Phytochemical profiling,antioxidant, enzyme inhibition and cytotoxic potential of Bougainvillea glabra flowers

Abstract

In this study, phytochemical composition, antioxidant, enzyme inhibition and cytotoxic activities of methanol and dichloromethane (DCM) extracts of Bougainvillea glabra (B. glabra) flowers were investigated. Methanol extract was found to have higher total bioactive contents and UHPLC-MS analysis of methanol extract revealed the presence of well-known phenolic and flavonoid compounds. Antioxidant activities were performed by radical scavenging (DPPH and ABTS), reducing power (FRAP and CUPRAC), phosphomolybdenum (TAC) and metal chelating assays. From our result, we observed that methanol extract had many antioxidant compounds. The DCM extract exhibited higher cholinesterases and α-glucosidase enzyme inhibition, while methanol extract showed significant urease inhibition. Both extracts exhibited strong to moderate cytotoxicity against MCF-7, MDA-MB-231, CaSki, DU-145 and SW-480 cancer cells with IC₅₀ values ranging from 88.49 to 304.7 µg/mL. The findings showed the B. glabra to possess considerable antioxidant, enzyme inhibition and cytotoxic potentials and therefore has potential to discover novel bioactive molecules.     

Two new sesquiterpenes from Sarcandra glabra

Phytochemical study of the ethanol extract of Sarcandra glabra resulted in the isolation of two new sesquiterpenes, glabranols A (1) and B (2). Their structures were elucidated as 8alpha,9alpha,15-trihydroxylinden-4,7(11)-dien-12,8beta-olide (1) and 1beta,4alpha,7beta,11-tetrahydroxyeudesmane (2), by spectroscopic methods including 1D- and 2D-NMR and FTICR-MS.     

Polyketides and Meroterpenoids from Neosartorya glabra

Two new polyketides, neosarphenols A and B ( 1 and 2 , resp.), were isolated from Neosartorya glabra, together with six known polyketides, 3 – 8 , and two meroterpenoids, 9 and 10 . The structures of the new compounds were elucidated by comprehensive spectroscopic analysis, especially by HR‐ESI‐MS and NMR experiments. All compounds were evaluated for their cytotoxic activities against MDA‐MB‐231, MCF‐7, and PANC‐1 tumor cell lines; 1 and 6 exhibited selective and moderate cytotoxicities against PANC‐1 cell line.     

A Flavonol Glycoside from Smilax glabra

A new flavonol glycoside,named neosmitibin was isolated the rhizome of Smilax glabra. Its structure and absolute configuration were elucidated on the basis of spectroscopic studies.     

Three new sesquiterpenes from Ainsliaea glabra

Three new sesquiterpenes: 4-acrylic-6-methyl-α-tetralone (1), ainsliaea acid A (2) and ainsliaea acid B (3), together with 8 known compounds (4-11) were isolated from the whole herb of Ainsliaea glabra and their structures were established by means of 1D and 2D NMR spectroscopy and HR-ESIMS. Compounds 1–6 were tested for the inhibition of nuclear factor kappa B (NF-κB) in the 293-NF-κB-luciferase reporter cell line induced by lipopolysaccharide (LPS), and compound 2 was further tested for the production of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6 and IL-10 in RAW264.7 macrophages induced by LPS. The isolated compound 2 exhibited significant anti-inflammatory activity.     

New Flavanonglycoside from Glycyrrhiza glabra -

A new flavanonglycoside pinocembroside, 2(S)-7-O--D-glucopyranosyl-5-hydroxyflavanone, was isolated from the aerial part ofGlycyrrhiza glabraL. Its structure was determined using chemical transformations and spectral data     

Three new compounds from Sarcandra glabra

One new sesquiterpene lactone,1 α,8 α,9 α-trihydroxyeudesman-3(4),7(11)-dien-8 β,12-olide(1) and two new phenylpropanoidsubstituted catechin glycosides,glabraoside C(2) and glabraoside D(3) were isolated from the whole plant of Sarcandra glabra. Their structures were established by the analyses of spectral and chemical evidences.     

New Triterpene Saponins from Herniaria glabra

Three new saponins 1–3 were isolated from Herniaria glabra by means of prep. HPLC and TLC. The structures were established mainly by a combination of 2D-NMR techniques (COSY, TOCSY, ROESY, HMQC, and HMBC) as O-α-L -rhamnopyranosyl-(1→4)-O-β-D -glucopyranosyl-(1-→6)-O-[β-D -glucopyranosyl-(1→2)]-β-D -glucopyranosyl medicagen-28-ate (herniaria saponin 4; 1 ), O-β-D -glucopyranosyl-(1→3)-O-α-L -rhamnopyranosyl-(1→2)-O-[β-(3R)-D -apiofuranosyl-(1→3)]-β-D -4-O-acetylfucopyranosyl 3-O-(β-D -glucuronopyranosyl)-16α-hydroxymedicagen-28-ate (herniaria saponin 5; 2 ), and O-α-L -rhamnopyranosyl-(1→4)-O-β-D -glucopyranosyl-(1→6)-O-[β-D -6-O-acetylglucopyra nosyl-(1→2)]-β-D -glucopyranosyl medicagen-28-ate (herniaria saponin 6; 3 ).     

Iridoid Glycosides from Lamiophlomis rotata

The seven new iridoid diglycosides 1 – 7 , together with eleven known iridoid and phenylpropanoid glycosides, were isolated from the 50% EtOH extract of the roots of Lamiophlomis rotata. Their structures were elucidated by chemical and spectroscopic methods.     

Cucurbitane Glycosides from Siraitia grosvenorii

Systematic phytochemical studies of the extract of Luo Han Go (Siraitia grosvenorii) furnished six known cucurbitane glycosides, namely, mogrosides IVa, mogrosides V and VI, isomogroside V, 11-oxomogroside V, and siamenoside I. The structures of all the isolated compounds were characterized on the basis of extensive spectral and chemical studies. Though the partial NMR spectral data has been reported for some of the isolated compounds previously, the complete ¹H and ¹³C NMR spectral assignments of all the isolated compounds are reported herewith for the first time based on COSY, HSQC, HMBC, and NOESY spectroscopic data.     

New Glycosides from Cistanche salsa

Six new glycosides, salsasides A–F ( 1 – 6 , resp.), were isolated from the stems of Cistanche salsa, together with seven known glycosidic compounds. Their structures were elucidated by means of ester hydrolysis and chemical derivatization, in‐depth NMR spectroscopic and mass spectrometric analyses, and by comparison with literature data of related compounds. The new glycosides are based on β‐D ‐glucose (Glc) and α‐L ‐rhamnose (Rha), carrying acetyl (Ac), benzyl (Bn), phenethyl, coumaroyl (Cou), and caffeoyl (Caf) substituents.     

Macrocyclic Glycosides from Clematis hexapetala

Two new macrocyclic glycosides, clemahexapetoside A ( 1 ) and B ( 2 ), along with the known compound clemochinenoside A ( 3 ), were isolated from the roots and rhizomes of Clematis hexapetala. Their structures were elucidated on the basis of chemical, physicochemical, and spectroscopic evidence.     

阿拉善马先蒿中新木脂素甙成分研究

阿拉善马先蒿中新木脂素甙成分研究高建军，刘自民，王继和，贾忠建（兰州大学有机化学研究所应用有机化学国家重点实验室，兰州，７３００００）关键词阿拉善马先蒿，玄参科，新木脂素甙前文［１］报道了从阿拉善马先蒿（ＰｅｄｉｃｕｌａｒｉｓａｌａｓｃｈａｎｉｃａＭ...     

Secolridoids Glycosides from Jasminum amplexicaule

In addition to jaslanceosides B ( 1 ) and E ( 2 ), and jasminoside ( 3 ), a new secoiridoid glucoside, isojasminoside ( 4 ) was isolated from the leaves of Jasminum amplexicaule (Oleaceace). The structure of 4 was determined on the basis of spectral analysis and chemical reactions. Chemotaxonomy for some selected plants in Jasminum is also discussed.     

Phenylethyl Glycosides from Digitalis lanata

Three new phenylethyl glycosides, 3′′′′‐O‐methylmaxoside (=2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→6)]‐4‐O‐(E)‐feruloyl‐β‐D ‐glucopyranoside; 1 ), digilanatosides A (=2‐(3,4‐dihydroxyphenyl)ethyl O‐6‐O‐(E)‐sinapoyl‐β‐D ‐glucopyranosyl‐(1→3)‐4‐O‐(E)‐caffeoyl‐β‐D ‐glucopyranoside; 2 ), and digilanatoside B (=2‐(3,4‐dihydroxyphenyl)ethyl O‐6‐O‐(E)‐p‐coumaroyl‐β‐D ‐glucopyranosyl‐(1→3)‐4‐O‐(E)‐caffeoyl‐β‐D ‐glucopyranoside; 3 ) were isolated from the aerial parts of Digitalis lanata, along with two known phenylethyl glycosides, purpureaside A and maxoside, a phenylpropanoid glucose ester, 1‐O‐(E)‐feruloyl‐β‐glucopyranose, a benzoquinolethanoid glucoside, cornoside, a cardenolide, lanatoside C, a furostane‐type steroidal saponin, purpureagitoside, and a disaccharide, sucrose. Their structures were elucidated on the basis of spectroscopic evidence (1D‐ and 2D‐NMR, and HR‐MALDI‐MS).     

Iridoid Glycosides from Hedyotis corymbosa

Three new iridoid glycosides, hedycorysides A–C ( 1 – 3 , resp.), were isolated from the whole plant of Hedyotis corymbosa (Linn .) Lam ., along with four known compounds. Their structures were elucidated by extensive 1D‐ and 2D‐NMR analysis, as well as by HR‐ESI‐MS experiments. The three new compounds are the first benzoylated geniposide derivatives from Hedyotis.     

Secoiridoid Glycosides from Swertia mileensis

From the MeOH extract of the aerial parts of Swertia mileensis, four new secoiridoid glycosides were isolated, 4′‐O‐[(E)‐caffeoyl]swertiamarin ( 1 ), 4′‐O‐[(Z)‐coumaroyl]swertiamarin ( 7 ), 6′‐O‐[(E)‐coumaroyl]swertiamarin ( 8 ), and 6′‐O‐[(Z)‐coumaroyl]swertiamarin ( 9 ), together with five known compounds. Their structures were elucidated by NMR spectroscopy and tandem mass spectrometry. Detailed HPLC/MS analyses and MS/MS fragmentation pathways are discussed for the identification of the swertiamarin‐derived (E)/(Z) isomers 6 / 7 and 8 / 9 .