A short synthesis of ambrox® from sclareol

Decorzant, René; Vial, Christian; Näf, Ferdinand; Whitesides, George M.

doi:10.1016/s0040-4020(01)81499-x

Cited by 64 publications

(25 citation statements)

References 30 publications

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“…Z ‐abienol belongs to a group of diterpenoids that have attracted interest because of their use as synthesis precursors of ambergris substitution fragrance products such as (−)‐Ambrox ® . (−)‐Ambrox ® is currently synthesized from sclareol, a labdane diterpene related to Z ‐abienol and extracted from clary sage, Salvia sclarea (Decorzant et al. , 1987; Martres et al.…”

Section: Discussionmentioning

confidence: 99%

Characterization of two genes for the biosynthesis of the labdane diterpene Z‐abienol in tobacco (Nicotiana tabacum) glandular trichomes

et al. 2012

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SUMMARYLeaves of tobacco (Nicotiana tabacum) are covered with glandular trichomes that produce sucrose esters and diterpenoids in varying quantities, depending on cultivar type. The bicyclic diterpene Z-abienol is the major labdanoid present in some oriental tobacco cultivars, where it constitutes a precursor of important flavours and aromas. We describe here the identification and characterization of two genes governing the biosynthesis of Z-abienol in N. tabacum. As for other angiosperm labdanoid diterpenes, the biosynthesis of Z-abienol proceeds in two steps. NtCPS2 encodes a class-II terpene synthase that synthesizes 8-hydroxy-copalyl diphosphate, and NtABS encodes a kaurene synthase-like (KSL) protein that uses 8-hydroxy-copalyl diphosphate to produce Z-abienol. Phylogenetic analysis indicates that NtABS belongs to a distinct clade of KSL proteins that comprises the recently identified tomato (Solanum habrochaites) santalene and bergamotene synthase. RT-PCR results show that both genes are preferentially expressed in trichomes. Moreover, microscopy of NtCPS2 promoter-GUS fusion transgenics demonstrated a high specificity of expression to trichome glandular cells. Ectopic expression of both genes, but not of either one alone, driven by a trichomespecific promoter in transgenic Nicotiana sylvestris conferred Z-abienol formation to this species, which does not normally produce it. Furthermore, sequence analysis of over 100 tobacco cultivars revealed polymorphisms in NtCPS2 that lead to a prematurely truncated protein in cultivars lacking Z-abienol, thus establishing NtCPS2 as a major gene controlling Z-abienol biosynthesis in tobacco. These results offer new perspectives for tobacco breeding and the metabolic engineering of labdanoid diterpenes, as well as for structure-function relationship studies of terpene synthases.

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Section: Discussionmentioning

confidence: 99%

Characterization of two genes for the biosynthesis of the labdane diterpene Z‐abienol in tobacco (Nicotiana tabacum) glandular trichomes

et al. 2012

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“…Sclareol has been reported to exhibit potent antibacterial activity [3] as well as fungal-growth-regulating and plant-growth-inhibiting properties [4 ± 6]. It is also being used commercially as a fixative in perfumery, a flavoring agent in tobacco industry, and a synthon for the synthesis of a series of amber odorants [7] [8]. Biotransformations of sclareol (1) have been reported by various fungal and bacterial strains [9 ± 19], resulting in hydroxylations at 2a-, 3a-, 3b-, 6a-, 18-, and 19-positions.…”

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Structure Elucidation and Antibacterial Activity of New Fungal Metabolites of Sclareol

Choudhary

Siddiqui

Hussain

et al. 2006

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The transformation of the antibacterial diterpene sclareol (1) by two different fungal strains was investigated (Scheme). In the presence of Rhizopus stolonifer, (3beta)-3-hydroxysclareol (2), 18-hydroxysclareol (3), (6alpha)-6,18-dihydroxysclareol (4), and (11S)-11,18-dihydroxysclareol (5) were formed. Fermentation of 1 with Fusarium lini afforded (1beta)-1-hydroxysclareol (6) and (12S)-12-hydroxysclareol (7). Compounds 4-7 were identified as new compounds, and some of them were active against Bacillus subtilis (Table 3).

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“…One of the most important is Salvia sclarea (clary sage), a biennial plant which produces both an essential oil rich in linalyl acetate and linalool, and a concrete with high amounts of the labdanoid diterpene sclareol. Sclareol is currently used in the fragrance industry as a synthesis precursor for Ambrox®, a highly valued compound with amber-like fragrance und excellent fixative properties (Decorzant et al, 1987;Martres et al, 1993;Koga et al, 1998;Moulines et al, 2001;Barrero et al, 2004;Moulines et al, 2004). Salvia sclarea possesses two types of glandular trichomes, capitate and peltate.…”

Section: Sagementioning

confidence: 99%

Trichome Specific Expression: Promoters and Their Applications

Tissier¹

2012

Transgenic Plants - Advances and Limitations

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A short synthesis of ambrox® from sclareol

Cited by 64 publications

References 30 publications

Characterization of two genes for the biosynthesis of the labdane diterpene Z‐abienol in tobacco (Nicotiana tabacum) glandular trichomes

Characterization of two genes for the biosynthesis of the labdane diterpene Z‐abienol in tobacco (Nicotiana tabacum) glandular trichomes

Structure Elucidation and Antibacterial Activity of New Fungal Metabolites of Sclareol

Trichome Specific Expression: Promoters and Their Applications

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