A verticillane‐type diterpene from<i>Boswellia carterii</i>essential oil

Basar, Simla; Koch, Angelika; König, Wilfried Α.

doi:10.1002/ffj.992

Cited by 69 publications

(45 citation statements)

References 12 publications

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“…Basar et al [13] Obermann (1977) [6] Basar (2005) [8] Al-Harasi and Al-Saidi (2008) [21] Marongiu et al [9] Mikhaeil et al [22] Camarda (2007) [20] 136 Naphthalene [13] Obermann (1977) [6] Basar (2005) [8] Al-Harasi and Al-Saidi (2008) [21] Marongiu et al [9] Mikhaeil et al [22] Camarda (2007) [20] 160 a-Selinene [23] Basar (2005) [8] Camarda (2007) [20] Baser et al [23] Basar (2005) [8] Camarda (2007) [20] Dekebo (2002) [24] Baser et al [23] Basar (2005) [8] 176 [23] Basar (2005) [8] Camarda (2007) [20] Baser et al [23] Basar (2005) [8] Camarda (2007) [20] Dekebo (2002) [24] Baser et al [23] Basar (2005) [8] 189 Eucalyptol [23] Basar (2005) [8] Camarda (2007) [20] Baser et al [23] Basar (2005) [8] Camarda (2007) [20] Dekebo (2002) [24] Baser et al [23] Basar (2005) [8] 210 [23] Basar (2005) [8] Camarda (2007) [20] Baser et al [23] B...…”

Section: B Carteri (B Sacra)mentioning

confidence: 98%

“…a-Pinene was found in all samples, with relative amounts in the range 3. [18] Verghese (1987) [19] Basar (2005) [8] Camarda (2007) [20] [13] Obermann (1977) [6] Basar (2005) [8] Al-Harasi and Al-Saidi (2008) [21] Marongiu et al [9] Mikhaeil et al [22] Camarda (2007) [20] 76 Abieta-8,12-diene Table 2.…”

Section: Quantitative Characterization Of Boswellia Volatilesmentioning

confidence: 98%

“…Basar et al [13] Obermann (1977) [6] Basar (2005) [8] Al-Harasi and Al-Saidi (2008) [21] Marongiu et al [9] Mikhaeil et al [22] Camarda (2007) [20] 104 p-Cymen-8-ol Table 2.…”

Section: B Carteri (B Sacra)mentioning

confidence: 98%

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The volatile constituents of frankincense – a review

Mertens

Buettner

Kirchhoff

2009

Flavour & Fragrance J

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The smell of frankincense resin and powder, as well as burned frankincense, has been linked to a series of health effects since ancient times. Additionally, frankincense and its fumes are used as a means to induce positive psychophysical effects and well-being, not only in an ecclesiastical setting but also in traditional medical applications. This review aims to provide an overview of current knowledge of the volatile constituents of frankincense, with explicit consideration concerning the diverse Boswellia varieties. Altogether, more than 300 volatiles in frankincense have been reported in the literature. In particular, a broad diversity has been found in the qualitative and quantitative composition of the volatiles with respect to different varieties of Boswellia. A detailed discussion of the various analytical approaches applied to isolating and analysing the volatile fractions of frankincense is also presented

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Section: B Carteri (B Sacra)mentioning

confidence: 98%

Section: Quantitative Characterization Of Boswellia Volatilesmentioning

confidence: 98%

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The volatile constituents of frankincense – a review

Mertens

Buettner

Kirchhoff

2009

Flavour & Fragrance J

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“…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. ent-Verticillanes might be useful as chemical markers of J. javanica.…”

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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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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“…Using different chromatographic methods (Paul, et al, 2012;Fei, et al, 2011;Paul, et al, 2011;Mertens, et al, 2009;Pozharitskaya, et al, 2006;Basar, 2005;Büchele, et al, 2003a;2003b;Hamm, et al, 2003;Brody, et al, 2002;Sane, et al, 1998), 311 (Mertens, et al, 2009) to 340 (Hussain, et al, 2013) chemical compounds in Boswellia genus have been found in its oleo-gum resin, including compounds new to science (Büchele, et al, 2003;Culioli, et al, 2003;Dekebo, et al, 2002a;2002b;2002c;2002d;2002e;Basar, et al, 2001;Dekebo, et al, 2000;Klein, et al, 1978). Similarly, in Commiphora, more than 300 chemical compounds have been found (Shen, et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Volatile Compounds in Oleo-gum Resin of Socotran Species of Burseraceae

Maděra

Paschová

Ansorgová

et al. 2017

Acta Univ. Agric. Silvic. Mendelianae Brun.

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Socotra Island is well known for its high rate of plant species endemism and having the highest concentration of frankincense species in the world. Thirteen species in Burseraceae occur on the island, of which 12 are endemic. A total of only four species from the island have had the chemical compositions of their resins published. Moreover, in general, most studies on chemical composition of frankincense and myrrh resins have analysed samples that were not freshly collected (including some of considerable age). Our study therefore aimed at analysing the volatile compound composition of all Socotran Burseraceae species, using fresh resin sample analysis. We found a total of 103 volatile compounds in all the species, with 53 of them fully identified, 27 of them partially determined and 23 still unidentified. These include four compounds (α-fenchene, calarene, trans-β-farnesene, α-elemene) newly reported from Boswellia and two (phytol and ledene) newly reported from Commiphora. Our results suggested the huge potential to find new chemical compounds among endemic Burseracean species.

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A verticillane‐type diterpene fromBoswellia carteriiessential oil

Abstract: The essential oil of Boswellia carterii resinoid (olibanum) was investigated by GC-MS. In addition to known compounds, a new verticillane-type diterpene was isolated and identified by NMR investigations as verticilla-4(20),7,11-triene.

Cited by 69 publications

References 12 publications

The volatile constituents of frankincense – a review

The volatile constituents of frankincense – a review

New ent-Verticillane Diterpenoids from the Japanese Liverwort Jackiella javanica

Volatile Compounds in Oleo-gum Resin of Socotran Species of Burseraceae

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