Screening of anti-HIV-1 inophyllums by HPLC-DAD of Calophyllum inophyllum leaf extracts from French Polynesia Islands

Various pyranocoumarins, calophyllolide, inophyllums B, C, G₁, G₂ and P, from Calophyllum inophyllum (Clusiaceae) leaves of French Polynesia (Austral, Marquesas, Society and Tuamotu archipelagos) have been determined in 136 leaf extracts using a high pressure liquid chromatography-UV-diode array detection (HPLC-UV-DAD) technique. Results show a wide range in chemical composition within trees growing on eighteen islands. The use of multivariate statistical analyses (PCA) shows geographical distribution of inophyllums and indicate those rich in HIV-1 active (+)-inophyllums. Inophyllum B and P contents (0.0-39.0 and 0.0-21.8 mg kg⁻¹, respectively) confirm the chemodiversity of this species within the large area of French Polynesia. The study suggests the presence of interesting chemotypes which could be used as plant source for anti-HIV-1 drugs.     

红厚壳中两个新呫酮类化合物的结构研究

呫酮类化合物存在于很多藤黄科植物中，并具有多样的生物活性．为了进一步发现其活性成分，本文对藤黄科植物红厚壳根的化学成分进行了研究，从中分离得到11个呫酮类化合物，其中两个为新化合物．经多种光谱方法确定了各化合物的结构，两个新化合物分别命名为红厚壳呫酮C（Calophyllumin C)(1)和红厚壳呫酮M(Caloxanthone)(2)．     

New Coumarins and Triterpenes from Calophyllum inophyllum

Four new coumarins, 1 – 4 , and two new triterpenes, 5 and 6 , along with nine known compounds have been identified from the leaves of Calophyllum inophyllum on the basis of spectroscopic analyses and chemical methods. The structure of apetalolide ( 7 ), previously reported from C. apetalum, was revised by means of 2D‐NMR, and the absolute configuration of the known compound inophyllum D ( 8 ) was established by a modified Mosher's method.     

Phenolic and flavonoid compounds extraction from Calophyllum inophyllum leaves

Calophyllum inophyllum has been known as a part of the mangrove forest area. This species is distributed primarily in the coastal regions of Indonesia and Africa. It is rich in bioactive compounds and has been used as a traditional medication. This work employed a single replicate of the one-factor-at-a-time experiment method to investigate optimum conditions, which resulted in the highest TPC. The three factors studied were organic solvent type (acetone, ethanol, and methanol), organic solvent concentration in water (50–100%, v/v), and extraction temperature (30–60 °C). The extraction was conducted with the percolation method. The result shows that organic solvent type, organic solvent concentration in water, and extraction temperature significantly affect the TPC, TFC, and the yield of crude extract obtained. The highest TPC (289.12 mg GAE/g of the residue of C. inophyllum leaves) was achieved with 80% methanol in water at 30 °C for 48 h. Under this condition, TFC value of 410.4 mg QE/g of the residue of C. inophyllum leaves, the yield of 2.41%, and IC₅₀ value of 0.054 µg/mL were achieved. Moreover, bis (2-ethylhexyl) phthalate was firstly detected in the extract.     

Inophyllin A, a new pyranoxanthone from Calophyllum inophyllum (Guttiferae)

In the authors' continuing search for new natural products, their recent studies on the roots of Calophyllum inophyllum (Guttiferae) have yielded a new prenylated pyranoxanthone, Inophyllin A together with the common triterpenes friedelin and stigmasterol. Structural elucidations of these compounds were achieved through (1)H, (13)C, DEPT, COSY, HSQC and HMBC experiments. The molecular mass was determined using MS techniques. The authors report here the isolation of and structural elucidation for Inophyllin A as well as its toxicity test result. The discovery of this new natural product from the unexploited Malaysian forest will certainly contribute to the search for potential natural larvicides.     

Two New Chromanone Acid Derivatives from Calophyllum inophyllum

Chemistry of Natural Compounds - Two new chromanone acid derivatives, calophinophyllins A and B (1 and 2), together with a known one (3), were isolated from Calophyllum inophyllum. The structures...     

New tricyclic and tetracyclic pyranocoumarins with an unprecedented C‐4 substituent. Structure elucidation of tamanolide,tamanolide D and tamanolide P from Calophyllum inophyllum of French Polynesia

Three new pyranocoumarin derivatives, tamanolide (1), tamanolide D (2) and tamanolide P (3), were isolated from the almond seeds of Calophyllum inophyllum L. (Clusiaceae) grown in French Polynesia. These compounds, having an unprecedented C‐4 isobutyl substituent, have been characterized as a new class of pyranocoumarins called tamanolides. Their structures were elucidated on the basis of 1D and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) in association with MS (HR‐ESI‐MS) data analysis. Copyright © 2009 John Wiley & Sons, Ltd.     

海棠果种子油脂肪酸成分研究

用乙醚萃取海棠果种子油,油脂皂化后的脂肪酸采用三氟化硼-甲醇溶液进行甲酯化.采用气相色谱-质谱-计算机联用技术分离、鉴定出7种主要脂肪酸,进一步采用气相色谱法定量测定脂肪酸,分别为肉豆蔻酸0.02%,软脂酸8.64%,硬脂酸8.96%,油酸37.7%,亚油酸20.1%,亚麻酸0.38%,二十碳酸0.85%.结果表明,海棠果种子油不饱和脂肪酸质量分数高达58%,值得作为不饱和脂肪酸食用油来源开发.     

A novel prenylated xanthone from the stems and leaves of Calophyllum inophyllum

A novel prenylated xanthone, caloxanthone Q, was isolated from the stems and leaves of Calophyllum inophyllum. The structure elucidation was carried out by detailed spectroscopic analysis.     

Inocalophyllins A,B and their methyl esters from the seeds of Calophyllum inophyllum

Fractionation of the ethanolic extract of the seeds of Calophyllum inophyllum L. has resulted in the isolation of four novel pyranocoumarin derivatives, designated as inocalophyllins A (1), B (2) and their methyl esters (3, 4) in addition to the known calophyllolide. The structures of these compounds have been determined on the basis of spectroscopic analysis including MS, heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and two dimensional incredible natural abundance double quantum transfer experiment (2D-INADEQUATE). Two new methylated products, 5 and 6 were also prepared by methylation of compounds 1 and 2, respectively.     

Phylattrin, a new cytotoxic xanthone from Calophyllum soulattri

Our continuing studies on secondary metabolites from the stem bark of Calophyllum soulattri has led to the isolation of another new diprenylated xanthone, phylattrin (1), in addition to five other xanthones and two common sterols. The xanthones are soulattrin (2), caloxanthone C (3), macluraxanthone (4), brasixanthone B (5) and trapezifolixanthone (6) while the sterols are stigmasterol (7) and β-sitosterol (8). The structures of these compounds were determined on the basis of spectroscopic analyses such as 1D and 2D-NMR, HRESIMS, IR and UV. Compounds 1-7 exhibited moderate cytotoxic activities against SNU-1, HeLa, Hep G2, NCI-H23, K562, Raji, LS174T, IMR-32 and SK-MEL-28 cells.     

Two new xanthones from Calophyllum nodusum (Guttiferae)

The air-dried powdered stem bark of Calophyllum nodusum (Guttiferea) collected from Sandakan (Sabah, Malaysia), was extracted sequentially with hexane, chloroform and methanol. The solvents were removed by rotary evaporator to give dark viscous extracts. Detailed and repeated chromatographic separation of the extracts lead to isolation of two new xanthones, identified as nodusuxanthone and trapezifolixanthone A. Other common terpenoids such as betulinic acid, lupeol, stigmasterol and friedelin were also isolated from the extracts and identified. The structures of the compounds were established by detailed spectral analysis and comparison with previously reported data.     

Three new friedelane lactones from the bark of gynocardia odorata (flacourtiaceae)

Three new triterpenes - odolactone, acetylodollactone and odollactone from the bark of Gynocardia odorata have been characterised as 3-keto, 3,α-O-acetyl and 3α(-hydroxyl derivatives of friedelan-26→12β-lactone respectively.     

Structure elucidation of a new friedelane triterpene from the mangrove plant Hibiscus tiliaceus

From the stem and bark of the mangrove plant Hibiscus tiliaceus, a new friedelane-type triterpene named 27-oic-3-oxo-28-friedelanoic acid (1) together with eight known triterpenoids involving five friedelane-type derivatives was isolated. The structure of 1 was determined by extensive 2D NMR (DQF-COSY, HMQC, HMBC, and NOESY) data analyses. All the compounds were obtained from mangrove plants for the first time.     

A new friedelane triterpenoid and saponin with moderate antimicrobial activity from the stems of Drypetes laciniata

A new friedelane-type triterpene named 3β-hydroxyfriedelane-7,12,22-trione,as well as nine known compounds were isolated from the whole stems of Drypetes laciniata Hutch.(Euphorbiaceae).Their structures were established on the basis of spectroscopic methods.The new triterpene derivative and a known saponin were tested for antimicrobial and antifungal activities and they appeared to be moderate active.     

A new chromanone acid from the stem bark of Calophyllum teysmannii

A new chromanone acid, namely caloteysmannic acid (1), along with three known compounds, calolongic acid (2), isocalolongic acid (3) and stigmasterol (4) were isolated from the stem bark of Calophyllum teysmannii. All these compounds were evaluated for their cytotoxic and antioxidant activities in the MTT and DPPH assays, respectively. The structure of compound 1 was determined by means of spectroscopic methods including 1D and 2D NMR experiments as well as HR-EIMS spectrometry. The stereochemical assignment of compound 1 was done based on the NMR results and X-ray crystallographic analysis. The preliminary assay results revealed that all the test compounds displayed potent inhibitory activity against HeLa cancer cell line, in particular with compound 1 which exhibited the highest cytotoxic activity comparable to the positive control used, cisplatin. However, no significant antioxidant activity was observed for all the test compounds in the DPPH radical scavenging capacity assay.     

Glucosinolates of the only three Brassicales indigenous to French Polynesia

Abstract

The glucosinolate (GL) profiles in leaf and stem of Rorippa sarmentosa (G.Forst. ex DC.) J.F.Macbr., Lepidium bidentatum Montin var. bidentatum, and Capparis spinosa subsp. cordifolia (Lam.) Fici indigenous to French Polynesia were investigated for the first time using LC-MS analysis. In the present study, we have established the presence of 8 known GLs in R. sarmentosa: 4-(methylsulfinyl)butyl- (1), but-3-enyl- (2), 5-(methylsulfinyl)pentyl- (3), 6-(methylsulfinyl)hexyl- (4), indol-3-ylmethyl- (6), 2-phenylethyl- (7), 8-(methylsulfinyl)octyl- (8), and 9-(methylsulfinyl)nonyl- (9) GLs. We have also tentatively identified for the first time the presence in R. sarmentosa of 7-(methylsulfinyl)heptyl GL (5). In addition, we have identified two known GLs in L. bidentatum var. bidentatum: benzyl- (10) and 4-methoxybenzyl- (11) GLs. Finally, the known methyl GL (12) was shown to be largely predominant in C. spinosa subsp. cordifolia.