Constituents of ayou essential oil (Aydendron barbeyana Mez)

Abstract

From Ayou oil (essential oil of Aydendron barbeyana Mez. 50 constituents could be identified by 1H‐NMR spectra and GC‐MS. Main constituents are β‐bisabolol (8%), (E)‐nerolidol (6%), ar‐curcumene (6%), and δ‐cadinene (5%). The structures of a new sesquiterpene ether 1,11‐oxidocalamenene (29a) and of trans‐sesquisabinene hydrate (41b) could be confirmed by 1H‐ and 13C‐NMR spectra.

A Gold‐Catalyzed Entry into the Sesquisabinene and Sesquithujene Families of Terpenoids and Formal Total Syntheses of Cedrene and Cedrol

“…Reaction of ketone 5 with MeMgBr in Et 2 O at 08C afforded alcohol 33 as a single isomer in high yield. Its spectra matched those of cis-sesquisabinene hydrate, an ingredient of the essential oils of Zingiber officinale, [15] Hedychium gardnerianum Roscoe ("Kahili ginger"), [35] Nectandra globosa ("Ayou" or "canella preta"), [36] and the sub-Himalayan aromatic shrub Strobilanthes auriculatus. [37] Whereas the [a] D of synthetic (À)-33 and the natural product are in good agreement, the literature actually depicts the opposite enantiomer.…”

“…The NMR spectra are sufficiently different from those of 33 and were found to be in accord with the data of trans-sesquisabinene hydrate published in the literature. [35,36] As no chiroptical data of this particular natural product are available, the assignment of the absolute configuration must remain open.…”

“…[ α ]${{{20\hfill \atop {\rm D}\hfill}}}$ =−10.3 ( c =1.2 in CHCl 3 ); [ α ]${{{22\hfill \atop {\rm D}\hfill}}}$ =−10.4 ( c =0.4 in CHCl 3 ), lit. :36 [ α ]${{{20\hfill \atop {\rm D}\hfill}}}$ =−12 ( c =1.3 in CHCl 3 ); 1 H NMR (400 MHz, CDCl 3 ): δ =5.10–5.06 (m, 1 H), 2.07–1.98 (m, 1 H), 1.95–1.85 (m, 1 H), 1.68 (s, 3 H), 1.64–1.52 (m, 3 H), 1.60 (s, 3 H), 1.49–1.38 (m, 2 H), 1.35 (s, 3 H), 1.30–1.22 (m, 2 H), 1.10 (dd, J =7.6, 3.4 Hz, 2 H), 0.89 (d, J =6.8 Hz, 3 H), 0.65 (dd, J =4.8, 3.7 Hz, 1 H), 0.29 ppm (dd, J =7.6, 5.1 Hz, 1 H); 13 C NMR (100 MHz, CDCl 3 ): δ =131.3, 124.8, 79.4, 37.6, 36.1, 34.3, 33.9, 33.2, 28.1, 26.1, 25.8, 25.7, 17.7, 17.1, 11.3 ppm; IR (film): $\tilde \nu $ = 3349, 2959, 2924, 2866, 1451, 1374, 1127, 985, 925 cm −1 ; MS (70 eV): m / z (%): 222 (5) [ M + ], 207 (36), 189 (10), 161 (30), 151 (11), 137 (26), 119 (60), 109 (29), 93 (54), 82 (82), 69 (100), 55 (43), 29 (11); HRMS (ESI): m / z : calcd for C 15 H 26 ONa [ M + +Na]: 245.1876, found: 245.1877.…”

“…Compounds 5 and 6 were then converted into a host of different members of the sesquisabina-and sesquithuja families of terpenoids, inter alia with the aid of iron-catalyzed cross-coupling reactions. As the relative and absolute configuration of 5 and 6 could be unambiguously established, the synthetic samples allowed the previously unknown stereostructures of various such terpenoids to be unraveled, including cis-sesquisabinene hydrate (33), 7-epi-sesquithujene (36), sesquisabinene B (37) and epoxysesquithujene (45). Moreover, the preparation of 6 also constitutes a formal total synthesis of cedrene (11) and cedrol (12).…”

Chemical volatiles present in cotton gin trash: A by-product of cotton processing

“…Although, not as common as its stereoisomer, β-bisabolol has been reported to be one of the major sesquiterpenoids extracted from cotton plants [16,19], and most notably from the cotton bolls [60]. The compound has also been identified in the essential oil of Santalum album [61], and in trace amounts in ayou oil from Aydendron barbeyana Mez [62]. β-Bisabolol acts as an insect attractant, particularly for boll weevils, and stimulates the production of sex pheromones in the insects, thereby promoting mating between opposite sexes.…”