Neo-clerodane diterpenoids from Scutellaria alpina

Bozov, Petko I.; Papanov, Georgi Y.; Malakov, Peter Y.

doi:10.1016/s0031-9422(00)94838-6

Cited by 22 publications

(26 citation statements)

References 9 publications

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“…Test compounds: All tested neo-clerodane diterpenoids ( Figure 1) were taken from previous work: Scupolin I (9), scutaltisin A (10),scutaltisin B (11), scutaltisin D (12), scutecyprin (13), scupolin H (19) and scutecyprol A (20) were isolated from Scutellaria altissima, as described previously [13,14]. Neoajugapyrin A (14), 14,15-dihydrojodrellin T (15), scutegalerin A (16), scutegalerin B (17) and scutecolumnin C (18) were extracted from S. galericulata [15,16]. The diterpenoids scutalpin A (21), scutalpin E (22) and scutalpin F (23) were obtained from S. alpina [17,18].…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms

Bozov

Girova

Prisadova

et al. 2015

Natural Product Communications

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Antimicrobial activity of nineteen neo-clerodane diterpenoids, isolated from the acetone extracts of the aerial parts of Scutellaria and Salvia species (Lamiaceae) were tested against thirteen strains belonging to nine different species of pathogenic and food spoilage bacteria Aeromonas hydrophila, Bacillus cereus, Escherichia coli, Listeria monocytogenes, Proteus vulgaris, Pseudomonas aeruginosa, Pseudomonas fluorescens, Salmonella abony and Staphylococcus aureus as well as against two yeast strains belonging to species Candida albicans. Seven of the evaluated compounds scutalpin A, scutalpin E, scutalpin F, salviarin, splenolide A, splenolide B and splendidin demonstrated antimicrobial activity against used test microbial strains, the rest of the compounds were inactive within the studied concentration range. Among all of the tested compounds the highest antimicrobial activity was detected for scutalpin A against Staphylococcus aureus (MIC 25 µg/mL).

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Section: Methodsmentioning

confidence: 99%

Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms

Bozov

Girova

Prisadova

et al. 2015

Natural Product Communications

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“…In fact, in the case of all other taxa of Scutellaria from which 8b,13-epoxy-neoclerodan-15,16-olides have been isolated, i.e. Scutellaria alpina (Bozov et al, 1993(Bozov et al, , 1994de la Torre et al, 1995), Scutellaria orientalis subsp. pinnatifida (Malakov et al, 1997), S. alpina subsp.…”

Section: Resultsmentioning

confidence: 99%

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

et al. 2010

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“…), who has practical experience for isolation of plant compounds and their structure elucidation, we additionally composed a small validation set of spectra of 10 compounds isolated by P.B. [4][5][6][7][8]. These ten compounds were isolated from plants and are suitable for checking the efficiency of the interpretive search.…”

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confidence: 99%

“…In rows (B) are shown the corresponding substructure generated with highest precision, embedded into the reference structure (bold bonds); for them the precision and correctness (Y/N) are given. Compounds: scutalpin E (1) [4], scutalpin F (2) [4], scutorientalin E (3) [5], formyl methyl ursolate (4) [6], formyl methyl oleanolate (5) [6], scutalpin A (6) [7], salviarin (7) [8], splenolide A (8) [8], splenolide B (9) [8], and splendidin (10) [8].…”

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confidence: 99%

Interpretive Library Search of Plant Compound Spectra in a 13C NMR Database#

et al. 2015

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The derivation of structural characteristics of a compound of unknown structure from its spectral data is a central procedure for modern structure elucidation. Computer searching in spectral libraries of fully-assigned 13 C NMR spectra of substructures or full structures is an essential part of structure elucidation and has been widely applied because this type of spectra reflects the nature of the skeletal backbone of an organic compound, information not as readily available by other spectroscopic techniques [1]. In this paper we describe an extensive test of a previously developed method for interpretive search in spectral libraries of fully-assigned 13 C NMR spectra [2]. The method is implemented into a Windows-based userfriendly program, called Infer C NMR.The program input consists of the 13 C NMR spectrum of the unknown compound (chemical shift and multiplicity of each signal) and molecular formula. The search algorithm retrieves a list of connected substructures from the reference compounds in such a way that only atoms with matched signals are included into the inferred substructures. The substructures are explicitly defined in terms of atom type, hydrogen multiplicity, and bond type. They are presented embedded into the reference structures and are sorted according to their reliability (estimation of their correctness, usually called accuracy). This accuracy is calculated by a multivariate function that was obtained in advance by comprehensive statistics. The parameters that restrict the search algorithm are the tolerance of signal matching (Tol) in ppm and the minimum number of carbon atoms in the inferred (retrieved) substructures (m.n.c.); the latter is set to six for this study.Although our program for interpretive library search is intended to serve as a useful stand-alone application for the spectroscopist, its output can be sent as input to a computer-enhanced structure elucidation system, such as SESAMI [3]. In this mode, one or more of the retrieved substructures act as constraints on the structure generation process, serving to reduce the number of plausible alternative structures that are presented to the chemist by the structure generator. The greater the number and information content of the constraints, the greater the efficiency of the structure generator and the fewer the structures produced. It is important to recognize that if a substructure predicted as present is handed to the structure generator, every structure output will contain that substructure. Thus, if even only one of the retrieved substructures used as constraints is incorrect, every structure produced by structure generator will be invalid (the worst scenario) or no output structures will be generated because the constraints contradict each other or other spectral data (a better scenario). That is why the output from the interpretive 13 C NMR library search must have two very important features: high information content and high reliability.As described in a previous paper [2], the accuracy function was tested with a large ...

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Neo-clerodane diterpenoids from Scutellaria alpina

Cited by 22 publications

References 9 publications

Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms

Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms

Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia

Interpretive Library Search of Plant Compound Spectra in a 13C NMR Database#

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