Über inhaltsstoffe des rosskastaniensamens VI

Wagner, Josef; Hoffmann, Hartmut; Löw, Irmentraut

doi:10.1016/s0040-4039(01)99139-7

Cited by 7 publications

(3 citation statements)

References 6 publications

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“…Silica gel chromatographic separation of a small-scale sample from a repository extract of C. racemif lora yielded two new compounds, (+)-cyrillins A (1) and B (2), and six known compounds, (+)-barringtogenol B (3), 6 (+)-22-O-acetylbarringtogenol B (4), 7 (+)-22-O-angeloyl-A1-barrigenol (5), 8 (+)-22-O-angeloyl-R1-barrigenol (6), 9 (+)-3β-O-trans-feruloylbetulinic acid, 10 and (+)-betulinic acid. 11 Compound 1 was isolated as an amorphous, colorless powder.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The identities of the known compounds (Figure S5, Supporting Information) isolated from C. racemiflora were determined by analysis of their spectroscopic data and by comparison of these data with reference values, − with the full assignments of their 1 H and 13 C NMR spectroscopic data being listed in Tables S1–S3 (Supporting Information). The absolute configuration of the 1,2-diol unit of 5 and 6 was confirmed by Snatzke’s method, − , and the overall absolute configurations of the known compounds were corroborated by comparison of their NOESY NMR and ECD spectra with those of reference compounds (Figures S7, S8, and S10, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Ren¹,

VanSchoiack²,

Chai³

et al. 2015

J. Nat. Prod.

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Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3–6), along with betulinic acid and (+)-3β-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the electronic circular dichroism (ECD) spectrum induced with [Mo2(OAc)4]. In the case of (+)-cyrillin B (2), which was found to contain a di-angeloylated glucose residue, the structure proposed was supported by analysis of its MS2 and MS3 spectra. All compounds isolated were evaluated for their cytotoxicity against HT-29 human colon cancer cells, and the known compound, (+)-barringtogenol B (3), was found to be the most potent, exhibiting an IC50 value of 1.7 µM. This compound also showed inhibitory activity toward the CCD-112CoN human normal colon cell line, with an IC50 value of 5.9 µM, indicating a lack of cytotoxic selectivity.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Ren¹,

VanSchoiack²,

Chai³

et al. 2015

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…were heated under high vacuum before use. Aliquots (3 cm3) of solutions of samples and hexan-2-one actinometer 22 were introduced into the Pyrex tubes, degassed by freeze-pump-thaw method (five cycles) t o a reduced pressure < 5 x Torr, and then irradiated with an Eikosha PIH-300 high-pressure mercury lamp using a ' merry-go-round ' apparatus immersed in water at 20 f 1 "C. Potassium chromate solutions of different concentration in a Pyrex vessel were used t o isolate the 313 nm light and change the intensity of the incident light.…”

Section: Details Of Niensure-mentioning

confidence: 99%

Redox-photosensitised reactions. Part 6. Stereospecific ring cleavage of 1-phenoxy-1,2,2a,3,4,8b-hexahydrocyclobuta[a]naphthalene-8b-carbonitrile and its 2-methyl derivatives by redox-photosensitisation

Majima¹,

Pac²,

Sakurai³

1980

J. Chem. Soc., Perkin Trans. 1

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Acylwanderungen am Protoäscigenin Über Inhaltsstoffe des Rosskastaniensamens, X

Wagner

Hoffmann

Löw

1971

Archiv der Pharmazie

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Wagner, Hoffmonn und LowArch. Pharmaz. 6.) Reduktion des 2,2',2",4',4"-Penrahydrox~juchsons VEine nach 4) hergestelltc Losung von V wird mit 30 ml Wasser bis zur Entf&bung mit schwefliger Same versetzt. Das abgeschiedene Reduktionsprodukt ist farblos und wird schon beini Umkristallisieren aus k h a n o l unter R o t f~b u n g oxidativ verandert. Eine Chaxakterisierung des Reduktionsproduktes ist deshalb nicht moglich.Bei den Protoascigeninacetaten wandert der Acetylrest an den Ringen D und E nur zwischen den Hydroxylgruppen in Stellung 2 1 p, 22 a und 28. Unter Isomerisierungsbedingungen findet bei den Ascinen ausschliedlich ein Acetylaustausch zwischen 22 a-OH und 28-OH statt. Aeyl Group Migration in Roto-eseigeninIn the protoescigenin acetates the acetyl group migrates at the D and E rings only between the hydroxy groups in the 21 p-, 22 a-and 28-position. Under conditions of isomerisation. an exchange of acetyl occurs in escins exclusively between 22 a-OH and 28-OH.Die Saponine aus dem Samen von Aesculus hippocastanum L. stellen ein Gemisch diacylierter Barringtogenol Cund Protoascigeninglykoside dar, die in 3-Stellung eine mit zwei Zuckerresten substituierte Glucuronsaure tragen. Sie existieren in stellungsisomeren Formen und lassen sich reversibel ineinander umlagern2).In ihrer hamolytisch wirksamen p-Ascinform (1) tragen sie eine langkettige Saure (Angelica-, Tiglin-, a-Methylbutter-oder Isobuttersaure) esterartig am 2 1 0-OH und die Essigsaure am 22 a-OH3). Dagegen ist in der hamolytisch inaktiven Kryptoascin-1 IX. Mitt.:

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Über inhaltsstoffe des rosskastaniensamens VI

Cited by 7 publications

References 6 publications

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Redox-photosensitised reactions. Part 6. Stereospecific ring cleavage of 1-phenoxy-1,2,2a,3,4,8b-hexahydrocyclobuta[a]naphthalene-8b-carbonitrile and its 2-methyl derivatives by redox-photosensitisation

Acylwanderungen am Protoäscigenin Über Inhaltsstoffe des Rosskastaniensamens, X

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