A new macrocyclic spermidine alkaloid from the aerial part of Hyssopus cuspidatus Boriss.

Abstract

Hyssopus cuspidatus Boriss. grows in Xinjiang, China. A new macrocyclic spermidine alkaloid, namely hyssopusizine (1), along with sixteen known compounds were isolated and identified from the aerial parts of H. cuspidatus. Their structures were elucidated on the basis of spectroscopic data and comparison with literatures. Among them, fifteen compounds were isolated from H. cuspidatus for the first time. The absolute configuration of compound 1 was established by comparing the calculated and experimental ECD spectroscopic data. All isolated compounds were tested for their antioxidant and antimicrobial activities. Among them, compound 10 exhibited significant effects on ABTS free-radical scavenging activity with an IC50 value of 15.6 μM.Compounds 5−7 exhibited potent antioxidant activities against ABTS and DPPH. Most compounds exhibited moderate antimicrobial activities. Hyssopusizine ( 1) is the first macrocyclic spermidine alkaloid discovered from the Hyssopus genus.

Polyamine-containing natural products: structure, bioactivity, and biosynthesis

“…112 Hyssopusizine ( 111 ) as a Spd alkaloidal glycoside from the Hyssopus cuspidatus aerial part, similar to the scaffold of dracotanoside, contains a 13-membered macrocyclic lactam, linking β- d -glucose via a moiety of ( Z )-4-hydroxycinnamyl at N 9 , and connects directly a phenyl group at C 4 . 113 The moderate antifungal activity of 111 against C. albicans was reported. 113…”

“…112 Hyssopusizine (111) as a Spd alkaloidal glycoside from the Hyssopus cuspidatus aerial part, similar to the scaffold of dracotanoside, contains a 13-membered macrocyclic lactam, linking b-D-glucose via a moiety of (Z)-4-hydroxycinnamyl at N 9 , and connects directly a phenyl group at C 4 . 113 The moderate antifungal activity of 111 against C. albicans was reported. 113 Meehanines A-W (112-134), a series of Spd alkaloid glycosides isolated from the whole plant Meehania urticifolia (Lamiaceae), like hyssopusizine 111, contain a 13-membered lactam ring that connects a para-hydroxylphenyl-mediated mono-or di-saccharide (all but meehanine T 131 are disaccharides).…”

“…113 The moderate antifungal activity of 111 against C. albicans was reported. 113 Meehanines A-W (112-134), a series of Spd alkaloid glycosides isolated from the whole plant Meehania urticifolia (Lamiaceae), like hyssopusizine 111, contain a 13-membered lactam ring that connects a para-hydroxylphenyl-mediated mono-or di-saccharide (all but meehanine T 131 are disaccharides). 114,115 The overall scaffold of the meehanines is highly conserved and differs mainly in three specied positions: C 8 that varies between the hydroxy group and O-acetyl…”

The Genus Hyssopus: Traditional Use, Phytochemicals and Pharmacological Properties

“…The new glycoside hyssopuside 117 was isolated together with other phenolic glycosides 118-123 from H. cuspidatus [83]. In addition, the lignan-type compounds syringaresinol 4′-O-β-D-glucopyranoside 109, dihydrodehydrodiconiferyl alcohol 9′-O-β-D-glucopyranoside 110, dihydrodehydrodiconiferyl alcohol 111 and (7R, 8S)-4,3′,9-trihydroxyl-3-methoxyl-7,8-dihydro-benzofuran-1′-propyl-neolignan 9′-O-β-D-glucopyranoside 112 were isolated from this compound [91].…”

“…In addition, Chinese scientists isolated a new macrocyclic spermidine alkaloid, hyssopusizine 106 , from an H. cuspidatus 95% ethanol extract [ 91 ] with 16 known compounds; this included for the first time the nitrogen-containing compounds ( Figure 11 ) pyrrolezanthine-6-methylether 107 and n-butyl pyroglutamate 108 from the plants of the genus Hyssopus .…”