Eight New Cucurbitane Glycosides,Kuguaglycosides A – H,from the Root of Momordica charantia L.

Eight new cucurbitane glycosides, kuguaglycosides A–H ( 1 – 8 , resp.), together with five known analogues, 3β,23‐dihydroxycucurbita‐5,24‐dien‐7β‐yl β‐D ‐glucopyranoside ( 9 ), karaviloside III ( 10 ), karaviloside V ( 11 ), karaviloside XI ( 12 ), and momordicoside K ( 13 ), were isolated from the root of Momordica charantia L. The structures of the new compounds were determined on the basis of spectroscopic and chemical methods.     

Cucurbitane Triterpenoids from the Fruit Pulp of Momordica charantia and Their Cytotoxic Activity

Two new cucurbitane‐type triterpenes, 25‐methoxycucurbita‐5,23(E)‐diene‐3β,19‐diol ( 1 ) and 7β‐ethoxy‐3β‐hydroxy‐25‐methoxycucurbita‐5,23(E)‐dien‐19‐al ( 2 ), together with three known cucurbitane‐type triterpenes, 3β,7β,25‐trihydroxycucurbita‐5,23(E)‐dien‐19‐al ( 3 ), (23E)‐3β‐hydroxy‐7β,25‐dimethoxycucurbita‐5,23‐dien‐19‐al ( 4 ), and 3β‐hydroxy‐25‐methoxycucurbita‐6,23(E)‐dien‐19,5β‐olide ( 5 ), were isolated from the fruit pulp of Momordica charantia. The structures of two new compounds were elucidated on the basis of 1D and 2D NMR, MS, IR, optical rotation. Among these isolates, compounds 1 , 2 , and 5 showed slight cytotoxic activity against the SK‐Hep 1 cell line with IC₅₀ values of 33.1, 24.3, and 38.7 μM, respectively.     

Triterpenoids from the Stems of Momordica charantia

Two new cucurbitane triterpenes, (23E)‐7β‐methoxycucurbita‐5,23,25‐trien‐3β‐ol ( 1 ) and 23,25‐dihydroxy‐5β,19‐epoxycucurbit‐6‐ene‐3,24‐dione ( 2 ), and a new D : C‐friedooleanane triterpene, 3α‐[(E)‐feruloyloxy]‐D : C‐friedooleana‐7,9(11)‐dien‐29‐oic acid ( 3 ), together with two known D : C‐friedooleanane triterpenes, 3β‐[(E)‐feruloyloxy]‐D : C‐friedooleana‐7,9(11)‐dien‐29‐oic acid ( 4 ) and 3‐oxo‐D : C‐friedooleana‐7,9(11)‐dien‐29‐oic acid ( 5 ), were isolated from the stems of Momordica charantia. The structures of the new compounds 1 – 3 were determined by spectroscopic methods.     

Two New Cucurbitane Triterpenoids from Immature Fruits of Momordica charantia

Two new cucurbitane triterpenoids, kuguacin X ( 1 ) and kuguaglycoside I ( 2 ), together with three known analogs, were isolated from immature fruits of Momordica charantia. By detailed analysis of IR, NMR, and MS data, acid hydrolysis, and comparison with spectroscopic data of known compounds, the new compounds were determined to be (23E)‐5β,19‐epoxycucurbita‐6,23‐diene‐3β,22ξ,25‐triol ( 1 ) and (23E)‐5β,19‐epoxycucurbita‐6,23‐dien‐19‐on‐3β,25‐diol 3‐O‐β‐D ‐allopyranoside ( 2 ).     

Sterols from the Stems of Momordica charantia

A new sterol, 5α,6α‐epoxy‐3β‐hydroxy‐(22E,24R)‐ergosta‐8,22‐dien‐7‐one ( 1 ), together with eight known sterols, 5α,6α‐epoxy‐(22E,24R)‐ergosta‐8,22‐diene‐3β,7α‐diol ( 2 ), 5α,6α‐epoxy‐(22E,24R)‐ergosta‐8,22‐diene‐3β,7β‐diol ( 3 ), 5α,6α‐epoxy‐(22E,24R)‐ergosta‐8(14),22‐diene‐3β,7α‐diol ( 4 ), 3β‐hydroxy‐(22E,24R)‐ergosta‐5,8,22‐trien‐7‐one ( 5 ), ergosterol peroxide ( 6 ), clerosterol ( 7 ), decortinol ( 8 ), and decortinone ( 9 ), were isolated from the stems of Momordica charantia. Their structures were elucidated by mean of extensive spectroscopic methods, including ¹H, ¹³C, 2D‐NMR and HR‐EI‐MS, as well as comparison with the literature data. Compounds 1 , 4 , 5 , 8 , and 91 were not cytotoxic against the SK‐Hep 1 cell line.     

Cucurbitane‐type triterpene glycosides from the fruits of Momordica charantia

The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1–3). The structures of these compounds were determined to be (19R, 23R)‐5β, 19‐epoxy‐19‐methoxycucurbita‐6,24‐diene‐3β, 23‐diol 3‐O‐β‐D‐allopyranoside (1), (23R)‐5β, 19‐epoxycucurbita‐6,24‐diene‐3β, 23‐diol 3‐O‐β‐D‐allopyranoside (2), and (19R)‐5β, 19‐epoxy‐19,25‐dihydroxycucurbita‐6,23(E)‐diene‐3β‐ol 3‐O‐β‐D‐glucopyranoside (3), by chemical and spectroscopic methods. Copyright © 2010 John Wiley & Sons, Ltd.     

Bioactives of Momordica charantia as Potential Anti-Diabetic/Hypoglycemic Agents

Momordica charantia L., a member of the Curcubitaceae family, has traditionally been used as herbal medicine and as a vegetable. Functional ingredients of M. charantia play important roles in body health and human nutrition, which can be used directly or indirectly in treating or preventing hyperglycemia-related chronic diseases in humans. The hypoglycemic effects of M. charantia have been known for years. In this paper, the research progress of M. charantia phytobioactives and their hypoglycemic effects and related mechanisms, especially relating to diabetes mellitus, has been reviewed. Moreover, the clinical application of M. charantia in treating diabetes mellitus is also discussed, hoping to broaden the application of M. charantia as functional food.     

Inhibitory Effects of Cucurbitane-Type Triterpenoids from Momordica charantia Fruit on Lipopolysaccharide-Stimulated Pro-Inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

The bitter melon, Momordica charantia L., was once an important food and medicinal herb. Various studies have focused on the potential treatment of stomach disease with M. charantia and on its anti-diabetic properties. However, very little is known about the specific compounds responsible for its anti-inflammatory activities. In addition, the in vitro inhibitory effect of M. charantia on pro-inflammatory cytokine production by lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) has not been reported. Phytochemical investigation of M. charantia fruit led to the isolation of 15 compounds (1−15). Their chemical structures were elucidated spectroscopically (one- and two-dimensional nuclear magnetic resonance) and with electrospray ionization mass spectrometry. The anti-inflammatory effects of the isolated compounds were evaluated by measuring the production of the pro-inflammatory cytokines interleukin IL-6, IL-12 p40, and tumor necrosis factor α (TNF-α) in LPS-stimulated BMDCs. The cucurbitanes were potent inhibitors of the cytokines TNF-α, IL-6, and IL-12 p40, indicating promising anti-inflammatory effects. Based on these studies and in silico simulations, we determined that the ligand likely docked in the receptors. These results suggest that cucurbitanes from M. charantia are potential candidates for treating inflammatory diseases.     

One new 19-nor cucurbitane-type triterpenoid from the stems of Momordica charantia

One new 19-nor cucurbitane-type triterpenoid (3β,9β,25-trihydroxy-7β-methoxy-19-nor-cucurbita-5,23(E)-diene) (1), together with other six known cucurbitane-type triterpenoids (2–7), were isolated from the stems of Momordica charantia L. The chemical structure of 1 was elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY and ROESY), MS experiments. Using MTT assay, compound 1 exhibited weak cytotoxicity against HL-60, A-549, and SK-BR-3 cell lines with the IC₅₀ values at 27.3, 32.7 and 26.6 μM, respectively.     

Four New Nortriterpenoids from Schisandra lancifolia

Four new highly oxygenated nortriterpenoids, lancifodilactones O–R ( 1 – 4 ), together with six known ones, i.e., 5 – 10 , were isolated from the leaves and stems of Schisandra lancifolia. Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments and mass spectrometry. Compounds 1 – 3 were evaluated for their cytotoxicity against NB4, A549, SHSY5Y, PC‐3, and MCF‐7 cell lines. No compounds exhibited significant cytotoxicity, the IC₅₀ values being above 50 μM .     

Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Flamvelutpenoids A–D ( 1 – 4 ), four new cuparene‐type sesquiterpenes, were isolated from the solid culture of Flammulina velutipes. Their structures were elucidated by NMR experiments. The absolute configurations of 1 and 2 were assigned via the circular dichroism data of the [Rh₂(OCOCF₃)₄] complex, whereas that of C(3) of 3 was determined by applying the octant rule for the α,β‐unsaturated ketone moiety. Compounds 1 – 4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillin‐resistant Staphylococcus aureus with MIC values larger than 100 μM .     

Further Withaphysalin Derivatives from Acnistus arborescens

Two new epimeric chlorinated withaphysalins, rel‐(4β,5β,6α,18S,22R)‐ and rel‐(4β,5β,6α,18R,22R)‐6‐chloro‐18,20‐epoxy‐18‐ethoxy‐4,5‐dihydroxy‐1‐oxowitha‐2,24‐diene‐26,22‐lactone ( 1 and 2 resp.), together with the new rel‐(4β,5β,6α,18R,22R)‐6‐chloro‐18,20‐epoxy‐4,5‐dihydroxy‐18‐methoxy‐1‐oxowitha‐2,24‐diene‐26,22‐lactone ( 3 ) and rel‐(3β,4β,5β,6β,18R,22R)‐5,6:18,20‐diepoxy‐3,18‐diethoxy‐4‐hydroxy‐1‐oxowith‐24‐ene‐26,22‐lactone ( 4 ) were isolated from the leaves of Acnistus arborescens and named withaphysalins T–W, respectively. The final structures and the complete ¹H‐ and ¹³C‐NMR assignments of the three chlorowithaphysalins 1 – 3 were performed by means of HR‐ESI‐MS and 1D‐ and 2D‐NMR experiments, including COSY, HSQC, and HMBC, beside comparison with spectral data of analogous compounds from the literature. The structure of 4 was also confirmed by means of a single‐crystal X‐ray diffraction analysis.     

Characterization of Antioxidant Activity of Momordica Charantia Fruit by Infrared-Based Fingerprinting

Momordica charantia is widely consumed edible fruit. The food and pharmaceutical industries use it as a natural antioxidant. However, the quality control of M. charantia-based medicinal products is questionable due to the complexity of metabolites in this fruit. Hence, this study has developed a statistical model in predicting the antioxidant value through the 2, 2-diphenyl-1 picrylhydrazyl radical scavenging activity and ferric reducing antioxidant power based on infrared spectroscopy with attenuated total reflectance. This technique was reliably used for quality control. Six ethanol extracts (0, 20, 40, 60, 80, and 100% in water) of this plant’s fruit were prepared. The radical scavenging and ferric reducing antioxidant power activities were measured and the chemical profiling of the extracts was fingerprinted by infrared spectroscopy between 4,000 and 600?cm^?1 at a resolution of 4?cm^?1. Statistical analysis was developed by correlating the bioactivity and infrared spectra of each extract using orthogonal partial least square discriminant analysis. The C–N, C?O, C–O, C–H, and OH infrared signals were positively correlated with biological activity. The antioxidant activity of the fruit of M. charantia may be due to the presence of several antioxidants that work synergistically.     

Four New Briarane Diterpenoids from the Gorgonian Coral Junceella fragilis

Chemical investigation of the gorgonian coral Junceella fragilis, collected by scuba diving in Taiwan, resulted in the isolation of four new briarane‐type diterpenoids, frajunolides A–D ( 1 – 4 ), along with three known briaranes. Their structures were elucidated on the basis of spectroscopic studies, especially 1‐ and 2D‐NMR as well as HR‐MS experiments. The inhibitory effect of all isolated metabolites towards superoxide‐anion generation and elastase release by human neutrophils in response to formylmethionyl‐leucyl‐phenylalanine/dihydrocytochalasin B (FMLP/CB) was evaluated.     

Anti-Inflammatory,Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of Momordica charantia L.

Diabetes mellitus is a chronic disease and one of the fastest-growing health challenges of the last decades. Studies have shown that chronic low-grade inflammation and activation of the innate immune system are intimately involved in type 2 diabetes pathogenesis. Momordica charantia L. fruits are used in traditional medicine to manage diabetes. Herein, we report the purification of a new 23-O-β-d-allopyranosyl-5β,19-epoxycucurbitane-6,24-diene triterpene (charantoside XV, 6) along with 25ξ-isopropenylchole-5(6)-ene-3-O-β-d-glucopyranoside (1), karaviloside VI (2), karaviloside VIII (3), momordicoside L (4), momordicoside A (5) and kuguaglycoside C (7) from an Indian cultivar of Momordica charantia. At 50 µM compounds, 2–6 differentially affected the expression of pro-inflammatory markers IL-6, TNF-α, and iNOS, and mitochondrial marker COX-2. Compounds tested for the inhibition of α-amylase and α-glucosidase enzymes at 0.87 mM and 1.33 mM, respectively. Compounds showed similar α-amylase inhibitory activity than acarbose (0.13 mM) of control (68.0–76.6%). Karaviloside VIII (56.5%) was the most active compound in the α-glucosidase assay, followed by karaviloside VI (40.3%), while momordicoside L (23.7%), A (33.5%), and charantoside XV (23.9%) were the least active compounds. To better understand the mode of binding of cucurbitane-triterpenes to these enzymes, in silico docking of the isolated compounds was evaluated with α-amylase and α-glucosidase.     

Four New Pregnane Steroids from Aglaia abbreviata and Their Cytotoxic Activities

Four new pregnane steroids, aglaiasterols A–D ( 1 – 4 ), have been isolated from the EtOH extract of stems of Aglaia abbreviata. They were identified as (3α,5α,17Z)‐3‐hydroxypregn‐17‐en‐16‐one ( 1 ), (3β,5α,17E)‐3‐hydroxypregn‐17‐en‐16‐one ( 2 ), (3β,5α,17Z)‐3‐hydroxypregn‐17‐en‐16‐one ( 3 ), and (3α,5α,20S*)‐3‐hydroxy‐16‐oxopregnan‐20‐yl acetate ( 4 ) on the basis of spectroscopic methods, including 1D‐ and 2D‐NMR techniques. Compounds 1 – 4 were evaluated for their cytotoxic activities against K562 (human leukemia), MCF‐7 (human breast cancer), and KB (human oral epithelium cancer) cells, and drug‐resistant cells of K562/A02, MCF‐7/ADM, and KB/VCR. These isolates showed weak to moderate inhibitory effects on the growth of the tested cell lines.     

Four New Nor‐Diterpenoid Alkaloids from Aconitum brachypodum

Four new C₁₉‐nor‐diterpenoid alkaloids, named brachyaconitines A–D ( 1 – 4 ), were isolated from the roots of Aconitum brachypodum Diels. Their structures were elucidated as 3‐O‐acetyl‐20‐deethyl‐20‐formylaconitine ( 1 ), 3‐O‐acetyl‐19,20‐didehydro‐20‐deethylaconitine ( 2 ), 3‐O‐acetyl‐8‐de(acetyloxy)‐7,8,17,20‐tetradehydro‐20‐deethyl‐7,17‐secoaconitine ( 3 ), and 1‐O‐methylflavaconitine ( 4 ) by means of MS, IR, 1D‐ and 2D‐NMR analyses. The structure of compound 1 was confirmed by an X‐ray diffraction experiment.     

Study of pancreatic lipase inhibition kinetics and LC–QTOF–MS‐based identification of bioactive constituents of Momordica charantia fruits

The different parts of Momordica charantia have been reported to have several therapeutic applications against hyperglycemia and hypercholesterolemia associated with pancreatic lipase (PL). Inhibition of this enzyme prevents the absorption of dietary triglyceride in the intestine, and thus exerts an anti‐obesity effect. This study aimed to investigate the bioactive constituents of the fruits of M. charantia (MCF) extract and fractions against pancreatic PL followed by study of their inhibition kinetics. The PL inhibitory assay was performed spectrophotometrically by measuring the change in absorbance of the products at 405 nm, using p‐nitrophenylcaprylate as substrate. The results indicated that the ethyl acetate fraction of MCF (EFMC) offered significant, dose‐dependent inhibition against PL, compared with the positive control, Orlistat. The enzyme kinetics study revealed the inhibition to be a mixed type in nature. Additionally, the total phenol and flavonoid content of the fractions was estimated. A positive correlation between phenolic content of EFMC and its PL inhibitory activity was established statistically, which implied that higher inhibition potential was contributed by the phenolic compounds. The identification of the bioactive constituents was further confirmed by LC–QTOF–MS study. This finding suggested that phenolic compounds of MCF can serve as functional food components to address obesity‐related disorders linked with PL.     

Monoterpenoids from the Fruit of Gardenia jasminoides

Eight new monoterpenoids, jasminoside J ( 1 ), jasminoside K ( 2 ), 6′‐O‐trans‐sinapoyljasminoside B ( 3 ), 6′‐O‐trans‐sinapoyljasminoside L ( 4 ), jasminosides M–P ( 5 – 8 ), together with three known analogues, jasminoside C ( 9 ), jasminol E ( 10 ), and sacranoside B ( 11 ), were isolated from the fruit of Gardenia jasminoides Ellis (Rubiaceae). Their structures were elucidated by spectral and chemical methods.