Pimarane Diterpenes and a Sesquiterpene from Salzmmania nitida

Carvalho, Mário Geraldo de; Alves, Josinete S.; Cunha, Emídio Vasconcelos Leitão da; Barbosa-Filho, José Maria; Silva, Marcelo Sobral da

doi:10.1590/s0001-37652006000100003

Cited by 5 publications

(6 citation statements)

References 7 publications

(4 reference statements)

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“…HMBC of the methyl groups at d H 1.00, 1.42 and 1.44 with the quaternary carbon at d C 77.2 (C-5) was consistent with pimarane or isopimarane-type of skeletons. The 13 C NMR data of compound 1 were similar to those of the previously isolated pimaran-8b-ol (Carvalho et al 2006) and isopimarane-8b-ol (Lorimer & Weavers 1987). Analysis for 13 C NMR data of the two known compounds revealed 13 C NMR shifts of carbons in the vicinity of C-13 to be diagnostic in distinguishing between the pimarane and isopimarane types with trans-fused B and C rings.…”

Section: Resultssupporting

confidence: 71%

New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus

Kulkarni

Shurpali

Khedkar

et al. 2015

Natural Product Research

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Phytochemical investigation of the acetone extract of the aerial parts of Anisochilus verticillatus afforded a new 8,9-secopimarane diterpene (1), two new isopimarane diterpenes (2, 3) and the known ursolic acid (4), α-amyrin (5), β-amyrin (6), stigmast-5-en-3-one (7) and hydroxychavicol (8). Structures of the new compounds were elucidated with the help of 1D and 2D nuclear magnetic resonance spectroscopic data, and single crystal X-ray crystallography of compound 3. Compounds 2 and 8 inhibited Mycobacterium tuberculosis H37Ra with an IC50 of 11.3 (IC90 of 20.0 μg/mL) and 12.5 μg/mL, respectively. Correspondingly, molecular docking studies with Extra Precision Glide revealed a correlation between score and biological activity for these compounds to describe the molecular basis for the most significant SAR results.

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Section: Resultssupporting

confidence: 71%

New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus

Kulkarni

Shurpali

Khedkar

et al. 2015

Natural Product Research

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“…Its stereochemistry can also be deduced from the carbon chemical shift of methyl group C-17 (cis relationships δ C-17 < 25 ppm, trans orientation δ C-17 > 32 ppm) [65,66]. Modern techniques can be used to perform the same assignment; the position of the tertiary 8-hydroxyl group can be confirmed by the cross-peaks signals due to the long-range coupling of C-8 with H-6, and H-9 and H-14 in HMBC experiments [26]. Also, in the 1 H NMR spectra in pyridine-d 6 , either the signals profile of H-15 and H-16 [39] or the observed downfield shifts of the methyl groups at C-13 and C-10 for 8β-OH in the isopimar-15-ene skeleton [55], and on C-10 and C-4 for 8α-OH in the ent-pimar-15-ene skeleton [66] can be used to confirm the orientation of an 8-hydroxyl group.…”

Section: C-1 C-2 C-3 C-4 C-5 C-6 C-7 C-8 C-9 C-10 C-11 C-12 C-13 C-14 C-mentioning

confidence: 98%

“…García-Alvarez and coworkers [70] studied the influence of the acetylation of the equatorial 11-hydroxyl group (26) and found that it causes a downfield (paramagnetic) shift on C-1, C-9 and C-12, and an upfield (diamagnetic) shift on C-8 and C-13. Naturally, there are also results on the more obvious shifts of the carbon attached to the oxygen atom caused by hydroxyl group acetylation [59,71].…”

Section: C-1 C-2 C-3 C-mentioning

confidence: 99%

“…The presence of a diterpene skeleton, as well as the number of methyl, methylene, methine and quaternary carbons present can be deduced from the combined analysis of 13 C and DEPT NMR spectra. From these data, the hydrogen deficiency index and consequently the number of double bonds can be deduced [17][18][19][20][21][22][23][24][25][26]. Other authors used the 13 C NMR spectrum, by PND (proton noise decoupled) and APT (attached proton test) technique, to identify the methyl, methylene, methine and quaternary carbons [11,27].…”

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confidence: 99%

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Structural Elucidation of Pimarane and Isopimarane Diterpenoids: The ¹³C NMR Contribution

Seca

Pinto

Silva

2008

Natural Product Communications

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This paper is dedicated to Professor P. Joseph-Nathan for his 65 th birthday. 13 C NMR spectroscopy is actually one of the first tools used for the structural elucidation of natural and synthetic compounds and it is also used in biosynthetic studies. The aim of this review is to present the 13 C NMR assignments of a large number of pimarane diterpenoids, describing the most significant effects caused by different substitution patterns and different stereochemistry at their chiral centers.

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“…Rubiaceae has species of great economical importance which are exploited as food, ornamental and in the pharmaceutical industry too (Carvalho et al, 2006). In addition, several species are popularly referred to as toxic and/or medicinal and among these latter there are species of the genus Richardia (Coelho et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

Chemical constiuents from Richardia grandiflora (Cham. & Schltdl.) Steud. (Rubiaceae)

Tomaz¹,

Nogueira²,

Pinto³

et al. 2008

Rev. bras. farmacogn.

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RESUMO: "Constituintes químicos de Richardia grandifl ora (Cham. & Schltdl.) Steud. (Rubiaceae)". Dentre as diversas formas de terapia para a prevenção e cura de doenças, as plantas foram, indubitavelmente, as mais amplamente utilizadas desde o início da humanidade. O Brasil tem grande diversidade de plantas com potenciais medicinais, ainda não pesquisados, e que são promissoras fontes de inovações terapêuticas e farmacológicas. A família Rubiaceae, considerada a maior da ordem Gentianales, possui cerca de 637 gêneros e 10.700 espécies. Richardia grandifl ora (Cham. & Schltdl.) Steud., conhecida popularmente como ervanço, poaia ou ipeca-mirim, tem indicações etnofarmacológicas para uso contra hemorróidas e como vermífugo na forma de decocto. Visando a contribuir com o estudo quimiotaxonômico da família Rubiaceae e tendo em vista a ausência de dados na literatura acerca da constituição química de Richardia grandifl ora, esta foi submetida a um estudo fi toquímico para o isolamento de seus constituintes químicos, através dos métodos cromatográfi cos usuais, e posterior identifi cação estrutural dos mesmos, utilizando-se os métodos espectroscópicos de RMN 1 H e 13 C uni e bidimensionais, além de comparações com modelos da literatura. Deste estudo pioneiro com R. grandifl ora foram isolados e identifi cados cinco constituintes: uma mistura dos esteróides -sitosterol e estigmasterol, o ácido o-hidroxibenzóico, o ácido m-metoxi-p-hidroxi-benzóico e a feofi tina A, todos inéditos no gênero Richardia. Unitermos:Richardia grandifl ora, Rubiaceae, -sitosterol, estigmasterol, ácido o-hidroxibenzóico, ácido m-metoxi-p-hidroxi-benzóico, feofi tina A. ABSTRACT:Amongst the different forms of therapy to prevent and cure illnesses, plants have been, undoubtedly, the most utilized ones since the beginning of mankind. Brazil has a great diversity on plants that possess non-researched medicinal potential and are promising sources of therapeutic and pharmacological innovations. The Rubiaceae family is considered the biggest one of the order Gentianales, presenting around 637 genera and 10,700 species. Richardia grandifl ora (Cham. & Schltdl.) Steud., known popularly as "ervanço", "poaia" or "ipeca-mirim", has ethnopharmacological indications to use as decoction against hemorrhoids and as vermifuge. Aiming at contributing to the chemotaxonomic study of the family Rubiaceae and considering the absence of data in literature about the chemical constitution of the species Richardia grandifl ora, the latter was submitted to a phytochemical study to isolate its chemical constituents, through usual chromatographic methods, and after identifying them by means of spectroscopic methods such as 1 H and 13 C NMR, with the add of two-dimensional techniques, besides comparison with literature data. Five constituents were isolated through this fi rst phytochemical study with R. grandifl ora: a mixture of the steroids -sitosterol and stigmasterol, o-hydroxy-benzoic acid, m-methoxy-p-hydroxy-benzoic acid and phaeophitin A, all of them isolated for th...

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Pimarane Diterpenes and a Sesquiterpene from Salzmmania nitida

Cited by 5 publications

References 7 publications

New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus

New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus

Structural Elucidation of Pimarane and Isopimarane Diterpenoids: The ¹³C NMR Contribution

Chemical constiuents from Richardia grandiflora (Cham. & Schltdl.) Steud. (Rubiaceae)

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Pimarane Diterpenes and a Sesquiterpene from Salzmmania nitida

Cited by 5 publications

References 7 publications

New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus

New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus

Structural Elucidation of Pimarane and Isopimarane Diterpenoids: The 13C NMR Contribution

Chemical constiuents from Richardia grandiflora (Cham. & Schltdl.) Steud. (Rubiaceae)

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Structural Elucidation of Pimarane and Isopimarane Diterpenoids: The ¹³C NMR Contribution