Five New Steroidal Saponins from Solanum chrysotrichum Leaves and Their Antimycotic Activity

Zamilpa, Alejandro; Tortoriello, Jaime; Navarro, Vı́ctor; Delgado, Guillermo; Álvarez, Laura

doi:10.1021/np020261h

Cited by 62 publications

(61 citation statements)

References 14 publications

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“…Extensive searches for bioactive steroidal glycosides have been done in more than 40 solanaceous plant species. A large number of compounds have been identified and their activities evaluated (Honbu et al, 2002;Zamilpa et al, 2002;Ikeda et al, 2003). Second, transgenic studies can be performed in Solanum (Ikenaga et al, 1995) more easily than in other plant species, such as Dioscorea or Yucca, which are the sources of the raw materials used in commercial steroid production.…”

Section: Introductionmentioning

confidence: 99%

A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum

et al. 2005

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Steroidal saponins are widely distributed in many plant species. Their diverse structures have resulted in a wide range of applications, including drug and medicine production. It has been suggested that the nature of the non-saccharide and oligosaccharide portions of the saponin molecule both contribute to the properties of individual saponins. Despite numerous studies on the occurrence, chemical structure, and varying pharmaceutical activities of steroidal saponins, their biosynthesis pathway is poorly understood. Glycosylation is thought to be the final step in steroidal saponin biosynthesis and it is thought to be involved in regulating the biological activities of saponins. Isolation of the glycosyltransferases that catalyze the transfer of sugar molecules to steroidal compounds will help to clarify the mechanisms that produce diverse saponins and control their activities in plants. In this study, we obtained three cDNAs encoding putative glycosyltransferases from Solanum aculeatissimum. One of the three, SaGT4A showed UDP-glucosyltransferase activity. This is the first cloned glucosyltransferase involved in steroidal saponin biosynthesis. SaGT4A catalyzes the 3-O-glucosylation of steroidal sapogenins, such as diosgenin, nuatigenin, and tigogenin. This enzyme also glucosylates steroidal alkaloids, such as solanidine, solasodine, and tomatidine. Gene expression analysis revealed that the accumulation of SaGT4A transcripts showed a unique response to wounding stress indicating the involvement of SaGT4A in plant defense system.

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Section: Introductionmentioning

confidence: 99%

A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum

et al. 2005

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“…Thus, from the perspective of structure-activity relationships (SAR), 22 steroidal saponins with a spirostanol skeleton and 6 steroidal sapogenins isolated from several monocotyledonous plants (8)(9)(10)(11)(12)(13)(14)(15)(16) and belonging to different chemotypes were selected for this study. This selection was particularly based on the structures of several saponins containing hecogenin, neohecogenin, tigogenin, neotigogenin, chlorogenin, or diosgenin as an aglycone moiety that have been demonstrated to be antifungal (1,30,32,37,39). (15), agamenoside C (compound 5) (9), cantalasaponin 1 (compound 6) (9), agamenoside A (compound 7) (12), agavesides A (compound 8) (11) and B (compound 9) (11), (11), agamenosides D (compound 12) (11) and E (compound 13) (11) (25,26).…”

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confidence: 99%

Antifungal Activity of C-27 Steroidal Saponins

Yang

Zhang

Jacob

et al. 2006

Antimicrob Agents Chemother

191

164

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As part of our search for new antifungal agents from natural resources, 22 C-27 steroidal saponins and 6 steroidal sapogenins isolated from several monocotyledonous plants were tested for their antifungal activity against the opportunistic pathogens Candida albicans, Candida glabrata, Candida krusei, Cryptococcus neoformans, and Aspergillus fumigatus. The results showed that the antifungal activity of the steroidal saponins was associated with their aglycone moieties and the number and structure of monosaccharide units in their sugar chains. Within the 10 active saponins, four tigogenin saponins (compounds 1 to 4) with a sugar moiety of four or five monosaccharide units exhibited significant activity against C. neoformans and A. fumigatus, comparable to the positive control amphotericin B. The antifungal potency of these compounds was not associated with cytotoxicity to mammalian cells. This suggests that the C-27 steroidal saponins may be considered potential antifungal leads for further preclinical study.

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“…1 H NMR data of 2 suggested a glycoside of the Δ 25(27) -spirostan steroidal type skeleton, disclosed by the olefi nic hydrogen signals at C27 of the aglycone at δ 4.74 (s) and 4.78 (s), along with signals of the sugar residue between δ 3.2 and 4.4. Characteristic A/B trans-ring fusion, indicating that 2 is a 5R-steroidal spirostanol deriva-tive, was inferred from 13 C NMR data with signals at δ 41.81 (C5), 54.27 (C9) and 11.54 (C19) (Acharya et al, 2009;Zamilpa et al, 2002;Bernardo et al, 1996). Further evidence of the trans stereochemistry between A/B rings was accomplished by NOESY data, which showed correlations between H3 (δ 3.96) and H5 (δ 1.89, m).…”

Section: Resultsmentioning

confidence: 99%

Antiviral Activity of Solanum paniculatum Extract and Constituents

Valadares

Brandão

Kroon

et al. 2009

Zeitschrift Für Naturforschung C

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Solanum species are traditionally employed as antiherpes and anticancer agents in different countries. S. paniculatum has widespread ethnomedical uses in Brazil, including the treatment of viral infections. This paper reports on the isolation of neotigogenin (1) and the new compound Δ25(27)-tigogenin-3-O-β-D-glucopyranoside (2), obtained as a mixture of R and S diastereoisomers at C22 from an ethanol extract of S. paniculatum leaves, along with the determination of their cytotoxicity against Vero cells and antiviral effect against human herpes virus type 1 (HHV-1), murine encephalomyocarditis virus (EMCv), and vaccinia virus strain Western Reserve (VACV-WR). The extract of S. paniculatum inhibited HHV-1 replication [EC50 = (298.0 ± 11.2) μg/ml] and showed no effect on EMCv and VACV-WR. On its turn, 1 was inactive against the assayed strains but presented high cytotoxicity [CC50 = (2.03 ± 0.03) μg/ml], whereas 2 exhibited signifi cant antiherpes [EC50 = (170.8 ± 1.7) μg/ml] and antivaccinia virus effects [EC50 = (177.0 ± 3.3) μg/ml], with low cytotoxicity (CC50 > 400 μg/ml). The results corroborate Solanum paniculatum as a source of cytotoxic and antiviral compounds.

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Five New Steroidal Saponins from Solanum chrysotrichum Leaves and Their Antimycotic Activity

Cited by 62 publications

References 14 publications

A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum

A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum

Antifungal Activity of C-27 Steroidal Saponins

Antiviral Activity of Solanum paniculatum Extract and Constituents

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