Two New Steroid Glycosides and a New Sesquiterpenoid Glycoside from the Underground Parts of Trillium kamtschaticum

Ono, M.; Takamura, Chika; Sugita, Fumie; Masuoka, Chikako; Yoshimitsu, Hitoshi; Ikeda, Tsuyoshi; Nohara, Toshihiro

doi:10.1248/cpb.55.551

Cited by 64 publications

(48 citation statements)

References 16 publications

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“…Although compounds 7 and 8 shared the same saccharide moiety, the transformation of configuration of OH-24 and the transference of the acetyl group from C-21 to C-24 could evidently strengthen the cytotoxicity of the latter one. In summary, eleven steroidal glycosides including eight new structures (1)(2)(3)(4)(5)(6)(7)(8) were isolated from the 30% EtOH elution from a macroporous resin of the crude extract of T. kamtschaticum. The aglycone of saponin 1, 16-oxaandrost-5-en-3-ol-17-one, is reported as a natural occurrence for the first time.…”

Section: Ar T Ic Le In F O Abstractmentioning

confidence: 99%

“…1 Its rhizomes have been used as a traditional Chinese medicine for the treatment of hypertension, waist-leg pain, and traumatic haemorrhage. 2 Previous phytochemical and pharmacological investigations indicated that T. kamtschaticum is an abundant resource of steroidal saponins [3][4][5][6] with few information regarding their biological activity. Our recent study revealed that 70% EtOH elution from a macroporous resin of the crude extract of T. kamtschaticum 7 showed significant hemostatic effect and clarified that the bioactive constituents were pennogenin saponins (such as Tb, Tc, and Tg).…”

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confidence: 99%

“…This stimulated us to conduct the phytochemicals of the 30% EtOH eluent by several chromatographic techniques. 9 As a result, eight new steroidal saponins, named trillikamtosides K-R (1)(2)(3)(4)(5)(6)(7)(8), along with three known analogues (Fig. 1) were obtained and characterized.…”

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Cytotoxic steroidal saponins from Trillium kamtschaticum

Qin

Chen

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Section: Ar T Ic Le In F O Abstractmentioning

confidence: 99%

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Cytotoxic steroidal saponins from Trillium kamtschaticum

Qin

Chen

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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“…(Liliaceae) and, further, that four phenolic compounds among these compounds had a stronger antioxidative activity than L-cysteine. 1,2) In a further investigation of this extract, we now report the isolation and structural elucidation of three new steroid glycosides along with two known 18-norspirostanol glycosides.…”

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confidence: 96%

“…The MeOH extract of the underground parts of T. kamtschaticum was successively subjected to Diaion HP20 and silica gel column chromatography as well as HPLC on ODS to afford five compounds (1)(2)(3)(4)(5) (Fig. 1).…”

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Three New Steroid Glycosides from the Underground Parts of Trillium kamtschaticum

Ono

Sugita

Shigematsu

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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In preceding papers, we reported the isolation and structural elucidation of 22 steroids, two sesquiterpenoid glycosides, one phenylpropanoid, one flavonoid glycoside, and three phenylpropanoid sucrose esters from the MeOH extract of the underground parts of Trillium kamtschaticum PALL. (Liliaceae) and, further, that four phenolic compounds among these compounds had a stronger antioxidative activity than L-cysteine.1,2) In a further investigation of this extract, we now report the isolation and structural elucidation of three new steroid glycosides along with two known 18-norspirostanol glycosides.The MeOH extract of the underground parts of T. kamtschaticum was successively subjected to Diaion HP20 and silica gel column chromatography as well as HPLC on ODS to afford five compounds (1-5) (Fig. 1).Compounds 4 and 5 were identified as trillenosides A and B, respectively, based on their physical and spectral data. 1)Compound 1, named trikamsteroside C, was obtained as an amorphous powder. The IR spectrum of 1 showed absorptions due to hydroxyl groups (3404 cm Ϫ1) and an a,b-unsaturated ketone group (1693 cm Ϫ1 ). In the positive FAB-MS, 1 exhibited an [MϩNa] ϩ ion peak at m/z 1041; the high-resolution ( H correlation spectroscopy (COSY), heteronuclear multiple-quantum coherence (HMQC), and heteronuclear multiple-bond correlation (HMBC) techniques, and 1 was characterized as a tetraglycoside of 18-norspirostanol. Further, the 13 C-NMR data of the aglycone moiety and the sugar moiety were superimposable on those of epitrillenoside C (6) 3) and 4, 1) respectively. The structure of 1 was therefore defined as epitrillenogenin 1-O-Compound 2, named trikamsteroside D, was obtained as an amorphous powder and the molecular formula of 2 was analyzed as C 48 H 74 O 24 by HR-positive FAB-MS. Its IR spectrum revealed absorptions at 3386 and 1741 cm Ϫ1 due to hydroxyl groups and a five-membered ketone group, respectively. The 1 H-NMR spectrum of 2 was analogous to that of 4, with an additional signal due to one methyl group. The 13 C-NMR spectrum of 2 was also similar to that of 4 except for the appearance of signals due to one each of methyl carbon, methine carbon, and quaternary carbon and the lack of signals due to two olefinic carbons. These 1 H-and 13 C-NMR signals were assigned in detail by 2D-NMR techniques similar to those of 1. In the HMBC spectrum of 2, key correlations were observed between H-1 of the arabinopyranosyl group and C-1, between H-17 and C-15, between H-14 and C-15, between H 2 -26 and C-22, between H 3 -27 and C-24, between H-24 and C-23, and between H-23 and C-24, and the planar structure of 2 was determined as illustrated in Fig. 2. Further, the 13 C-NMR assignments of the sugar moiety and A-ring of the aglycone moiety were quite similar to those of 4, indicating the same sugar chain as 4 was attached to C-1 of aglycone. The configurations of the aglycone moiety were confirmed by the following evidence. On acidic hydrolysis, 2 afforded an aglycone (2a) Sciences, Sojo University; 4-22-2 Ikeda, Kumamo...

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Synthesis of Non‐Classical Arylated C‐Saccharides through Nickel/Photoredox Dual Catalysis

et al. 2018

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The development of synthetic tools to introduce saccharide derivatives into functionally complex molecules is of great interest, particularly in the field of drug discovery. Herein, we report a new route toward highly functionalized, arylated saccharides, which involves nickel‐catalyzed cross‐coupling of photoredox‐generated saccharyl radicals with a range of aryl‐ and heteroaryl bromides, triggered by an organic photocatalyst. In contrast to existing methods, the mild reaction conditions achieve arylation of saccharide motifs while leaving the anomeric carbon available, thus providing access to a class of arylated glycosides that has been underexplored until now. To demonstrate the potential of this strategy in late‐stage functionalization, a variety of structurally complex molecules incorporating saccharide moieties were synthesized.

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Two New Steroid Glycosides and a New Sesquiterpenoid Glycoside from the Underground Parts of Trillium kamtschaticum

Cited by 64 publications

References 16 publications

Cytotoxic steroidal saponins from Trillium kamtschaticum

Cytotoxic steroidal saponins from Trillium kamtschaticum

Three New Steroid Glycosides from the Underground Parts of Trillium kamtschaticum

Synthesis of Non‐Classical Arylated C‐Saccharides through Nickel/Photoredox Dual Catalysis

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