Two new glycosides from Leonurus japonicus

Two new glycosides, 1,6-di-O-syringoyl-β-d-glucopyranose (1) and quercetin 3-O-[(3-O-syringoyl-α-l-rhamnopyranosyl)-(1 → 6)-β-d-glucopyranoside] (2), along with seven known compounds were isolated from the MeOH extract of Leonurus japonicus. The structures of these compounds were elucidated by spectral analysis.     

Two new oleanane derivatives from the fruits of Leonurus japonicus and their cytotoxic activities

Two new oleanane derivatives, leonuronins A and B (1 and 2), along with three known oleanane triterpenes (3–5) were isolated from the fruits of Leonurus japonicus. Their structures were elucidated on the basis of NMR, MS, IR and UV spectroscopic data. The new compounds were tested for cytotoxic activities against A549 and Hela cancer cell lines. Compounds 1 and 2 exhibited weak cytotoxicity with IC₅₀ values ranging from 6.97 to 18.13 μM.

     

Two new furostanol glycosides from the fibrous root of Ophiopogon japonicus (Thunb.) Ker-Gawl

Two new furostanol glycosides, ophiopogonins H (1) and I (2), were isolated from the fibrous root of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside and (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-20α-hydroxyfurost-5,22-diene-3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside on the basis of spectroscopic means including HR-ESI-MS, 1D and 2D NMR experiments.     

Two new furostanol saponins from the fibrous root of Ophiopogon japonicus

Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-14-hydroxy-furost-5,20(22)-diene 3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1), and (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-furost-5,20(22)-diene 3-O-α-l-rhamnopyranosyl-(1 → 2)[(β-d-xylopyranosyl-(1 → 4)-β-d-glucopyranoside)] (2) on the basis of spectroscopic means including HRESIMS, 1D, and 2D NMR experiments.     

Triterpene saponins with α-glucosidase inhibition and cytotoxic activity from the leaves of Schefflera sessiliflora

From the leaves of Schefflera sessiliflora De P. V., two new triterpene saponins including one oleanane-type saponin, named scheffleraside C (1) and one lupane-type saponin scheffleraside D (2), together with six known triterpene saponins (3–8), were isolated by various chromatography methods. Among them, 3 was found for the first time from natural sources, while 6–8 were isolated for the first time from the genus Schefflera. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments, and comparison of their NMR data with previously reported data. Their α-glucosidase inhibition and cytotoxic activity against MCF-7 human breast cancer cell lines were evaluated. The isolates (1, 3–5, 8) showed stronger α-glucosidase inhibitory activity (IC₅₀ = 5.99–76.58 μM) than the standard drug acarbose (IC₅₀ = 214.50 μM). At the concentration of 100 μg/ml, the isolates (1, 2) showed appreciable cytotoxic activity (67.92, 63.83%, respectively).     

Isoflavanones from Desmodium oxyphyllum and their cytotoxicity

Two new isoflavanones, (3R)-7-hydroxy-4′-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R)-8-hydroxy-4′-methoxy-7-methoxycarbonyl-isoflavanone (2), together with seven known isoflavanones (3–9) were isolated from Desmodium oxyphyllum of the Leguminosae family. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compound 1 showed good cytotoxicity against NB4 and SHSY5Y cell lines with IC₅₀ values of 3.1 and 2.5 μM; compound 2 exhibited cytotoxicity against PC3 cell lines with a IC₅₀ value of 3.6 μM; compound 4 showed cytotoxicity against A549 and SHSY5Y cell lines with IC₅₀ values of 3.6 and 2.8 μM; and compound 5 displayed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 2.6, 3.8, and 2.8 μM, respectively. Other compounds also showed moderate cytotoxicity for some tested cell lines with IC₅₀ values between 5.4 and 8.8 μM.     

Three new diterpenoid alkaloids from the roots of Aconitum duclouxii

Three new C₁₉-diterpenoid alkaloids, ducloudines C (1), D (2), and E (3), were isolated from the roots of Aconitum duclouxii. Their structures were established on the basis of extensive spectroscopic analyses. Ducloudine C (1) is the first aconitine-type C₁₉-diterpenoid alkaloid with a C = O group at C-3 and a C = C bond between C-1 and C-2. All compounds were tested for their biological activities against one pathogenic fungi and two pathogenic bacteria.     

Cytotoxic prenylated xanthones from Calophyllum inophyllum

A new prenylated xanthone (1), named caloxanthone N, together with two known constituents, gerontoxanthone C (2) and 2-hydroxyxanthone (3), was isolated from the ethanolic extract of the twigs of Calophyllum inophyllum. Their structures were completely elucidated using a combination of 1D, 2D NMR techniques (COSY, HMQC, HMBC, and ROESY) and HR-ESI-MS analyses. Compounds 1 and 2 exhibited cytotoxicity against chronic myelogenous leukemia cell line (K562) with IC₅₀ values of 7.2 and 6.3 μg ml^? 1, respectively.     

Two new homoisoflavonoids from the fibrous roots of Ophiopogon japonicus (Thunb.) Ker-Gawl

Two new homoisoflavonoids ophiopogonone D (1) and ophiopogonanone G (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of these two compounds were determined on the basis of spectroscopic means including HR-ESI-MS, 1D, and 2D NMR experiments. The cytotoxic activities of 1 and 2 against Hela and Hep2 cells are described.     

Acylphloroglucinol derivatives from Decaspermum gracilentum and their antiradical and cytotoxic activities

Two new acylphloroglucinol derivatives, 1-(hexanoyl)phloroglucinol-α-d-arabinopyranoside (1) and 1-(hexanoyl)phloroglucinol-β-d-glucopyranoside (2), along with two known ones, 1-(acetyl)phloroglucinol-β-d-glucopyranoside (3) and ethyl 2,4,6-trihydroxybenzoate (4), were isolated from the EtOAc soluble fraction of EtOH extract of Decaspermum gracilentum. The structures of the new compounds were determined by extensive spectroscopic analyses including HRESIMS, 1D and 2D NMR data. Interestingly, all of the compounds showed ABTS^·+ radical scavenging activity with the IC₅₀ values less than 10 μM. Furthermore, compounds 3 and 4 displayed moderate cytotoxicity on human non-small-cell lung carcinoma cell line A549 (IC₅₀ = 50.9 μΜ) and human renal carcinoma cell line 786-O (IC₅₀ = 38.6 μΜ), respectively.     

A novel 3,4-dihydronaphthalen-1(2H)-one with spiro-butyrolactone and a new isocoumarin isolated from the endophytic fungus Phoma sp. YN02-P-3

A novel 3,4-dihydronaphthalen-1(2H)-one with spiro-butyrolactone phomol (1) and a new isocoumarin phomasatin (2), together with two known compounds (3–4) were isolated from the solid culture of the endophytic fungus Phoma sp. YN02-P-3. Their structures including the absolute configurations were characterized on the basis of extensive 1D, 2D NMR (HSQC, HMBC, NOESY), MS, and CD spectral data. Compound 1 showed selective cytotoxic activity against HL-60 cell line with the IC₅₀ value of 29.05 μM.     

Two new triterpenoid saponins from rhizome of Anemone amurensis

Two new triterpenoid saponins were isolated from the 70% ethanol extract of the rhizome of Anemone amurensis, they are oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1) and 23,27-dihydroxy oleanolic acid 3-O-α-l-arabinopyranoside (2). The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR data and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against three human cancer cell lines (A549, Hep-G2, and MCF-7). Compound 1 showed potent cytotoxicity with IC₅₀ values of 34.76, 41.17, and 28.92 μM, respectively, while compound 2 with IC₅₀>100 μM.     

Phorbol ester-type diterpenoids from the twigs and leaves of Croton tiglium

Phytochemical investigation of the ethanol extract from the twigs and leaves of Croton tiglium led to the isolation of two new phorbol esters (1–2) and seven known ones (3–9). Their structures were elucidated by the analyses of extensive spectroscopic data (IR, MS, and 1D and 2D NMR) and comparing with related compounds. Meanwhile, compounds 1–9 were determined for their cytotoxic activities on human lung cancer cell line A549. Among them, 1–2 were inactive against the cell line A549 (IC₅₀ > 100 μM), but compounds 3 and 7 showed weak activities.     

Lanostane triterpenoids and ergostane-type steroids from the cultured mycelia of Ganoderma capense

Abstract

Two new lanostane triterpenoids (1 and 2), two new ergostane-type steroids (3 and 4) together with two known lanostane triterpenoids (5 and 6) and one known steroid (7) were isolated from the cultured mycelia of Ganoderma capense (CGMCC 5.71). Their structures were determined on the basis of extensive spectroscopic (HRESIMS, 1D NMR, 2D NMR) data analyses. Compound 1 exhibited moderate cytotoxic activity against the human cancer cell line NCI-H1650 with an IC₅₀ value of 22.3 μM, and 7 displayed cytotoxic activity against the human cancer cell line HCT116 with an IC₅₀ value of 17.4 μM. In addition, compounds 2, 3, 5, and 6 displayed weak anti-HIV activity with IC₅₀ values of 23.5, 46.7, 21.6, and 30.1 μM, respectively.     

Two new steroidal glycosides from Cynanchum amplexicaule

Two new C₂₁ steroidal glycosides were isolated from the EtOAc fraction of Cynanchum amplexicaule. Their structures were elucidated as amplexicogenin d-3-O-β-d-cymaropyranoside (1) and stauntogenin -3-O-α-l-oleandropyranosyl-(1 → 4)-O-β-d-digitoxopyranosyl-(1 → 4)-O-β-d-oleandropyranoside (2) by spectroscopic analysis including 1D and 2D NMR experiments.     

Phenolic acid derivatives with neuroprotective effect from the aqueous extract of Clerodendranthus spicatus

Two new phenolic acid helisterculins C (1) and D (2) were isolated from the whole plant of Clerodendranthus spicatus. Their structures were elucidated on the basis of 1D and 2D NMR, MS, and CD analysis. Compound 1 possesses an unusual bicyclol [2. 2. 2] octane moiety which is rare in the previously isolated phenolic acid derivatives. The two compounds were tested in vitro for neuroprotective activities against 6-OHDA-induced cell death in SH-SY5Y cells, and the result showed that compounds 1 and 2 displayed moderate neuroprotective activity with the IC₅₀ values of 17.4 and 21.3 μM, respectively.     

Two new monoterpenes from Sibiraea laevigata

Two new monoterpenes, 3-(2-oxo-4-methyl-3-pentenyl)furan-5H-2-one (1) and 3-[(2E)-4-hydroxyl-4-methyl-2-pentenyl)]furan-5H-2-one (2), along with eight known compounds (3–10), were isolated from the stalks and infructescence of Sibiraea laevigata. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques. In addition, all of these isolates were evaluated for their cytotoxic and antioxidant activities. The results showed that compounds 5–7 displayed cytotoxicity with IC₅₀ values ranging from 34.8 to 43.2 μg ml^?1 against tumor cell lines. Furthermore, 5 and 9 showed antioxidant activities.     

Two pairs of rare naturally occurring 4-hydroxy-4-methyl-2,5-heptanedione derivatives from the red alga Chondria crassicaulis

Two pairs of rare naturally occurring racemic lipids, (±)-4,7-dihydroxy-4-methyl-2,5-heptanedione (1), and (±)-7-butoxy-4-hydroxy-4-methyl-2,5-heptanedione (2) were isolated from the red alga Chondria crassicaulis Harv. The structures of the racemic mixtures of 1 and 2 were elucidated by detailed spectroscopic techniques, including 1D and 2D NMR (¹H and ¹³C NMR, ¹H–¹H COSY, HSQC, and HMBC) as well as mass spectrometry and optical rotation experiments, and by comparison with data for related known analogs. This is the first report of naturally occurring 4-hydroxy-4-methyl-2,5-heptanedione derivatives. Antifungal, PTP1B inhibitory, and receptor tyrosine kinase inhibitory activities of these two compounds were investigated. The results showed that compounds 1 and 2 exhibited good selective inhibition against RET tyrosine kinase activity with IC₅₀ values of 9.56 and 8.93 μM, respectively. Compound 1 also displayed moderate antifungal activity against Cryptococcus neoformans (32609), showing a MIC₈₀ value of 32 μg/ml.     

Two new morphinane alkaloids from Sinomenium acutum

Two new morphinane alkaloids, 1-hydroxy-10-oxo-sinomenine (1) and 4,5-epoxy-14-hydroxy sinomenine N-oxide (2), have been isolated from the stems of Sinomenium acutum. Their structures were established by various spectral analyses, especially 2D NMR experiments. The structure of 2 was confirmed by single crystal X-ray diffraction. The absolute configurations of 1 and 2 were deduced by comparison of CD spectra with the known alkaloid sinomenine (3). Compound 1 was tested for DPPH inhibition and gave IC₅₀ of 27.9 μM. Compound 2 was tested for neuroprotective effect and showed significant activity against β-amyloid_25–35-induced oxidative injury (*P < 0.05) at 10 μM in PC-12 cells.     

A new thiophene and two new monoterpenoids from Xanthium sibiricum

Three new compounds (1–3), together with six known compounds (4–9), were isolated from the fruits of Xanthium sibiricum. The structures and the absolute configurations of sibiricumthionol (1), (+)-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [(+)-2], ( ? )-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [( ? )-2], (2E,4E,1′S, 2′R, 4′S, 6′R)-dihydrophaseic acid (3), (+)-xanthienopyran [(+)-4] and ( ? )-xanthienopyran [( ? )-4] were established by extensive spectroscopic analyses, X-ray crystallographic analysis, ECCD analysis and ECD calculations. Caffeic acid (7) and caffeic acid ethyl ester (8) weekly inhibited α-glucosidase enzymatic activity by 44.5% and 40.2%, respectively, at 40 μM. Protocatechuic acid (9) selectively exhibited cytotoxicity against HepG2 cell lines, with an IC₅₀ value of 2.92 μM.