A new ursane-type triterpene,cymosic acid from Rosa cymosa

A new ursane-type triterpene, cymosic acid (1) together with two known compounds, 3β,19α-dihydroxy-2-oxo-12-ursen-28-oic acid (2) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (3), were isolated from Rosa cymosa Tratt. The structure of compound 1 was elucidated by analyzing its ¹H and ¹³C NMR, ¹H–¹H COSY, HSQC, HMBC, NOESY, and HR-ESI-MS values. The three compounds were found to display moderate inhibitory activities against nitric oxide production in lipopolysaccharide-activated macrophage cell lines, RAW 264.7 cells.     

A new ganoderic acid from Ganoderma lucidum mycelia

A new ganoderic acid (GA), 7-O-ethyl ganoderic acid O (GA-O) (1), together with two known compounds, GA-T (2) and GA-Me (3), was isolated and purified from fermented mycelia of Ganoderma lucidum. The structure of the new triterpenoid was elucidated on the basis of the interpretation of extensive spectroscopic data (HR-MS, IR, UV, 1D and 2D NMR) as 3α,15α,22-triacetoxy-7α-ethoxy-5α-lanost-8,24E-dien-26-oic acid. The new compound was found to contain a rare ethoxyl group at C-7. In addition, its cytotoxicity against 95D and HeLa human cancer cell lines was also evaluated.     

Three new sesquiterpenes from Pterocarpus santalinus

Three new sesquiterpenes of canusesnol K (1), canusesnol L (2) and 12, 15-dihydroxycurcumene (3), along with five known ones (4–8), were isolated from the heartwood extract of Pterocarpus santalinus. Their structures were established by extensive analyses of 1D and 2D NMR spectroscopy, including ¹H NMR, ¹³C NMR, HSQC, HMBC and NOESY, and HRESI-MS. The absolute configurations of the new compounds were established with Modified Mosher’s method. The cytotoxic activities of all these compounds against HepG2 (human liver cancer), MCF-7 (human breast cancer), MDA-MB-231 (human breast cancer), and Hela (human cervical carcinoma) cancer cell lines were evaluated. Compound 1 exhibited moderate cytotoxic activity toward MDA-MB-231 cell lines.     

Ergostane steroids from the ethanol extract of Dysoxylum mollissimum

Three new ergostane steroids, 7α-acetoxyl-ergosta-5,24(28)-diene-3β,4β,20S-triol (1), 7α-acetoxyl-ergosta-5,24(28)-diene-3β,4β-diol (2), and 7α-acetoxyl-ergosta-5,24(28)-3β-ol (3) were isolated from the ethanol extract of stem bark of Dysoxylum mollissimum BI. Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (¹H-¹H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. All the isolated steroids were in vitro evaluated for their anti-inflammatory activity against COX-1 and COX-2. As a result, steroids 1–3 exhibited modest selective inhibition for COX-1 (>60%).     

Two new flavonol glycosides from the leaves of Cleome chelidonii L.f.

From the leaves of Cleome chelidonii L.f., two new flavonol glycosides, named cleomesides A (1) and B (2), and four known compounds, quercetin 3-O-β-glucopyranosyl(1 → 2)-α-rhamnoside-7-O-α-rhamnoside (3), ethyl α-galactopyranoside (4), adenine (5) and glycerol monostearate (6), were isolated. The structures of all isolated compounds (1–6) were determined by NMR spectroscopy and mass spectrometry. The data of known compounds (3–6) were further compared with the reported data for these compounds.     

C28 sterols with a cyclopentane ring at C-22 and 26 from cape gooseberry (berries of Physalis pubeacens L.)

Two new C₂₈ sterols with a cyclopentane ring at C-22 and 26, alkesterol A (1) and alkesterol B (2), along with β-sitosterol (3), were isolated from the berries of Physalis pubeacens L. (cape gooseberry). The structures of the new compounds were established by HR-EI-MS, 1D and 2D (¹H–¹H COSY, HSQC, HMBC) NMR experiments. The known compound was identified by comparison of spectral data with published references. The two new compounds showed some cytotoxic activities by MTT assay.     

Two new compounds from Bombyx batryticatus

Two new compounds beauvericins M1 (1) and S1 (2) were isolated from Bombyx batryticatus. Their structures were established as (3α,6α)-3-benzyl-6-secbutyl-4-methylmorpholine-2,5-dione (1) and (5α,8α)-epidioxyergosterol-24-one-6,22-dien-3β-ol (2) by various spectroscopic techniques including 1D NMR (¹H NMR and ¹³C NMR), 2D NMR (HSQC, HMBC, ¹H–¹H COSY, NOESY), and HR-ESI-TOF-MS.     

Diterpenoids from the freshwater green algae Rhizoclonium hieroglyphicum with antibacterial activity

Three new isopimarane diterpenes 7β-hydroxy-19α-methylmalonyloxy-isopimara-8(14),15-diene (1), 7β-hydroxy-14-oxo-isopimara-8(9),15-dien-19oic acid (2), and 7β-hydroxy-14-oxo-19α-methylmalonyloxy-isopimara-9(11),15-diene (3) in addition to the known compounds isopimaric acid (4), 7oxo-13-epi-pimara-14,15-dien-18oic acid (5), 7oxo-13-epi-pimara-8,15-dien-18oic acid (6), and 6β-hydroxyisopimaric acid (7) were isolated from the hexane extract of Rhizoclonium hieroglyphicum. The structures of compounds 1–7 were established by 1D and 2D NMR techniques. The isolated diterpenoids were screened for antimicrobial activity against gram-positive and gram-negative bacteria and yeast strains.     

Four new minor taxanes from cell cultures of Taxus chinensis

Four new minor taxanes (1–4) have been isolated from Ts-19 cell cultures of Taxus chinensis together with five known taxanes (5–9) by silica gel chromatography combined with semi-preparative HPLC chromatography. On the basis of the analyses of the chemical and spectroscopic (IR, MS, 1D, and 2D NMR) data, the structures of new compounds were elucidated as 5α-hydroxy-2α,10β-diacetoxy-14β-(3-hydroxy-2-methyl-butyryl)oxytaxa-4(20),11-diene (1), 2α,5α,10β-triacetoxy-14β-(2-hydroxy-propionyl)oxytaxa-4(20),11-diene (2), 2α,5α,10β-triacetoxy-14β-(2-hydroxy-3-methyl-butyryl)oxytaxa-4(20),11-diene (3), and 2α-benzoxy-4α,9α,10β,13α-tetraacetoxytax-11-ene (4), respectively. Compounds 1–5 were pharmacologically evaluated for their cytotoxicities against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) and their reversing activity towards multi-drug resistance A549/taxol tumor cell line, and the results showed that all of the tested compounds exhibited very low cytotoxicities, while compound 4 possessed twice the reversing activity as that of verapamil at 10 μM.     

Polyanthumin,a novel cyclobutane chalcone trimmer from Memecylon polyanthum

A novel unusual trimmer chalcone, polyanthumin (1), together with five known compounds myricetin 3-O-(3″-O-galloyl)-α-l-rhamnopyranoside (2), sulfuretin (3), fustin (4), gallic acid (5), and ethyl gallate (6), was isolated from the dry stems of Memecylon polyanthum H.L. Li. Among them, compound 1 is a new chalcone trimmer with a novel cyclobutane skeleton in nature. Compounds 3 and 4 are flavonoids carrying a single 7-OH in A ring, which provided the first example of these class flavonoids from the family Melastomataceae. In addition, the antitumor activities for 2–4 were reported for the first time in this study. The antitumor effects of the isolated compounds 1–6in vitro were assayed by the SRB method using human cancer K562 cells, with the inhibition rates ranging from 39.4% to 54.5% at 100 μg/ml. The IC₅₀ values of compounds 1 and 3 for the inhibition of K562 cell proliferation were determined to be 45.4 and 30.5 μg/ml, respectively. To the best of our knowledge, compound 1 was the second sample as chalcone trimer. In addition, the antitumor activities for 2–4 were reported for the first time in this study.     

Limonoid constituents of Euodia rutaecarpa var. bodinieri and their inhibition on NO production in lipopolysaccharide-activated RAW264.7 macrophages

A new limonoid compound, named evorubodinin (1), was isolated from the dried and nearly ripe fruits of Euodia rutaecarpa (Juss.) Benth. var. bodinieri (Dode) Huang (family Rutaceae), together with two known limonoid compounds, limonin (2) and evolimorutanin (3). The chemical structure of 1 was elucidated by spectroscopic method and single-crystal X-ray diffraction. The inhibitory effects of the isolated compounds 1–3 and the structurally related compounds evodol (4), shihulimonin A1 (5), evodirutaenin (6), 12α-hydroxyrutaevin (7), and rutaevin (8) on nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 macrophages were also assayed. All compounds 1–8 showed the inhibitory activity, in which both 7 and 8 with the uncommon 5β-H configuration more efficiently inhibited NO production. The results provided valuable information for further investigation of compounds 1–8 as anti-inflammatory agents or lead compounds.     

Two new phenylpropanoids and one new sesquiterpenoid from the bioactive fraction of Sambucus williamsii

Two new phenylpropanoids, samwirin (1) and samwiphenol (2), and a new sesquiterpenoid, 2β,4β,10α-trihydroxy-1αH,5βH-guaia-6-ene (3), together with six known compounds were isolated from the bioactive fraction of Sambucus williamsii Hance. Their structures including the absolute configurations were characterized on the basis of extensive 1D, 2D-NMR, MS, and CD spectral data. In vitro proliferation effects of all compounds on osteoblast-like UMR 106 cells were examined. Compounds 1, 4–9 significantly promoted cell proliferation. Compounds 5, 6, and 8 increased osteoblastic cell numbers separately by 24.3%, 25.2%, and 29.1% at 10^–10 M, 10^–10 M, and 10^–8 M, respectively.     

New diterpenoids from Semiaquilegia adoxoides

Two new ent-kaurane-type diterpenoids, E-semiaquilegin (1) and Z-semiaquilegin (2), together with eight known compounds (3–10) were isolated from the dried roots of Semiaquilegia adoxoides (DC.) Makino. The structures of compounds 1 and 2 were elucidated mainly by 2D NMR techniques including ¹H–¹H COSY, HSQC, HMBC, NOESY as 16α-hydroxy-ent-kaurane-17,20-di-(3,4-dihydroxy-E-cinnamoyl) ester and its (Z)-isomer.     

Three minor valepotriate isomers from Valeriana jatamansi and their cytotoxicity

Three new minor valepotriate isomers, jatamanvaltrates Z1 (1), Z2 (2), and Z3 (3), have been isolated from the whole plants of Valeriana jatamansi (syn. Valeriana wallichii.). Their structures were elucidated by extensive spectroscopic analysis, especially 2D NMR and ESI-MS/MSⁿ. All isolated compounds displayed moderate cytotoxicity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC-3 M), colon cancer (HCT-8), and hepatoma (Bel7402) cell lines with IC₅₀ values of 2.8–8.3 μM.     

Feruhermonins A–C: three daucane esters from the seeds of Ferula hermonis (Apiaceae)

Seventeen daucane esters have been isolated from the seeds of Ferula hermonis Boiss (Apiaceae). Three of these sesquiterpenes, 4β-hydroxy-6α-benzoyl-7-daucen-9-one (1), 4β, 8β-dihydroxy-6α-benzoyl-dauc-9-ene (2), and 4β, 9α-dihydroxy-6α-benzoyl-dauc-7-ene (4), named feruhermonins A–C, respectively, are novel natural products. The structures of these compounds were elucidated unequivocally by a series of 1D and 2D NMR analyses. Although 4β, 8β-dihydroxy-6α-(4-hydroxy-3-methoxybenzoyl)-dauc-9-ene (3) was reported previously, the complete spectroscopic data for this compound are presented here for the first time.     

New cycloartanes and new iridoids from Dolichandrone spathacea collected in the mangrove forest of Soc Trang province,Vietnam

Abstract

Two new cycloartanes, named dolichandrone A (1) and dolichandrone B (2), as well as two new iridoids, named [6-O-[(E)-4-methoxycinnamoyl]-1β-hydroxy-dihydrocatalpolgenin (3) and 6-O-[(E)-4-methoxycinnamoyl]-1α-hydroxy-dihydrocatalpolgenin (4), together with four known iridoids (5–8), were isolated from the leaves and barks of Dolichandrone spathacea. Their structures were elucidated by means of extensive analysis of their HRESIMS, 1D and 2D NMR spectroscopic data. All of these compounds have been isolated for the first time from this plant. Compounds 1, 2, 5, and 7 were evaluated for their cytotoxic activity in vitro against four human cancer cell lines KB, Lu, HepG2, and MCF7. The results showed that only compound 2 exhibited a good cytotoxicity against KB cell line with IC₅₀ of 18.77 μM.     

Antioxidant and α-amylase inhibitory activities of extract and isolates from Zygogynum pancheri subsp. arrhantum

One new sesquiterpenoid (5R^*,8R^*,9R^*,10R^*)-cinnamolide (8), and seven known compounds, 5-hydroxy-7-methoxyflavonone (1), 8-hydroxy-3-(4′-hydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (2), 8-hydroxy-3-(3′,4′-dihydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (3), 1β-E-O-p-methoxycinnamoyl-bemadienolide (4), 1β-O-(E-cinnamoyl)-6α-hydroxy-9-epi-polygodial (5), 1β-O-(E-cinnamoyl)-6α-hydroxypolygodial (6), and 1β-O-E-cinnamoylpolygodial (7) were isolated from the ethyl acetate extract of barks of Zygogynum pancheri subsp. arrhantum (Winteraceae). The structures of these molecules were assigned predominantly based on spectral data. The structure of compound 8 was confirmed by X-ray crystallographic analysis. Compounds 2 and 3 exhibited significant antioxidant activity, whereas compounds 1 and 4–7 showed significant α-amylase inhibitory activity.     

Two new casbane diterpenoids from the roots of Euphorbia pekinensis

From the roots of Euphorbia pekinensis, two new casbane diterpenoids, named pekinenins A (1) and B (2), were isolated. Their structures were elucidated as 18-hydroxy-1βH,2αH-casba-3E,7E,11E-trien-5-one (1), 5α-methoxy-1βH,2αH-casba-3Z,7E,11E-trien-18-oic acid (2) by a combination of 1D and 2D NMR spectroscopy and mass spectrometry. In the cytotoxicity assay of the two new compounds against Hela, MCF-7, and C6 human cancer cell lines, compound 1 showed moderate cytotoxic activity against two human cancer cell lines, Hela and C6, with IC₅₀ values of 42.97 and 50.00 μM, respectively.     

Triterpenoids from the stems of Schisandra grandiflora and their biological activity

One new ursane-type triterpenoid (1), named granditriol, along with 14 known compounds (2–15), was isolated from the organic extracts of Schisandra grandiflora stems. The structure of the new compound was elucidated by extensive spectroscopic methods as 28-norursa-12,17,19,21-tetraen-2α,3α,23-triol. These isolates were evaluated for anti-phytopathogenic fungi activity and cytotoxicity against human cancer cell line (HepG2). Asiatic acid (8) and 2α,3α,19α-trihydroxyurs-12-en-28-oic acid (9) inhibited the growth of two plant pathogens, Alternaria alternata and Alternaria solani. In addition, compounds 12, 15, and 11 displayed notable anti-proliferative activity against HepG2 cells. Compound 1 is the first report of 28-nortriterpenoid from the Schisandraceae family. All these were obtained from this plant for the first time.     

Several chromones from the stems of Polygonum aubertii Henry

Two new 2-alkylchromanones, 2-tricosyl-2,5,7-trihydroxy-chromanone (6) and 2-pentacosyl-2,5,7-trihydroxy-chromanone (7), together with five known 2-alkylated chromones and chromanones (1–5), were isolated from the stems of Polygonum aubertii Henry. The structures of these compounds were established by spectroscopic methods including extensive 1D, 2D NMR (¹H-¹H COSY, HSQC, and HMBC), and HR-ESI-MS techniques. In addition, a plausible biosynthetic pathway for these compounds is described.