Zizyphus mauritiana Lam. (Rhamnaceae) and the chemical composition of its floral fecal odor

Abstract

As flores de Zizyphus mauritiana Lam. (Rhamnaceae) exalam um forte odor fecal, e sua análise por micro-extração em fase sólida (SPME) associada a cromatografia gasosa-espectrometria de massas (CG-EM), co-injeção de padrões e índices de retenção revelou o benzaldeído como constituinte majoritário. Foram observados ainda benzenóides, ácidos carboxílicos, aldeídos, hidrocarbonetos alifáticos e monoterpenóides. A avaliação olfatométrica do SPME realizada por CG-olfatometria em sniffing port indicou o escatol (3-metil-indol) como o responsável pelo odor fecal das flores e a vanilina pelo seu odor adocicado.When in blossom, jujube (Zizyphus mauritiana Lam., Rhamnaceae) emanates a strong fecal odor. The substances responsible for this scent were analysed by headspace solid-phase microextraction and gas chromatography-mass spectrometry (SPME-GC-MS) associated to standard co-injection and retention indexes, which showed benzaldehyde as major constituent. Minor benzenoids, aliphatic carboxylic acids, aldehydes, hydrocarbons and oxygenated monoterpenes were also observed. Olfactometric evaluation of the SPME using GC-sniffing port indicated skatole (3-methyl-indole) as responsible for the fecal odor and vanillin for the sweety odor. Keywords:Zizyphus mauritiana, Rhamnaceae, aroma, skatole, headspace solid-phase microextraction IntroductionAround 170 tropical and subtropical species of Zizyphus Mill. are known. Z. mauritiana Lam. is popularly known as Aprin, Ber, Dunks or Indian jujube and belongs to the family Rhamnaceae. The plants vary from bushy shrubs 1.2-1.8 m tall to trees up to 12 m and about five yellowish-green flowers with 4-5 petals are borne on short inflorescences at the leaf axils. During the week of blossom, the thousands of flowers emanate a strong scent reminiscent of human excrement, which is detectable over 30 m from the tree, attracting hundreds of flies. We have seen small green dung-beetles visiting the flowers as well.Many publications deal with the varieties, cultivars, cultivation, propagation and analyses of the constituents present on Z. mauritiana, 1 and more rarely with pollination of the Indian jujube.2 However, we were unable to find any mention of the strong fecal odor of the flowers and vegetative parts of any Zizyphus species, and decided to study the chemical constituents responsible for this notable character. Materials and Methods Plant materialFlowers were collected from a single specimen of Zizyphus mauritiana Lam. cultivated at the Botanical Orchard of the Museu Nacional, Rio de Janeiro, during 2 successive blossoms. A voucher specimen (R. J. V. Alves, 6990), was deposited in the herbarium of Museu Nacional. InstrumentationAn Agilent 6890 gas chromatograph was used coupled to an Agilent 5973 quadrupole mass spectrometer with electron ionization mode (EI) generated at 70 eV (ion source at 230 °C and transfer line at 280 °C). GC was performed on , where it was held for 20 min. At the end of the column, the effluent was split 1:1 (by volume) into the mass detector and the sniffing port,...

Headspace Volatile Composition of the Flowers of Caralluma europaea N.E.Br. (Apocynaceae)

“…α-Terpinene and linalool are also present in the club-shaped organs of Sauromatum guttatum , where they account for 0.2% and 5.5%, respectively [ 17 ], while 0.8% of linalool has been found in the pistillate-stage spate of Peltandra virginica (L.) Kunth (Araceae) [ 18 ], and 1.5% in flowers of Zizyphus mauritiana Mill. (Rhamnaceae) [ 19 ]. Hexanoic acid and octanoic acid are present in Desmidorchis flava and, according to Jürgens at al .…”

Antifungal Activity of Iranian Honeybees Against C andida, A spergillus Species and T richophyton R ubrum

“…Also gas chromatography mass spectrometry showed low rate of phenolic and flavonoid components in Chamaemelum and Zizyphus (Alves et al . ; Ansari Dezfooli et al . ).…”

Dung mimicry: the function of volatile emissions and corolla patterning in fly‐pollinated Wurmbea flowers

“…Emission of skatole is much less common in plants and has been reported mainly from members of the Araceae (Knudsen et al , 2006 list only Araceae). Aside from the Araceae, emission of skatole is known for Desmidorchis flava (Jürgens et al , 2006), Orbea verrucosa (Johnson & Jürgens, 2010), and Stapelia gigantea (F. Geers, S. D. Johnson, A. Shuttleworth & T. van der Niet, unpublished), all in the Apocynaceae, and in Zizyphus mauritiana (Rhamnaceae; Alves et al , 2005).…”