Terpenoids of the volatile oil of <i>Bursera graveolens</i>

The characteristic spicy, sweet and balsamic aroma components of the woods of Bursera graveolens (palo santo) were measured using GC-MS. The characteristic four compounds, 1-4, were isolated from the diethyl ether extract. The structure of compounds 1 and 2 was elucidated by means of NMR studies, and confirmed to be 1-acetyl-4-isopropenyl-1-cyclopentene (1) and 2-methyl-5-isopropenyl-1-cyclopenten-1-carboxaldehyde (2) by synthesis from limonene oxide derivatives. The structure of compounds 3 and 4 was determined to be 6,10-epoxy-7(14)-isodaucane (3) and 10-hydroxy-6,10-epoxy-7(14)-isodaucane (4) by NMR experiments. Of these, compound 4 is a new sesquiterpenoid with a weak woody note, and the presence of compounds 1-4 in B. graveolens is reported here for the first time.

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“…6,7 In this report, we describe mono-and sesquitrpenoids found in B. graveolens, including a new sesquiterpenoid with a woody note.…”

Section: Introductionmentioning

confidence: 95%

Mono- and sesquiterpenoids of the volatile oil ofBursera graveolens

et al. 2005

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“…Also 10‐ epi ‐γ‐eudesmol ( 35 ) was first obtained by synthesis from dihydrocarvone (+)‐ 19 , unfortunately without reporting the optical rotation of 35 , [131] but the first isolation paper mentions the identity of (−)‐ 35 from vetiver oil ( Vetiveria zizanioides ) and the synthetic material [132] . The compound was also isolated from Amyris balsamifera , [38] Aquilaria malaccensis ([α] D =−68.8), [133] Alpinia japonica , [122] Hedychium spicatum [134] and Bursera graveolens [135] …”

Section: Eudesmolsmentioning

confidence: 99%

“…[132] The compound was also isolated from Amyris balsamifera, [38] Aquilaria malaccensis ([α] D = À 68.8), [133] Alpinia japonica, [122] Hedychium spicatum [134] and Bursera graveolens. [135] Scheme 8. Eudesmols derived from I1 and 1,2-hydride shift to M1.…”

Section: Eudesmols From Cation I2mentioning

confidence: 99%

“…[176] The absolute configuration was evident through a synthesis from 35 (prepared as shown in Scheme 12) by epoxidation and reductive epoxide opening (Scheme 17B). [149] Isodihydroagarofuran ( 52), also named α-dihydroagarofuran, was isolated from Phonus arborescens, [147] Bursera graveolens, [135] Bulnesia sarmientoi, [177] and identified in the cyanobacterium Calothrix by GC/MS in comparison to standards of 52 and its stereoisomer 40, albeit without determination of absolute configuration. [178]…”

Section: Eudesmols From Cation I3mentioning

confidence: 99%

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Hedycaryol – Central Intermediates in Sesquiterpene Biosynthesis, Part II

Dickschat

2022

Chemistry A European J

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The known sesquiterpenes that arise biosynthetically from hedycaryol are summarised. Reasonings for the assignments of their absolute configurations are discussed. The analysis provided here suggests that reprotonations at the C1=C10 double bond of hedycaryol are directed toward C1 and generally lead to 6–6 bicyclic compounds, while reprotonations at the C4=C5 double bond occur at C4 and result in 5–7 bicyclic compounds. Read more in the Review by H. Xu and J. S. Dickschat (DOI: 10.1002/chem.202200405).

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“…(−)-Carvone has been used as starting material in the first asymmetric total synthesis of 1a,6a-dihydroxyeudesm-3-ene. 236 The eudesmane derivatives 229 and 230 have been obtained from Bursera graveolens 237 and Cedrolepsis grevei, 238 respectively. Several polyacylated dihydroagarofuran derivatives have been isolated from Celastrus angulatus, 239 Celastrus orbiculatus, 240 Celastrus paniculatus, 241 Euonymus nanoides, 242, 243 Maytenus chiapensis, 244 Maytenus chuchuhuasca, 245 Maytenus laevis 246 and Salacia chinensis.…”

Section: Eudesmane and Valeranementioning

confidence: 99%