Lycopodium alkaloids from Huperzia serrata.

A new lycopodane-type Lycopodium alkaloid, 6α-hydroxy-5,15-oxide-lycopodane (1), and seven known alkaloids were isolated from the whole plants of Huperzia serrata. Their structures were elucidated by means of spectroscopic methods. 12-Deoxyhuperzine O (2) was reported as a naturally occurring alkaloid for the first time, and showed an antagonist effect on the N-methyl-d-aspartate receptor with an IC(50) value of 0.92 µM.

Preoperative evaluation and outcome of corneal transplantation for limbal dermoids: a ten-year follow-up study.

AIM: To summarize preoperative evaluation and outcome of corneal transplantation for limbal dermoids for ten years. METHODS: Eighty-five patients diagnosed with limbal dermoids and treated with corneal transplantation were analyzed retrospectively. All patients were further divided into two groups according to absence or presence of neovascularization surrounding the dermoids in the corneal stroma. Eighty-two eyes were treated with tumor excision combined with partial lamellar sclerokeratoplasty, and the other three eyes were performed by penetrating keratoplasty. The size and location of the tumor, the associated ocular and systemic anomalies, the depth of the corneal penetration of tumor tissues, the preoperative and postoperative best-corrected visual acuity (BCVA), graft survival and cosmetic outcome, and surgical complications were recorded respectively. RESULTS: The average age at surgery was 5.3y (range, 3mo-36y). The mean size of dermoids was 6.1±1.6 mm. The 43.5% of eyes (37/85) were present with hair at the surface of the dermoid and 72.9% of dermoids were located inferotemporal of the eye. Amplyopia was present in 34.1% of patients (29/85) and 9.4% of patients (8/85) had lipodermoids. Eighteen patients suffered from Goldenhar's syndrome with an accessory ear. The 75% of patients in group 1 had involvement of the corneal deep stroma down to Descemet's membrane without involving it, but 71.4% of patients had Descemet's membrane involvement in group 2. Preoperative BCVA ranged from counting fingers to 20/20. Postoperatively 81.1% had a BCVA of 20/800 or better. There was no significant difference between the post-surgical BCVA of the two groups (t=1.584, P>0.05). The grafts of 70.5% patients were present as 1+ opacity, 21.1% as 2+ opacity, 8.2% as 3+ opacity and none as 4+ opacity. Surgical complications included graft rejection, microperforation, prolonged reepithelialization, steroid glaucoma, interface neovascularization, and interface hemorrhage. CONCLUSION: The dermoids with neovascularization surrounding them in the corneal stroma invaded deeper tissues in the cornea than those with no neovascularization surrounding them in the corneal stroma. Therefore, surgeons should take care to avoid corneal perforation during the corneal transplantation operation. The majority of patients markedly improved their cosmetic appearance after surgery.

Serratane-type triterpenoids from Huperzia serrata.

Sixteen serratane-type triterpenoids including three new compounds, 14beta,15beta-epoxyserratan-3beta,21beta,29-triol (1), serrat-14-en-3beta,21beta,29-triol (2) and serrat-14-en-3alpha,21beta,24,29-tetraol (3), were isolated from the whole plant of Huperzia serrata (Thunb) Trev. The structures of these new compounds (1-3) were elucidated on the basis of spectral analysis.

[Studies on chemical constituents in the peels of Citrus changshan-huyou (I)].

OBJECTIVE: To reveal the pharmacological activities of the components for their further utilization and development by studying the chemical constituents of Citrus changshan-huyou. METHOD: The structures were determined by repeated silica gel chromatographic separation and spectral analysis. RESULT: Five compounds were obtained, and identified as 3-oxo friedelin (I), limonin (II), beta-sitosterol (III), 8-(2',3'-dihydroxy-4'-methylbutane)-7-methoxycoumarin (IV), sucrose (V). CONCLUSION: The five compounds were obtained from this plant for the first time.

Two new N-oxide Lycopodium alkaloids from Huperzia serrata.

Two new Lycopodium alkaloids, N-oxidehuperzine E (1) and N-oxidehuperzine F (2), along with two known alkaloids, huperzines E (3) and F (4), were isolated from Huperzia serrata (Thunb.) Trev. Their structures were elucidated by spectroscopic and chemical transformations.

Two new isomeric alpha-tetralones from Pyrola calliantha.

Callianthones A ( 1) and B ( 2), a pair of new isomeric alpha-tetralones, together with a known alpha-tetralone ( 3) and four known flavonoids ( 4 - 7) were isolated from the 50 % EtOH extract of Pyrola calliantha. The structures and absolute configurations of the two new isomers were established to be (2 S,4 R) - and (2 S,4 S)-2,4-dihydroxy-2,7-dimethyl-3,4-dihydronaphthalen-1(2 H)-one ( 1 and 2, respectively) on the basis of spectral analysis, including 2 D NMR, model studies, and CD spectra.

New indole N-oxide alkaloids from Evodia fargesii.

Three new indole N-oxide alkaloids, fargesine (5-hydroxy-12-methyl-10,11,12,13-tetrahydro-1 H-azepino[5,4,3-cd]indole N(12)-oxide, 1), plectocomine 12-methyl-5- O-beta-D-glucopyranoside N(12)-oxide (2), and bufotenine 5-O-beta-D-glucopyranoside N(12)-oxide (3), were isolated from the root and stem of Evodia fargesii Dode along with five known compounds. The structures of the new alkaloids were elucidated on the basis of spectroscopic analysis.

New eremophilane-type sesquiterpenes from Ligularia hodgsonii.

Four new eremophilanlides (1- 4) together with a known sesquiterpene were isolated from the roots and rhizomes of Ligularia hodgsonii. The structures of these new compounds were established as 6beta-(2'-methylbutanoyloxy)-10beta-acetoxy-3 beta, 8beta-dihydroxyeremophil-7(11)-en-8,12-olide (1), 6beta,10 beta-dihydroxyeremophil-7(11)-en-8alpha,12-olide (2), 3beta-acetoxy-6,9-dien-8-oxoeremophil-12-nor-11-ketone (3), and 3beta-acetoxy-6alpha, 8alpha-dihydroxyeremophil-7(11), 9-dien-8,12-olide (4) by means of mass, IR and NMR spectroscopy.

Three new hydroxylated serratidine alkaloids from Huperzia serrata.

A known compound, serratidine (1), along with three hydroxylated serratidine alkaloids, 6alpha-hydroxyserrati dine (2), 4alpha-hydroxyserratidine (3) and 4alpha,6alpha-dihydroxyserratidine (4) were isolated from the CHCl3 fraction of basic materials of whole plant of the Chinese medicinal herb Huperzia serrata. The relative configurations of the above compounds were determined based on 2D NMR studies.

New epoxyserratanes from Huperzia serrata.

Three new serratane-type epoxytriterpenoids were isolated from the whole plant of Huperzia serrata. The structures of these new compounds were characterized as 14 beta,15 beta-epoxy-3 beta-hydroxyserratan-21 beta-ol (1), 14 beta,15 beta-epoxy-3 beta-hydroxyserratan-21alpha-ol (2), and 14 beta,15 beta-epoxy-3 beta-hydroxyserratan-21alpha-ol-3 beta-O-acetate (3), respectively, on the basis of spectral data and for 1 by single-crystal X-ray analysis.

Serratene-type triterpenoids from Huperzia serrata.

Seven new and 15 known serratene-type triterpenoids were isolated from the whole plant of Huperzia serrata. The structures of these new triterpenoids were elucidated as 21alpha-hydroxyserrat-14-en-3beta-yl p-dihydrocoumarate (1), 21alpha-hydroxyserrat-14-en-3beta-yl dihydrocaffeate (2), 21alpha-hydroxyserrat-14-en-3beta-yl propanedioic acid monoester (3), 3alpha,21alpha-dihydroxyserrat-14-en-24-oic acid (4), 16-oxo-3alpha,21beta-dihydroxyserrat-14-en-24-al (5), 16-oxo-3alpha,21beta-dihydroxyserrat-14-en-24-oic acid (6), and 16-oxo-21beta-hydroxyserrat-14-en-3alpha-yl acetate (7), respectively, by means of spectroscopic analysis.

New lycopodium alkaloids from Huperzia serrata.

Three new lycopodium alkaloids, 11alpha-hydroxyphlegmariurine B (2), 7alpha-hydroxyphlegmariurine B (3) and 7alpha,11alpha-dihydroxyphlegmariurine B (4) along with a known compound, phlegmariurine B (1), were isolated from the herb Huperzia serrata. The structures of the above compounds were elucidated based on spectroscopic studies.

Two norditerpenoid ester alkaloids from Aconitum bulleyanum.

Two new norditerpenoid alkaloids, 8-acetyl-14-p-methoxybenzoate of talatisamine (1) and 14-p-methoxybenzoate of talatisamine (2), were isolated from Aconitum bulleyanum Diels. The structures were elucidated on the basis of spectroscopic and chemical studies.

Terrestrinins A and B, two new steroid saponins from Tribulus terrestris.

Two new steroid saponins, named terrestrinins A (1) and B (2), along with six known compounds were isolated from the Chinese medicine herb Tribulus terrestris, and their chemical structures were elucidated as 26-O-beta-D-glucopyranosyl-(25S)-furostan-4(5),20(22)-diene-3,12-dione (1) and 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furostane-3beta,22alpha,26-triol-3-O-beta-D-xylopyranosyl(1 --> 3)-[(beta-D-xylopyranosyl(1 --> 2)]-beta-D-glucopyranosyl(1 --> 4)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-galactopyranoside (2) on the basis of spectroscopic techniques.

Miyoshianines A and B, two new lycopodium alkaloids from Huperzia miyoshiana.

Two new Lycopodium alkaloids, miyoshianines A and B, together with five known alkaloids, lycopodine, lycodoline, 12-epilycodoline, clavolonine, and flabelliformine, were isolated from Huperzia miyoshiana (Makino) Ching (Huperziaceae). Their structures were determined by means of spectroscopic techniques.

Halophilols A and B, two new stilbenes from Iris halophila.

A new monomeric stilbene, halophilol A (1), and a new tetrastilbene, halophilol B (2), along with three known oligostilbenes were isolated from the seeds of Iris halophila. Their structures were established on the basis of the spectral data. The oligostilbene skeleton is encountered for the first time in the Iridaceae family. Bioactivity tests showed that 1 had moderate cytotoxicity against KB and HMEC cell lines (IC50 = 17.28 microM, 22.47 microM respectively), while 2 was inactive.

Huperzine R, a novel 15-carbon Lycopodium alkaloid from Huperzia serrata.

Huperzine R (2), a novel 15-carbon Lycopodium alkaloid, was isolated from the whole plant of Huperzia serrata, and the relative configuration was established using spectroscopic and X-ray crystallographic techniques.

Three new phlegmariurine B type lycopodium alkaloids from Huperzia serrata.

Phlegmariurine B (1), a known alkaloid, along with three new analogous compounds, 2alpha-hydroxyphlegmariurine B (2), 2-oxoyphlegmariurine B (3) and 11-oxophlegmariurine B (4), were isolated from the CHCl3 fraction of total alkaloids of whole plant of the Chinese medicinal herb Huperzia serrata. Their structures were elucidated by spectral analysis.

Identification of three sulfate-conjugated metabolites of berberine chloride in healthy volunteers' urine after oral administration.

AIM: To identify the structure of unknown metabolites of berberine (Ber) in human urine after oral administration. METHODS: Urine samples were obtained from 5 volunteers after they orally took Ber chloride 0.9 g per day for three days. Metabolites in urine samples were isolated and purified by polyporous resin column chromatography. The individual metabolites were identified mainly using electrospray ionization mass spectroscopy (ESI-MS) and proton nuclear magnetic resonance (1H NMR) spectroscopy. RESULTS: Three unknown metabolites (M1, M2, and M3) were isolated. They were susceptible to arylsufatase. ESI-MS measurements of M1, M2, and M3 produced quasimolecular ions [M+H]+, m/z 17.9, 404.0, and 402.0 respectively. Especially, each of them produced a characteristic protonated ion [M-80+H]+, which can be ascribed as quasimolecular ions lost a SO3 fragment. 1H NMR spectra of the metabolites were also obtained and each of 1H signals was assigned. CONCLUSION: Structures of M1, M2, and M3 were firmly identified as jatrorrhizine-3-sulfate, demethyleneberberine-2-sulfate, and thalifendine-10-sulfate, and the major metabolite was M2.