Isolation and Immunomodulatory Effect of Homoisoflavones and Flavones from Agave sisalana Perrine ex Engelm.

Abstract

Three known flavones and seven known homoisoflavonoids were isolated from the methanolic extract of the leaves of Agave sisalana Perrine ex Engelm. Their structures were elucidated on the basis of spectroscopic analysis. The isolated compounds were also evaluated for immunopharmacological activity. PBMC were used as target cells, and cell proliferation was determined by 3H-thymidine uptake. (±)-3,9-Dihydroeucomin (4), dihydrobonducellin (5), and 5,7-dihydroxy-3-(4′-hydroxybenzyl)-4-chromanone (7) showed inhibitory effects on PBMC proliferation activated by PHA with IC50 values 19.4, 73.8, and 58.8 µM, respectively. All three compounds significantly inhibited the production of IL-2 and IFN-γ in activated PBMC in a concentration-dependent manner.

Sappanin-type homoisoflavonoids from Sansevieria trifasciata Prain

“…The 1 H NMR chemical shifts of 2 (Table 1) was closely related to those of 1, especially for signals due to the A and B rings as shown by the pair of ortho-coupled protons at d 7.50 (1H, d, J = 8.8 Hz, H-5) and 6.61 (1H, d, J = 8.8 Hz, H-6), and the ABX system at d 6.72 (1H, d, J = 8.0 Hz, H-5 0 ), 6.76 (1H, brs, H-2 0 ), and 6.68 (1H, dd, J = 8.0, 1.3 Hz, H-6 0 ). The C ring part of the 1 H NMR spectrum exhibited the typical proton signals for a À ÀCH 2 À ÀCÀ ÀCH 2 À À moiety of 3-hydroxy-3-benzyl-4-chromanone with the H 2 -2 signals occurring at d 4.07 (d, 11.2) and 4.22 (d, 11.2), and the H 2 -9 signals occurring at d 2.86 (d, 14.1) and 2.93 (d, 14.1) (Koorbanally et al, 2007;Chen et al, 2009;Li et al, 2012). Intensive inspection of the 13 C NMR spectra of both compounds revealed that the signal of the methine carbon present in 1 (d 48.7, C-3) was absent in 2 and was replaced by the carbon signal at (d 74.1, C-3).…”

Variability of the Foliar Phenol Profiles of the Agave victoriae-reginae Complex (Agavaceae).

“…The presence of phenolic acids in the species here studied, all of them belonging to Agave subgenus Littaea, contrasts with their absence in A. americana (Parmar et al, 1992), A. asperrima, A. durangensis, A. shrevei, A. wocomahi, (Almaraz-Abarca et al, 2009, and A. sisalana (Chen et al, 2009), which belong to Agave subgenus Agave. If those tendencies are found in more species of both subgenera, it could be suggested that the relative abundance of phenolic acids may have some taxonomic relevance at the subgeneric level in Agave.…”

Chemical Constituents from the Roots of <i>Furcraea bedinghausii</i> Koch

“…Column chromatography of the EtOAc and n-butanol soluble fractions of the MeOH extract from the dried roots of Furcraea bedinghausii led to the isolation and structure elucidation of a mixture of two new homoisoflavonoids together with the known β-sitosterol (1) [7], 7,4'-dihydroxy-homoisoflavane (2) [8], dihydrobonducellin (3) [9], kaempferol (5) [17] and (25R)-3β-hydroxy-5α-spirost-9-en-12-one [16] were isolated from the roots of Furcraea bedinghausii Koch (Fig. 1).…”

“…Furthermore, homoisoflavonoids were previously isolated from plants of the Agavaceae family, especially Agave sisalana and Agave tequilana [9,22]. 7,4'-dihydroxy-homoisoflavane (2), dihydrobonducellin (3), and 5,7-dihydroxy-3-(4-hydroxybenzyl)-chromone (6) were isolated from Dracaena cambodiana [8], Agave sisalana [9], and Dracaena draco [11], respectively which belong to the families Dracaenaceae and Agavaceae. Agavaceae and Dracaenaceae are placed in Asparagales, an order of the monocotyledoneous plants.…”