Four new saponins from the root bark of Aralia elata

Four new saponins, 3-O-[beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl]-16a lpha-hydroxyoleanolic acid 28-O-beta-D-glucopyranosyl ester (called aralia-saponin I), 3-O-[beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl]-16a lpha-hydroxyhederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin II), 3-O-[beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->3)-alpha-L-+ ++arabinopyranosyl]-16alpha-hydroxyoleanolic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin III), 3-O-[beta-D-glucopyranosyl(1-->3)-beta-D-gucopyranosyl(1-->3)-beta -D-glucucopyranosyl]-16alpha-hydroxyoleanolic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin IV), were isolated from the root bark of Aralia elata (Miq.) Seem., together with nineteen known compounds including glycosides of (20S)-protopanaxadiol and (20S)-protopanaxatriol. Their structures were determined on the basis of chemical and spectroscopy methods.     

Aralosides A,B, and C from Aralia elata

Conclusions The triterpene glycosides isolated from the roots ofAralia elata are identical with the aralosides A, B, and C.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1338–1340, July, 1964     

Phenolic constituents from the rhizomes of Gastrodia elata

Gastrodia elata Bl. (Orchidaceae) is an important traditional medicinal plant as well as a famous foodstuff in China. In the present article, the HPLC chromatograms of different preparation processes were reported, and structures of nine phenolic compounds, isolated from Gastrodia elata, were assigned. The isolated compounds were identified as 1,3-bis(4-hydroxybenzyl)citrate (1), gastrodin (2), 4-hydroxybenzyl alcohol (3), 1-(4-beta-D-glucopyranosyloxybenzyl)citrate (4), 4-hydroxybenzaldehyde (5), parishin B (6), 4-hydroxybenzyl methyl ether (7), 4-hydroxybenzyl ethyl ether (8), and 4-(4'-hydroxybenzyl)phenol (9). Compounds 1 and 4, named as parishin D and E, were new. Their structures were elucidated on the basis of spectral analyses, including 2D NMR spectroscopy.     

3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and other glycosidic constituents from apple leaves

3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside 1 has been isolated from a methanolic extract of apple (Malus domestica) leaves by XAD-2 adsorption chromatography and subsequent purification by high speed countercurrent chromatography (HSCCC) and HPLC. Under acidic conditions this glycoside gives rise to a number of volatile compounds including 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2, which is known as an off-flavor compound in wine. In the course of the study, six additional glycoconjugates were isolated from apple leaves, i.e. roseoside 3, 3-oxo-alpha-ionol beta-D-glucopyranoside 4, benzoic acid beta-D-glucose ester 5, kaempferol 3-O-rhamnoside 6, (+)-syringaresinol beta-D-glucopyranoside 7 and 4-hydroxy-5-(3'-methyl-2'-butenyl)-benzoic acid methylester 3-beta-D-glucopyranoside 8. The latter compound has been isolated for the first time in nature. In order to avoid the 'kerosene-off-flavor' caused by TDN, the methanolic extract has been subjected to yeast fermentation. This treatment reduced the amount of TDN formed and resulted in an improved flavor impression of the methanolic extract.     

Four new phenolic constituents from the rhizomes of Gastrodia elata Blume

Four new gastrodin derivatives containing a trans-cinnamoyl unit (1–4) and nine known compounds (5–13) were isolated from the rhizomes of Gastrodia elata Blume. All these compounds were evaluated for their neuroprotective effects against 6-hydroxydopamine-induced cell death, and compounds 7 and 12 showed potent activities with EC₅₀ values of 10.5 and 10.2 μM, respectively.     

New flavonoid glycosides and other chemical constituents from Clerodendrum phlomidis leaves: isolation and characterisation

Phytochemical investigation of the plant Clerodendrum phlomidis Linn. F. (Lamiaceae) has now led to the isolation of two new flavonoid glycosides (1, 2) together with six known compounds identified as pectolinaringenin (3), pectolinaringenin-7-O-β-d-glucopyranoside (4), 24β-ethylcholesta-5,22E,25-triene-3β-ol (5), 24β-ethylcholesta-5,22E,25-triene-3β-O-β-D-glucopyranoside (6), (2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (7) and andrographolide (8) mainly by spectroscopic analysis. Compounds 4 and 6–8 are reported for the first time from C. phlomidis.     

Saponins from leaves of Acanthopanax hypoleucus Makino.

From the leaves of Acanthopanax hypoleucus Makino (Araliaceae), five triterpenoidal saponins, having oleanolic acid and hederagenin as sapogenins, were isolated. On the basis of chemical and spectral data, the structures of two new saponins, named hypoleucosides A (1), and B (5) were elucidated as follows: 1; 3-O-beta-D-glucopyranosyl 11 alpha-methoxy-oleanolic acid 28-O-beta-D-glucopyranosyl ester, 5; 3-O-beta-D-glucopyranosyl-(1----2)-alpha-L-arabinopyranosyl-(1---- 4)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1----6)-beta-D-glucopyranosyl ester.     

Chemical constituents from the leaves of Psidium guajava

Five constituents including one new pentacyclic triterpenoid guajanoic acid (1) and four known compounds beta-sitosterol (2), uvaol (3), oleanolic acid (4), and ursolic acid (5) have been isolated from the leaves of Psidium guajava. The new constituent 1 has been characterized as 3beta-p-E-coumaroyloxy-2alpha-methoxyurs-12-en-28-oic acid through 2D NMR techniques and chemical transformations. This is the first report of isolation of compound 3 from the genus Psidium.     

Chemical constituents from the leaves of Melia azedarach

Six compounds, benzyl 3-O-β-D-glucopyranosyl-7-hydroxybenzoate (1), spathulenol (2), 1,7,8-trihydroxy-2-naphtaldehyde (3), quercetin (4), astragalin (5) and 2-methoxy-4-(2-propenyl)phenyl β-D-glucoside (6), were isolated from the leaves of Melia azedarach L. The structure elucidation of compound 1 was discussed in detail based on its 2D-NMR data. Compound 1 showed weak cytotoxicity against the cell lines of T-24, NCI-H460, HepG2, SMMC-7721, CNE, MDA-MB-231 and B16F10 with the inhibition rates from 10.01% to 34.05% at the concentration of 80?μM.     

New constituents from the leaves of Morinda citrifolia

A new iridoid glycoside, citrifoside (1), and a new anthraquinone, 1,5,15-trimethylmorindol (2), together with 24 known compounds, were isolated from the leaves of Morinda citrifolia. The structures of the new compounds were elucidated by spectral data. 1,5,15-Trimethylmorindol (2) did not show significant cytotoxic activity by itself but showed cytotoxicity when combined with tumor necrosis factor-related apoptosis-inducing ligand (TRAIL), while citrifoside (1) did not show any activity even with TRAIL.     

Cytotoxic constituents from the leaves of Cinnamomum subavenium

Two new butanolides, subamolide D (1) and subamolide E (2), and a new secobutanolide, secosubamolide A (3), along with 21 known compounds were isolated from the leaves of Cinnamomum subavenium. The structures of 1-3 were determined by spectroscopic analysis. Propidium iodide staining and cytometry analysis were used to evaluate the cell cycle progression of the treated SW480 cells and it was found that 1 and 2 caused DNA damage in a dose- and time-dependent manner.     

Antitumor constituents from the leaves of Carya cathayensis

This study aimed to find cytotoxic chemical constituents from Carya cathayensis leaves (LCC) by using various chromatographic procedures. Identification of the chemical constituents was carried out by various spectroscopic techniques and classical chemical methods. The cytotoxic activity of the constituents was assayed on HeLa and HepG2 cell lines by staining with 3-(4,5-dimethylthiahiazol-2-y1)-2,5-di-phenytetrazolium bromide (MTT). Six flavanoids, namely (1) pinostrobin, (2) pinostrobin chalcone, (3) wogonin, (4) cardamonin, (5) alpinetin and (6) tectochrysin were identified from this species. Compounds 2-6 were isolated from this kind of plant for the first time. MTT results showed that wogonin has a moderate cytotoxic activity with IC(50) values of 17.03?±?2.41 and 44.23?±?3.87?μM against HeLa and HepG2 cell lines, respectively. According to the correlation of primary the structure and activity, 8-methoxy substituent in these flavones may be a major factor of the antitumor activity.     

Antifungal agent and other constituents from Cynanchum otophyllum

Seven constituents were isolated from the ethyl acetate extract of the rhizome of Cynanchum otophyllum Schneid (Asclepiadaceae). Their structures were determined as 1-(4-methoxy-3-(6-methoxy-3-acetylphenylperoxy)phenyl)ethanone (1), 1-(3-hydroxy-7-acetylnaphthalen-2-yl)ethanone (2), 1-(3,4-dihydroxyphenyl)ethanone (3), 1-(2,4-dihydroxyphenyl)ethanone (4), 1-(3-(3,6-dihydroxy-2-methylbenzoyl)-2,4-dihydroxyphenyl)ethanone (beishouwubenzophenone) (5), N,N-dimethylethanamine (6), and 2-oxo-2-phenylacetic acid (7), respectively, by spectral methods. Among them, 1 and 2 were new compounds; 1 had antifungal activity.     

Isoswertisin flavones and other constituents from Peperomia obtusifolia

A phytochemical investigation of the leaves and stems of Peperomia obtusifolia (Piperaceae) yielded a new flavone C-diglycoside isoswertisin-4'-methyl-ether-2'α-L-rhamnoside (1), along with four known compounds: isoswertisin-2'α-L-rhamnoside (2), (+)-diayangambin (3), 2-episesalatin (4) and corchoionoside C (5). The structures of the two flavone C-diglycosides (1, 2) were elucidated on the basis of 1D and 2D NMR spectroscopy and MS spectrometric data. These flavones were evaluated by bioautographic assay against Cladosporium cladosporioides and C. sphaerospermum and showed weak antifungal activity.