Triterpenoid Glycosides of Fatsia japonica. II. Isolation and Structure of Glycosides from the Leaves

The previously known triterpenoid 3-O--L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ethers of the 3-O--L-arabinopyranoside of hederagenin, and 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves ofFatsia japonica(Araliaceae). The structures of the glycosides are confirmed by chemical methods and ¹³ C NMR spectroscopy     

Triterpene Glycosides of Tetrapanax papyriferum. II. Isolation and Structure Determination of Glycosides St-E2, St-F2, St-J2, and St-K2 from Stem Bark

Stem bark ofTetrapanaxpapyriferum yielded the new triterpene glycosides 3-O-[-D-glucopyranosyl-(13)]--D-galactopyranosyl-(12)-O--L-arabinopyranosides of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters. Their structures were established using chemical and physicochemical methods     

Triterpene glycosides ofScheffleropsis angkae. II. Structure of glycosides L-E1, L-E2, L-K1, and L-K2

The structures of four triterpene glycosides from leaves ofScheffleropsis angkae (Araliaceae) are established using chemical and NMR methods. The structures 3-O--D-glucopyranosyl-(1-3)-O--L-arabinopyranosides of oleanic and ursolic acids and their 28-O--L-rhamnopyranosyl-(1-4)-O--gentiobiosyl ethers are proposed for L-E₁, L-E₂, L-K₁, and L-K₂, respectively. L-K₁ and L-K₂ are new triterpene glycosides.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 239–241, May–June, 2000.     

Triterpene Glycosides of Fatsia japonica. IV. Structure of Glycosides D1 and D2 from Seeds

Seeds ofFatsia japonica(Araliaceae) afforded the known hederagenin 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranoside and the new triterpene glycoside D ₂ , for which the structure hederagenin 3-O--D- galactopyranosyl-(12)-O--L-arabinopyranoside was proposed based on chemical methods and NMR spectroscopy     

Triterpene glycosides ofScheffleropsis angkae. I. Structure of glycosides L-B1, L-B2, L-H1, and L-H2

The structures of four triterpene glycosides from the leaves ofScheffleropsis angkae (Araliaceae) are found by chemical methods and NMR spectroscopy to be the 3-O--L-arabinopyranosides of oleanic and ursolic acids and their 28-O--L-rhamnopyranosyl-(14)-O--gentiobiosyl esters, which are designated L-B₁, L-B₂, L-H₁, and L-H₂, respectively. The glycoside L-H₂ is new.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 136–138, March–April, 2000.     

Triterpene Glycosides of Fatsia japonica. VI. Structures of Glycosides D3a and D3b

Seeds of Fatsia japonica (Araliaceae) yielded the new glycosides of gypsogenin: 3-O--D-glucopyranosyl-(12)-O--D-glucopyranoside and 3-O--D-galactopyranosyl-(12)-O--D-glucopyranoside. The structures of these compounds were established by chemical methods and NMR spectroscopy.     

Triterpene glycosides ofHedera helix III. Structure of the triterpene sulfates and their glycosides

From the leaves of English ivyHedera helix L. we have isolated the known 3-sulfates of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters and the new 3-sulfate of 28-O--gentiobiosyl oleanolate — helicoside L-8a. The structures of the compounds isolated were deduced from the results of chemical transformations and NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 87–90, January–February, 1999.     

Triterpene Glycosides of Tetrapanax papyriferum. I. Isolation and Structure of Glycosides St-H2 and St-I2 from Stem Bark

Stem bark ofTetrapanax papyriferumC. Koch., Araliaceae, yielded new triterpene glycosides 28-O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosyl esters of the 3-O-[-D-glucopyranosyl-(13)-[-D-galactopyranosyl-(12)]-O--L-arabinopyranosides of oleanolic and echinocystic acids. The structures of these substances were established using chemical and physicochemical methods     

Triterpene glycosides ofHedera canariensis IV. Structures of glycosides L-F3, L-G0, and L-Gla from the leaves of Algerian ivy

Three minor partially acetylated glycosides have been isolated from the leaves of Algerian ivy, Hedera canariensis Willd. (Araliaceae) — the previously known {3-O-[-L-rhamnopyranosyl-(12)-O--L-arabinopyranoside] 28-O-[-L-rhamnopyranosyl-(14)-O-(6-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranoside}s of oleanolic acid and of hederagenin (ciwujianoside C₄ and kizuta saponin K₁₁) and the new 3-O-[-L-rhamnopyranosyl-(12)--O-L-arabinopyranoside] 28-O-[-L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranoside of echinocystic acid (glycoside L-G₀). The structures of the glycosides isolated have been established on the basis of chemical transformations and¹H and¹³C NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 81–86, January–February, 1999.     

Steroid saponins X. Glycosides of Allium narcissiflorum the structure of glycosides A and B

Summary FromAllium narcissiflorum Wells have been isolated for the first time trillin and a glycoside B, which proved to be 3-O-[-O-D-glucopyranosyl-(1 3)-O--D-glucopyranosyl-(1 6)-O--D-glucopyranosyl-(1 ]-26-O-[-D-glucopyranosyl-(1 ]-25R-furost-5-ene-3,22 , 26-triol.Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 55–58, January–February, 1976.     

Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A,L-B1, L-B2, L-C,L-D,L-E1 1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis

From the leaves of Algerian ivyHedera canariensis Willd. (fam. Aralaceae) we have isolated 13 triterpene glycosides: the 3-O--L-arabinopyranosides of oleanolic acid (A), of echinocystic acid (B₁), and of hederagenin (B₂); the 3-O-[O--L-rhamnopyranosyl-(2)--L-arabinopyranoside]s of oleanolic acid (C), of echinocystic acid (D), and of hederagenin (E₁); the 3-O--L-rhamnopyranoside] 28-O-[O--L-rhamnopyranosyl-(14)--gentiobioside of hederagenin (G₁); the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside] 28-O--gentiobioside of hederagenin (G3); the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside] 28-O-[O--L-rhamnopyranosyl-(14)--gentiobioside]s of oleanolic acid (G₂), of echinocystic acid (H₁), and of hederagenin (H₂); the 3-O-[O--L-rhanmopyranosyl-(12)--D-glucopyranoside] 28-O-(O--L-rhamno-pyranosyl-(14)--gentiobioside] of hederagenin (H₂); and the 3-O-(O--L-rhamnopyranosyl-(12)-O-gentiobiosyl)-O-(14)--L-rhamnopyranosyl-(12)-a-L-arabinopyranoside] of hederagenin (G₄). The structures of the substances isolated have been established on the basis of chemical transformations and¹³C NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 377–383, May–June, 1996. Original article submitted December 3, 1995.     

Triterpene Glycosides of Astragalus and Their Genins. LXI. Occurrence of Cycloartane 6-O-Monodesmosides

Cyclosiversigenin 6-O--L-rhamnopyranoside and 6-O--D-glucopyranoside were isolated fromAstragalus coluteocarpusBoiss. (Leguminosae) andAstragalus dissectusB. Fedtsch. et N. Ivanova, respectively. Cyclosiversigenin 5-O--L-rhamnopyranoside was shown to be an artifact forAstragalus coluteocarpus.Thus, the cyclosiversigenin 6-O--D-glucopyranoside that was isolated from certainAstragalusspecies is hypothesized also to be an artifact. Glycosylation of the 6 -hydroxyl group of cycloartanes by D-glucose and D-xylose, in contrast with other substituents, does not change the low-field position of the PMR signal of the 4-CH ₃ group (1.65 2.01 ppm) that is caused by the influence of deuteropyridine directly on the 6 -hydroxyl. Obviously one of the hydroxyls of the -D-glucopyranoside or -D-xylopyranoside residues has the same effect in this instance.     

Triterpene Glycosides of Tragacantha Stipulosa and Their Genins. Structures of Askendosides G and D and Cycloglobiceposide B from One- and Two-Dimensional 1H and 13C NMR Spectroscopy

Roots of Tragacantha stipulosa Boriss yielded three triterpene glycosides of the cycloartane series: askendoside G (1), askendoside D (2), and cycloglobiceposide B (3). Glycoside 1 is 3-O--L-arabinopyranosyl-(12)--D-xylopyranoside; 16-O--D-glucopyranoside-24R-cycloartan-3,6,16,24,25-pentaol; 2 - 3-O--L-arabinopyranosyl-(12)--D-xylopyranoside; 6-O--D-xylopyranoside-20R,24S-epoxycycloartan-3,6,16,25-tetraol; 3 - 3-O--D-xylopyranoside; 16-O--D-glucopyranoside; 25-O--D-glucopyranoside-24R-cycloartan-3,6,16,24,25-pentaol.     

Triterpene glycosides ofHedera taurica. XI. Structures of taurosides St-G1, St-H1, and St-H2 from the stems of Crimean ivy

The previously known glycosides 3-O--L-arabinopyranosyl-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin and 3-O-[-L-rhamnopyranosyl-(12)-O--L-arabinopyranosyl]-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin and the new triterpene glycoside tauroside St-H₁ — 3-O--D-glucopyransyl-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin — have been isolated from the stems ofHedera taurica Carr.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 571–579, July–August, 1993.     

Polysaccharides ofUngernia. VII. Partial hydrolysis of the mannan of the bulbs ofU. vvedenskyi

4-O--D-Manopyranosyl-D-mannose, O--D-mannopyranosyl-(l4)-O--D-mannopyranosyl-(14)-D-mannose, and 0--D-mannopyranosyl-(14)-O--D-mannopyranosyl-(l4)-O--D-mannopyranosyl-(l4)-D-mannose have been isolated fron the products of the partial hydrolysis of ungeromannan-V, obtained fron the bulbs ofUngernia vvedneskyi, and have been identified. This set of oligosaccharides confirms the regular structure of the carbohydrate chain of ungeromannan-V, which consists of a linear sequence of -14-bound D-mannose residues.DeceasedTranslated from Khimiya Prirodnykh Soedineii, No. 4, pp. 434–436, July–August, 1981.     

On theC v toC p conversion for solid linear macromolecules

TheC _v toC _p conversion for solid linear macromolecules via the Nernst-Lindemann equationC _p -C _v =A ₀,C _p ² T/T_m is discussed on hand of data for 10 crystals and seven glasses. An average value ofA ₀=(5.11±2.41) · 10^–3 mol K J^–1 was calculated if the mole is assumed to refer to heavy atoms only. ThisA ₀ is numerically equal to the original Nernst—Lindemann constant.

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Zusammenfassung An Hand von sich auf 10 Kristalle und 7 Gläser beziehenden Daten wird die Umrechnung vonC _v -inC _p -Werte für feste lineare Makromoleküle mittels der Nernst-Lindemann-GleichungC _p -C _v =A ₀ C _p ² T/T _m diskutiert. Ein Durchschnittswert vonA ₀=(5.11±2.41) · 10^–3 mol K J^–1 wurde unter der Annahme berechnet, daß sich das Mol nur auf schwere Atome bezieht. DieserA ₀-Wert ist numerisch gleich der ursprünglichen Nerns-Lindemann-Konstanten.

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10 , - C _v C _p , —C _p –C _v = _{0 p} ² / . , , ₀ (5.11±2.41) · 10^–3 · ^–1. ₀ — .

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Support by the National Science Foundation, Polymers Program (Grant No. DMR 83-17097) is gratefully acknowledged.     

Steroids of the furostan and spirostan series from Nolina microcarpa II. structures of nolinospiroside D and nolinofurosides D, E, and F

Proofs are given of the structures of two new glycosides of the furostan series isolated from the leaves of the plantNolina microscarpa S. Wats. (family Dracaenaceae). Nolinofuroside D is (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-galactopyranoside 26-O--D-glucopyranoside (I), and nolinofuroside F is (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-fucopyranoside 26-O--D-glucopyranoside 3-O--L-rhamnopyranoside (VII). The latter was characterized as its 22-O-methyl ether (VIII). Nolinofuroside E (IV) has the structure of (25S)-furost-5-ene-1,3,22,26-tetraol 26-O--glucopyranoside 1-O-[O--L-rhamnopyranosyl-(12)--D-fucopyranoside], which followed from the structure of the fermentation product (VI). The products of the fermentation of the above-named compounds were present in the plant in only trace amounts. Only one of them — nolinospiroside D (III) — has not been described previously. This monoside of the spirostan series is (25S)-spirost-5-ene-1,3-diol 1-O--D-galactopyranoside.M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 678–686, September–October, 1991.     

Frequencies, anharmonicities, and dissociation energies of OH groups in H-mordenite

Harmonic frequencies, anharmonicities and dissociation energies of surface hydroxy groups in H-mordenite have been determined. The application of the Lippincott-Schroeder potential function for similar problems is proposed.

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, -. - .

     

Non quasi-stationary state pyrolysis. Induction period of neopentane pyrolysis

The principle of an apparatus using an isothermal continuous flow stirred tank reactor to study homogeneous gas phase reactions at space times of the order of 1 sec is given. With this apparatus, the induction period of neopentane pyrolysis (as an example) has been clearly shown.

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, , 1 . , , .

     

Formation and thermal decomposition of silicon oxynitride compounds. Part III

The formation of a previously unknown compound with stoichiometry Li₆SiN₂O₂ was found during studies on the reactivity of Li₂SiN₂ with Li₂O, of SiO₂ with Li₃N and of Li₃SiNO₂ with Li₃N.

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Zusammenfassung Die Bildung einer bisher unbekannten Verbindung der Stöchiometrie Li₆SiN₂O₂ wurde bei Untersuchungen der Reaktivität von Li₂SiN₂ mit LiO, von SiO₂ mit Li₃N und von Li₃SiNO₂ mit Li₃N beobachtet.

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Li₆SiN₂O₂ Li₂SiN₂ , , Li₃SiNO₂ .