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Biomedical subjects

Sheng-Ping Yang

Publications and source records attributed to Sheng-Ping Yang.

17 recordsLinked to original sources

Flueggenines A and B, two novel C,C-linked dimeric indolizidine alkaloids from Flueggea virosa.

[structure: see text] Two unprecedented C,C-linked dimeric indolizidine alkaloids, flueggenines A (1) and B (2), as well as their biosynthetic precursor (-)-norsecurinine, were isolated from the roots of Flueggea virosa. Their structures and absolute configurations were elucidated by spectroscopic methods, especially 2D NMR and CD spectral analyses, and supported by their unique biosynthetic pathway as proposed. Both 1 and 2 were tested against two tumor cell lines, and alkaloid 1 showed weak activity against the P-388 cell line.

Alkaloids↗

Terpenoid indole alkaloids from Winchia calophylla.

Three new indole alkaloids, N(4)-demethyl-12-methoxyalstogustine (1), 17-carboxyl-N(4)-methylechitamidine chloride (2), and 17-carboxyl-12-methoxy-N(4)-methylechitamidine chloride (3), along with 15 known alkaloids, were isolated from the ethanolic extract of the stem bark of Winchia calophylla. The structures of 1-3 were elucidated on the basis of spectroscopic means and chemical methods. The determination of relative configurations at C-19 and C-20 for 1-3 was aided by 13C NMR spectroscopic data. The absolute configurations of alkaloids 1-3 were determined by direct comparison of their CD spectra with those of known alkaloids. All the alkaloids were tested in cytotoxic assays against P-388 and A-549 tumor cell lines, and only two of them showed weak activity against the A-549 cell line.

Animals↗

Alkaloids from Daphniphyllum longeracemosum.

Four new Daphniphyllum alkaloids, daphnilongeranins A-D (1-4), along with four known ones, daphniphylline, longistylumphylline A, deoxyisocalyciphylline B, and daphnicyclidin D, were isolated from the leaves and stems of Daphniphyllum longeracemosum. Daphnilongeranin A (1) is the first seco-10,17-longistylumphylline A type Daphniphyllum alkaloid, and daphnilongeranin B (2) is a new C-22 nor-Daphniphyllum alkaloid based on a new C21 skeleton. Their structures and stereochemistry were determined using spectroscopic data and chemical methods.

Alkaloids↗

Daphniyunnines A-E, alkaloids from Daphniphyllum yunnanense.

The first chemical study on the stems and leaves of Daphniphyllum yunnanense led to the isolation of five new alkaloids, daphniyunnines A-E (1-5). Daphniyunnines B-E (2-5) are four unusual C-22 nor-Daphniphyllum alkaloids. The structures of these alkaloids were characterized by spectroscopic methods, especially 2D NMR techniques. A single-crystal X-ray diffraction analysis was used to confirm the structure of 1. Daphniyunnine D (4) showed cytotoxicity against two tumor cell lines, P-388 and A-549, with IC(50) values of 3.0 and 0.6 microM, respectively.

Alkaloids↗

Alkaloids from Gelsemium elegans.

Three new alkaloids, gelsebanine (1), 14alpha-hydroxyelegansamine (2), and 14alpha-hydroxygelsamydine (3), and a new extraction artifact , gelsebamine (4), together with 12 known alkaloids, were isolated from the stems and leaves of Gelsemium elegans. The structures of 1-4 were determined by spectroscopic methods, especially 2D NMR techniques. Compounds 1-4 were evaluated for cytotoxic activity against four tumor cell lines, and gelsebamine (4) selectively inhibited the A-549 human lung adenocarcinoma cell line.

Antineoplastic Agents, Phytogenic↗

Lathyranoic acid A: first secolathyrane diterpenoid in nature from Euphorbia lathyris.

[structures: see text] Lathyranoic acid A (1), the first secolathyrane diterpenoid with an unprecedented skeleton, and a new diterpenoid Euphorbia factor L11 (2) were isolated from the seeds of Euphorbia lathyris. Their structures were elucidated by spectroscopic analysis and chemical methods. A biogenetic route involving an enzymatic Baeyer-Villiger oxidation as the key step was postulated for the transformation of 2 to 1 and mimicked by an unusual chemical Baeyer-Villiger oxidation.

Diterpenes↗

Lignans and their degraded derivatives from Sarcostemma acidum.

Four lignans, sacidumlignans A-D (1-4), and two degraded lignan derivatives, sacidumols A (5) and B (6), along with four known compounds, (+)-pinoresinol, 9alpha-hydroxypinoresinol, perforatic acid, and peucenine-7-O-methyl ether, were isolated from the ethanolic extract of the whole plant of Sarcostemma acidum. The structures and relative configuration of these new compounds were elucidated on the basis of spectroscopic and chemical data, especially 2D NMR techniques. Sacidumlignan D (4) was assigned as a rearranged tetrahydrofuran lignan with an unprecedented skeleton. Sacidumlignan A (1) showed moderate antimicrobial activities against two Gram-positive bacteria in vitro.

Anti-Bacterial Agents↗

First diamino Daphniphyllum alkaloid, daphnipaxinin, with an unprecedented heterohexacyclic skeleton from Daphniphyllum paxianum.

[structure: see text] The first diamino Daphniphyllum alkaloid, daphnipaxinin (1), with an unprecedented hexacyclic fused skeleton, along with a known alkaloid, daphnicyclidin A (2), was isolated from the stem of Daphniphyllum paxianum Rosenth. The structure and absolute stereochemistry of 1 were established by spectral methods, especially two-dimensional NMR techniques and CD analysis.

Alkaloids↗

Novel antibacterial diterpenoids from Larix chinensis Beissn.

Two novel labdane-type diterpenoids, butanedioic acid mono[(13S)-13-hydroxylabda-8(17),14-dien-19-yl] ester (1) and butanedioic acid bis[(13S)-13-hydroxylabda-8(17),14-dien-19-yl] ester (2), along with the eleven known diterpenoids 3-13 and three other known compounds, were isolated from the bark of Larix chinensis. Their structures were elucidated both spectroscopically and chemically. The major diterpenoids 1-9, 11, and 13, as well as the very abundant phenolic compound 16, were subjected to antibacterial and cytotoxic bioassays. Compounds 7 and 9 showed remarkable in vitro inhibition of Staphylococcus aureus and S. epidermidis (MIC = 37-73 microM).

Anti-Bacterial Agents↗

Cytotoxic sesquiterpenoids from Eupatorium chinense.

Ten new sesquiterpenoids, namely, eupachinilides A-J (1-10), together with seven known sesquiterpenoids, eupachifolin D (11), budlein B (12), 8 beta-(4'-hydroxytiglyloxy)-2 beta-hydroxy-1 alpha H,5 alpha H,6 beta H,7 alpha H-guai-3,10(14),11(13)-trien-6,12-olide (13), 1,10-hydrobahia (14), 2 alpha-hydroxyeupatolide (15), eupaserrin (16), and mollisorin B (17), were isolated from the whole plant of Eupatorium chinense. Their structures were elucidated mainly by spectral methods, especially 2D NMR techniques. Eupachinilides A (1), E (5), F (6), and I (9) exhibited moderate cytotoxic activities against several tumor cell lines. The structures assigned previously for eupachifolins B (11a), C (13a), and D (11) were revised by spectral analysis and 2D NMR techniques.

Antineoplastic Agents, Phytogenic↗

Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum.

Ten new guaiane type sesquiterpene lactones, namely, eupalinilides A-J (1-10), as well as nine known compounds, eupachinilide C (11), eupachifolin D (12), eupachinilide E (13), 2alpha-hydroxyeupatolide (14), 3-deacetyleupalinin A (15), heliangine (16), 8beta-tigloyloxy-2,3-seco-6betaH,7alphaH-helianga-4Z,11(13)-diene-3,10beta;6, 12-diolid-2-oic acid (17), 8beta-(4'-hydroxytigloyloxy)-3beta,14-dihydroxy-6betaH,7alphaH-germacra-1(10)Z,4Z,11(13)-trien-6,12-olide (18), and 8beta-tigloyloxy-3beta,14-dihydroxy-6betaH,7alphaH-germacra-1(10)Z,4E,11(13)-trien-6,12-olide (19), were isolated from the whole plant of Eupatorium lindleyanum. Eupalinilides B (2), C (3), E (5), F (6), and I (9) have been tested for cytotoxicity against P-388 and A-549 tumor cell lines. The results showed that eupalinilides B (2) and E (5) demonstrated potent cytotoxicity. The structures of these compounds were determined by spectroscopic methods including 1D and 2D NMR spectra.

Animals↗

Alkaloids from the fungus Lactarius subplinthogalus.

A new alkaloid, namely laccarin A (1), along with four known alkaloids, laccarin (2), adenosine (3), indole-3-carboxaldehyde (4) and nicotinamide (5), was isolated from the fungus Lactarius subplinthogalus. The structure of laccarin A (1) was established mainly by spectroscopic methods.

Alkaloids↗

Chemical constituents from Pseudolarix kaempferi.

A novel degraded triterpenoid isopseudolaritone A (1) and one new oligosaccharide, 1-O-isopropyl-6-O-[2-O-methyl-alpha-L-rhamnopyranosyl(1 --> 6)]-beta-D-glucopyranose (2), two new artefacts, 9-O-formacyl cedrusin (5) and 9,9'-O-diformacyl cedrusin (6), as well as 12 known phenolic Compounds (3-4, 7 16), were isolated from the root bark of Pseudolarix kaempferi. Their structures were elucidated mainly by spectroscopic methods.

Humans↗

Two novel alkaloids with a unique fused hexacyclic skeleton from Daphniphyllum subverticillatum.

Two novel major alkaloids, deoxycalyciphylline B (1) and deoxyisocalyciphylline B (2) with a unique fused hexacyclic skeleton, together with a quite recently reported alkaloid calyciphylline B (3), were isolated from the stem of Daphniphyllum subverticillatum. Their structures were established by spectral methods and chemical evidence, especially 2D NMR techniques. The structure of 1 was further confirmed by a single-crystal X-ray diffraction determination.

Alkaloids↗

Antifungal diterpenoids of Pseudolarix kaempferi, and their structure-activity relationship study.

The in vitro antifungal activities of 19 structurally diversified analogues of pseudolaric acids tested against the major pathogenic fungus Candida albicans has led to the establishment of a very clear structure-activity relationship of pseudolaric acids derivatives. Pseudolaric acid A was first found to be a potent antifungal component comparable with pseudolaric acid B. Among the tested 19 diterpenoids, pseudolaric acids A2 (1), B2 (3), B3 (4) and methyl pseudolarate A2 (2) are new isolates of the root bark of Pseudolarix kaempferi, and their structures were elucidated mainly by 2D-NMR techniques and chemical methods. Compounds 12-19 were first semi-synthesized by efficient routines from pseudolaric acid B.

Animals↗

Five new diterpenoids from Pseudolarix kaempferi.

Five new diterpenoids, pseudolaric acids F (1), G (2), and H (3), 2',3'-dihydroxy-1'-propoxypseudolarate B (4), and 6'-O-acetylpseudolaric acid B O-beta-D-glucopyranoside (5), along with nine known diterpenoids, pseudolaric acids A, B, and C(1), deacetylpseudolaric acid C(2), deacetylpseudolaric acid A, methyl pseudolarate A, methyl pseudolarate B, pseudolaric acid A-O-beta-D-glucopyranoside, and pseudolaric acid B-O-beta-D-glucopyranoside, were isolated from the root bark of Pseudolarix kaempferi. Their structures and stereochemistry were elucidated mainly by spectral data, especially 2D NMR techniques.

Chromatography, Thin Layer↗