New antifungal constituents from Terminalia alata

The roots of Terminalia alata yielded three new glycosides: 3,3'-di-O-methylellagic acid 4-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranoside (1), 5,7,2'-tri-O-methylflavanone 4'-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside (2), and 2alpha,3beta, 19beta,23-tetrahydroxyolean-12-en-28-oic acid 3-O-beta-D-galactopyranosyl-(1-->3)-beta-D-glucopyranoside-28-O-beta-D-glucopyranoside (3). Compounds 2 and 3 displayed antifungal activity.     

New constituents of Terminalia alata

The roots of Terminalia alata yielded a new terpene glycoside, 2α, 3β, 19α-trihydroxy-olean-12-en-28-oic acid methylester 3β-O-rutinoside (1), a new flavanone, 8-methyl-5,7,2′, 4′-tetramethoxy-flavanone (2) and a new chalchone glycoside, 2-O-β-glucosyloxy-4,6,2′,4′-tetramethoxychalchone (3).     

Triterpenoid saponins from the roots of Silene cucubalus

A new triterpenoid saponin was isolated from the roots of Silene cucubalus and its structure was determined on the basis of one- and two-dimensional NMR spectroscopy as gypsogenin 3-O-beta-xylopyranosyl-(1-->3)-[beta-galactopyranosyl-(1-->2)]-beta-glucuronopyranoside. A known saponin, quillaic acid 3-O-beta-xylopyranosyl-(1-->3)-[beta-galactopyranosyl-(1-->2)]-beta-glucuronopyranoside, was also isolated.     

A new cardenolide from the roots of Terminalia arjuna

A new cardenolide, 16,17-dihydroneridienone 3-O-beta-D-glucopyranosyl-(1-->6)-O-beta-D-galactopyranoside (1), was isolated from the roots of Terminalia arjuna.     

A new phenolic glycoside from the roots of Lygodium japonicum

A new phenolic glycoside, 3,4-dihydroxybenzoic acid 4-O-(4'-O-methyl)-beta-D-glucopyranoside (1), was isolated from the roots of Lygodium japonicum. The structure was elucidated on the basis of spectroscopic methods.     

A new naphthalene glycoside from the roots of Smilax bockii

From the roots of Smilax bockii a new compound, 7-hydroxymethyl-1, 4, 5-trihydroxynaphthalene-4-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside, was isolated. The structure of the new compound was elucidated on the basis of spectroscopic methods.     

A new aromatic glycoside from the roots of Prunus armeniaca

A new aromatic glycoside, 4-O-glycosyloxy-2-hydroxy-6-methoxyacetophenone (1), has been isolated from the roots of Prunus armeniaca.     

Triterpenoid p-aminobenzoates from the seeds of zucchini

An investigation of the triterpenoid fraction of zucchini seeds afforded two novel multiflorane p-aminobenzoates, identified as 7-epi zucchini factor A and debenzoyl zucchini factor B. Multiflorane p-aminobenzoates could not be detected in zucchini sprouts, which contained bryonolic acid as the only multiflorane constituent. No compound of this type could be obtained from adult plant parts (roots, stems, leaves).     

A new cardenolide from the seeds of Terminalia bellerica

A new cardenolide, cannogenol 3-O-beta-D-galactopyranosyl-(1-->4)-O-alpha-L-rhamnopyranoside (1), was isolated form the seeds of Teminalia bellerica.     

Anti-acne activity of tannin-related compounds isolated from Terminalia laxiflora

In our investigation to find out new anti-acne agent, we focused on Terminalia laxiflora Engl & Diels (Combretaceae) methanolic wood extract, which has been selected during previous screening experiments for anti-acne agents, which included 29 species of Sudanese medicinal plants. Based on the biologically guided fractionation using an antibacterial assay against Propionibacterium acnes, a lipase inhibitory assay and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity assay; five tannin-related compounds were isolated, such as ellagic acid, flavogallonic acid dilactone, terchebulin and gallic acid. Terchebulin showed good antibacterial activity; minimum inhibitory concentration (MIC) = 125 μg/ml and minimum bactericidal concentration (MBC) = 250 μg/ml. Gallic acid exhibited lipase inhibitory activity with IC₅₀ value of 149.3 μM, which showed strong inhibition compared with terchebulin, IC₅₀ 260.7 μM. However, all compounds exhibited better or equal DPPH radical scavenging activity to (+)-catechin as positive control. Ellagic acid and terchebulin showed the best DPPH radical scavenging activities, IC₅₀ 4.86 and 4.90 μM, respectively. This study demonstrated that terchebulin has potentiality as an anti-acne agent.     

Additional pregnane glycoside from Baseonema acuminatum

The isolation of baseonemoside C (1), a new pregnane glycoside from the aerial parts of Baseonema acuminatum is reported.     

Hepatitis C virus inhibitory hydrolysable tannins from the fruits of Terminalia chebula

Two new hydrolysable tannins, chebumeinin A (1) and chebumeinin B (2), together with eight known related compounds (3-10), were isolated from the fruits of Terminalia chebula. The new compounds were structurally determined by analysis of their spectroscopic data and the known compounds characterized by comparing their spectroscopic data with literature values. All isolates were evaluated by an HCV protease inhibition assay, and some compounds were found to be potently active.     

Acylated flavonol glycoside from Platanus orientalis

The ethylacetate and n-butanol fractions of ethanolic extract of Platanus orientalis leaves led to the isolation of new acylated flavonol glycoside as 3',5,7-trihydroxy-4'-methoxyflavonol 3-[O-2-O-(2,4-Dihydroxy)-E-cinnamoyl-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl (1→2)]-β-D-glucopyranoside, along with seven known compounds. All the compounds were characterized by NMR including 2D NMR techniques. The isolates were evaluated for NF-κB, nitric oxide (NO), aromatase and QR2 chemoprevention activities and some of them appeared to be modestly active.     

A novel isoflavone glycoside from the leaves of Sphaeranthus indicus

A novel isoflavone glycoside, 5,4′-dimethoxy-3′-prenylbiochanin 7-O-β-d-galactoside (1), was isolated from the leaves of S. indicus.     

A new flavonoid glycoside from the leaf of Cephalotaxus koreana

A new flavone glycoside, apigenin 5-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside (1), along with four known flavonol glycosides (2-5), were isolated from the leaf of Cephalotaxus koreana. The new glycoside 1 showed inhibitory activity in superoxide radical scavenging assay with IC(50) value of 13.0 microM, while it showed weak activity in 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay. Compounds 2-5 exhibited antioxidant activity in scavenging DPPH and superoxide radicals with IC(50) values ranging from 5.7 to 22.3 microM.     

A new flavone glycoside from the fruits of Luffa cylindrica

The methyl ester of diosmetin 7-O-beta-D-glucuronide (1) was isolated from the fruits of Luffa cylindrica. Its structure was determined by spectroscopic methods.     

A new flavone glycoside from the seeds of Tecoma undulata

The new flavonoid 5,7-dihydroxy-6-methoxyflavone 7-O-α-l-rhamnopyranoside (1) was isolated from the seeds of Tecoma undulata.     

A new coumarin glycoside from the husks of Xanthoceras sorbifolia

From the husks of Xanthoceras sorbifolia, a new coumarin glycoside, isofraxetin-6-O-beta-D-glucopyranoside (1), was isolated. The structure was established on the basis of spectroscopic methods.     

A new secoiridoid glycoside from Lonicera angustifolia

A new secoiridoid glycoside, 6'-O-beta-apiofuranosylsweroside (1), together with the known compounds sweroside, loganin, beta-sitosterol, oleanolic acid, ursolic acid and methyl-4-hydroxy benzoate have been identified from the leaves of Lonicera angustifolia. The structure of the new compound has been elucidated on the basis of spectroscopic and chemical evidence.