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Page 1
Exploring novel bacterial terpene synthases.
Reddy GK, Leferink NGH, Umemura M, Ahmed ST, Breitling R, Scrutton NS, Takano E. Reddy GK, et al. PLoS One. 2020 Apr 30;15(4):e0232220. doi: 10.1371/journal.pone.0232220. eCollection 2020. PLoS One. 2020. PMID: 32353014 Free PMC article.
Several terpenoid products not previously detected in bacteria were identified, including aromandendrene, acora-3,7(14)-diene and longiborneol. Overall, we have identified promiscuous terpene synthases in bacteria and demonstrated that terpene synthases with substrate prom …
Several terpenoid products not previously detected in bacteria were identified, including aromandendrene, acora-3,7(14)-diene and longibo
Strategy Evolution in a Skeletal Remodeling and C-H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids.
Lusi RF, Sennari G, Sarpong R. Lusi RF, et al. J Am Chem Soc. 2022 Sep 21;144(37):17277-17294. doi: 10.1021/jacs.2c08136. Epub 2022 Sep 13. J Am Chem Soc. 2022. PMID: 36098550 Free PMC article.
Detailed herein are our synthesis studies of longiborneol and related natural products. Our overarching goals of utilizing a "camphor first" strategy enabled by skeletal remodeling of carvone, and late-stage diversification using C-H functionalizations, led to divergent sy …
Detailed herein are our synthesis studies of longiborneol and related natural products. Our overarching goals of utilizing a "camphor …
Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy.
Lusi RF, Sennari G, Sarpong R. Lusi RF, et al. Nat Chem. 2022 Apr;14(4):450-456. doi: 10.1038/s41557-021-00870-4. Epub 2022 Feb 14. Nat Chem. 2022. PMID: 35165424 Free PMC article.
Here, we demonstrate that an orthogonal strategy where topological complexity is introduced at the outset leads to the short synthesis of the longifolene-related terpenoid longiborneol. To implement this strategy, we access a bicyclo[2.2.1] starting material through scaffo …
Here, we demonstrate that an orthogonal strategy where topological complexity is introduced at the outset leads to the short synthesis of th …
Chemical composition and antibacterial activity of the essential oil of Drimys granadensis L.f. leaves from Colombia.
Gaviria M, Quijano C, Pino J, Madriñán S. Gaviria M, et al. Chem Biodivers. 2011 Mar;8(3):532-9. doi: 10.1002/cbdv.201000170. Chem Biodivers. 2011. PMID: 21404436
A total of 85 components were identified, with the major compounds germacrene D (1, 14.7%), sclarene (9.5%), a-cadinol (7.3%), longiborneol acetate (2, 6.3%), drimenol (4.2%), (Z)-beta-ocimene (3, 4.2%), a-pinene (4, 3.2%), and beta-elemene (5, 2.7%). ...
A total of 85 components were identified, with the major compounds germacrene D (1, 14.7%), sclarene (9.5%), a-cadinol (7.3%), longiborne
Total synthesis of (+/-)-culmorin and (+/-)-longiborneol: an efficient construction of Tricyclo[6.3.0.0(3,9)]undecan-10-one by intramolecular double Michael addition.
Takasu K, Mizutani S, Noguchi M, Makita K, Ihara M. Takasu K, et al. J Org Chem. 2000 Jun 30;65(13):4112-9. doi: 10.1021/jo000185s. J Org Chem. 2000. PMID: 10866628
The methodology was further elaborated to achieve efficient total syntheses of (+/-)-culmorin (1) and (+/-)-longiborneol (2). The common precursor 13 of them was obtained from 14 in 94% yield as a single isomer by the treatment with LHMDS. After the conversion of 13 into t …
The methodology was further elaborated to achieve efficient total syntheses of (+/-)-culmorin (1) and (+/-)-longiborneol (2). The com …
Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum.
Bahadoor A, Schneiderman D, Gemmill L, Bosnich W, Blackwell B, Melanson JE, McRae G, Harris LJ. Bahadoor A, et al. J Nat Prod. 2016 Jan 22;79(1):81-8. doi: 10.1021/acs.jnatprod.5b00676. Epub 2015 Dec 16. J Nat Prod. 2016. PMID: 26673640
Clm2 encodes a regio- and stereoselective cytochrome P450 monooxygenase for C-11 of longiborneol (1). Clm2 gene disruptants were grown in liquid culture and assessed for culmorin production via HPLC-evaporative light scattering detection. ...
Clm2 encodes a regio- and stereoselective cytochrome P450 monooxygenase for C-11 of longiborneol (1). Clm2 gene disruptants were grow …
C-C Bond Cleavage of α-Pinene Derivatives Prepared from Carvone as a General Strategy for Complex Molecule Synthesis.
Lusi RF, Perea MA, Sarpong R. Lusi RF, et al. Acc Chem Res. 2022 Mar 1;55(5):746-758. doi: 10.1021/acs.accounts.1c00783. Epub 2022 Feb 16. Acc Chem Res. 2022. PMID: 35170951 Free PMC article.
We, then, present several total syntheses using these synthetic intermediates, beginning with the bridged, polycyclic sesquiterpenoid longiborneol, which was synthesized from a carvone-derived [2.2.1]bicycle following a key semipinacol rearrangement. ...
We, then, present several total syntheses using these synthetic intermediates, beginning with the bridged, polycyclic sesquiterpenoid lon
Stereoselective Construction of Copaborneol and Longiborneol Frameworks by Intramolecular Double Michael Reaction.
Ihara M, Makita K, Fujiwara Y, Tokunaga Y, Fukumoto K. Ihara M, et al. J Org Chem. 1996 Sep 6;61(18):6416-6421. doi: 10.1021/jo960698s. J Org Chem. 1996. PMID: 11667485
Stereoselective syntheses of tricyclo[5.3.0.0(3,8)]decane 22 and tricyclo[6.3.0.0(3,9)]undecane 26, the basic skeletons of copaborneol and longiborneol, were achieved by the intramolecular double Michael reactions of 2-cyclopenten-1-ones 15-17. ...The intramolecular double …
Stereoselective syntheses of tricyclo[5.3.0.0(3,8)]decane 22 and tricyclo[6.3.0.0(3,9)]undecane 26, the basic skeletons of copaborneol and …
Structural Insights into Three Sesquiterpene Synthases for the Biosynthesis of Tricyclic Sesquiterpenes and Chemical Space Expansion by Structure-Based Mutagenesis.
Lou T, Li A, Xu H, Pan J, Xing B, Wu R, Dickschat JS, Yang D, Ma M. Lou T, et al. J Am Chem Soc. 2023 Apr 5. doi: 10.1021/jacs.3c00278. Online ahead of print. J Am Chem Soc. 2023. PMID: 37018048
We here determined the crystal structures of three sesquiterpene synthases (STSs, namely, BcBOT2, DbPROS, and CLM1) catalyzing the biosynthesis of the tricyclic sesquiterpenes presilphiperfolan-8beta-ol (1), delta(6)-protoilludene (2), and longiborneol (3). All three STS s …
We here determined the crystal structures of three sesquiterpene synthases (STSs, namely, BcBOT2, DbPROS, and CLM1) catalyzing the biosynthe …
Efficacy of Mandarin Crust Oil, Marigold Extract and Their Nanoemulsions, on Spodoptera littoralis (Boisd.) Larvae.
E Marouf A. E Marouf A. Pak J Biol Sci. 2022 Jan;25(8):688-697. doi: 10.3923/pjbs.2022.688.697. Pak J Biol Sci. 2022. PMID: 36098194
The major constituents identified by GC-MS analysis in marigold extract and mandarin crust oil were, 6-epi-shyobunol (Longiborneol) and D-Limonene, respectively. Furthermore, at LC<sub>50</sub>, all treatments decreased AST/GOT and ALT/GPT activ …
The major constituents identified by GC-MS analysis in marigold extract and mandarin crust oil were, 6-epi-shyobunol (Longiborneol) a …
19 results