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Volumn 6, Issue 10, 2015, Pages 5740-5745

Biosynthetic insights provided by unusual sesterterpenes from the medicinal herb Aletris farinosa

(6) Challinor, Victoria L a Johnston, Ryne C a Bernhardt, Paul V a Lehmann, Reginald P b Krenske, Elizabeth H a De Voss, James J a

a UNIVERSITY OF QUEENSLAND (Australia)

b Integria Healthcare Pty Ltd ^* (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CARBON; COMPUTATION THEORY; CRYSTALLOGRAPHY; DENSITY FUNCTIONAL THEORY;

CARBON SKELETON; COMPUTATIONAL MODEL; ENZYME ACTIVE SITES; HYDRIDE MIGRATION; MEDICINAL HERB; PREORGANIZATION; SESTERTERPENES; THEORETICAL CALCULATIONS;

X RAY CRYSTALLOGRAPHY;

EID: 84941641536 PISSN: 20416520 EISSN: 20416539 Source Type: Journal
DOI: 10.1039/c5sc02056e Document Type: Article

Times cited : (11)

References (29)

1
- 36348934977
- Y. Liu L. Wang J. H. Jung S. Zhang Nat. Prod. Rep. 2007 24 1401 1429
- (2007) Nat. Prod. Rep. , vol.24 , pp. 1401-1429
- Liu, Y.¹ Wang, L.² Jung, J.H.³ Zhang, S.⁴

2
- 0034637608
- M. K. Renner P. R. Jensen W. Fenical J. Org. Chem. 2000 65 4843 4852
- (2000) J. Org. Chem. , vol.65 , pp. 4843-4852
- Renner, M.K.¹ Jensen, P.R.² Fenical, W.³

3
- 84888877969
- The biosynthetic origins of diterpenes can be complex. Class I terpene cyclases catalyse the formation of a reactive cationic intermediate via pyrophosphate ionization as is typical of mono- and sesquiterpene biosynthesis. Class II diterpene synthases use protonation of an alkene to initiate cyclisation. Some enzymes combine both these functions, with pyrophosphate ionization followed by a protonation step or vice versa. For reviews see
- J. Shinozaki M. Shibuya Y. Ebizuka K. Masuda Biosci., Biotechnol., Biochem. 2013 77 2278 2282
- (2013) Biosci., Biotechnol., Biochem. , vol.77 , pp. 2278-2282
- Shinozaki, J.¹ Shibuya, M.² Ebizuka, Y.³ Masuda, K.⁴

4
- 84871576542
- Y. Gao R. B. Honzatko R. J. Peters Nat. Prod. Rep. 2012 29 1153 1175
- (2012) Nat. Prod. Rep. , vol.29 , pp. 1153-1175
- Gao, Y.¹ Honzatko, R.B.² Peters, R.J.³

5
- 0000502773
- in, ed. D. E. Cane, Elsevier Science, Oxford, ch. 2.08, Enzyme-induced conformational control of the fates of cationic intermediates in terpene biosynthesis has recently been proposed by Tantillo in his seminal studies of the bisabolyl cation: see
- J. MacMillan and M. H. Beale, in Comprehensive Natural Products Chemistry, ed., D. E. Cane, Elsevier Science, Oxford, 1999, vol. 2, ch. 2.08, pp. 217-243
- (1999) Comprehensive Natural Products Chemistry , vol.2 , pp. 217-243
- MacMillan, J.¹ Beale, M.H.²

6
- 84894145298
- Y. J. Hong D. J. Tantillo J. Am. Chem. Soc. 2014 136 2450 2463
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 2450-2463
- Hong, Y.J.¹ Tantillo, D.J.²

7
- 84924942301
- For the role of post-TS dynamic effects in determining product selectivities, see
- R. P. Pemberton K. C. Ho D. J. Tantillo Chem. Sci. 2015 6 2347 2353
- (2015) Chem. Sci. , vol.6 , pp. 2347-2353
- Pemberton, R.P.¹ Ho, K.C.² Tantillo, D.J.³

8
- 84893021866
- Y. J. Hong D. J. Tantillo Nat. Chem. 2014 6 104 111
- (2014) Nat. Chem. , vol.6 , pp. 104-111
- Hong, Y.J.¹ Tantillo, D.J.²

9
- 25844476888
- Briza Publications, Pretoria, South Africa
- B. van Wyk, M. Wink, Medicinal Plants of the World, Briza Publications, Pretoria, South Africa, 2004
- (2004) Medicinal Plants of the World
- Van Wyk, B.¹ Wink, M.²

10
- 84890571290
- C. L. Butler C. H. Costello J. Am. Pharm. Assoc. 1944 33 177 183
- (1944) J. Am. Pharm. Assoc. , vol.33 , pp. 177-183
- Butler, C.L.¹ Costello, C.H.²

11
- 79959485788
- N. J. Matovic J. M. U. Stuthe V. L. Challinor P. V. Bernhardt R. P. Lehmann W. Kitching J. J. de Voss Chem.-Eur. J. 2011 17 7578 7591
- (2011) Chem.-Eur. J. , vol.17 , pp. 7578-7591
- Matovic, N.J.¹ Stuthe, J.M.U.² Challinor, V.L.³ Bernhardt, P.V.⁴ Lehmann, R.P.⁵ Kitching, W.⁶ De Voss, J.J.⁷

12
- 79960734976
- V. L. Challinor V. M. U. Stuthe P. V. Bernhardt R. P. Lehmann W. Kitching J. J. De Voss J. Nat. Prod. 2011 74 1557 1560
- (2011) J. Nat. Prod. , vol.74 , pp. 1557-1560
- Challinor, V.L.¹ Stuthe, V.M.U.² Bernhardt, P.V.³ Lehmann, R.P.⁴ Kitching, W.⁵ De Voss, J.J.⁶

13
- 84865504622
- V. L. Challinor J. M. U. Stuthe P. G. Parsons L. K. Lambert R. P. Lehmann W. Kitching J. J. De Voss J. Nat. Prod. 2012 75 1469 1479
- (2012) J. Nat. Prod. , vol.75 , pp. 1469-1479
- Challinor, V.L.¹ Stuthe, J.M.U.² Parsons, P.G.³ Lambert, L.K.⁴ Lehmann, R.P.⁵ Kitching, W.⁶ De Voss, J.J.⁷

14
- 0342978211
- R. E. Marker D. L. Turner A. C. Shabica E. M. Jones J. Krueger J. D. Surmatis J. Am. Chem. Soc. 1940 62 2620 2621
- (1940) J. Am. Chem. Soc. , vol.62 , pp. 2620-2621
- Marker, R.E.¹ Turner, D.L.² Shabica, A.C.³ Jones, E.M.⁴ Krueger, J.⁵ Surmatis, J.D.⁶

15
- 84876947330
- The planar structures of 1-4 have been reported in the patent literature
- V. L. Challinor S. Chap R. P. Lehmann P. V. Bernhardt J. J. De Voss J. Nat. Prod. 2013 76 485 488
- (2013) J. Nat. Prod. , vol.76 , pp. 485-488
- Challinor, V.L.¹ Chap, S.² Lehmann, R.P.³ Bernhardt, P.V.⁴ De Voss, J.J.⁵

16
- 84941723329
- Jpn. Kokai Tokkyo Koho JP 2012206962) albeit with differing, apparently erroneous stereochemistry of the Δ17(18) double bond 8 PCM
- H. Takikawa and M. Sugiyama, Jpn. Kokai Tokkyo Koho JP 2012206962, 2012
- (2012)
- Takikawa, H.¹ Sugiyama, M.²

17
- 84946893847
- B3LYP
- S. MiertuŠ E. Scrocco J. Tomasi Chem. Phys. 1981 55 117 129
- (1981) Chem. Phys. , vol.55 , pp. 117-129
- Miertuš, S.¹ Scrocco, E.² Tomasi, J.³

18
- 0000189651
- mPW1PW91
- A. D. Becke J. Chem. Phys. 1993 98 5648 5652
- (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
- Becke, A.D.¹

19
- 11244326290
- C. Adamo V. Barone J. Chem. Phys. 1998 108 664 675
- (1998) J. Chem. Phys. , vol.108 , pp. 664-675
- Adamo, C.¹ Barone, V.²

20
- 79959190033
- Quantum mechanical calculations were performed in Gaussian 09:, Gaussian, Inc., Wallingford CT
- Quantum mechanical calculations were performed in Gaussian 09: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT, 2013
- (2013) Gaussian 09, Revision D.01
- Frisch, M.J.¹ Trucks, G.W.² Schlegel, H.B.³ Scuseria, G.E.⁴ Robb, M.A.⁵ Cheeseman, J.R.⁶ Scalmani, G.⁷ Barone, V.⁸ Mennucci, B.⁹ Petersson, G.A.¹⁰ Nakatsuji, H.¹¹ Caricato, M.¹² Li, X.¹³ Hratchian, H.P.¹⁴ Izmaylov, A.F.¹⁵ Bloino, J.¹⁶ Zheng, G.¹⁷ Sonnenberg, J.L.¹⁸ Hada, M.¹⁹ Ehara, M.²⁰ more..

21
- 84856301655
- M. W. Lodewyk M. R. Siebert D. J. Tantillo Chem. Rev. 2012 112 1839 1862
- (2012) Chem. Rev. , vol.112 , pp. 1839-1862
- Lodewyk, M.W.¹ Siebert, M.R.² Tantillo, D.J.³

22
- 84869458987
- M. W. Lodewyk C. Soldi P. B. Jones M. M. Olmstead J. Rita J. T. Shaw D. J. Tantillo J. Am. Chem. Soc. 2012 134 18550 18553
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 18550-18553
- Lodewyk, M.W.¹ Soldi, C.² Jones, P.B.³ Olmstead, M.M.⁴ Rita, J.⁵ Shaw, J.T.⁶ Tantillo, D.J.⁷

23
- 77956630251
- ESI This has also been suggested in the case of the sesterterpene ophiobolin F
- S. G. Smith J. M. Goodman J. Am. Chem. Soc. 2010 132 12946 12959
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12946-12959
- Smith, S.G.¹ Goodman, J.M.²

24
- 84873391260
- and β-geranylfarnesene
- R. Chiba A. Minami K. Gomi H. Oikawa Org. Lett. 2013 15 594 597
- (2013) Org. Lett. , vol.15 , pp. 594-597
- Chiba, R.¹ Minami, A.² Gomi, K.³ Oikawa, H.⁴

25
- 84877038326
- T. Sato H. Yamaga S. Kashima Y. Murata T. Shinada C. Nakano T. Hoshino ChemBioChem 2013 14 822 825
- (2013) ChemBioChem , vol.14 , pp. 822-825
- Sato, T.¹ Yamaga, H.² Kashima, S.³ Murata, Y.⁴ Shinada, T.⁵ Nakano, C.⁶ Hoshino, T.⁷

26
- 0034683034
- Class II diterpene synthases are also known to utilise alkene protonation to initiate biosynthesis. 3 Although 1-4 possess a Z configured C-17 alkene which might arise from 2Z-geranylfarnesol, we chose to show the 2E-geranylfarnesol as the precursor as previous work with the squalene-hopene cyclase had shown it to be a much better precursor of cyclized products. 2 However, either the 2E or 2Z isomer could lead to the same cationic intermediates (C, Scheme 1) via cyclisation. Indeed, the precursor may be the (pyro)phosphate ester of geranylfarnesol as this would not be expected to significantly affect the chemistry shown and would provide a strong interaction with the cyclase active site For reviews of quantum mechanical studies of terpene biosynthetic pathways, see
- K. U. Wendt G. E. Schulz G. E. E. J. Corey D. R. Liu Angew. Chem., Int. Ed. 2000 39 2812 2833
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2812-2833
- Wendt, K.U.¹ Schulz, G.E.² Corey, G.E.E.J.³ Liu, D.R.⁴

27
- 80051584607
- D. J. Tantillo Nat. Prod. Rep. 2011 28 1035 1053
- (2011) Nat. Prod. Rep. , vol.28 , pp. 1035-1053
- Tantillo, D.J.¹

28
- 84887788807
- Interconversion between the twist-boat and chair conformers of β- C entails significant molecular motions, especially of the C-17 methyl and C-18 hydroxymethyl groups. Steric and hydrogen-bonding interactions between these groups and active-site residues could disfavor twist-boat → chair conversion relative to hydride migration. While the initial 1,2-hydride shift leading from β- C to β- D is computed to be uphill by 4.5 kcal mol^-1, the next step in the cascade is significantly downhill, thereby limiting reversion of β- D back to β- C. That is, the intermediate derived from 1,2-methyl migration from C-13 to C-18 in β- D is 9.3 kcal mol^-1 lower in energy than the twist-boat form of β- C (see the ESI)
- D. J. Tantillo Nat. Prod. Rep. 2013 30 1079 1086
- (2013) Nat. Prod. Rep. , vol.30 , pp. 1079-1086
- Tantillo, D.J.¹

29
- 0345112540
- G. Brownlie F. S. Spring R. Stevenson W. S. Strachan J. Chem. Soc. 1956 2419 2427
- (1956) J. Chem. Soc. , pp. 2419-2427
- Brownlie, G.¹ Spring, F.S.² Stevenson, R.³ Strachan, W.S.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.