3-O-[β- d -galactopyranosyl -(1 → 2)-β- d -glucuronopyranosyl ]-28-O-[β- d -glucopyranosyl -(1 → 2)-α- l - rhamnopyranosyl -(1 → 2)-β- d -4-O-trans-p- methoxycinnamoyl-fucopyranosyl ] quillaic acid and its cis-isomer, respectively. They did not show any activity in the in vitro chemoluminescence granulocytes assay, but exhibited only a weak inhibito…
A new biologically active acylated triterpene saponin from Silene fortunei.
1998
A new acylated triterpene-saponin (1), together with a mixture of the known jenisseensosides C and D, has been isolated from the roots of Silene fortunei. The structure of the new compound was established by chemical means and spectroscopic methods as 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28 -O- [[alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl- (1-->3)-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)]-[beta-D- glucopyranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyranosyl]quillaic acid. This saponin showed a significant enhancement of granulocyte phagocytosis in vitro.
Three new acylated triterpene saponins from Acanthophyllum squarrosum.
2001
Three new triterpenoid saponins, 1-3, were isolated from the roots of Acanthophyllum squarrosum. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1--3)-beta-D-xylopyranosyl-(1--4)-beta-D-xylopyranosyl-(1--4)-3-O-acetyl-alpha-L-rhamnopyranosyl-(1--2)-3,4-di-O-acetyl-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1--4)-alpha-L-rhamnopyranosyl-(1--2)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1--3)]-4-O-acetyl-beta-D-fucopyranoside (2), and 3-O-beta…
Glucuronide triterpene saponins from Bersama engleriana
2006
Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-…
Squarroside A, a biologically active triterpene saponin from Acanthophyllum squarrosum.
1993
A new bioactive saponin has been isolated from the roots of Acanthophyllum squarrosum. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis, and on chemical transformations, the structure of this new compound was elucidated as 3-O-beta-D-galactopyranosyl-(1--2)-[beta-D-xylopyranosyl-(1--3)]-beta- D-glucuronopyranosyl gypsogenin 28-O-beta-D-xylopyranosyl-(1--4)-alpha-L- rhamnopyranosyl-(1--2)-[alpha-L-arabinofuranosyl-(1--3)]-beta-D-4-O- acetylfucopyranoside for which we proposed the name squarroside A. This molecule showed a concentration dependent immunomodulatory effect in the in vitro lymphocyte transformation test.
Jenisseensosides C and D, biologically active acylated triterpene saponins from Silene jenisseensis
1997
Abstract We previously reported the isolation and structure elucidation of a new trans - p -methoxycinnamoyl triterpene-saponin along with its cis - p -methoxycinnamoyl isomer as an inseparable mixture from the roots of Silene jenisseensis . In a continuing study on this plant, two additional new acylated triterpene-saponins were obtained as an inseparable mixture. Their structures have been established by chemical means and spectroscopic methods including 1D and 2D homonuclear and heteronuclear correlation NMR spectroscopy as 3- O -[β- d -galactopyranosyl-(1 → 2)-β- d -glucuronopyranosyl]-28- O -[{α- l -rhamnopyranosyl-(1 → 2)}- {4- O - trans - p -methoxycinnamoyl}-β- d -fucopyranosyl] qui…
Anti-inflammatory activity of saikosaponins from Heteromorpha trifoliata.
1995
By means of activity-directed chromatographic fractionation using the 12-O-tetradecanoylphorbol acetate (TPA)-induced edema test, two saikosaponins were isolated from the MeOH extract of Heteromorpha trifoliata leaves. They were identified as 16 beta, 23-dihydroxy-13,28-epoxyolean-11-en-3 beta-yl-[beta-D-glucopyranosyl (1-->2)]-[beta-D-glucopyranosyl (1-->3)]-beta-D-fucopyranoside [1] and 16 beta, 23,28-trihydroxy-11 alpha-methoxyolean-12-en-3 beta-yl-[beta-D-glucopyranosyl (1-->2)]-[beta-D-glucopyranosyl (1-->3) [beta-D-fucopyranoside [2]. Compound 1 showed activity in the TPA and ethylphenylpropiolate (EPP) mouse ear edema and the serotonin paw edema tests, whereas compound 2 was active o…