Studies on the constituents of Luffa acutangula Roxb. I. Structures of acutosides A-G, oleanane-type triterpene saponins isolated from the herb.

Nagao, Tsuneatsu; Tanaka, Ryuichiro; Iwase, Yukiko; Hanazono, Hiroshi; Okabe, Hikaru

doi:10.1248/cpb.39.599

Cited by 29 publications

(17 citation statements)

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“…The assignments of the 1 H and 13 C signals of the triterpene moiety were secured by HSQC, 1 H- 1 H COSY, and HMBC experiments, which allowed for the identification of the aglycon as oleanolic acid. The presence of an oleanolic acid moiety in 1 was further supported by 1 H and 13 C NMR data, which were similar to those obtained for the other triterpene saponins isolated in this study, including 3- O -[ β -D-glucopyranosyl (1→2)]- β -D-glucopyranosyl oleanolic acid ( 5 ),6,7 3- O -[ α -L-arabinopyranosyl (1→2)- α -L-arabinopyranosyl (1→6)]- β -D-glucopyranosyl oleanolic acid ( 6 ),8 and 3- O -[ β -D-xylopyranosyl (1→2)- α -L-arabinopyranosyl (1→6)]- β -D-glucopyranosyl oleanolic acid ( 7 ) 8. The structure of 1 was confirmed by a complete acid hydrolysis of this compound which afforded the aglycon oleanolic acid as identified by co-TLC with an authentic sample available in our laboratory.…”

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confidence: 87%

Cytotoxic Oleanane-Type Saponins from Albizia inundata

et al. 2011

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Bioassay-guided fractionation of a CH2Cl2-MeOH extract of the aerial parts of Albizia inundata resulted in the isolation of two new natural oleanane-type triterpene saponins {3-O-[α-L-arabinopyranosyl( 1→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl oleanolic acid (1) and 3-O-[α-L-arabinopyranosyl(1→2)-α-L-arabinopyranosyl(1→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl acacic acid lactone (2)} along with seven known saponins {3-O-[α-L-arabinopyranosyl(1→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl echinocystic acid (3), 3-O-[β-D-xylopyranosyl (1→2)-α-L-arabinopyranosyl (1→6)]-2-acetamido-2-deoxy-β-Dglucopyranosyl acacic acid lactone (concinnoside D) (4), 3-O-[β-D-glucopyranosyl (1→2)]-β-D-glucopyranosyl oleanolic acid (5), 3-O-[α-L-arabinopyranosyl (1→2)-α-L-arabinopyranosyl (1→6)]-β-D-glucopyranosyl oleanolic acid (6), 3-O-[β-D-xylopyranosyl (1→2)-α-L-arabinopyranosyl (1→6)]-β- D-glucopyranosyl oleanolic acid (7), 3-O-[α-L-arabinopyranosyl- (1→2)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranoside echinocystic acid (8) and 3-O-[β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranoside echinocystic acid (9)}. The structures of 1 and 2 were established on the basis of extensive 2D NMR (1H-1H COSY or DQF-COSY, HSQC, HMBC, TOCSY, and HSQC-TOCSY) spectroscopic, ESIMS, and chemical methods. Saponins 1, 3, 6, and 7 showed cytotoxicity against human head and neck squamous cells (JMAR, MDA1986) and melanoma cells (B16F10, SKMEL28) with IC50 values in the range of 1.8–12.4 μM, using the MTS assay.

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confidence: 87%

Cytotoxic Oleanane-Type Saponins from Albizia inundata

et al. 2011

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“…Compounds 1 and 2 showed two anomeric proton signals at δ 4.88 (Sotheeswaran et al, 1989). The sugar moiety of compound 2 also consisted of two glucoses, however, the linkage between glucose was proved to be (1 → 2) by comparison with reported NMR data (Nagao et al, 1991). Thus, compound 2 was identified as…”

Section: Resultsmentioning

confidence: 90%

Retracted:Matrix metalloproteinase-1 expression inhibitory compound from the whole plants ofViola ibukiana Makino

et al. 2005

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Bioassay-guided fractionation has led to the isolation of two triterpenoid saponins 3-O-[O-beta-D-glucopyranosyl-(1 --> 3)-O-beta-D-glucopyranosyl] oleanolic acid (1), and 3-O-[O-beta-D-glucopyranosyl-(1 --> 2)-O-beta-D-glucopyranosyl] oleanolic acid (2) from the whole plants of Viola ibukiana Makino. Compound 2 showed matrix metalloproteinase-1 expression inhibition activities in a dose-dependent manner.

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“…The interglycosidic linkage of this disaccharide was deduced to be Glc(1→2)Glc from the deshielding in the 13 C NMR spectrum of 4 of one of the CH units of this moiety (δ 83.4). Thus, 4 was determined to be 3-O-β-D-gluco-pyranosyl-(1→2)-β-D-glucopyranosyl-oleanolic acid, already isolated from Passiflora quadrangularis 17 and Luffa acutangula 18 .…”

Section: Resultsmentioning

confidence: 99%

Steroidal and triterpenoidal glucosides from Passiflora alata

Reginatto¹,

Kauffmann²,

Schripsema³

et al. 2001

J. Braz. Chem. Soc.

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Cinco glicosídeos foram isolados a partir das folhas de P. alata. Após extensivas análises espectroscópicas, as estruturas 1-5 foram identificadas como sendo o 3Adicionalmente, foram analisados, através de CCD, extratos hidroetanólicos de espécies de Passiflora existentes no sul do Brasil (P. actinia, P. caerulea, P. edulis var. flavicarpa, P. elegans, P. foetida, P. misera e P. tenuifila). A acumulação de saponinas foi verificada somente em Passiflora alata.Five glycosides were isolated from leaves of P. alata. The structures 1-5 were obtained through extensive spectral analyses as 3 (4) and 9 ,19-cyclolanost-24Z-en-3β,21,26-trihydroxy-3,26-di-O-gentiobiose (5). Comparison of the TLC profiles of the hydroethanolic extracts from leaves of other Passiflora species found in the south of Brazil (P. actinia, P. caerulea, P. edulis var. flavicarpa, P. elegans, P. foetida, P. misera and P. tenuifila) showed that only P. alata presented saponin accumulation.

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Studies on the constituents of Luffa acutangula Roxb. I. Structures of acutosides A-G, oleanane-type triterpene saponins isolated from the herb.

Cited by 29 publications

References 0 publications

Cytotoxic Oleanane-Type Saponins from Albizia inundata

Cytotoxic Oleanane-Type Saponins from Albizia inundata

Retracted:Matrix metalloproteinase-1 expression inhibitory compound from the whole plants ofViola ibukiana Makino

Steroidal and triterpenoidal glucosides from Passiflora alata

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