[Chromosomes of the seeds of Trigonellae (Trigonella foenumgraecum L.) and vaccariae Vaccaria segetalis (Neck.) Garcke].
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Chromosomes↗
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Saponin biosynthesis in Saponaria vaccaria. cDNAs encoding beta-amyrin synthase and a triterpene carboxylic acid glucosyltransferase.
Saponaria vaccaria (Caryophyllaceae), a soapwort, known in western Canada as cowcockle, contains bioactive oleanane-type saponins similar to those found in soapbark tree (Quillaja saponaria; Rosaceae). To improve our understanding of the biosynthesis of these saponins, a combined polymerase chain reaction and expressed sequence tag approach was taken to identify the genes involved. A cDNA encoding a beta-amyrin synthase (SvBS) was isolated by reverse transcription-polymerase chain reaction and characterized by expression in yeast (Saccharomyces cerevisiae). The SvBS gene is predominantly expressed in leaves. A S. vaccaria developing seed expressed sequence tag collection was developed and used for the isolation of a full-length cDNA bearing sequence similarity to ester-forming glycosyltransferases. The gene product of the cDNA, classified as UGT74M1, was expressed in Escherichia coli, purified, and identified as a triterpene carboxylic acid glucosyltransferase. UGT74M1 is expressed in roots and leaves and appears to be involved in monodesmoside biosynthesis in S. vaccaria.
Amino Acid Sequence↗
The hemocyanin of the Californian black sea hare, Aplysia vaccaria Winkler.
The hemocyanin of the Californian black sea hare. Aplysia vaccaria exists in solution largely as a di-decameric protein with a molecular weight of close to 8.0 x 10(6) and a sedimentation coefficient of about 92 S. Light-scattering measurements at pH 8.0, 0.1 M Tris, 0.05 M Mg2+, 0.01 M Ca2+ gave a molecular weight of 8.0 +/- 0.6 x 10(6), and scanning transmission electron microscopic determinations (STEM) gave a slightly higher particle mass of 8.49 +/- 0.41 x 10(6) daltons. Measurements using the STEM method gave a particle mass of 4.27 +/- 0.26 x 10(6) daltons for the dissociated half-molecules or decamers. Light-scattering measurements on the dissociated monomers at pH 11.1 and in 8.0 M urea gave molecular weights of 4.74 x 10(5). Sedimentation measurements in the presence of 0.01 M Mg2+ indicate that the hemocyanin of A. vaccaria is largely in the di-decameric form in the pH region from about 5.0 to 8.0. Above pH 8.0 the hemocyanin di-decamers are found to dissociate to half-molecules or decamers, followed by dissociation to dimers and monomers as the pH is increased above pH 9.0.
Animals↗
Structure of a new cyclic nonapeptide, segetalin F, and vasorelaxant activity of segetalins from Vaccaria segetalis.
A new cyclic nonapeptide, segetalin F, has been isolated from the seeds of Vaccaria segetalis and the structure including absolute stereochemistry was elucidated by using 2D NMR and chemical means. A series of segetalins showed a vasorelaxant activity against norepinephrine (NE)-induced contractions of rat aorta.
Animals↗
A new triterpenoid saponin with inhibition of luteal cell from the seeds of Vaccaria segetalis.
A new triterpenoid saponin, named segetoside B, showing inhibition of luteal cell activity, has been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reactions and spectral analyses, its structure has been established as 28-O-[beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)]-[alpha-L-(5-O-acetyl)arabinofuranosyl-(1 --> 3)]-beta-D-(4-O-acetyl)fucopyranosyl-gypsogenin-3-O-beta-D-galactopyranosyl-(1 --> 2)-beta-D-(6-O-methyl ester)-glucuronopyranoside.
Animals↗
[Studies on the flavonol glycosides from the seeds of Vaccaria segetalis].
OBJECTIVE: To study the chemical constituents of the seeds of Vaccaria segetalis. METHOD: Chromatography and spectral analysis were used to isolate the constituents and elucidate their structure. RESULT: Three compounds were isolated from alcohol extract of the seeds of V. segetalis, and identified as apigenin-6-C-arabinosylglucoside(1), apigenin-6-C-glucosylglucoside(2), vaccarin(3). CONCLUSION: Compound 1 and 2 were isolated from the seeds of this plant for the first time.
Apigenin↗
Analysis of bisdesmosidic saponins in Saponaria vaccaria L. by HPLC-PAD-MS: identification of new quillaic acid and gypsogenin 3-O-trisaccharides.
A high-performance liquid chromatographic method using photodiode array and single quadrupole electrospray mass detection for analysis and profiling of bisdesmosidic saponins in Saponaria vaccaria seed was developed. Profiles of seed extract from three different plant sources were obtained and found to contain the same saponins, albeit in different proportions. Several known saponins were identified by selected ion extraction of quasi-molecular ions from the total ion chromatogram and confirmed by their mass spectra. Application of high cone voltages afforded mass spectra containing key diagnostic fragments and relatively strong singly charged quasi-molecular ions. In addition to previously identified saponins, several new quillaic acid and gypsogenin bisdesmosides could be detected via mass spectral analysis. Five of these were tentatively identified as pentose homologues of known saponins, having an added xylosyl residue linked to the 3-O-glucuronyl group (1 --> 3). The stereochemistry and identity of the xylosyl linkage in the new saponins was determined by chemical means. Previously reported vaccaric or segetalic acid-type bisdesmosides could not be detected in any of the extracts.
Carbohydrate Conformation↗
Microspore embryogenesis and the development of a double haploidy protocol for cow cockle (Saponaria vaccaria).
Factors affecting microspore embryogenesis of cow cockle (Saponaria vaccaria) were evaluated including donor plant growing conditions, genotype, bud size, density, medium composition, and culture conditions. Of the two donor plant (day/night) temperature regimes evaluated (10/5 degrees C and 20/15 degrees C), plants grown at 20/15 degrees C were the most embryogenic. An embryogenic frequency of greater than 350 embryos/100 buds was observed in the most embryogenic genotype, cv. 'White Beauty'. Buds from 3-9 mm in length were evaluated for their embryogenic potential; buds that were 4-7.9 mm produced the most embryos/100 buds. Of all the media compositions evaluated, NLN medium with 15% sucrose resulted in the most embryos. Cow cockle microspores required an initial period of 32 degrees C for 3 days for production of microspore-derived embryos (MDEs).
Culture Media↗
A cyclic heptapeptide from Vaccaria segetalis.
A new cyclic heptapeptide, segetalin E, cyclo(-Gly-Tyr-Val-Pro-Leu-Trp-Pro-), has been isolated from the seeds of Vaccaria segetalis and the structure elucidated by extensive two-dimensional NMR methods and chemical degradation.
Amino Acid Sequence↗
Triterpenoid saponin from Vaccaria segetalis.
A new triterpenoid saponin, vaccaroid B, has been isolated from the seeds of Vaccaria segetalis and its structure was elucidated to be 3beta-hydroxyolean-12-en-23, 28-dioic acid-28-O-beta-D-glucopyranosyl-(1-->3)- beta-D-glucopyranosyl-(1-->6)-[6- O-(3-hydroxy-3-methylglutaryl)-beta-D-glucopyranosyl-(1-->2)]- beta-D-glucopyranoside by spectroscopic methods.
Carbohydrate Conformation↗
Triterpenoid saponins from Vaccaria segetalis.
Four novel triterpenoid saponins were isolated from the seeds of Vaccaria segetalis. Their structures were established as vaccaroside A, gypsogenic acid-28-O-beta-D- glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)-[beta-D- glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; vaccaroside B, gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-[3-hydroxyl-3- methylglutaroyl-(1-->6)]-beta-D-glucopyranosyl-(1-->6)-[beta-D- glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; vaccaroside C, 23-O-beta-D-glucopyranosyl-gypsogenic acid-28-O-beta-D- glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)- [beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside and vaccaroside D, 3,4-secogypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)- [beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC and NOESY) studies and chemical degradation.
Carbohydrate Conformation↗
Triterpenoid saponins and sapogenins from Vaccaria segetalis.
Four new triterpenoid saponins, vaccarosides E, F, G and H were isolated from the seeds of Vaccaria segatalis and were respectively defined to be 3-O-beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl] quillaic acid 28-O-beta-D-xylopyranosyl-(1-->4)-chi-L-rhamnopyranosyl-(1-->2)- [chi-L-arabinofuranosyl-(1-->3)]-beta-D-4-O-acetylfucopyranoside; 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl] 3beta,4chi,16chi-trihydroxy-23-norolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-chi-L-rhamnopyranosyl-(1-->2)- [chi-L-arabinofuranosyl-(1-->3)]-beta-D-4-O-acetylfucopyranoside; 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl] gypsogenin 28-O-beta-D-xylopyranosyl-(1-->4)-chi-L-rhamnopyranosyl-(1-->2)- [chi-L-arabinofuranosyl (1-->3)]-beta-D-4-O-acetylfucopyranoside; and 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl] 3beta,4chi-dihydroxy-23norolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-chi-L-rhamnopyranosyl-(1-->2) -chi-L-arabinofuranosyl-(1-->3)]-beta-D-4-O-acetyfucopyranoside. Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC AND NOESY), FAB-MS and ESI-MS studies as well as chemical strategies and enzymatic degradation. The new aglycones of two of the saponins have been designated as segetalic acid and vaccaric acid, respectively.
Carbohydrate Conformation↗
Conformational preference for segetalins G and H, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis.
Three-dimensional structures in DMSO-d0 of segetalins G [cyclo(-Gly-Val-Lys-Tyr-Ala-)] and H [cyclo(-Gly-Tyr-Arg-Phe-Ser-)], cyclic pentapeptides from seeds of Vaccaria segetalis, showing estrogen-like activity, were determined by the distance geometry calculation and restrained energy minimization from NMR data. The backbone structure of segetalin G contains one beta-turn: a beta II-like turn at Tyr4-Ala5, and that of segetalin H one beta-turn: a beta II' turn at Gly1-Tyr2 and one gamma-turn at Arg3-Phe4-Ser5 sequence. The results of distance comparison analysis proposed a pharmacophore model of estrogen-like cyclic peptides, segetalins.
Binding Sites↗
Cyclic peptides from higher plants. 34. Segetalins G and H, structures and estrogen-like activity of cyclic pentapeptides from Vaccaria segetalis.
Segetalins G and H (1-2) possessing estrogen-like activity are cyclic pentapeptides from the seeds of Vaccaria segetalis. Their structures, cyclo(-Gly-Ala-Lys-Tyr-Val) (1) and cyclo(-Gly-Phe-Ser-Tyr-Arg-) (2), were determined by interpretation of spectral data.
Animals↗
Immunoconjugates made of an anti-EGF receptor monoclonal antibody and type 1 ribosome-inactivating proteins from Saponaria ocymoides or Vaccaria pyramidata.
The present paper describes two immunoconjugates consisting of an anti-epidermal growth factor receptor (EGFR) monoclonal antibody (MAb), named Mint5, covalently linked to the type 1 ribosome-inactivating proteins (RIPs) ocymoidine (Ocy) and pyramidatine (Pyra) from Saponaria ocymoides and Vaccaria pyramidata respectively. Both antibody and toxins are shown to retain their respective biological properties upon chemical conjugation. The immunoconjugates exert specific inhibition of EGFR expressing target cell proliferation and protein synthesis in in vitro assays and also inhibit the growth of grafted human tumour cells in nude mice.
Animals↗
Estrogen-like activity of cyclic peptides from Vaccaria segetalis extracts.
Methanol and ethyl acetate extracts of Wang Bu Liu Xing (seeds of Vaccaria segetalis, Caryophyllaceae) and cyclic peptides (named segetalins A and B) obtained from the extracts were shown to have an estrogen-like activity.
Amino Acid Sequence↗
Three new triterpenoid saponins from the seeds of Vaccaria segetalis.
Three new triterpenoid saponins, named segetoside G(1), H(2) and I(3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, their structures have been established as: 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinofuranosyl (1-->3)]-beta-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-(6-O-butyl ester)-glucuronopyranoside (1), 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-(5-O-acetyl)-arabinofuranosyl-(1-->3)]-beta-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (2) and 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-(5-O-acetyl)-arabinofuranosyl-(1-->3)]-beta-D-(4-O-acetyl)-fucopyranosyl-quillaic acid-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (3).
China↗
Triterpenoid saponins from Vaccaria segetalis.
A new triterpenoid saponin, named segetoside C (1), and two known saponins, vaccaroid A (vaccaroside A) (2) and dianoside G (3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, the structure of segetoside C (1) has been established as: gypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[6-O-acetyl-beta-D-glucopyra-nosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside.
Carbohydrate Sequence↗