A new triterpenoid from Azadirachta indica

A new triterpenoid, 1α,7α-diacetoxyapotirucall-14-ene-3α,21,22,24,25-pentaol (1), and the two known compounds odoratone (2) and 2β,3β,4β-trihydroxypregnan-16-one (3) were isolated from a methanolic extract of the seed kernels of Azadirachta indica. Their structures were elucidated on the basis of spectral methods.     

Two new furostanol saponins from Tribulus terrestris L.

Two new furostanol glycosides, named tribufurosides I (1) J (2), were isolated from the fruits of Tribulus terrestris L. by a combination of chemical and spectroscopic methods. Its structures were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl (1 → 4)-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5α-furost-20(22)-en-12-one-2α,3β,26-triol-3-O-β-d-glucopyranosyl (1 → 4)-β-d-galactopyranoside (2).     

Cycloartane saponins from Astragalus peregrinus as modulators of lymphocyte proliferation

From Astragalus peregrinus, four cycloartane-type saponins have been isolated and their structures elucidated by spectral means as 20(R),24(S)-epoxy-9β,19-cyclolanostane-3β,6α,16β,25-tetrol 3-O-β- -glucopyranoside (1), 20(R),24(S)-epoxy-9β,19-cyclolanostane-3β,6α,16β,25-tetrol 3-O-α- -rhamnopyranosyl-(1→4)-β- -glucopyranoside (2), 20(R),24(S)-epoxy-9β,19-cyclolanostane-3β,6α,16β,25-tetrol 3-O-α- -rhamnopyranosyl-(1→2)-β- -glucopyranoside (3) and 20(R),25-epoxy-9β,19-cyclolanostane-3β,6α,16β,24(S)-tetrol (24-O-acetyl)- 3-O-α- -rhamnopyranosyl-(1→2)-(6′-O-acetyl)-β- -glucopyranoside (4). Compounds 2 and 3 showed to stimulate the proliferation of mouse splenocytes and were not significantly cytotoxic.     

New clerodane diterpenoids from Casearia sylvestris

Two new clerodane diterpenoids 2β-methoxy-cleroda-3,13-dien-18-carboxy-15,16-olide (1) and 15ξ-methoxy-cleroda-3,12-dien-18-carboxy-15,16-olide (2) and one new nitrogen-containing clerodane diterpenoid 15-oxo-echinophyllin A (3), along with six known compounds, namely, echinophyllin A, (−)-patagonic acid, tyrosol, oplopanone, 4-hydroxy-4-methyl-2-[(1R)-1-(1-methylethyl)-4-oxopentyl]-2-cyclohexen-1-one and 1β,6α-dihydroxy-eudesman-4(15)-ene were isolated from the leaves of Casearia sylvestris. Their structures were determined by extensive NMR techniques.     

Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma

Phytochemical investigation of the stem bark of Terminalia mollis afforded friedelin (1), catechin with epicatechin (2), gallocatechin with epigallocatechin (3) and 3-O-methylellagic acid 4'-O-α-rhamnopyranoside (4). Arjunolic acid with 2α, 3β, 23-trihydroxy-urs-12-en-28-oic acid (5), 2α-hydroxyursolic acid (6), gallic acid (7), chebulanin (8) and 2'-O-galloylvitexin (9) were isolated from the leaf. Chebulanin (8), betulinic acid (10), ursolic acid (11), catechin (12), isoorientin (13), orientin (14), isovitexin (15) and punicalagin (16) were isolated from Terminalia brachystemma leaf. The first full unambiguous NMR assignments for (4) and (8), and revised assignments for (9), are reported. Compound (16) showed good activity against three Candida species.     

A new ent-kaurane diterpenoid from Rabdosia pseudo-irrorata

A new kaurenoid, ent-3β,7α,14β-trihydroxykaur-16-ene-12,15-dione (1), named pseurata G, was isolated from the ethanol extract of the whole plant of Rabdosia pseudo-irrorata.     

In vivo hypoglycemic effects of phenolics from the root bark of Morus alba

Moracin M (1), Steppogenin-4′-O-β-D-glucosiade (2), Mullberroside A (3) were isolated from the root bark of Morus alba L. and identified by spectral evidence. Compounds 1, 2 and 3 were studied in hypoglycemic effects on alloxan-diabetic mice. The results showed that compounds 1, 2 and 3 all produced hypoglycemic effects. The compound 2 in a dose of 50 mg/kg exerted significant effect (p < 0.05), 2 and 3 in a dose of 100 mg/kg exerted obviously effect (p < 0.01). Meantime, the compound 1 in a dose of 100 mg/kg can make the fasting blood glucose level have decreasing tendency.     

Two new flavonoids from Retama raetam

Two new flavones were isolated from the aerial parts of Retama raetam subsp. raetam. Their structures were established as luteolin 4′-O-neohesperidoside (1) and 5,4′-dihydroxy-(3″,4″-dihydro-3″,4″-dihydroxy)-2″,2″-dimethylpyrano-(5″,6″:7,8)-flavone (2) by means of spectroscopic methods. Also present was ephedroidin (4′,5,7-trihydroxy-8-(2-hydroxy-3-butenyl)-flavone).     

Biochanin A triglycoside from Andira inermis

A new isoflavonol triglycoside, biochanin A 7-O-β- -apiofuranosyl-(1→5)-β- -apiofuranosyl-(1→6)-β- -glucopyranoside (1), was isolated from Andira inermis roots in addition to the known compounds genistein 7-O-β- -apiofuranosyl-(1→6)-β- -glucopyranoside and lanceolarin.     

A new chiratane type triterpenoid from the rhizomes of Drynaria fortunei

Chiratone (1), a rare new chiratane type triterpenoid, together with five known triterpenoids were isolated from the rhizomes of Drynaria fortunei (Kunze) J. Sm. The structure was characterized as 20β-hydroxychiratan-22-one on the basis of extensive 1D and 2D NMR, and MS spectroscopic analyses, and was further confirmed by X-ray crystal diffraction. Primary bioassays showed that compound 1 had significant cytotoxic activity against Hela, PC3 and HepG2 cells, with IC₅₀ of 2.92 μM, 1.08 μM and 2.45 μM, respectively.     

A new flavonoid from the aerial part of Thalictrum atriplex

A new flavone glycoside, identified as kaempferol 3-O-[3′″-acetyl-α- -arabinopyranosyl-(1′″–6″)]-β- -glucopyranoside (1), has been isolated from the aerial part of Thalictrum atriplex.     

A new biflavonoid from Daphniphyllum angustifolium Hutch

An investigation of the flavonoids in Daphniphyllum angustifolium Hutch. resulted in the identification of a new biflavonoid, 5,7,4′-trihydroxyflavan (2α→O→7, 4α→8) kaempferol (1), together with five known flavonoids. Their structures were determined by spectroscopic method.     

A new flavone glycoside from the seeds of Shorea robusta

A new flavonoid, 3,7-dihydroxy-8-methoxyflavone 7-O-α- -rhamnopyranosyl-(1→4)-α- -rhamnopyranosyl-(1→6)-β- -glucopyranoside (1), was isolated from the seeds of Shorea robusta.     

A new norlignan from Taxodium ascendens

A new norlignan, (2R,3R,4S,5S)-2,4-bis(4-hydroxyphenyl)-3,5-dihydroxy-tetrahydropyran (1), together with 9 known compounds were isolated from the branches and leaves of Taxodium ascendens. Their structures were mainly determined on the basis of MS, IR, 1D and 2D NMR spectral evidences. Methanol extract showed inhibitory activity on carbonic anhydrase II with an IC₅₀ value of 4.27 µg/ml, acetone extract and methanol extract inhibited activity of cathepsin B with IC₅₀ values of 2.12 and 3.71 µg/ml, respectively.     

Effects of Pithecellobium clypearia Benth extract and its main components on inflammation and allergy

The ethanol extract of Pithecellobium clypearia Benth (PCE) was characterized to be rich in polyphenols by HPLC analysis, and investigated for its anti-inflammatory and anti-allergic activities. In our assay, PCE showed anti-inflammatory activity in both acute and auto-immune inflammation animal models. Administration of PCE can effectively inhibit the croton oil-induced ear edema and capillary permeability, the carrageenin-induced paw edema, and the liver injury caused by propionibacterium acnes plus lipopolysaccharide. PCE was also found to possess anti-allergic activity in inhibiting the DNFB-induced delayed hypersensitivity reaction. Meanwhile, seven main components (1–7) from PCE were studied for their effect on histamine release stimulated by compound 48/80 from rat peritoneal mast cells in vitro. Compound 2 ((−)-epigallocatechin-7-gallate), 3 ((−)-5, 7, 3′, 4′, 5′-pentahydroxyflavan), and 5 ((−)-tetra hydroxyflavan-7-gallate) showed significant inhibition effect on histamine release.     

A new cerebroside from Gynura divaricata

A new cerebroside, 1-O-β-d-glucopyranosyl-(2S,3S,4R,10E)-2-[(2′R)-2′-hydroxyltricosanoyl-amino]-10-octadecene-1,3,4-triol was isolated from the aerial parts of Gynura divaricata DC.     

New steroids from Clerodendrum colebrookianum

Five new steroids, colebrin A–E (1–5) were isolated from the aerial parts of Clerodendrum colebrookianum. The structures of the new compounds were elucidated on the basis of spectral evidence.     

Bioactive constituents from the stems of Dalbergia parviflora

From the stems of Dalbergia parviflora, three known flavonoids, six known isoflavonoids, a new isoflavone, dalparvone (2) and a new cinnamyl derivative, dalparvinene (6) were isolated and characterized. Isoflavan 3 exhibited strong cytotoxicity against KB and NCI-H187 cell lines with IC₅₀ values of 0.53 and 2.04 μg/ml, respectively. Compound 6 demonstrated strong cytotoxicity against NCI-H187 with an IC₅₀ value of 1.46 μg/ml. Compounds 4 and 6 possessed moderate cytotoxicity against KB cells with IC₅₀ values of 6.78 and 9.89 μg/ml, respectively. In addition, 2 exhibited moderate antiplasmodial activity with an IC₅₀ value of 8.19 μg/ml.     

Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes (Zingiber officinale)

The atomic ratios (¹⁴C/³H) obtained in ar-curcumene, α-zingiberene, β-bisabolene obtained from the essential oil of rhizomes of Zingiber officinale which were fed with [2-¹⁴C, 2-³H₂], [2-¹⁴C, 4R-³H₁] and [2-¹⁴C, 5-³H₂]mevalonic acid and [1-³H₂]farnesylpyrophosphate (FPP) revealed that (a) (2E,6E)-isomer of FPP is isomerised to (2Z,6E)-isomer without loss of epimeric hydrogen that means without a redox process; (b) (2Z,6E)-FPP is cyclised to bisabolyl cation which is the penultimate precursor of α-zingiberene, ar-curcumene and β-bisabolene; and (c) two 1,2-hydrogen shifts take place during the formation of α-zingiberene whereas one 1,2 shift has been observed during the formation of ar-curcumene.     

Dammarane-type glycosides and long chain sesquiterpene glycosides from Gynostemma yixingense

A new dammarane-type glycoside and a new long chain sesquiterpene glycoside, along with nine known compounds 20(S)-ginsenoside Rh1 (3), 20(R)-ginsenoside Rh1 (4), ginsenoside F1 (5), amarantholidoside IV (6), ginsenoside Rc (7), 20(S)-ginsenoside Rg2 (8), 20(R)-ginsenoside Rg2 (9), ginsenoside Rd (10) and gypenoside XLVI (11) were isolated from Gynostemma yixingense. The structures of the new compounds were determined on the basis of spectroscopic analysis, including 1D-, 2D-NMR and ESI-MS techniques as well as by comparison of the spectral data with those of related compounds as 2α,3β,20(S)-trihydroxydammar-24-ene-3-O-[β-d-glucopyranosyl((1 → 2)-β-d-glucopyranosyl]-20-O-[β-d-xylopyranosyl((1 → 6)-β-d-glucopyranoside] (1) (2E,6E)-10-β-d-glucopyranosyl-1,10,11-trihydroxy-3,7,11-trimethyldodeca-2,6-diene (2).