1-octen-3-O-alpha-L-arabinopyranosyl-(1 -> 6)-beta-glucopyranoside, a minor substance from the leaves of Kalanchoe pinnata (Crassulaceae)

Abstract

RESUMO:"1-Octeno-3-O--L-arabinopiranosil-(1 6)--glicopiranosídeo, u m a substância minoritária das folhas de Kalanchoe pinnata (Crassulaceae)". A partir das folhas de Kalanchoe pinnata (Crassulaceae), uma planta medicinal amplamente utilizada contra processos infl amatórios e que apresenta importante atividade imunossupressora e antileishmania, foi isolado um álcool vinílico diglicosilado minoritário, caracterizado como 1-octeno-3-O--L-arabinopiranosil-(1 6)--glicopiranosídeo baseado em RMN mono e bi-dimensional e em CG-EM, após sucessivos processos cromatográfi cos em coluna. Esta molécula é um derivado hidrossolúvel da aglicona 1-octen-3-ol, molécula que atua como atrativo para polinizadores e sinalizador de defesa contra herbivoria. Unitermos:Kalanchoe pinnata, Crassulaceae, extrato etanólico, 1-octeno-3-O--Larabinopiranosil-(1 6)--glicopiranosídeo, defesa da planta, atrativo para polinizadores.ABSTRACT: From the leaves of Kalanchoe pinnata (Crassulaceae), a medicinal plant widely used against infl ammatory processes which exhibit a important immunosuppressive and antileishmanial activities, was isolated a minor vinylic aliphatic alcohol diglycoside which structure was proposed as the known 1-octen-3-O--L-arabinopyranosyl-(1 6)--glucopyranoside based on 1 H and 13 C mono and bi-dimensional NMR experiments and GC-MS analysis, after successive chromatographic column procedures. This molecule is a water-soluble derivative of the volatile aglicone 1-octen-3-ol that appears to be attractant of pollinators and signalling of defence against herbivores.

1-Octen-3-ol Is Formed from Its Glycoside during Processing of Soybean [Glycine max (L.) Merr.] Seeds

“…All of the carbon signals of the sugar moiety fit with those of aroma β-primeveroside with only a small difference. , The aglycone moiety of 1-octen-3-yl β-primeveroside was confirmed by 13 C NMR data [heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond coherence (HMBC)] and 1 H NMR and GC–MS analyses of hydrolyzed 1-octen-3-yl β-primeveroside. The aglycone moiety of 13 C and 1 H NMR data fit with that of 1-octen-3-yl vicianoside in the leaves of Kalanchoe pinnata (Crassulaceae) with less than 0.13 ppm of 1 H NMR . The NMR and MS data supported a structure of 1-octen-3-yl 6- O -β- d -xylopyranosyl-β- d -glucopyranoside (1-octen-3-yl β-primeveroside).…”

“…Because the formation of 1-octen-3-ol from linoleic acid needs molecular oxygen in most organisms, − oxygen-independent formation of 1-octen-3-ol in the hydrated seed powder implied that 1-octen-3-ol was formed from a stored, non-volatile compound. Glycosides of 1-octen-3-ol have been isolated in several plant species. − On the basis of this knowledge, we prepared a glycoside-rich fraction from the dry soybean powder and hydrolyzed this fraction with almond β-glycosidase (Figure ). As expected, 1-octen-3-ol was formed continuously with increasing incubation time.…”

Bryophyllum pinnatum and Related Species Used in Anthroposophic Medicine: Constituents, Pharmacological Activities, and Clinical Efficacy

“…4-OEthylgallic acid, syringic acid, vanillic acid, methyl gallate, 3,4-dimethoxyphenol, phloroglucinol, and 3,4-dihydroxyallylbenzene were reported in B. delagoense [38]. The presence of n-alkanols and n-alkanes, such as n-hentriacontane and n-tritriacontane [39], bryophollenone (52) [41], and a minor constituent, 1-octen [47], have been reported in B. pinnatum. In B. daigremontianum, ferulate esters of C 22 -C 30 alcohols were found in the roots, and triacontanol was detected in the leaves [48].…”

Vitamin C and aroma composition of fresh leaves from Kalanchoe pinnata and Kalanchoe daigremontiana

“…1-octen-3-ol did not give a mushroom-like effect in the aroma profile of the samples from K. daigremontiana , which contained very small amounts of it. According to Almeida, Muzitano & Costa 33 1-octen-3-ol occurs in the leaves of K. pinnata as an aglycone of a minor vinylic aliphatic alcohol diglycoside with the proposed structure: 1-octen-3-O-α-L-arabinopyranosyl—(1→6)-ß-glucopyranoside. The presence in the aroma of K. pinnata of a few other eight-atom compounds (mentioned above) not found in K. daigremontiana is interesting.…”