Verticillane Derivatives from Bursera suntui and Bursera kerberi

Hernández‐Hernández, Juan D.; Román-Marín, Luisa U.; Cerda-Garcı́a-Rojas, Carlos M.; Joseph‐Nathan, Pedro

doi:10.1021/np050323e

Cited by 31 publications

(37 citation statements)

References 31 publications

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“…[12][13][14] The structures of the known compounds were determined by comparison of authentic 1 H-and 13 C-NMR spectra and/or reference data.…”

Section: Resultsmentioning

confidence: 99%

“…The absolute structure of 8, which has been reported as the epoxy derivative given by the oxidation of 9, 6) was also revised to (7R,8R,12R)-ent-7,8-epoxy-3E-verticillen-12-ol (25). Additionally, the previously reported epoxy derivatives 6) The verticillane-type diterpenoids, which are known as precursors to taxanes, have been isolated from the conifer Sciadopitys verticillata, 8) the soft coral Cespitularia hypotentaculata, 15) and the dicotyledons Bursera suntui, 14) B. kerberi 14) and Boswellia carterii. 16) However, the ent-verticillanes have been isolated as the main components only in the liverwort J. javanica.…”

Section: -Ol (ϭEnt-isoverticillenol) (22) (1s)-ent-verticilla-3e7ementioning

confidence: 99%

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New ent-Verticillane Diterpenoids from the Japanese Liverwort Jackiella javanica

Nagashima

Wakayama

Ioka

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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In our search for novel compounds possessing biological activity, we are currently studying the chemical constituents of Japanese, European, New Zealand and Argentine liverworts.1,2) To date, we have reported a number of novel carbon skeletal, sesqui-and diterpenoids or bisbibenzyl compounds, and enantiomers of known terpenoids. Some of them show interesting biological activities.3) Moreover these compounds are often valuable as chemosystematic and genetic markers. 1,2)The sesqui-and diterpenoids of Jackiella javanica SCHIFFN., that is known as only one genus and one species in Japan, have previously been reported by our group. 4,5) Reinvestigation of the Japanese J. javanica resulted in the isolation of the very rare natural products, ent-verticillane diterpenoids 1-8 as main components, together with known sesquiterpenoids and ent-kaurane diterpenoids. 6) Recently, Coates et al. 7) reported that the absolute configuration of (ϩ)-verticillol which had been isolated from Sciadopitys verticillata 8) should be corrected from structure 9 to 1 by X-ray crystallographic analysis of the p-iodobenzoate derivative. Inevitably, the absolute configuration of ent-verticillol, the enantiomer of (ϩ)-verticillol, must be corrected from structure 1 to 9. Furthermore, the absolute structures of the other ent-verticillanes might also be reversed. Continuing the study of the chemical constituents of J. javanica resulted in the isolation of three additional new ent-verticillanes 10-12, together with the four known sesquiterpenoids 13-16 and a known ent-verticillene diterpenoid 17.Here, we report on the isolation and structural characterization of the new compounds from J. javanica and revision of their absolute configurations. Results and DiscussionA combination of chromatography on silica gel, Sephadex LH-20 and preparative HPLC of the ether extract of J. javanica afforded three new ent-verticillanes 10-12 as well as known sesquiterpenoids, ent-ledene (13), 9) ent-4,10-aromadendrandiol (14), 10) (1R,7R)-germacra-4(15),5E,10(14)-trien-1-ol (15) 4) and ent-11-hydroxy-5-guaien (16), 11) and a diterpene hydrocarbon, ent-exo-verticillene (17). [12][13][14] The structures of the known compounds were determined by comparison of authentic 1 H-and 13 C-NMR spectra and/or reference data.The IR spectrum of compound 10 showed the presence of hydroxy and carbonyl groups (3466, 1709 cm Ϫ1 ). Electron impact mass spectrometry (EI-MS) showed a molecular ion peak at m/z 304 [M] ϩ and the molecular formula was confirmed as C 20 H 32 O 2 by high resolution EI-MS (HR-EI-MS). The 1 H-NMR spectrum (Table 1) (Table 2) and distortionless enhancement by polarization transfer (DEPT) spectra indicated the presence of two trisubstituted olefinic carbons (d 124.3, 128.9 each CH, 132.9, 134.3 each C), a carbonyl carbon (d 205.7) originating from the aldehyde group, a quaternary carbon (d 76.6) bearing a hydroxy group, and also four methyls, seven methylenes, two methines and a quaternary carbon. These spectral data are similar to those of verticillene-type...

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“…[12][13][14] The structures of the known compounds were determined by comparison of authentic 1 H-and 13 C-NMR spectra and/or reference data.…”

Section: Resultsmentioning

confidence: 99%

Section: -Ol (ϭEnt-isoverticillenol) (22) (1s)-ent-verticilla-3e7ementioning

confidence: 99%

New ent-Verticillane Diterpenoids from the Japanese Liverwort Jackiella javanica

Nagashima

Wakayama

Ioka

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Many Bursera species are important in Mexican folk medicine. Their use is related to fragrance in addition to its medicinal properties against diarrhea, fever, gingivitis, cough and measles (Hernández-Hernández et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Bursera Morelensis Ramírez Essential Oil

Canales-Martínez¹,

Rivera-Yañez²,

Salas-Oropeza³

et al. 2017

Afr J Tradit Complement Altern Med

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Background: Bursera morelensis, known as "Aceitillo", is an endemic tree of Mexico. Infusions made from the bark of this species have been used for the treatment of skin infections and for their wound healing properties. In this work, we present the results of a phytochemical and antimicrobial investigation of the essential oil of B. morelensis. Materials and Methods:The essential oil was obtained by a steam distillation method and analyzed using GC-MS. The antibacterial and antifungal activities were evaluated. Results: GC-MS of the essential oil demonstrated the presence of 28 compounds. The principal compound of the essential oil was α-Phellandrene (32.69%). The essential oil had antibacterial activity against Gram positive and negative strains. The most sensitive strains were S. pneumoniae, V. cholerae (cc) and E. coli (MIC 0.125 mg/mL, MBC 0.25 mg/mL). The essential oil was bactericidal for V. cholera (cc). The essential oil inhibited all the filamentous fungi. F. monilifome (IC 50 = 2.27 mg/mL) was the most sensitive fungal strain. Conclusions: This work provides evidence that confirms the antimicrobial activity of the B. morelensis essential oil and this is a scientific support about of traditional uses of this species.

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“…It has been demonstrated that the cyclization mechanism from (E,E,E)-geranylgeranyl diphosphate to taxa-4,11-diene proceeds through a verticillen-12-yl carbocation intermediate [5]. Some hydroxylated verticillane derivatives have been isolated from diverse sources such as the conifer Sciadopitys verticillata [6], the dicotyledons Bursera suntui and B. kerberi [7], the soft coral Cespitularia hypotentaculata [8 -11], and the liverworts Jackiella javanica and Jungermannia infusca [12] [13]. Several polyfunctionalized derivatives of this bicyclic diterpene have also been isolated from Taxus species [14 -16].…”

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confidence: 99%

“…rosea Whole plant [19] (þ)-(1S,11S,12S)-verticilla-3,7-dien-12-ol (3), which was later isolated also from liverwort Jackiella javanica along with other eight analogues 5 -12 [12] [13] [18]. In 2005, five verticillane diterpenes, 13 -17, along with 4 were isolated from the stems of Bursera suntui and B. kerberi [7]. Besides the verticillane diterpenes 1 -17, a ,7E )-2a,10b-Diacetoxy-5a,13a,20-trihydroxy-3,8-secotaxa-3,7,11-trien-9-one 63 T. chinensis Leaf [33] (3E,7E )-2a,10b,13a-Triacetoxy-5a,20-dihydroxy-3,8-secotaxa-3,7,11-trien-9-one 64 T. chinensis Leaf [33] verticillane dimer, dihypoestoxide (18), was isolated from hexane extracts of Hypoestes rosea [19].…”

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confidence: 99%

Verticillane Derivatives from Natural Sources

Wang

et al. 2009

Chemistry & Biodiversity

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Verticillane Derivatives from Bursera suntui and Bursera kerberi

Cited by 31 publications

References 31 publications

New ent-Verticillane Diterpenoids from the Japanese Liverwort Jackiella javanica

New ent-Verticillane Diterpenoids from the Japanese Liverwort Jackiella javanica

Antimicrobial Activity of Bursera Morelensis Ramírez Essential Oil

Verticillane Derivatives from Natural Sources

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