Effects of immersing treatment of curcumin and piperine combined with vacuum packaging on the quality of salmon (Salmo salar) during cold chain logistics.

In order to study the effects of the compound preservatives (curcumin and piperine (CP)) and vacuum packaging (VP) on the quality of salmon during cold chain logistics suffered from temperature abuse, the physiochemical indexes (texture, water holding capacity (WHC), total volatile basic nitrogen (TVB-N), thiobarbituric acid reactive substances (TBARS), free amino acids (FAA) contents), microbial indicators (total mesophilic bacteria count (MBC), total psychrotrophic bacteria count (PBC), H2S-producing bacteria count (HSBC)) were determined, and the moisture changes were explored by near-infrared (NIR) spectroscopy and low-field nuclear magnetic resonance (LF-NMR). The results showed that the treatment of curcumin and piperine in combination with vacuum packaging could maintain the quality of salmon suffered from temperature abuse most effectively. At the end of storage, the MBC of VP+CP was only 4.95 log CFU/g, which was about 1 log CFU/g lower than the control sample stored at the same condition. The combined treatment also retarded the increase of TVB-N, TBARS, and the decrease of hardness, springiness, and a* value, as well as water migration in salmon, contributing to higher water holding capacity and better appearance. Besides, VP+CP retarded the decrease of free glutamate, which contributed to umami taste. Due to the biological activity and safety of the preserves, the combined treatment could be a promising method for preservation of seafood.

Japonisine A, a fawcettimine-type Lycopodium alkaloid with an unusual skeleton from Lycopodium japonicum Thunb.

Japonisine A, a novel fawcettimine-type Lycopodium alkaloid with an unusual skeleton and two new fawcettimine-type ones, along with 20 known Lycopodium alkaloids, were isolated from the whole plants of Lycopodium japonicum Thunb. Their structures were determined by extensive spectroscopic analysis, including 1D and 2D NMR, and HR-ESIMS, as well as by comparison with the literature data. Notably, japonisine A (1) was the first example of fawcettimine-related Lycopodium alkaloid with a 2-oxopropyl attached at C-6. All the isolates were evaluated for their inhibitory effects on acetylcholinesterase (AChE) and α-glucosidase. Unfortunately, the results indicated that all the compounds were inactive against the acetylcholinesterase (AChE) and α-glucosidase.

Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina.

Three new bisindole alkaloids, 3'-(2-oxopropyl)-19,20-dihydrotabernamine (1: ), 3'-(2-oxopropyl)-ervahanine B (2: ), 19,20-dihydrovobparicine (3: ), and 20 known compounds were isolated from the aerial parts of Tabernaemontana bufalina. The structures of these alkaloids were elucidated using spectroscopic methods. The absolute configurations of 1: -3: were determined by the circular dichroic exciton chirality method. Compounds 1: -23: were screened for their cytotoxicity against two human cancer cell lines, A-549 and MCF-7. Ten compounds (1: -3, 10, 14, 16, 17, 19, 22: , and 23: ) exhibited inhibitory effects against the two human cancer cells with IC50 values of 1.19 ~ 6.13 µM.

Eucarobustols A-I, Conjugates of Sesquiterpenoids and Acylphloroglucinols from Eucalyptus robusta.

Nine new conjugates of sesquiterpenoids and acylphloroglucinols, named eucarobustols A-I (1-9), as well as 11 known analogues were isolated from the leaves of Eucalyptus robusta. The sesquiterpenoid motifs furnishing the new conjugates included four structural types of aristolane (1 and 2), guaiane (3), eudesmane (4), and aromadendrane (5-9) moieties. Compounds 1 and 2 were found to represent the first examples of conjugates of aristolane and acylphloroglucinol units. In turn, compound 3 features a new coupling model of guaiane and acylphloroglucinol via the C-4-C-7' bond. Compounds 1, 7, and 9 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 1.3, 1.8, and 1.6 µM, respectively.

Limonoids and Triterpenoids from Dysoxylum mollissimum var. glaberrimum.

Seven new limonoids, dysomollides A-G (1-7), and two new cycloapotirucallane-type triterpenoids, dysomollins A and B (8 and 9), together with three known compounds, dysoxylumin A (10) and toonapubesins A (11) and B (12), were isolated from the twigs of Dysoxylum mollissimum var. glaberrimum. The structures of 1-9 were elucidated on the basis of spectroscopic methods. Compound 10 showed inhibitory activity against A549 cells with an IC50 value of 2.1 µM, and compound 11 exhibited activity against P388 cells with an IC50 value of 6.7 µM.

Triterpenoids from Aglaia odorata var. microphyllina.

Five new apotirucallane-type triterpenoids (1-5), named agladorals A-E, and 28 known compounds (20 triterpenoids and 8 rocaglamides) were isolated from the twigs of Aglaia odorata var. microphyllina. Their structures were elucidated by spectroscopic analysis.

Potent HGF/c-Met axis inhibitors from Eucalyptus globulus: the coupling of phloroglucinol and sesquiterpenoid is essential for the activity.

Eucalyptin A (1), together with two known compounds 2 and 3 exhibiting potent inhibition on HGF/c-Met axis, was discovered from the fruits of Eucalyptus globulus. 1 possessed an unprecedented carbon framework of phloroglucinol-coupled sesquiterpenoid, and its structure was elucidated by spectroscopic method and ECD calculation. A brief structure-activity relationship discussion indicated that the coupling of a phloroglucinol and a sesquiterpenoid is essential for the activity.

Discovery of structurally diverse and bioactive compounds from plant resources in China.

This review describes the major discoveries of structurally diverse and/or biologically significant compounds from plant resources in China, mainly from the traditional Chinese medicines (TCMs) since the establishment of our research group in 1999. In the past decade, a large array of biologically significant and novel structures has been identified from plant resources (or TCM) in our laboratory. The structural modification of several biologically important compounds led to more than 400 derivatives, some of which exhibited significantly improved activities and provided opportunities to elucidate the structure-activity relationship of the related compound class. These findings are important for drug discovery and help us understand the biological basis for the traditional applications of these plants in TCM.

Sesquiterpenes from Dysoxylum oliganthum and Dysoxylum excelsum.

Three new sesquiterpenes (1-3), (6R,7S,11R,10S)-15-hydroxy-sesquisabinene hydrate (1), (6R,7R,11S,10S)-15-hydroxy-sesquisabinene hydrate (2), and (6R,7R,10S)-15-hydroxy-zingiberenol (3), along with three known compounds, were isolated from the stems of Dysoxylum oliganthum; and three new isodaucane (salvionane) sesquiterpenes, namely isodauc-6-ene-10ß,14-diol (4), 4-epi-isodauc-6-ene-10ß,14-diol (5), and 4-epi-6α,10ß-dihydroxy-artabotrol (6) together with 15 known compounds were isolated from the twigs and leaves of D. excelsum. Their structures were established on the basis of extensive spectroscopic analysis and chemical shifts. The absolute configuration of C-10 in compounds 1-3 of a rare class was determined by using Snatzke's method.

Limonoids from the stems of Toona ciliata var. henryi (Meliaceae).

Ten limonoids, toonacilianins A-J, and two norlimonoids, toonacilianins K and L, together with seven known compounds were isolated from the stems of Toona ciliata var. henryi (Meliaceae). Their structures were elucidated by spectroscopic analysis. Two compounds showed strong cytotoxic activities.

Trigoxyphins A-G: diterpenes from Trigonostemon xyphophylloides.

Six new oxygenated daphnane-type diterpenoids, trigoxyphins A-F (1-6), a phenanthrene-type diterpenoid, trigoxyphin G (7), and two known compounds were isolated from twigs of Trigonostemon xyphophylloides. Their structures were established using spectroscopic methods. Compounds 1 and 2 exhibited strong cytotoxic activity against HL60 (IC(50): 0.27 and 0.49 microM) and A549 (IC(50): 7.5 and 4.9 microM) tumor cell lines, respectively.

Four sesquiterpenoids from Chloranthus multistachys.

Four new sesquiterpenoids, chlomultins A-D (1-4), were isolated from the whole plant of Chloranthus multistachys. Their structures were established on the basis of spectroscopic analysis.

Limonoids and triterpenoids from Khaya senegalensis.

Seven new limonoids (1-7), named khayalenoids C-I, three new triterpenoids (8-10), named senegalenes A-C, and eight known limonoids have been isolated from stems of Khaya senegalensis. The structures of these compounds were elucidated on the basis of spectroscopic analyses.

Limonoids from Khaya ivorensis.

Four limonoids, 1-O-deacetyl-6-deoxykhayanolide E (1), 1-O-deacetyl-2 alpha-hydroxykhayanolide E (2), 3-acetyl-khayalactone (3), 11 alpha-acetoxy-2 alpha-hydroxy-6-deoxy-destigloylswietenine acetate (4), along with 12 known limonoids, were isolated from the stems of Khaya ivorensis. Their structures were elucidated on the basis of spectroscopic analysis.

Phenolic compounds with cell protective activity from the fruits of Livistona chinensis.

Two new depsidones, livistones A (1) and B (2), and a new benzofurane, livistone C (3), together with the 11 known compounds including three stilbenes (4-6), four steroids, three flavan-3-ols, and an alkaloid were isolated from the fruits of Livistona chinensis. The structures of the new compounds were determined by spectroscopic methods. Compounds 1, 4-6 exhibited remarkable cell protective activities against H(2)O(2)-induced SH-SY5Y cell damage.

Terpenoids from Toona ciliata.

Three new norlimonoids (1-3), two new tirucallane-type triterpenoids (4 and 5), and a new pimaradiene-type diterpenoid (6), along with two known limonoids and eight known tirucallane-type triterpenoids, were isolated from the leaves and twigs of Toona ciliata. Their structures were elucidated on the basis of spectroscopic data. Toonaciliatin M (6) showed moderate antifungal activity against Trichophyton rubrum with an MIC of 12.5 microg/mL.

Sesquiterpenoids and phenylpropanoids from Chloranthus serratus.

Seven new sesquiterpenoids, chlorantenes A-G (1-7), two new phenylpropanoids (8 and 9), and six known sesquiterpenoids were isolated from the whole plants of Chloranthus serratus. Their structures were elucidated on the basis of spectroscopic analyses. Chlorantene A (1) was a sesquiterpene with a unique C-4 and C-10 linkage, and chlorantene B (2) possessed a nitro group at C-1. The structure of a eudesmane-type sesquiterpene previously isolated from Chloranthus henryi was revised as its 4-epimer (3a).

Alkaloids from the twigs of Daphniphyllum calycinum.

Twelve new alkaloids, caldaphnidines G-R (1-12), along with 24 known ones, were isolated from the twigs of Daphniphyllum calycinum. Their structures were elucidated by spectroscopic methods, especially two-dimensional NMR techniques.

Walsucochins A and B with an unprecedented skeleton isolated from Walsura cochinchinensis.

Walsucochins A (1) and B (2) with an unprecedented skeleton were isolated from Walsura cochinchinensis. Their structures including absolute configuration were elucidated by spectral methods. A biosynthetic pathway of 1 and 2 was postulated. Both 1 and 2 exhibited significant cell protecting activities against H2O2-induced PC12 cell damage.

Structural modification of an angiogenesis inhibitor discovered from traditional Chinese medicine and a structure-activity relationship study.

Pseudolaric acid B (PAB), discovered as a promising angiogensis inhibitor, was served as the anticancer drug lead, and a series of its derivatives were synthesized. Among them, some derivatives, such as 13c- 13k, exhibited potent inhibition on the HMEC-1 cell proliferation and strong cytotoxic activities against the tested six tumor cell lines. The PAB derivatives 13c- 13k also showed significant and specific inhibition on HMEC-1 cell migration in vitro, and only 13d expressed moderate activity against HMEC-1 cell tube formation. The in vitro anticancer tests of the selected natural PAB analogs and the structurally modified PAB derivatives have led to the establishment of a clear structure-activity relationship.