A new polycyclic polyprenylated acylphloroglucinols from Hypericum lagarocladum N. Robson / 药学学报

Silica gel column chromatography, reversed phase C18 column chromatography, Sephadex LH-20 gel column chromatography, high performance liquid chromatography and medium performance semi preparative liquid chromatography were performed to separate and purify the chemical constituents of Hypericum lagarocladum N. Robson. Spectroscopic methods such as MS and NMR combined with physicochemical properties were applied in identifying the structures of the isolated compounds. A total of 11 compounds were isolated and identified as hyperlagarone A (1), hyperpatulone E (2), hyperbeanol G (3), uralione D (4), tomoeone F (5), pyramidatone A (6), tomoeone A (7), tomoeone B (8), hyperbeanol C (9), hyperbeanol A (10), and hypercohone G (11), respectively. Compound 1 is a new polycyclic polyprenylated acylphloroglucinol derivative, and compounds 2-11 are isolated from this plant for the first time. 11 compounds were tested for glucose uptake in L6 cells, and the results showed that compounds 7 and 8 had significant effect on glucose uptake.

Antipromastigote and cytotoxic activities of some chemical constituents of Hypericum lanceolatum Lam. (Guttifereae)

Phytochemical investigation of the ethanol extract of the stem bark of Hypericum lanceolatum Lam. (Guttifereae)afforded eight known compounds including 2,2ʹ,5,6ʹ-tetrahydroxybenzophenone (1), 5-hydroxy-3-methoxyxanthone(2), 3-hydroxy-5-methoxyxanthone (3), betulinic acid (4), hydroquinone (5) 6,7-dihydroxy-1,3-dimethoxyxanthone(6), calophyllumin A (7), and 1,3,5,6-tetrahydroxy-4-prenylxanthone (8). Compound 1 was submitted to acetylationreaction to give 5-acetoxy-2,2ʹ,6ʹ-trihydroxybenzophenone (9), a new hemisynthetic derivative. Compounds 5 and8 were isolated for the first time from this plant. The structures were established by extensive analysis of their massspectrometry and nuclear magnetic resonance (NMR) spectroscopic data and comparison with those from the literature.The isolated compounds (1, 2, 4, 5, and 8) and the derivative of benzophenone (9) were tested for their antipromastigoteand cytotoxic activities against visceral leishmaniasis parasite Leishmania donovani and macrophage RAW 264.7 cellline, respectively. Compound 9 was the most active with an IC50 value of 6.1 µg/ml, while compounds 1, 2, 4, and 8were moderately active with IC50 values ranging from 11.4 to 34.8 µg/ml against L. donovani and were not cytotoxicexcept compound 5 that was very toxic and not active. The findings of the present study suggested that compounds 1,2, 4, and 8 could be considered as a potential source of therapeutic medicine for the treatment of leishmaniasis.

A Conformational Isomer of Soulattrolide from the Stem Bark of Calophyllum symingtonianum and Its Antibacterial Activity

Callophylum symingtonianum (Guttiferae), an evergreen broad-leaved tree that usually grows in hill forests, can be found distributed in the Malay Peninsula. The barks, leaves, flowers and seeds is often used medicinally to treat diarrhea and rheumatism. In the present study, we isolated two inophyllum type coumarins, 12-O-ethylinophyllum D (1) and iso-soulattrolide (2) from the stembarks of C. symingtonianum together with their antibacterial activity. The compounds were isolated by chromatographic methods on a silica gel. The structures were established by spectroscopic methods including UV, IR, (1D and 2D) NMR and mass spectrometry as well as by comparison with several literature sources. The antibacterial activity of those compounds was tested using a disc-diffusion assay against Staphylococcus aureus, Bacillus cereus, Escherichia coli and Pseudomonas aeruginosa. Both compound exhibited mild inhibition against P. aeruginosa with both 111 µg/ml MIC value. Compound 2 also inhibits S. aureus with 25 µg/ml MIC value.

Chemical constituents of Hypericum perforatum / 中国中药杂志

A chemical investigation on the aerial parts of Hypericum perforatum resulted in the isolation of a new phloroglucinol derivatives (1), and seven known compounds (2-8). The structures of the compounds were elucidated by means of spectroscopic methods (MS, IR, 1D NMR, and 2D NMR) as 3-methyl-4,6-di (3- methyl-2-butenyl)-3-(4-methyl-3-pentenyl)-2-(2-ethyl-1-oxobutyl)-cyclohexanone (1)，hyperforin (2)，(2R,3R,4S,6)-3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxo-propyl)-3-(4-methyl-3-pentenyl)-cyclohexanone (3)，hyperscabrin B (4)，hyperscabrin C (5)，furohyperforin isomer 1 (6)，furoadhyperforin (7)，and furohyperforin (8). Compound 1 was a new compound, and compounds 3-5 were obtained from H. perforatum for the first time.

Research in progress on natural polycyclic polyprenylated acylphoroglucinols / 中草药

As major active components of the plant of Guttiferae family, polycyclic polyprenylated acylphoroglucinols (PPAPs) have become a hot topic in natural product studies for their novel structures and varied bioactivities such as antibacterial, antiviral, antitumor, and antidepressant activities. In this paper, the chemical structures and bioactivities of 226 natural PPAPs have been summarized. It may provide the reference for the further studies of PPAPs.

Cytotoxic and Antibacterial Evaluation of Coumarins and Chromanone Acid from Calophyllum symingtonianum.

Calophyllum symingtonianum is a rare species from the Calophyllum genus that belongs to the Guttiferae family. Calophyllum has been recognized as a potential medicinal plant due to its many bioactive phytochemicals especially coumarins and chromanone acids. In this study, the cytotoxic activities against MCF-7 and A-549 and antibacterial activities towards S. aureus, B. subtilis, P. aeruginosa and E. Coli of three coumarins known as inophyllum D, inophyllum H and calanone as well as chromanone acid identified as isocordato-oblongic acid isolated from this plant were evaluated. Inophyllum H exhibited the highest IC50 values against MCF-7 at 25.56 μg/mL and A-549 at 26.41μg/mL. Isocordato-oblongic acid showed moderate antibacterial activity against S. aureus and B. subtilis at 125μg/mL and 62.5μg/mL, respectively. This study suggests C. symingtonianum as a potential plant for cytotoxic and antibacterial phytochemicals.

Banfoxanthone, a new prenylated xanthone from the stem bark of Garcinia ovalifolia (Guttiferaceae).

A detailed chemical investigation of the secondary metabolites from the extract of the stem bark of Garcinia ovalifolia led to the isolation of one new prenylated xanthone named banfoxanthone and five known compounds, namely friedeline, canophyllal, ovalifoloneA, 3-methoxycheffouxanthone, endodesmiadol. Prenylated xanthones isolated from Garcinia ovalifolia and others species of genus Garcinia appear to be useful as chemotaxonomic markers in Garcinia.

Determination of Isogarcinol in Seven Guttiferae Plant Species by HPLC / 世界科学技术-中医药现代化

This study was aimed to establish a HPLC method for the determination of isogarcinol. Daojin Inertsil WP300 C18 (4.6 mm× 150 mm, 5μm) was employed with methanol and water (75?25) as the mobile phase. The flow rate was 1.0 mL·min-1. The column temperature was set at 40°C. The detection wavelengthγ was set at 277 nm. The results showed that the linear range of isogarcinol was 0.005 7-0.039 9μg. The average recovery rate was 99.58%. The relative standard deviation (RSD) was 1.25%. The contents of isogarcinol inGarcinia mangostana,Garcinia oblongifolia,Garcinia oligantha,Cratoxylum cochinchinense andCalophyllum membranaceum were 0.285%, 0.199%, 0.857%, 0.161% and 0.006%, respectively. Isogarcinol was not detected inCratoxylum formosum orCalophyllum inophyllum. It was concluded that the method was convenient, accurate with high sensitivity, good stability and repeatability. It can be used for determination of isogarcinol content in Chinese herbal medicine.

Revisión bibliográfica sobre la composición química y actividades farmacológicas del género Vismia (Guttiferae) / A review on the chemical composition and pharmacological activities of Vismia genus (Guttiferae)

Vismia genus is an important source of natural medicinal products, thus, information collected in this review is an attempt to cover the most recent developments in the ethnopharmacology, pharmacology and phytochemistry of this genus. Anthraquinones and other quinonoid derivates, terpenoids and volatile constituents have been reported as the major constituents isolated from different Vismia species. On the other hand, pharmacological studies carried out to date have revealed the variety of anti-plasmodium, antioxidant, antimicrobial and antifungical properties of extracts and pure isolated compounds of the different species tested. The information summarized in this paper intends to serve as a reference tool to practitioners in the fields of etnopharmacology and chemistry of natural products.

El género Vismia es una fuente importante de productos naturales medicinales, es por esto que la información reunida en la presente revisión cubre los estudios más recientes en la etnofarmacología, farmacología y fitoquímica de este género. Antraquinonas y otros derivados quinoides, terpenos y constituyentes volátiles han sido reportados como los compuestos mayormente aislados de las diferentes especies de Vismia. Por otro lado, los estudios farmacológicos realizados hasta los momentos muestran las diversas propiedades antiplasmodicas, antioxidantes, antimicrobianas y antifúngicas que presentan tanto los extractos como los compuestos puros aislados de las diferentes especies ensayadas. La información resumida en este documento intenta servir de material de apoyo para investigadores en los campos de la etnofarmacologia y la química de productos naturales.

NMR elucidation and crystal structure analysis of 1-hydroxy-3, 6-dimethoxy-8-methyl-9h-xanthen-9-one (lichexanthone) isolated from Vismia baccifera (Guttiferae) / Elucidación por RMN y análisis de la estructura cristalina de 1-hidroxi-3,6-dimetox1-8-methil-9h-xanten-9-ona (lichexanthone)

In the present investigation the structural analysis of 1-hydroxy-3,6-dimethoxy-8-methyl-9h-xanthen-9-one (lichexanthone) isolated from Vismia baccifera var. dealbata collected in Mérida-Venezuela, was established by NMR (1H and 13C), mass spectrometry and single crystal X-ray diffraction. Lichexanthone crystallizes in the monoclinic system, space group P21/c (No 14) with unit cell parameters a = 11.6405(5) Å; b = 7.5444(3) Å; c = 15.2341(6) Å; = 102.280(1)°; V = 1307.26(9) Å3; Z = 4. The structure refinement converged to R = 0.0397, wR2 = 0.1076, S = 1.04. Lichexanthone had been isolated before from Parmotrema sp and Ruprechtia tangarana (Polygonaceae). However, to the best of our knowledge, this is the first report of this compound obtained from V. baccifera var. dealbata (Guttiferae).

En la presente investigación el análisis estructural de 1-hidroxi-3,6-dimetoxi-8-metil-9h-xanten-9-ona (lichexanthone) aislada de Vismia baccifera var. dealbata colectada en Mérida-Venezuela, fue determinado por RMN (1H y 13C), espectrometría de masas y difracción de rayos X. La lichexanthona cristaliza en un sistema monoclínico con un grupo espacial P21/c (No 14) y parámetros de celda de a = 11.6405 (5) Å; b = 7.5444 (3) Å; c = 15.2341 (6) Å; = 102.280(1)°; V = 1307.26(9) Å3; Z = 4. El refinamiento de la estructura convergió a los valores de R = 0.0397, wR2 = 0.1076, S = 1.04. La lichexanthona ha sido aislada de Parmotrema sp y Ruprechtia tangarana (Polygonaceae). Sin embargo, para nuestro conocimiento, esta es la primera vez que se reporta el aislamiento de este compuesto en la especie V. baccifera var. dealbata (Guttiferae).

Anti-inflammatory and analgesic activities of Hypericum brasiliense (Willd) standardized extract / Atividades anti-inflamatória e analgésica de extratos padronizados de Hypericum brasiliense (Willd)

As atividades antiinflamatória e antinociceptiva do extrato padronizado de Hypericum brasiliense (HBSE) (Guttiferae) foi avaliada em modelos animais. Ratos Wistar machos foram tratados com extrato de H. brasiliense (50, 250 e 500 mg/kg, v.o.) em solução 3 por cento Tween 80 0,9 por cento NaCl. O tratamento com HBSE (500 mg/kg) mostrou inibição significativa sobre o edema induzido por carragenina comparado ao grupo controle. Nessa dose, o edema foi reduzido em 31,25 por cento na terceira hora (pico do edema) após o tratamento, mas na dose de 50 mg/kg, o edema apresentou redução de 53,13 por cento (p < 0,05). Ainda com a dose de 50 mg/kg, a diminuição do edema induzido por dextrana foi similar ao controle positivo, ciproeptadina. Houve diminuição na formação do tecido granulomatoso (6,6 por cento) comparável ao grupo controle. O HBSE também inibiu o número de contorções abdominais em 46,4 por cento, estatisticamente igual ao controle positivo, tratado com indometacina (42,9 por cento). Na dose de 250 mg/kg, houve inibição do número de contorções em 70,7 por cento quando comparado ao grupo controle (p < 0,001). No teste da placa-quente, foi verificado aumento no tempo de latência com a dose de 50 mg/kg. Os resultados demonstram que o HBSE possui atividade antiinflamatória sobre processos agudos, principalmente quando sua gênese está relacionada à síntese dos derivados do ácido araquidônico, e seu efeito analgésico provavelmente envolve ação sobre o Sistema Nervoso Central.

The anti-inflammatory and antinociceptive activities of the standardized leaves extract (HBSE) of Hypericum brasiliense (Guttiferae) were evaluated in animal models. Male Wistar rats were treated with H. brasiliense extract (50, 250 and 500 mg/kg, p.o.) in 3 percent Tween 80 0.9 percent saline solution. The treatment of the edema induced by carrageenin with HBSE (500 mg/kg) showed significant inhibition when compared to the control group. At this dose, the edema decreased by 31.25 percent in the third hour after treatment (edema peak), but the dose of 50 mg/kg has inhibited the edema by 53.13 percent (p < 0.05). At the dose of 50 mg/kg, the decrease of the edema induced by dextran was similar to that caused by cyproheptadine. The decrease of the formation of granulomatous tissue (6.6 percent) was comparable to the control group. The HBSE inhibited the abdominal constrictions induced by acetic acid. At a dose of 50 mg/kg, the inhibition of the abdominal constrictions (46.4 percent) was comparable to that produced by indomethacin (42.9 percent). A dose of 250 mg/kg inhibited these constrictions by 70.66 percent when compared to control (p < 0.001). In the hot-plate test, an increase in the latency time was observed at a 50 mg/kg dose. These data suggest that HBSE has anti-inflammatory activity on acute process, developed principally by arachdonic acid derivates and analgesic effect due to its probable involvement in the Central Nervous System.

Flavonoids, benzophenones and a new euphane derivative from Clusia columnaris Engl / Flavonóides, benzofenonas e um novo eufano de Clusia columnaris Engl

The polyisoprenylated benzophenones machuone and clusiachromene A have been isolated from the fruits of Clusia columnaris. The hexane extract of the young branches with leaves afforded a new euphane derivative, whose structure was elucidated by spectroscopic methods. On the contrary, the most polar EtOAc and ButOH extracts were constituted of flavonoid C-glucosides (isovitexin, vitexin and vitexin-2"-xyloside) and seven biflavonoids of the so-called Garcinia group.

Dos frutos de Clusia columnaris foram isoladas as benzofenonas poliisopreniladas machuona e clusiacromeno A. Do extrato em hexano obtido de galhos e folhas novas, um novo triterpeno do tipo eufano foi isolado. Sua estrutura foi elucidada através de métodos espectroscópicos. Por outro lado, dos extratos mais polares - em acetato de etila e em butanol, foram isolados os flavonóides C-glicosilados isovitexina, vitexina e vitexina-2"-xilosídeo, além de sete bisflavonóides conhecidos como bisflavonóides do grupo da Garcinia.

PRENYLATED XANTHONES FROM Rheedia acuminata (reprinted from Acta Amazônica, 23(2/3):181-185)

Pyranojacareubin; 1,5-dihydroxy-6',6'-dimethyl-2H-pyran(2,,3':6,7) -6",6"-dime-thyl-2H,4H-pyran(2",3":2,3)xanthone and a new xanthone l,6-dihydroxy-5-methoxy-6',6'-dime-thyl-2H-pyran(2',3':3,2)-7-(3,3-dimethylprop-2-enyl)xanthone were isolated from the ether extract of the root bark of Rheedia acuminata together with friedelin and friedelanol.

Piranojacareubina; 1,5-diidroxi-6',6'-dimetil-2H-pirano(2',3':6,7)-6",6"-dimetil-2H,4H(2",3":2,3)xantona e uma xantona inédita 1,6-diidroxi-5-metoxi-6,6'-dimetil-2H-pirano(2',3':3,2)-7-(3,3-dimetilprop-2-enil) xantona foram isoladas do extrato etèreo da casca da raiz de Rheedia acuminata além de friedelina e friedelanol.

ena acuminata

Pyranojacareubin; 1,5-dihydroxy-6',6'-dimethyl-2H-pyran(2',3':6,7) -6",6"-dim-ethyI-2H,4H-pyran(2",3":2,3)xanthone and a new xanthone l,6-dihydroxy-5-methoxy-6',6'-dim-ethyl-2H-pyran(2',3':3,2)-7-(3,3-dimethylprop-2-enyl)xanthone were isolated from the ether extract of the root bark of Rheedia acuminata together with friedelin and friedelanol.

Piranojacareubina;l,5-diidroxi-6',6'-dimetil-2H-pirano(2',3':6,7)-6",6"-dimetil-2H,4H(2",3":2,3)xantona e uma xantona inédita l,6-diidroxi-5-metoxi-6',6'-dimetil-2H-pirano(2',3':3,2)-7-(3,3-dimetilprop-2-enil) xantona foram isoladas do extrato etéreo da casca da raiz de Rheedia acuminata além de friedelina e friedelanol.