Correction: Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus.

Correction for 'Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus' by Zan-Xin Xu et al., Org. Biomol. Chem., 2021, 19, 9844-9848, DOI: 10.1039/D1OB01973B.

Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus.

Two pairs of novel pentacyclic spermidine alkaloid enantiomers, (±)-orychoviolines A and B ((±)-1 and (±)-2), were isolated from the seeds of Orychophragmus violaceus and represented the first example of a 2-piperidinone-fused hydrodibenzofuran skeleton, constructed from a 6/5/6/6 tetracyclic system and an 18 atomic ring. The most unexpected novelty was the formation of one more piperidinone ring by a connection between C-6 and N-7. Their structures and absolute configurations were determined by spectroscopic analyses, X-ray crystallography, and ECD analysis. Compared to Ex-RAD (sodium salt of 4-carboxystyryl-4-chlorobenzylsulfone), (-)-1 exhibited a significant radioprotective effect on cell survival and DNA damage. (-)-1 also exhibited remarkable anti-inflammatory activity by inhibiting the production of NO in RAW 264.7 cells activated by lipopolysaccharide with an IC50 value of 20.3 ± 1.58 µM, which was equivalent to that of dexamethasone.

Anticancer Effects of Five Biflavonoids from Ginkgo Biloba L. Male Flowers In Vitro.

Ginkgo biloba L., an ancient dioecious gymnosperm, is now cultivated worldwide for landscaping and medical purposes. A novel biflavonoid-amentoflavone 7''-O-ß-D-glucopyranoside (1)-and four known biflavonoids were isolated and identified from the male flowers of Ginkgo. The anti-proliferative activities of five biflavonoids were evaluated on different cancer lines. Bilobetin (3) and isoginkgetin (4) exhibited better anti-proliferative activities on different cancer lines. Their effects were found to be cell-specific and in a dose and time dependent manner for the most sensitive HeLa cells. The significant morphological changes validated their anticancer effects in a dose-dependent manner. They were capable of arresting the G2/M phase of the cell cycle, inducing the apoptosis of HeLa cells dose-dependently and activating the proapoptotic protein Bax and the executor caspase-3. Bilobetin (3) could also inhibit the antiapoptotic protein Bcl-2. These might be the mechanism underlying their anti-proliferation. In short, bilobetin (3) and isoginkgetin (4) might be the early lead compounds for new anticancer agents.

New lignan glycosides from Justicia procumbens.

Four new lignan glycosides (1-4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6-10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.

New Anti-HBV C-Boivinopyranosyl Flavones from Alternanthera philoxeroides.

C-boivinopyranosyl flavones have rarely been isolated from nature. In the search for anti-HBV (hepatitis b virus) constituents of Alternanthera philoxeroides, two new compounds, luteolin-6-C-ß-D-boivinopyranosyl-3'-O-ß-D-glucopyranoside (1) and chrysoeriol-6-C-ß-D-boivinopyranosyl-4'-O-ß-D-glucopyranoside (2), along with three known C-boivinopyranosyl flavones (compounds 3-5) were isolated. Their structures were determined by spectroscopic analyses including 1D and 2D NMR, HR-ESI-MS, IR spectra. Compounds 1, 2 and 3 showed significant anti-HBV activities through specifically inhibiting the secretion of HBsAg in HepG2.2.15.

New cyclopeptide alkaloid and lignan glycoside from Justicia procumbens.

This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC50 value of 17.908 ± 1.949 µM.

Two new coumarins from the seeds of Solanum indicum.

Two new coumarins, (E)-2-(4-hydroxy-3-methoxybenzylidene)-5-methoxy-2H-[1,4]dioxino[2,3-h]chromene-3,9-dione (indicumin E, 1) and 7-hydroxy-6,8-dimethoxy-3-(4'-hydroxy-3'-methoxyphenyl)-coumarin (2), together with two known coumarins isofraxidin (3) and fraxetin (4), were isolated from the Solanum indicum seeds. Their structures were established on the basis of 1D and 2D spectroscopic data. Compound 1 was the rarest coumarinolignoid known to date.

Two new flavonols from Cudrania cochinchinensis.

Two new flavonols, 6-p-hydroxybenzyl kaempferol (1) and 6-p-hydroxybenzyl quercetin (2), together with six known compounds were isolated from the roots of Cudrania cochinchinensis and their structures elucidated on the basis of spectroscopic methods. Their antioxidant capacities were evaluated by 1,1-diphenyl-2-picryl-hydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical-scavenging assays. The results suggested that compounds 2, 4, and 7 showed significant radical-scavenging activities.

[Effect of the chelator Zn-DTPA on the excretion of lead in lead intoxication mice detected with ICP-MS].

To study the lead excretion effect of the chelator Zn-DTPA on the lead intoxication mice, inductively coupled plasma mass spectrometry (ICP-MS) was applied to detect the lead content of biological samples. The acute lead intoxication mice model was established by injecting lead acetate intraperitoneally with the dose of 1 mg. Zn-DTPA was administered intraperitoneally to mice once daily for five consecutive days 4 h after intoxication. Control group, model group, combination of Zn-DTPA and Ca-DTPA group were evaluated at the same time. The urine was collected every day. The mice were sacrificed in batches in the 2rd, 4th, 6th day. Biological samples including urine, whole blood, femur and brain were prepared and nitrated. Lead concentration was detected by ICP-MS. The result showed that Zn-DTPA could increase lead content in urine markedly and reduce lead content in blood, femur and brain.

Three new germacrane-type sesquiterpenes with NGF-potentiating activity from Valeriana officinalis var. latiofolia.

Three new germacrane-type sesquiterpenoids, volvalerenal F (1), volvalerenal G (2) and volvalerenic acid D (3), along with five known compounds 4-8, were isolated from the CHCl3 soluble partition of the ethanol extract of Valeriana officinalis var. latiofolia. The structures of the new compounds were determined on the basis of spectroscopic evidence, including their 1D- and 2D-NMR spectra, as well as mass spectrometry. The eight germacrane-type sesquiterpenoids showed nerve growth factor (NGF) potentiating activity, which mediates the neurite outgrowth in PC 12D cells. This study intends to reveal the chemical basis of the use of V. officinalis var. latiofolia as a dietary supplement.

[Chemical constituents of Cudrania cochinchinensis].

OBJECTIVE: To study the chemical constituents of Cudrania cochinchinensis. METHODS: Compounds were isolated and purified by silica gel column, sephadex LH-20 chromatography and recrystallization. Their structures were elucidated by physicochemical properties and spectral data. RESULTS: Thirteen compounds were isolated from the 70% ethanol extract of the root of Cudrania cochinchinensis and identified as beta-sitosterol (1), butyrospermol (2), butyrospermol acetate (3), (+) syringarenol (4), 1, 3, 6-trihydroxy-7-methoxy xanthone (5), 1, 3, 6, 7-tetrahydroxy-8-prenylxanthone (6), kaempferol (7), dihydrokaempferol (8), umbelliferone (9),4-hydroxybenzyl ethyl ether (10), 2,4-dihydroxybenzaldehyde (11), 4-hydrox-ybenzaldehyde (12) and vanillin (13). CONCLUSION: Compounds 2 - 6, 10 - 13 are isolated from Cudrania cochinchinensis for the first time.

Two novel secoiridoid glucosides from Tripterospermum chinense.

Two novel secoiridoid glucosides, tripterospermumcins C (1) and D (2), were isolated from the aerial parts of Tripterospermum chinense, along with four known compounds, tripterospermumcin B (3), sweroside (4), loganic acid (5), and 8-epi-kingiside (6). Their structures were determined by analysis of 1D and 2D NMR data, as well as by comparison with model compounds. Compound 1 was a rare iridoid tetramer with four glucosides.

A novel lactone from Tripterospermum chinense.

A novel lactone, tripterospermumcins E (1), along with four known compounds, sweroside (2), loganic acid (3), 8-epi-kingiside (4) and bergenin (5), were isolated from the aerial parts of Tripterospermum chinense. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and chemical methods. Compound 1 is rare beta-lactone with a glucoside.

[A new triterpenoid fom Radix Pittospori].

To investigate chemical constituents from Radix Pittospori, chloroform extract of the roots was subjected to column chromatography with various chromatographic techniques. The structures were elucidated on the basis of physico-chemical property and spectral analysis. Two triterpenoids were identified as 22-acetyl-21-(2-acetoxy-2-methylbutanoyl)-R1-barrigenol(1) and 3alpha-hydroxyl-20-demethylisoaleuritolic-14(15)-ene-28, 30-dioic acid (2). Compound 1 is a new triterpene and compound 2 is isolated from this plant for the first time.

[Triterpenoid saponins of Alternanthera philoxeroides (Mart.) Griseb].

In order to find the anti-virus constituents of Alternanthera philoxeroides (Mart.) Griseb, the investigation was carried out. The paper reported the five triterpenoid saponins isolated from n-BuOH fraction: 3-O-beta-D-glucopyranosyl (1-->3)-O-[beta-D-glucopyranosyl-oleanolic acid]-28-O-beta-D-glucuronopyranoside (1), oleanolic acid-3-O-beta-D-glucuronopyranoside (calenduloside E, 2), oleanolic acid-3-O-beta-D-glucopyranosyl-28-Obeta-D-glucopyranosyl ester (chikusetsusaponin-IVa, 3), 3-O-(6'-O-butyl-beta-D-glucuronopyranosyl)-oleanolic acid-28-O-beta-D-glucopyranosyl ester (4) and hederagenin-3-O-beta-D-glucuronopyranoside (HN-sapoins K, 5). 1 is a new compound, saponins 4 and 5 were isolated from the plant for the first time.

New cyclopeptide alkaloids from the whole plant of Justicia procumbens L.

Three novel 14-membered cyclopeptide alkaloids, justicianenes B-D (1-3), were isolated from the EtOH extract of the whole plant of Justicia procumbens L., and their structures were determined on the basis of detailed NMR spectroscopic data and the absolute stereochemistry of the ring-bonded α-amino acids in the cyclopeptide alkaloids were determined by ECD spectra. The isolated compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines, including brest cancer MCF-7, cervix carcinoma HeLa, lung cancer A549 and H460, and diphyllin (14) showed moderate cytotoxicity against the HeLa, A549 and H460 cells with IC50 of 9.13, 23.12, 42.34 µM, respectively, justicianene D showed weak cytotoxicity against the MCF-7 cell with inhibition rate of 50% at the concentration of 90 µM.

[Apigenin glycosides from Euphorbia humifusa wild].

The investigation on the herbal of Euphorbia humifusa Wild. was carried out in order to find its anti-HBV constituents. The isolation and purification were performed by chromatography such as Sephadex LH-20, MCI GEL CHP 20P, etc. Based on the spectral analysis, five apigenin glycosides were identified as apigenin-7-O-(6"-O-galloyl)-beta-D-glucopyranoside (1), apigenin-7-O-beta-D-apiofuranosyl (1-->2)-beta-D-glucopyranoside (2), apigenin-7-O-beta-D-lutinoside (3), apigenin-7-O-beta-D-glucopyranside (4) and apigenin (5). Among them, compound 1 is a new compound, compound 2 and 3 were isolated from this plant for the first time.

[A new secoiridoid from the flowers of Jasminum officinale L. var. grandiflorum].

To study the chemical constituents of the flowers of Jasminum officinale L. var. grandiflorum, the compounds were isolated and purified by HPLC, recrystallization and chromatography on silica gel and Sephadex LH-20 column. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Six secoiridoids were identified as jasgranoside (I), jaspolyoside (II), 8-epi-kingiside (III), 10-hydroxy-oleuropein (IV), 10-hydroxy-ligstroside (V), oleoside-7, 11-dimethyl ester (VI). Compound I is a new compound. Compounds II, III, IV, V and VI were isolated from Jasminum officinale L. var. grandiflorum for the first time.

[Triterpenoid saponins from flower bud of Jasminum officinale var. grandiflorum].

OBJECTIVE: To study the chemical constituent bud of the flowers of Jasminum officinale var. grandiflorum. METHOD: The compounds were isolated and purified by recrystallization and chromatography on silica gel and Sephadex LH - 20 column. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. RESULT: Six triterpenoid saponins were identified as 3-O-alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-xylopyranosyl- hederagenin-28-O-beta-D-galactopyranosyl (1 --> 6)-beta-D-galactopyranosyl ester (1), hederagenin-3-O-beta-D-glucopyranosyl (1 --> 3)-alpha-L-arabinopyranoside (2), 2alpha, 3beta, 23-trihydroxyolean-12-en-28-oic-O-beta-D-glucopyranosyl ester (3), hederagenin-3-O-beta-D-xylopyranosyl (1 --> 3)-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (4), 2alpha, 3beta, 23-trihydroxyolean-12-en-28-oic-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranosyl ester (5), hederagenin-3-O-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (6). CONCLUSION: Compound 1 is a new compound. Compounds 2, 3, 4, 5, 6 were isolated from the genus Jasminum for the first time.

[A new C-glycosylflavone from Peperomia dindygulensis].

OBJECTIVE: To study the chemical constituents of Peperomia dindygulensis. METHOD: Several column chromatographic methods were used to isolated compounds from P. dindygulensis and spectroscopic methods (1H-NMR, 13C-NMR, HMQC, HMBC, 1D- HOHAHA, NOE) were used to identify the structures of isolated compounds. RESULT: Compound 1 was isolated and identified as 2"-O-beta-D-galactosylisoswertisin. CONCLUSION: Compound 1 was a new compound.