Four new homoisoflavonoids from Caesalpinia pulcherrima.

Four new homoisoflavonoids, 7-hydroxy-3-[hydroxy(4'-methoxyphenyl)methyl]-benzopyran-4-one (1), (3R)-7, 8-dihydroxy-3-(4'-methoxybenzyl)-chroman-4-one (2), 7-hydroxy-3-(2'-hydroxy-4'-methoxybenzyl)-chroman-4-one (3), and 7-hydroxy-3-(2'-hydroxy-4'-methoxybenzyl)-benzopyran-4-one (4), were isolated from the seeds of Caesalpinia pulcherrima. The structures of new compounds were elucidated by MS and NMR spectra. Their absolute configurations were assigned using electronic circular dichroism spectrum. Compounds 2 and 4 exhibited cytotoxic effects on MCF-7/TAM cells with the IC50 values of 101.4 ± 0.03 and 93.02 ± 0.03 µM, respectively.

Three new caryophyllene-type sesquiterpenoid glycosides from Biebersteinia heterostemon maxim.

Three new caryophyllene-type sesquiterpenoid glycosides were isolated from Biebersteinia heterostemon. Their structures were elucidated by comprehensive analysis of NMR and MS spectroscopic data. All the isolated compounds were evaluated for MCF-7/TAM cytotoxic activity. The results indicated that compound 1 was found to exhibit the weak cytotoxicity against MCF-7/TAM with the IC50 value of 106.4 ± 0.04 µM.

Two new norcassane-type diterpenoids from Mezonevron sinense Hemsl.

Two new norcassane-type diterpenoids, named 6ß-hydroxy-bisnorcass-13-en-12-one (1) and 6ß-hydroxy-bisnorcassan-12-one (2), were isolated from the seeds of Mezonevron sinense Hemsl. The structures of compounds 1-2 were determined by extensive spectroscopic analysis. Two compounds exhibited immunosuppressive activity with the IC50 values of 19.35 ± 0.87 µM and 18.69 ± 0.88 µM in the ConA induced T cell model and 65.04 ± 0.83 µM and 48.06 ± 0.76 µM in LPS induced B cell model, respectively.

Three new cassane-type diterpenoids from Caesalpinia sinensis.

Three new cassane-type diterpenoids, namely, (4S)-6ß,12α,19-trihydroxy-cass-13(15)-en-16,12-olide (1), cass-13(15)-en-​16,12-olide (2), and 12α-hydroxy-cass-13(15)-en-16,12-olide (3), were isolated from the seeds of Caesalpinia sinensis. The structures of 1-3 were established by extensive spectroscopic analysis, and their absolute configurations were assigned by electronic circular dichroism (ECD) calculations. The inhibitory activities against PTP1B of the isolated compounds were evaluated. The results showed that compound 2 possessed PTP1B inhibitory activity with an IC50 value of 217.45 ± 36.4 µM.

Serratene triterpenoids from Lycopodium cernuum L. as α-glucosidase inhibitors: Identification, structure-activity relationship and molecular docking studies.

Phytochemical investigation of Lycopodium cernuum L. afforded seven undescribed serratene triterpenoids named 3ß, 21ß-dihydroxyserra-14-en-24-oic acid-3ß-(5'-hydroxybenzoate) (1), 3ß, 21ß, 24-trihydroxyserrat-14-en-3ß-(5'-hydroxyl benzoate) (2), 3ß, 14α, 15α, 21ß-tetrahydroxyserratane-24-methyl ester (3), 3ß, 14α, 21ß-trihydroxyserratane-15α-(4'-methoxy-5'-hydroxybenzoate)-24-methyl ester (4), 3ß, 14α, 21ß-trihydroxyserratane-15α-(4'-methoxy-5'-hydroxybenzoate) (5), 3ß-hydroxy-21ß-acetate-16-oxoserrat-14-en-24-oic acid (6), 3ß, 21ß-dihydroxy-16α, 29-epoxyserrat-14-en-24-methyl ester (7), together with eleven known compounds (8-18), whose chemical structures were elucidated through spectroscopic analysis of HRESIMS, 1D NMR, 2D NMR and comparison between the literature. All compounds were evaluated for their α-glucosidase inhibitory activity for the first time. The results showed that compounds 1, 2, 4, 5, 6, 10, 13, 15, and 16 were among the most potent α-glucosidase inhibitors, with IC50 values ranging from 23.22 ± 0.64 to 50.65 ± 0.82 µM. Structure-activity relationship (SAR) studies indicated that the combined properties of the 5-hydroxybenzoate moiety at C-3, ß-OH at C-21, COOH- at C-24, and Δ14,15 groups enabled an increase in the α-glucosidase inhibitory effect. In addition, molecular docking studies showed that the potential inhibitors mainly interact with key amino acid residues in the active site of α-glucosidase through hydrogen bonds and hydrophobic forces.

A new lignan from Pandanus tectorius.

A new lignan, named (8S, 8'S)-2,2',3,3'-tetramethoxy-4'-hydroxy-epoxylignan-4-O-ß-D-glucoside (1), together with eight known compounds (2-9), was isolated from the leaves of P. tectorius. Their structures were elucidated on the basis of spectral characteristics and comparison with the data of literatures. Besides, the absolute configuration of 1 was established by using ECD calculations. The cytotoxicity of 1 in vitro against three selected tumor cell lines (A549, HeLa and MCF-7) was evaluated by MTT assay. The results showed that compound 1 exhibited moderate cytotoxicity against HeLa cell with IC50 value of 19.30 ± 4.46 µM.

[Processing evolution,chemical components and pharmacological effects of Bufonis Venenum].

Bufonis Venenum,the dried secretion of Bufo bufo gargarizans or B. melanostictus,is toxic and hard with the efficacy of removing toxicity for detumescence and relieving pain. The processing of Bufonis Venenum dates back to the Song dynasty. In addition to the wine-processing,milk-processing and talcum powder-processing,there were some other kinds of processing methods in ancient times,such as baking,calcining,water-soaking and vinegar-processing. Modern studies have shown that the Bufonis Venenum has the main chemical components of bufadienolides,indole alkaloids sterols,and other compounds. It has the pharmacological effects of antitumor,cardiac,antibacterial,and analgesic activities,local anesthesia,and so on. This paper reviews the processing evolution,chemical components and pharmacological effects of Bufonis Venenum,providing references for its special processing and modern research as well as the theoretical basis for the research on its processing mechanism and quality control.

[Research advances in chemical constituents and pharmacological activities of Pueraria genus].

Kudzu plants in the subfamily sphenoideae of Leguminosae are commonly used herbs in China, Japan, Korea, India and Thailand, with a long history of medicinal use. They are recorded in Chinese Pharmacopoeia, Japanese Pharmacopeia, Korea Pharmacopeia, Ayurveda Pharmacopoeia of India and Flora of Thailand. There are 15-20 species of Pueraria in the world, including 7 species and 2 varieties in China. At present, there are 6 species with medicinal value, such as Pueraria lobata and P. thomsonii. The main chemical components of the genus are isoflavones, flavonoids, terpenes, steroids, coumarins, puerarin glycosides and benzopyrans. A total of 240 compounds have been isolated and identified from this genus, and their pharmacological effects mainly include improvement of the cardiovascular system, antioxidant, hypoglycemic, antipyretic, anti-inflammatory, anti-alcoholic and estrogen-like effects. In this study, chemical constituents and pharmacological activities of Pueraria at home and abroad were systematically summarized, in order to provide references for the material basis, quality control and further development of Pueraria genus.

Three new diterpenes from Dysoxylum lukii and their NO production inhibitory activity.

Three new diterpenes were isolated from the stems of Dysoxylum lukii Merr and characterized on the basis of spectral data. Neoclerod-13Z-ene-3α, 4ß, 15-triol (3) exhibited the inhibition of lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages with an IC50 value of 25.49 µM.[Formula: see text].

[Study on neoflavonoids from heartwood of Dalbergia latifolia].

Dalbergiae Odoriferae Lignum is derived from heartwood of Dalbergia odorifera,which is national Ⅱ level of rare and endangered protective plants in China. Its resources are scarce and its price is high. In order to find substitutes of D. odorifera,the chemical constituents of 70% ethanol extract of heartwood of D. catifolia were systematically studied by using silica gel,Sephadex LH-20 column chromatography,and semi-preparative HPLC. Sixteen neoflavanoids were isolated and identified as eight dalbergiphenols( 1-8),three dalbergiones( 9-11),two dalbergins( 12,13),two benzophenones( 14,15) and one other type neoflavanoids( 16) based on spectroscopic data analyses and/or comparing the spectroscopic data with those in literature. Among them,compounds 3,7 and 11 were isolated from the genus Dalbergia for the first time,and compounds 2,4-6,8,14 and 15 were isolated from the D. latifolia for the first time. Ten neoflavonoids were both discovered from D. latifolia and D. odorifera.

A new diaryl 1, 2-diketone from the heartwood of Dalbergia latifolia.

A new diaryl 1,2-diketone, named 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethane-1,2-dione (1), along with eight known compounds (2-9), were isolated from the heartwood of Dalbergia latifolia. They were identified on the basis of spectral data. Compounds 1-7 were obtained from the Dalbergia genus for the first time. Compounds 8 and 9 were firstly isolated from the plant. Compound 1 exhibited inactive against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 21530 with the minimum inhibitory concentrations of 10.0 and 10.0 mg/mL, respectively.

A new pyridine alkaloid from Zingiberis rhizoma.

A new alkaloid, named 2-methoxy-4-(2-(2-pyridine)-ethyl) phenol (1), together with two known compounds, was isolated from Zingiberis rhizoma. Their structures were elucidated on the basis of 1D and 2D NMR spectra and MS spectra. Compound 1 exhibited substantial bioactivity against Canidia albicans ATCC 10231 with a minimum inhibitory concentration of 1.0 mg/mL.

[Neoflavonoids and their pharmacological activities in Dalbergia genus].

Neoflavonoids are a kind of characteristic components in the Dalbergia genus. Based on the previous researches, 59 neoflavonoids have been obtained from the Dalbergia genus. According to their molecular skeleton, the neoflavonoids can be divided intodalbergiphenols, dalbergiones, dalbergins, benzophenones and other types. Modern research shows that neoflavonoids displayed a variety of pharmacological activities, such as anti-osteoporosis, anti-inflammatory, antitumor, anti-androgen, anti-allergic, antioxidation etc. This paper reviewed neoflavonoids and their pharmacological functions, which could provide the valuable reference for comprehensive utilization and new drug development in the Dalbergia genus.

Two new alkaloids from Melodinus hemsleyanus Diels.

Two new monoterpenoid indole alkaloids, named 14,15-dihydro-14ß,15ß-epoxy-10-hydroxyscandine (1) and 15α-hydroxy-meloscandonine (2), together with 12 known compounds, were isolated from the aerial parts of Melodinus hemsleyanus Diels. The structures of 1 and 2 were elucidated on the bases of 1D and 2D NMR spectra and MS. Two new compounds were evaluated for their PTP1B and Drak2 inhibitory effects, and inactivity.

Novel stilbenes from Artocarpus nanchuanensis.

Four new stilbene derivatives, hypargystilbenes B-E (1-4), together with seven known compounds (5-11), were isolated from the stems of Artocarpus nanchuanensis S.S. Chang. Their structures were elucidated on the basis of spectral data. Hypargystilbene B, hypargystilbene D, and hypargystilbene E exhibited protein tyrosine phosphatase 1B inhibitory effects with corresponding IC50 values of 3.23, 37.31, and 2.53 nM.

[Lignans from Stem Bark of Styrax perkinsiae].

OBJECTIVE: To study the chemical constituents in the stem bark of Styrax perkinsiae. METHODS: The chemical constituents were separated and purified by chromatographic methods after solvent extraction and identified by spectroscopic analyses. RESULTS: Ten lignans were isolated from the stem bark of Styrax perkinsiae and identified as following: pinoresinol 4-O-ß-D-glucopyranoside (1), matairesinoside (2), styraxlignolide B (3), 3- (ß-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl )-7-methoxy-(2R , 3S) -dihydrobenzofuran (4), burselignan (5), (+) -neo-olivil (6), threo-1-(4-hydroxy-3-methoxyphenyl )-2-[ 4-(3-hydroxypropyl)-2-methoxyphenoxy]-1, 3-propanediol (7), erythro-1-(4-hydroxy-3-methoxyphenyl )-2-[ 4-(3-hydroxypropyl )-2-methoxyphenoxy ] -1 ,3-propanediol (8), isolariciresinol(9) and (+) -lariciresinol (10). CONCLUSION: Compounds 5 - 10 are isolated from the plants of Styrax genus for the first time.

[Chemical Constituents from Dalbergia cochinchinensis].

OBJECTIVE: To investigate the chemical constituents from the heartwood of Dalbergia cochinchinensis. METHODS: Isolate and purify compounds by various column chromatographic methods. Spectral analysis were taken to identify the structures. RESULTS: Elev- en compounds were isolated and identified as dibutyl terephthalate (1), medicarpin (2), pterostilbene (3), 6-hydroxy-2-(2-hydroxy-4- methoxyphenyl)-benzofuran (4), pterocarpol (5), butyl isobutyl phthalate (6), pterolinus B (7), methyl 4-hydroxybenzoate (8), ethyl 4- hydroxybenzoate (9),2-(2'-methoxy-4'-hydroxy)-aryl-3-methyl-6-hydroxy-benzofuran (10) and 6α-hydroxycyclonerolidol (11). CONCLUSION: Compounds 1 and 6~10 are isolated from Dalbergia genus for the first time, and compounds 2, 4 and 11 are isolated from this plant for the first time.

[Chemical Constituents from Periplaneta americana].

OBJECTIVE: To study the chemical constituents in Periplaneta americana. METHODS: The chemical constituents were separated and purified by chromatographic methods after solvent extraction and identified by spectroscopic analyses. RESULTS: Ten compounds were isolated from Periplaneta americana and identified as following: 8-hydroxy-3,4-dihydroquinolin-2 (1H)-one (1), cyclo-( L-Phe-L-Pro) (2), cyclo-(Pro-Ile) (3), cyclo-(L-Pro-D-Leu) (4), brevianamide F (5), cyclo-(Ile-Ala) (6), cyclo-( L-Val-L-Pro) (7), cyclo-(L-Pro-L-Tyr) (8), cyclo-(Trp-Val)-dipeptide (9), and (-)-(1S, 3S)-1-methyl-1,2,3,4-tetrahydro-ß-carboline-3-carboxylic acid (10). CONCLUSION: Compounds 2 - 9 are isolated from Periplaneta americana for the first time.

Pregnane alkaloids from Sarcococca hookeriana var. digyna.

Fourteen pregnane-type steroidal alkaloids were isolated from the ethanolic extracts of whole Sarcococca hookeriana var. digyna plants. Their structures were elucidated on the basis of spectral data. Three of them were identified as new steroidal alkaloids: (S)-20-(N,N-dimethylamino)-16α,17α-epoxy-3ß-methoxy-pregn-5-ene (1), (20S)-20-(N,N-dimethylamino)-3ß-tigloylamino-5α-pregn-11ß-ol (2), and (20S)-2α,4ß-bis(acetoxy)-20-(N,N-dimethylamino)-3ß-tigloylamino-5α-pregnane (3). Some of the isolated compounds showed estrogen biosynthesis-promoting effects in human ovarian granulosa-like KGN cells. The EC50 values for the most effective compounds, vagnine B (6) and funtumafrine C (12), were 71 µM and 67 µM, respectively.

Identification, synthesis and quantification of process-related impurities in auraptene.

Impurities in chemically synthesized auraptene, an active pharmaceutical ingredient (API), were detected by a gradient reverse-phase high-performance liquid chromatography (RP-HPLC) method. Molecular weights and major product ions of these chemical compounds were determined by liquid chromatography/Triple Quadrupole (LC-MS/MS) analysis. Structural assignments were presumed as umbelliferone (Imp-I), (E)-6,7-dihydroxy-3,7-dimethyl-2-octene-umbelliferone (Imp-II), (E)-6,7-epoxy-3,7-dimethyl-2-octene-umbelliferone (Imp-III) and 4-methylauraptene (Imp-IV). The impurities were authentically synthesized, confirmed by nuclear magnetic resonance spectroscopy (NMR) and infrared spectroscopy (IR), and subsequently used as reference samples in routing HPLC system suitability testing for method specificity and detectability. Method specificity was further verified by forced degradation studies. The developed method was validated for characterization of impurities in synthesized auraptene according to the guidelines of the International Conference on Harmonization (ICH) in our laboratory.