Aquatidial, a new bis-Norsesquiterpenoid from Pachira aquatica Aubl.

Abstract

Aquatidial, um novo bis-norsesquiterpenóide assimétrico, hipoteticamente derivado da isoemigossipolona, foi isolado da casca externa das raízes de Pachira aquatica (Bombacaceae), juntamente com os compostos conhecidos isoemigossipolona, p-cumarato de triacontila e lupeol. As estruturas do aquatidial e dos demais compostos foram determinadas por análises espectroscópicas (EM-FAB, IV, RMN 1D e 2D) ou por comparação com dados publicados na literatura.Aquatidial, a new asymmetric bis-norsesquiterpenoid, hypothetically derived from isohemigossypolone, was isolated from the outer bark of Pachira aquatica (Bombacaceae) roots, along with the known compounds isohemigossypolone, triacontyl p-coumarate and lupeol. The structures of aquatidial and the known compounds were established by spectroscopic analyses (HRFABMS, IR, 1D and 2D NMR) or comparison with published data from literature.

Involucratusins A–H: Unusual Cadinane Dimers from Stahlianthus involucratus with Multidrug Resistance Reversal Activity

“…The skeleton of 1 – 3 is corresponded to novel cadinane sesquiterpenoid dimer with unusual 1-oxaspiro[4.5]decane ring ( 1 and 2 ) or seven-membered cyclic ether ring ( 3 ), and new manners of bond connection ( 1 and 2 : C-8 and C-14′, C-9 and oxygen on C-9′; 3 : C-8 and C-14′, C-9 and oxygen on C-1′). Although a series of cadinane dimers have been reported from natural sources, hitherto, only two nor-cadinane-dimers have been isolated 1 2 3 . Nor-cadinane-dimer ( 4 ), dinor-cadinane-dimer ( 5 and 6 ), dodecanor-cadinane-dimer ( 7 ), and tetradecanor-cadinane-dimer ( 8 ) represent four novel nor-cadinane-dimer carbon skeletons, which greatly enrich the structure of nor-cadinane-dimer.…”

“…In the Fig. 8 , it is revealed that the formation of nor-cadinane-dimer 4 is attributed to the decarboxylation reaction, which is the most common biogenetic pathway to form norterpenoids 2 9 33 34 35 . However, interesting, different from the most norterpeniods, the carbon skeletons of dinor-cadinane-dimers 5 and 6 , dodecanor-cadinane-dimer 7 , and tetradecanor-cadinane-dimer 8 were speculated to be produced by the key oxidative cleavage reaction.…”

“…Of these naturally occurring cadinane dimers, most are derived from two units of the corresponding monomers by the free-radical coupling reaction 1 , however, rare example that formed by nucleophilic addition reaction have been reported. The occurrence of nor-cadinane-dimer is also surprisingly low, with the only two, aquatidial 2 and parviflorene I 3 . Recently, we have reported three unprecedented cadinane dimers, involucratustones A–C 4 , from Stahlianthus involucratus , a folklore medicine to treat inflammation, pain, and fever 5 , as part of a continued program searching for novel terpenoids from Zingiberaceae plants 6 7 8 9 .…”

Fatty Acid Composition of Seed Oil from Pachira aquatica Grown in Nigeria

“…The plant is believed to originate from Brazil but has extended to almost all parts of the tropics and subtropics while in the temperate regions it is a component urban forests [1][2][3][4][5][6]. It can be found frequently in marshy lands and riparian forests, however, it easily adapts to diverse soils and climatic conditions [7,8].…”

“…-NMR spectrum ofSunday et al; JAERI, 18(4):[1][2][3][4][5][6][7][8][9] 2019; Article no. , the peak of the tertiary proton of the glycerol moiety (δ 5.21 ppm) was integrated as 100, leading to an integral value for vinyl proton (δ 5 36 .…”