Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis

Yun Soo Yeo; S. Eric Nybo; Amar G. Chittiboyina; Aruna D. Weerasooriya; Yan Hong Wang; Elsa Góngora-Castillo; Brieanne Vaillancourt; C. Robin Buell; Dean Dellapenna; Mary Dawn Celiz; A. Daniel Jones; Eve Syrkin Wurtele; Nick Ransom; Natalia Dudareva; Khaled A. Shaaban; Nidhi Tibrewal; Suman Chandra; Troy Smillie; Ikhlas A. Khan; Robert M. Coates; David S. Watt; Joe Chappell

doi:10.1074/jbc.M112.415836

Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis

Yun Soo Yeo, S. Eric Nybo, Amar G. Chittiboyina, Aruna D. Weerasooriya, Yan Hong Wang, Elsa Góngora-Castillo, Brieanne Vaillancourt, C. Robin Buell, Dean Dellapenna, Mary Dawn Celiz, A. Daniel Jones, Eve Syrkin Wurtele, Nick Ransom, Natalia Dudareva, Khaled A. Shaaban, Nidhi Tibrewal, Suman Chandra, Troy Smillie, Ikhlas A. Khan, Robert M. CoatesDavid S. Watt, Joe Chappell

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

Abstract

Background: Therapeutic values of Valeriana officinalis have been associated with sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.

Original language	English
Pages (from-to)	3163-3173
Number of pages	11
Journal	Journal of Biological Chemistry
Volume	288
Issue number	5
DOIs	https://doi.org/10.1074/jbc.M112.415836
State	Published - Feb 1 2013

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Cell Biology

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Yeo, Y. S., Nybo, S. E., Chittiboyina, A. G., Weerasooriya, A. D., Wang, Y. H., Góngora-Castillo, E., Vaillancourt, B., Buell, C. R., Dellapenna, D., Celiz, M. D., Daniel Jones, A., Wurtele, E. S., Ransom, N., Dudareva, N., Shaaban, K. A., Tibrewal, N., Chandra, S., Smillie, T., Khan, I. A., ... Chappell, J. (2013). Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis. Journal of Biological Chemistry, 288(5), 3163-3173. https://doi.org/10.1074/jbc.M112.415836

@article{1056021ca33047759a60573ce28e0930,

title = "Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis",

abstract = "Background: Therapeutic values of Valeriana officinalis have been associated with sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.",

author = "Yeo, {Yun Soo} and Nybo, {S. Eric} and Chittiboyina, {Amar G.} and Weerasooriya, {Aruna D.} and Wang, {Yan Hong} and Elsa G{\'o}ngora-Castillo and Brieanne Vaillancourt and Buell, {C. Robin} and Dean Dellapenna and Celiz, {Mary Dawn} and {Daniel Jones}, A. and Wurtele, {Eve Syrkin} and Nick Ransom and Natalia Dudareva and Shaaban, {Khaled A.} and Nidhi Tibrewal and Suman Chandra and Troy Smillie and Khan, {Ikhlas A.} and Coates, {Robert M.} and Watt, {David S.} and Joe Chappell",

year = "2013",

month = feb,

day = "1",

doi = "10.1074/jbc.M112.415836",

language = "English",

volume = "288",

pages = "3163--3173",

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Yeo, YS, Nybo, SE, Chittiboyina, AG, Weerasooriya, AD, Wang, YH, Góngora-Castillo, E, Vaillancourt, B, Buell, CR, Dellapenna, D, Celiz, MD, Daniel Jones, A, Wurtele, ES, Ransom, N, Dudareva, N, Shaaban, KA, Tibrewal, N, Chandra, S, Smillie, T, Khan, IA, Coates, RM, Watt, DS & Chappell, J 2013, 'Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis', Journal of Biological Chemistry, vol. 288, no. 5, pp. 3163-3173. https://doi.org/10.1074/jbc.M112.415836

Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis. / Yeo, Yun Soo; Nybo, S. Eric; Chittiboyina, Amar G. et al.
In: Journal of Biological Chemistry, Vol. 288, No. 5, 01.02.2013, p. 3163-3173.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis

AU - Yeo, Yun Soo

AU - Nybo, S. Eric

AU - Chittiboyina, Amar G.

AU - Weerasooriya, Aruna D.

AU - Wang, Yan Hong

AU - Góngora-Castillo, Elsa

AU - Vaillancourt, Brieanne

AU - Buell, C. Robin

AU - Dellapenna, Dean

AU - Celiz, Mary Dawn

AU - Daniel Jones, A.

AU - Wurtele, Eve Syrkin

AU - Ransom, Nick

AU - Dudareva, Natalia

AU - Shaaban, Khaled A.

AU - Tibrewal, Nidhi

AU - Chandra, Suman

AU - Smillie, Troy

AU - Khan, Ikhlas A.

AU - Coates, Robert M.

AU - Watt, David S.

AU - Chappell, Joe

PY - 2013/2/1

Y1 - 2013/2/1

N2 - Background: Therapeutic values of Valeriana officinalis have been associated with sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.

AB - Background: Therapeutic values of Valeriana officinalis have been associated with sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.

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SN - 0021-9258

VL - 288

SP - 3163

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JO - Journal of Biological Chemistry

JF - Journal of Biological Chemistry

IS - 5

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Yeo YS, Nybo SE, Chittiboyina AG, Weerasooriya AD, Wang YH, Góngora-Castillo E et al. Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis. Journal of Biological Chemistry. 2013 Feb 1;288(5):3163-3173. doi: 10.1074/jbc.M112.415836

Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis

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