Carapanolides C–I from the seeds of andiroba (Carapa guianensis,Meliaceae)

Five new mexicanolide-type limonoids, carapanolides C–G (1–5), together with two new phragmalin-type limonoids, carapanolides H–I (6, 7), were isolated from the oil of Carapa guianasis AUBLET (Meliaceae) seeds. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Carapanolides C (1), E (3), and I (7) exhibited moderate activity in the P388 (IC₅₀ 17.9 μM in 1, 15.8 μM in 3) and L1210 cell lines (IC₅₀ 13.3 μM in 1, 18.1 μM in 3, 16.9 μM in 7). On the other hand, Carapanolide D (2) exhibited a strong inhibitory effect in the HL-60 cell line (IC₅₀ 11.0 μM), Carapanolides F (4) showed inhibitory activity in the L1210 cell line (IC₅₀ 15.9 μM), and the cytotoxic activity of Carapanolides I (7) was moderate in all cell lines.     

Chemical constituents of Swertia yunnanensis and their anti-hepatitis B virus activity

Four new triterpenoids, sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4), along with nineteen known compounds (5–23) were isolated from Swertia yunnanensis. Based on extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, IR, [α]_D), the structures of sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4) were elucidated as taraxer-14-ene-3α,6β-diol, oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranoside, 2α,3β-di-hydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl (1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside and hederagenin 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside, respectively. Twenty-two compounds were evaluated for their anti-HBV activities on the HepG 2.2.15 cell line in vitro, of which nine compounds showed potent anti-HBV activities. Compounds 1, 5–6, 14–16 and 19 showed activities against the secretion of HBsAg (IC₅₀ values from 0.10 to 1.76 mM) and HBeAg (IC₅₀ values from 0.04 to 1.41 mM), and compounds 11 and 13–16 exhibited significant inhibition on HBV DNA replication (IC₅₀ values from 0.01 to 0.09 mM).     

Desmodeleganine,a new alkaloid from the leaves of Desmodium elegans as a potential monoamine oxidase inhibitor

Desmodeleganine (1), a new potential monoamine oxidase inhibitor, along with three known alkaloids, bufotenin (2), hydroxy-N, N-dimethyltryptamine N¹²-oxide (3), 2-(5-methoxy-1H-indol-3-yl)-N, and N-dimethylethylamine (4) were isolated from the leaves of Desmodium elegans. Their structures were elucidated by IR, MS, 1D and 2D NMR spectra. 1 showed strong monoamine oxidase inhibitory activity with IC₅₀ value of 13.92 ± 1.5 μM, when the IC₅₀ value of iproniazid as a standard was 6.5 ± 0.5 μM. The molecular modeling was also performed to explore the binding mode of compounds 1, 2 at the active site of MAO-A and MAO-B.     

Sesquiterpene coumarin and sesquiterpene chromone derivatives from Ferula ferulaeoides (Steud.) Korov.

Five novel compounds — three sesquiterpene coumarin derivatives, ferulin A (1), B (2), and C (3), and two sesquiterpene chromone derivatives, ferulin D (4) and E (5), together with eleven known compounds (6–16) have been isolated from the roots of Ferula ferulaeoides (Steud.) Korov. Their structures were established by comprehensive spectroscopic analysis. The biosynthetic pathways leading to these compounds were proposed. The cytotoxicity of all these isolates against HepG2, MCF-7, and C6 cancer cell lines was evaluated and compound 7 displayed the highest potency against HepG2, MCF-7, and C6 with IC₅₀ values 39.9 μM, 37.7 μM, and 16.0 μM, respectively.     

Japonicasins A and B,two new isoprenylated flavanones from Sophora japonica

Two new flavanones with a C₁₅ isoprenoid group, japonicasins A and B (1 and 2), were isolated from the leaves of Sophora japonica. This is the first report on the presence of the (2E,7E)-6-isopropyl-3,9-dimethyldeca-2,7,9-trien-1-yl group (C₁₅ isoprenoid group) in isoprenylated flavonoids. Their structures were determined by spectroscopic methods, including UV, IR, 1D and 2D NMR, HRESIMS, and CD experiments. In addition, the antioxidant activities of compounds 1 and 2 were determined through DPPH radical scavenging assays. They exhibited potential antioxidant activities, with IC₅₀ values of 35.1 ± 0.8 μM and 88.7 ± 1.1 μM for compounds 1 and 2, respectively.     

Cycloartane Triterpenes from Beesia calthaefolia (Maxim.)

Three new cycloartane triterpenoids (1–3) and two known compounds (4, 5) were isolated from the whole plant of Beesia calthaefolia. Their structures were elucidated by 1D and 2D NMR, HRESIMS and optical rotation spectral data. All isolates were investigated for their inhibitory effects on the classical pathway of the complement system. Among them, compound 4 showed stronger inhibitory activity (IC₅₀ 136.7 μM) than positive control (Rosmarinic acid, IC₅₀ 181.8 μM) while compounds 2 and 3 were moderately active with IC₅₀ value of 206 μM and 200.9 μM. Chemical compound studied in this article: Rosmarinic acid (PubChem CID: 5281792).     

Phenylethanoid glycosides from the stems of Callicarpa peii (hemostatic drug)

Two new trisaccharide intermediates of phenylethanoid glycosides, peiioside A₁/A₂ (1a/1b) and peiioside B (2), were isolated from the n-BuOH fraction of MeOH extract of the stems of Callicarpa peii H.T. Chang, together with five biogenetic relevant known compounds 3–7. The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques) and acid-catalyzed hydrolysis as O-α-l-rhamnopyranosyl-(1″ → 3′)-O-[β-d-apiofuranosyl-(1‴ → 6′)] -4′-O-[(E)-caffeoyl]-d-glucopyranoside] (1a/1b), 3,4-dihydroxy-β-phenylethoxy-O-[β-d-apiofuranosyl-(1‴ → 6′)-α-l-rhamnopyranosyl-(1″ → 3′)-O-β-d-glucopyranoside] (2), respectively. On the basis of the isolated compounds, a presumable biogenetic pathway of the biologically interesting phenylethanoid glycosides about forsythoside B (3) and acteoside (4) isolated from this species was proposed. Isolation of five related intermediates (1–2, 5–7) provided further support for the biogenetic path. This is the first report about phytochemical research on C. peii and the biogenetic hypothesis of forsythoside B and acteoside.     

Xanthine oxidase inhibitory lanostanoids from Ganoderma tsugae

Two new lanostanoids, 3α-acetoxy-22-oxo-5α-lanosta-8,24-dien-21-oic acid, named tsugaric acid D (1) and 16α-hydroxy-3-oxo-5α-lanosta-6,8,24(24¹)-trien-21-oic acid, named tsugaric acid E (2) were isolated from the fruit bodies of Ganoderma tsugae. The structures 1 and 2 were determined by spectroscopic methods. Compound 1 and known compounds 3 and 6 exhibited significant inhibitory effects on xanthine oxidase (XO) activity with an IC₅₀ values of 90.2 ± 24.2, 116.1 ± 3.0, and 181.9 ± 5.8 μM, respectively. Known compound 5 was able to protect human keratinocytes against damage induced by UVB light, which showed 5 could protect keratinocytes from photodamage. The 1 and 5 μM 1 combined with 5 μM cisplatin, respectively, enhanced the cytotoxicity induced by cisplatin. It suggested that 1 and 5 μM 1 combined with low dose of cisplatin may enhance the therapeutic efficacy of cisplatin and reduce side effect and cisplatin resistant.     

Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris

Three new polyacetylenes, 8-(Z)-decene-4, 6-diyne-1, 3, 10-triol (1), 1, 3S, 8S-trihydroxydec-9-en-4, 6-yne (2), 3S, 8S-dihydroxydec-9-en-4, 6-yne 1-O-β -D-glucopyranoside (3), and one new glucosyl caffeoate, 1-O-ethyl-6-O-caffeoyl-β -D-glucopyranose (4), together with 34 known compounds were isolated from Artemisia capillaris. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, [α]_D and CD experiments. Among them, 19 compounds showed activity inhibiting HBsAg secretion; 20 compounds showed activity inhibiting HBeAg secretion; and 25 compounds possessed inhibitory activity against HBV DNA replication according to our anti-HBV assay on HepG 2.2.15 cell line in vitro. The most active compound 12 could inhibit not only the secretions of HBsAg and HBeAg, but also HBV DNA replication with IC₅₀ values of 15.02 μM (SI = 111.3), 9.00 μM (SI = 185.9) and 12.01 μM (SI = 139.2).     

Cytotoxic steroidal glycosides from Allium flavum

Three new spirostane-type glycosides (1–3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-xylopyranosyl-(1 → 3)-[β-d-galactopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→4)-β-d-galactopyranoside (1), (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-xylopyranosyl-(1 → 3)-[β-d-glucopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→4)-β-d-galactopyranoside (2), and (20S,25R)-spirost-5-en-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480).     

Triterpenoids of Ganoderma theaecolum and their hepatoprotective activities

Five new lanostane triterpenoids, ganoderic acid XL₁ (1), ganoderic acid XL₂ (2), 20-hydroxy-ganoderic acid AM₁ (3), ganoderenic acid AM₁ (4) and ganoderesin C (5), together with five known triterpenoids (6–10) were isolated from the fruiting bodies of Ganoderma theaecolum. Chemical structures were elucidated on the basis of spectroscopic evidence, including 1D, 2D NMR, mass spectrometric data and circular dichroism spectra. Compounds 1, 4, 5, 8, 9 and 10 (10 μM) exhibited hepatoprotective activities against DL-galactosamine-induced cell damage in HL-7702 cells.     

Cytotoxic biflavones from Stellera chamaejasme

Bioassay-guided phytochemical studies on Stellera chamaejasme led to the isolation of two new biflavones, chamaejasmenin E (1) and chamaejasmin D (2), together with ten known compounds. The structures of new compounds were elucidated by extensive spectroscopic analyses and their absolute configurations on 2, 3, 2″ and 3″ were confirmed by TDDFT quantum chemical calculated ECD spectra combined with experimental ECD spectra. All isolated biflavones were evaluated for their cytotoxic activities against Bel-7402 and A549 tumor cell lines, and sikokianin D (3) was found to possess the most potential cytotoxic activities against both the two cell lines with IC₅₀ values of 1.29 ± 0.21 and 0.75 ± 0.25 μM, respectively. Moreover, some structure–function relationships of these bioflavones for cytotoxic activities were explored and summarized.     

A novel hepatoprotective saponin from Celosia cristata L.

A new saponin, cristatain (1), together with four other saponins, celosin A (2), celosin B (3), celosin C (4) and celosin D (5) were isolated from the seeds of Celosia cristata L. (Amaranthaceae). Their structures were established by chemical and spectroscopic analyses. For the first time, the saponins were found in C. cristata L. In addition, compound 1 exhibited significant hepatoprotective effect on carbon tetrachloride (CCl₄)- and N,N-dimethylformamide (DMF)–induced hepatotoxicity in mice, which were evidenced by significant decreases in the values of asparate aminotransferase (AST), alanine aminotransferase (ALT) and alkaline phosphatase (ALP) of serum and histopathological examinations compared to controls.     

Isolation,characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia

Two new alkaloids, named stenine A (1) and stenine B (2), along with the known compounds neostenine (3), stenine (4) and neotuberostemonine (5), were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1D- and 2D-NMR spectra and X-ray single-crystal diffraction experiment. Anti-acetylcholinesterase (AChE) activity of compounds 1–5 were also tested. Compounds 2 and 4 showed significant anti-acetylcholinesterase activities, with IC₅₀ values of 2.1 ± 0.2 μM and 19.8 ± 2.5 μM, resp. The mode of AChE inhibition by Compound 2 (the most potential AChE inhibitor) was reversible and competitive. In addition, molecular modeling was performed to explore the binding mode of compound 2 with AChE.     

Andirolides Q–V from the flower of andiroba (Carapa guianensis,Meliaceae)

Two new gedunins, an andirobin, two mexicanolides, and a phragmalin-type limonoid, named Andirolides Q (1), R (2), S (3), T (4), U (5), and V (6), were isolated from an oil of the flower of Carapa guianensis AUBLET (Meliaceae). Their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Andirolide S (3) and Andirolide T (4) showed significant cytotoxic activity against the murine P388 leukemia cell line (IC₅₀ of 1.4 μM for 3; 1.8 μM for 4) and the human HL-60 leukemia cell line (IC₅₀ of 1.3 μM for 3 and 4).     

Five new triterpenoidal saponins from the roots of Ilex cornuta and their protective effects against H2O2-induced cardiomyocytes injury

Five new ursane-type triterpenoidal saponins (1–5), together with five known ones (6–10), were isolated from the EtOH extract of the roots of Ilex cornuta. The structures of saponins 1–5 were elucidated as 19α-hydroxyurs-12-en-28-oic acid 3β-O-β-D-glucuronopyranoside (1), 19α-hydroxyurs-12-en-28-oic acid 3β-O-β-D-glucuronopyranoside-6-O-ethyl ester (2), 19α-hydroxyurs-12-en-28-oic acid 3β-O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranoside (3), 3β-O-[α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranosyl]-19α-hydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (4) and 3β-O-[α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranoside-6-O-methyl ester]-19α-hydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (5), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and chemical reactions. Protective effects of compounds 1–10 against H₂O₂-induced H9c2 cardiomyocyte injury were tested. Compounds 1–5, 7, and 10 showed cell-protective effects. Among them compound 5 exhibited the highest activity. No significant DPPH radical scavenging activity was observed for compounds 1–10.     

New α-glucosidase inhibitors with p-terphenyl skeleton from the mushroom Hydnellum concrescens

The purpose of this study is to elucidate the bioactive components responsible for the the α-glucosidase inhibitory activity detected in the EtOAc extract of the mushroom Hydnellum concrescens. Two new p-terphenyl derivatives, concrescenins A (1) and B (2), in along with six known compounds thelephantins L (3), I (4), J (5), K (6), dihydroauran-tiacin dibenzoate (7), and curtisian A (8) were isolated from the fruiting bodies of H. concrescens. Their chemical structures were elucidated by NMR experiments. Compounds 1–4 and 6–8 showed the inhibitory activity against α-glucosidase with the IC₅₀ of 0.99, 3.11, 4.53, 18.77, 2.98, 5.16, and 8.34 μM, respectively. Kinetic analysis of α-glucosidase indicated that compounds 1 and 2 inhibited the activity of α-glucosidase in a noncompetitive fashion with a Ki value of 0.02 and 0.21 μM, respectively. In antioxidant evaluation, compounds 1 and 4 showed weak DPPH scavenging activity (EC₅₀ = 82.50 and 161.75 μM) and weak reducing ability (EC₅₀ = 193.57 and 152.94 μM). The current research supports the potential use of mushroom-derived p-terphenyl derivatives for the treatment of diabetes.     

Cyclodepsipeptides from the ascocarps and insect-body portions of fungus Cordyceps cicadae

A new cyclodepsipeptide cordycecin A (1), together with four known ones beauvericin E (2), beauvericin J (3), beauvericin (4), and beauvericin A (5) was isolated from the ascocarps and insect-body portions of fungus Cordyceps cicadae. Their structures were identified by NMR and MS analyses. The absolute configuration of 1 was confirmed by crystal X-ray diffraction. Compounds 2–5 exhibited a significant inhibitory effect on HepG2 and HepG2/ADM cells with IC₅₀ values ranging from 2.40 ± 0.37 to 14.48 ± 1.68 μM. Interestingly, compounds 3–5 showed cytotoxic activity against multiple drug resistant HepG2 cell line (HepG2/ADM) with IC₅₀ value 25-fold more sensitive to doxorubicin.     

Cleistanthane diterpenes from the seed of Caesalpinia sappan and their antiausterity activity against PANC-1 human pancreatic cancer cell line

Three new cleistanthane diterpenes named tomocinon (1), tomocinol A (2), and tomocinol B (3), were isolated from the EtOAc extract of the seed of Caesalpinia sappan. Their structures were determined by extensive NMR spectroscopic analysis. The absolute stereochemistry of tomocinon (1) has been established by CD spectroscopic analysis. Cleistanthane diterpenes (1–3) represents the novel class of antiausterity agents having preferential cytotoxicity against PANC-1 human pancreatic cancer cell line under nutrient deprived condition with PC₅₀ value of 34.7 μM, 42.4 μM and 39.4 μM, respectively.     

Four new C18-diterpenoid alkaloids with analgesic activity from Aconitum weixiense

Four new C₁₈-diterpenoid alkaloids, weisaconitines A–D (1–4), were isolated from Aconitum weixiense. Based on extensive UV, IR, MS, 1D and 2D NMR analyses, their structures were elucidated as 8-O-ethyldolaconine (1), 4-demethylgenicunine B (2), 14-oxoaconosine (3), and 8-O-ethylaconosine (4). The analgesic activity of compound 4 was studied with CH₃COOH-induced writhing model in mice. Compound 4 showed writhing inhibitions of 24% (50 mg/kg), 26% (100 mg/kg) and 34% (200 mg/kg), respectively, as compared to the reference drug aspirin (63%) at a dose of 200 mg/kg.