Displaying publications 1 - 20 of 81 in total

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  1. Total Synthesis of (-)-Conolutinine
    Feng X, Jiang G, Xia Z, Hu J, Wan X, Gao JM, et al.
    Org. Lett., 2015 Sep 18;17(18):4428-31.
    PMID: 26315849 DOI: 10.1021/acs.orglett.5b02046
    The first enantioselective synthesis of (-)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac)2 was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (-)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.
    Matched MeSH terms: Indole Alkaloids/chemical synthesis*; Indole Alkaloids/chemistry
  2. Cannabinoid CB1 receptor binding and acetylcholinesterase inhibitory activity of Sceletium tortuosum L.
    Lubbe, A., Khatib, A., Yuliana, N.D., Jinap, S., Verpoorte, R.
    International Food Research Journal, 2010;17(2):349-355.
    MyJurnal
    The whole plant extract of plant Sceletium tortuosum, plant native to South Africa, has been known
    traditionally to have mood enhancing and stimulant properties. These properties have been confirmed before by proving serotonin-uptake inhibition activity. A further confirmation by using CB1 receptor binding assay has been performed in this study. The unfermented alkaloid extract was proved to posses a higher activity to bind CB1 receptor compared to that of the fermented one. GC-MS analysis confirmed that unfermented alkoloid extract contain more alkaloids than the fermented one. The ethanol extract was also more active than the fermented one, suggesting that non-alkaloid compounds in this extract could posses this activity. An additional test to check wether this extract can improve cognitive function and memory was performed by acetylcholinesterase inhibitory assay. Both fermented and unfermented alkaloid extracts could inhibit acetylcholinesterase with IC50 being 0.303 mg/ml and 0.330 mg/ml, respectively. However, the major alkaloid in the extract, mesembrine, did not show inhibition of the enzyme. A TLC based test proved that other alkaloids in the extract were responsible to the activity.
    Matched MeSH terms: Indole Alkaloids
  3. Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa
    Takayama H
    Chem Pharm Bull (Tokyo), 2004 Aug;52(8):916-28.
    PMID: 15304982
    The leaves of a tropical plant, Mitragyna speciosa KORTH (Rubiaceae), have been traditionally used as a substitute for opium. Phytochemical studies of the constituents of the plant growing in Thailand and Malaysia have led to the isolation of several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids, including new natural products. The structures of the new compounds were elucidated by spectroscopic and/or synthetic methods. The potent opioid agonistic activities of mitragynine, the major constituent of this plant, and its analogues were found in in vitro and in vivo experiments and the mechanisms underlying the analgesic activity were clarified. The essential structural features of mitragynines, which differ from those of morphine and are responsible for the analgesic activity, were elucidated by pharmacological evaluation of the natural and synthetic derivatives. Among the mitragynine derivatives, 7-hydroxymitragynine, a minor constituent of M. speciosa, was found to exhibit potent antinociceptive activity in mice.
    Matched MeSH terms: Indole Alkaloids/isolation & purification; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry*
  4. Antiproliferative and Microtubule-stabilizing Activities of Two Iboga-vobasine Bisindoles Alkaloids from Tabernaemontana corymbosa in Colorectal Adenocarcinoma HT-29 Cells
    Tan CH, Sim DSY, Lim SH, Mohd Mohidin TB, Mohan G, Low YY, et al.
    Planta Med, 2022 Nov;88(14):1325-1340.
    PMID: 35100653 DOI: 10.1055/a-1755-5605
    Two iboga-vobasine bisindoles, 16'-decarbomethoxyvoacamine (1: ) and its 19,20-dihydro derivative, 16'-decarbomethoxydihydrovoacamine (2: ) from Tabernaemontana corymbosa exhibited potent cytotoxicity against the human colorectal adenocarcinoma HT-29 cells in our previous studies. Bisindoles 1: and 2: selectively inhibited the growth of HT-29 cells without significant cytotoxicity to normal human colon fibroblasts CCD-18Co. Treatment with bisindoles 1: and 2: suppressed the formation of HT-29 colonies via G0/G1 cell cycle arrest and induction of mitochondrial apoptosis. Owing to its higher antiproliferative activity, bisindole 2: was chosen for the subsequent studies. Bisindole 2: inhibited the formation of HT-29 spheroids (tumor-like cell aggregates) in 3D experiments in a dose-dependent manner, while an in vitro tubulin polymerization assay and molecular docking analysis showed that bisindole 2: is a microtubule-stabilizing agent which is predicted to bind at the β-tubulin subunit at the taxol-binding site. The binding resulted in the generation of ROS, which consequently activated the oxidative stress-related cell cycle arrest and apoptotic pathways, viz., JNK/p38, p21Cip1/Chk1, and p21Cip1/Rb/E2F, as shown by microarray profiling.
    Matched MeSH terms: Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry
  5. Conodurine, conoduramine, and ervahanine derivatives from Tabernaemontana corymbosa
    Kam TS, Sim KM
    Phytochemistry, 2003 Jul;63(5):625-9.
    PMID: 12809725
    Four bisindole alkaloids, viz., 19'(S)-hydroxyconodurine, conodurinine, 19'(S)-hydroxyconoduramine, and 19'(S)-hydroxyervahanine A, in addition to conodurine and ervahanine A, were obtained from the leaf and stem-bark extracts of Tabernaemontana corymbosa. The structures of the new alkaloids were determined using NMR and MS analysis.
    Matched MeSH terms: Indole Alkaloids/isolation & purification; Indole Alkaloids/chemistry
  6. Five new iboga alkaloids from Tabernaemontana corymbosa
    Kam TS, Sim KM
    J Nat Prod, 2002 May;65(5):669-72.
    PMID: 12027738
    Five new indole alkaloids of the ibogan type (1-5), in addition to 12 other known iboga alkaloids, were obtained from the leaf and stem-bark extract of the Malayan species Tabernaemontana corymbosa, viz., 19(S)-hydroxyibogamine (1), 19-epi-isovoacristine (2), isovoacryptine (3), 3R/S-ethoxyheyneanine (4), and 3R/S-ethoxy-19-epi-heyneanine (5). The structures were determined using NMR and MS analysis and comparison with known related compounds.
    Matched MeSH terms: Indole Alkaloids/isolation & purification*; Indole Alkaloids/chemistry
  7. Black sea cucumber (Holothuria atra Jaeger, 1833) rescues Pseudomonas aeruginosa-infected Caenorhabditis elegans via reduction of pathogen virulence factors and enhancement of host immunity
    Lee WT, Tan BK, Eng SA, Yuen GC, Chan KL, Sim YK, et al.
    Food Funct, 2019 Sep 01;10(9):5759-5767.
    PMID: 31453615 DOI: 10.1039/c9fo01357a
    A strategy to circumvent the problem of multidrug resistant pathogens is the discovery of anti-infectives targeting bacterial virulence or host immunity. Black sea cucumber (Holothuria atra) is a tropical sea cucumber species traditionally consumed as a remedy for many ailments. There is a paucity of knowledge on the anti-infective capacity of H. atra and the underlying mechanisms involved. The objective of this study is to utilize the Caenorhabditis elegans-P. aeruginosa infection model to elucidate the anti-infective properties of H. atra. A bioactive H. atra extract and subsequently its fraction were shown to have the capability of promoting the survival of C. elegans during a customarily lethal P. aeruginosa infection. The same entities also attenuate the production of elastase, protease, pyocyanin and biofilm in P. aeruginosa. The treatment of infected transgenic lys-7::GFP worms with this H. atra fraction restores the repressed expression of the defense enzyme lys-7, indicating an improved host immunity. QTOF-LCMS analysis revealed the presence of aspidospermatidine, an indole alkaloid, and inosine in this fraction. Collectively, our findings show that H. atra possesses anti-infective properties against P. aeruginosa infection, by inhibiting pathogen virulence and, eventually, reinstating host lys-7 expression.
    Matched MeSH terms: Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry
  8. Fulltext The natural alkaloid Jerantinine B has activity in acute myeloid leukemia cells through a mechanism involving c-Jun
    Alhuthali HM, Bradshaw TD, Lim KH, Kam TS, Seedhouse CH
    BMC Cancer, 2020 Jul 07;20(1):629.
    PMID: 32635894 DOI: 10.1186/s12885-020-07119-2
    BACKGROUND: Acute myeloid leukemia (AML) is a heterogenous hematological malignancy with poor long-term survival. New drugs which improve the outcome of AML patients are urgently required. In this work, the activity and mechanism of action of the cytotoxic indole alkaloid Jerantinine B (JB), was examined in AML cells.

    METHODS: We used a combination of proliferation and apoptosis assays to assess the effect of JB on AML cell lines and patient samples, with BH3 profiling being performed to identify early effects of the drug (4 h). Phosphokinase arrays were adopted to identify potential driver proteins in the cellular response to JB, the results of which were confirmed and extended using western blotting and inhibitor assays and measuring levels of reactive oxygen species.

    RESULTS: AML cell growth was significantly impaired following JB exposure in a dose-dependent manner; potent colony inhibition of primary patient cells was also observed. An apoptotic mode of death was demonstrated using Annexin V and upregulation of apoptotic biomarkers (active caspase 3 and cleaved PARP). Using BH3 profiling, JB was shown to prime cells to apoptosis at an early time point (4 h) and phospho-kinase arrays demonstrated this to be associated with a strong upregulation and activation of both total and phosphorylated c-Jun (S63). The mechanism of c-Jun activation was probed and significant induction of reactive oxygen species (ROS) was demonstrated which resulted in an increase in the DNA damage response marker γH2AX. This was further verified by the loss of JB-induced C-Jun activation and maintenance of cell viability when using the ROS scavenger N-acetyl-L-cysteine (NAC).

    CONCLUSIONS: This work provides the first evidence of cytotoxicity of JB against AML cells and identifies ROS-induced c-Jun activation as the major mechanism of action.

    Matched MeSH terms: Indole Alkaloids/pharmacology*; Indole Alkaloids/therapeutic use
  9. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria
    Zhang Q, Zhao JJ, Xu J, Feng F, Qu W
    J Ethnopharmacol, 2015 Sep 15;173:48-80.
    PMID: 26091967 DOI: 10.1016/j.jep.2015.06.011
    The genus Uncaria belongs to the family Rubiaceae, which mainly distributed in tropical regions, such as Southeast Asia, Africa and Southeast America. Their leaves and hooks have long been thought to have healing powers and are already being tested as a treatment for asthma, cancer, cirrhosis, diabetes, hypertension, stroke and rheumatism. The present review aims to provide systematically reorganized information on the ethnopharmacology, phytochemistry and pharmacology of the genus Uncaria to support for further therapeutic potential of this genus. To better understanding this genus, information on the stereo-chemistry and structure-activity relationships in indole alkaloids is also represented.
    Matched MeSH terms: Indole Alkaloids
  10. New bisindole alkaloids from Tabernaemontana corymbosa
    Kam TS, Sim KM, Pang HS
    J Nat Prod, 2003 Jan;66(1):11-6.
    PMID: 12542336
    Ten new bisindole alkaloids of the vobasinyl-ibogan type, viz., conodiparines A-F (1-6), conodutarines A and B (7, 8), and cononitarines A and B (9, 10), were obtained from the leaf extract of the Malayan species Tabernaemontana corymbosa. The structures were determined using NMR and MS analysis.
    Matched MeSH terms: Indole Alkaloids/isolation & purification*; Indole Alkaloids/chemistry
  11. Antioxidant activity of methanol extract of tinospora crispa and tabernaemontana corymbosa
    Heida Nadia Zulkefli, Jamaludin Mohamad, Nurhayati Zainal Abidin
    Sains Malaysiana, 2013;42:697-706.
    Tinospora crispa and Tabernaemontana corymbosa have been used traditionally to treat fever, diabetes, rheumatism and sinusitis. The objective of this study was to evaluate the antioxidant activity of Tinospora crispa and Tabernaemontana corymbosa. The presence of apigenin and magnoflorine was detected using LCMS/MS in Tinospora crispa (Patawali) whereas appararicine, voafinine, conodusarine, conodurine, voacamine and voacangine were detected in Tabernaemontana corymbosa (Susur kelapa) methanol extract. The stem extract of Tinospora crispa showed high antioxidant activity in the following order: DPPH radical scavenging, reducing power and metal chelating assay (98.8%, 0.957, 81.97%) than Tabernaemontana corymbosa of leaves (90.04%, 0.652, 69.64%), stem (82.78%, 0.819, 36.70%) and root extracts (63.25%, 0.469, 51.56%), respectively. The high antioxidant activity in the stem extract of Tinospora crispa is due to the presence of apigenin and magnoflorine. The high antioxidant activity in Tabernaemontana corymbosa extract is due to its high phenol contents. There were significant linear positive correlation (r=0.788, p<0.001, r2=0.621) between the total phenolic content and DPPH free radical scavenging assay in the crude extracts of Tinospora crispa and Tabernaemontana corymbosa. Meanwhile, a significant moderate positive correlation was observed between the total phenolic content and ferric reducing power assay (r= 0.556, p<0.05, r2= 0.309). However, there was no significant difference in the correlation coefficient of total phenolic content and metal chelating assay.
    Matched MeSH terms: Indole Alkaloids
  12. Fulltext Characterisation of Silver Nanoparticles using a Standardised Catharanthus Roseus Aqueous extract
    Siti Zulaikha Ghozali, Mohd Nazri Ismail, Nor Hazwani Ahmad
    Malaysian Journal of Medicine and Health Sciences, 2018;14(102):1-6.
    MyJurnal
    The biosynthesis of nanoparticles has been proposed as a cost-effective and environmental friendly alternative to chemical and physical methods. The present study was aimed to characterise Catharanthus roseus (C. roseus)-silver nanoparticles (AgNPs) using a standardised C. roseus aqueous extract. Methods: The standardisation was performed by using Liquid Chromatography/Time-of-Flight ion trap Mass Spectrometry. An optimised C. roseus-AgNPs have been previously synthesised. Further characterisation of C. roseus-AgNPs was evaluated by zeta potential analysis and fourier transform infrared spectroscopy (FTIR). Results: The chromatography analysis has revealed presence of thirteen possible indole alkaloids in C. roseus extract which were lochrovicine, lochnerine, vinleurosine, vindolinine, tabersonine, catharanthine, serpentine, catharosine, vincristine, catharine, ajmalicine, vinleurosine, and vindolicine. Zeta potential analysis exhibited the value at -16.6 mV. FTIR spectrum of C. roseus aqueous extract showed the absorption band at 3210.83 cm-1 (C-H stretch), 2934.11 (C-H bond), 1578.15 (N=O stretch), 1388.76 and 1314.89 (N=O bend), 1119.29 (C-O bond) and 729.94 (C-Cl bond). In comparison, FTIR spectrum of C. roseus-AgNP s showed the absorption band at 2925.01 and 2924.97 (C-H bond), 1622.93 (C-C=C symmetric stretch), 1383.19 and 1384.13 (N-O bend), 1037.92/1038.76/1238.3/1117.2 (C-O bond), 3169.4 (O-H bond), 774.59 and 691.53 (C-Cl bond). Conclusion: The present findings have shown that the C. roseus aqueous extract contains alkaloids that may responsible as reducing and stabilising agents in the synthesis of AgNPs.
    Matched MeSH terms: Indole Alkaloids
  13. Fulltext Comparative metabolomics analysis reveals alkaloid repertoires in young and mature Mitragyna speciosa (Korth.) Havil. Leaves
    Veeramohan R, Zamani AI, Azizan KA, Goh HH, Aizat WM, Razak MFA, et al.
    PLoS One, 2023;18(3):e0283147.
    PMID: 36943850 DOI: 10.1371/journal.pone.0283147
    The fresh leaves of Mitragyna speciosa (Korth.) Havil. have been traditionally consumed for centuries in Southeast Asia for its healing properties. Although the alkaloids of M. speciosa have been studied since the 1920s, comparative and systematic studies of metabolite composition based on different leaf maturity levels are still lacking. This study assessed the secondary metabolite composition in two different leaf stages (young and mature) of M. speciosa, using an untargeted liquid chromatography-electrospray ionisation-time-of-flight-mass spectrometry (LC-ESI-TOF-MS) metabolite profiling. The results revealed 86 putatively annotated metabolite features (RT:m/z value) comprising 63 alkaloids, 10 flavonoids, 6 terpenoids, 3 phenylpropanoids, and 1 of each carboxylic acid, glucoside, phenol, and phenolic aldehyde. The alkaloid features were further categorised into 14 subclasses, i.e., the most abundant class of secondary metabolites identified. As per previous reports, indole alkaloids are the most abundant alkaloid subclass in M. speciosa. The result of multivariate analysis (MVA) using principal component analysis (PCA) showed a clear separation of 92.8% between the young and mature leaf samples, indicating a high variance in metabolite levels between them. Akuammidine, alstonine, tryptamine, and yohimbine were tentatively identified among the many new alkaloids reported in this study, depicting the diverse biological activities of M. speciosa. Besides delving into the knowledge of metabolite distribution in different leaf stages, these findings have extended the current alkaloid repository of M. speciosa for a better understanding of its pharmaceutical potential.
    Matched MeSH terms: Indole Alkaloids/analysis
  14. Fulltext Sustainable Syntheses of (-)-Jerantinines A & E and Structural Characterisation of the Jerantinine-Tubulin Complex at the Colchicine Binding Site
    Smedley CJ, Stanley PA, Qazzaz ME, Prota AE, Olieric N, Collins H, et al.
    Sci Rep, 2018 Jul 13;8(1):10617.
    PMID: 30006510 DOI: 10.1038/s41598-018-28880-2
    The jerantinine family of Aspidosperma indole alkaloids from Tabernaemontana corymbosa are potent microtubule-targeting agents with broad spectrum anticancer activity. The natural supply of these precious metabolites has been significantly disrupted due to the inclusion of T. corymbosa on the endangered list of threatened species by the International Union for Conservation of Nature. This report describes the asymmetric syntheses of (-)-jerantinines A and E from sustainably sourced (-)-tabersonine, using a straight-forward and robust biomimetic approach. Biological investigations of synthetic (-)-jerantinine A, along with molecular modelling and X-ray crystallography studies of the tubulin-(-)-jerantinine B acetate complex, advocate an anticancer mode of action of the jerantinines operating via microtubule disruption resulting from binding at the colchicine site. This work lays the foundation for accessing useful quantities of enantiomerically pure jerantinine alkaloids for future development.
    Matched MeSH terms: Indole Alkaloids/chemical synthesis; Indole Alkaloids/isolation & purification; Indole Alkaloids/pharmacology*; Indole Alkaloids/chemistry
  15. Eucophylline, a Tetracyclic Vinylquinoline Alkaloid from Leuconotis eugenifolius
    Deguchi J, Shoji T, Nugroho AE, Hirasawa Y, Hosoya T, Shirota O, et al.
    J Nat Prod, 2010 Oct 22;73(10):1727-9.
    PMID: 20836516 DOI: 10.1021/np100458b
    Eucophylline (1), a new tetracyclic vinylquinoline alkaloid, was isolated from the bark of Leuconotis eugenifolius together with leucophyllidine (2). The structure and absolute configuration of 1 were elucidated on the basis of 2D NMR correlations and simulated CD analysis. Leucophyllidine (2) showed iNOS inhibitory activity and decreased the iNOS protein expression dose-dependently.
    Matched MeSH terms: Indole Alkaloids/isolation & purification; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry
  16. Bisnicalaterine A, a vobasine-vobasine bisindole alkaloid from Hunteria zeylanica
    Nugroho AE, Hirasawa Y, Kawahara N, Goda Y, Awang K, Hadi AH, et al.
    J Nat Prod, 2009 Aug;72(8):1502-6.
    PMID: 19388660 DOI: 10.1021/np900115q
    A new bisindole alkaloid, bisnicalaterine A (1), consisting of two vobasine-type skeletons, and 3-epivobasinol (2) and 3-O-methylepivobasinol (3), with vobasine-type skeletons, were isolated from the leaves of Hunteria zeylanica, and their structures were elucidated on the basis of spectroscopic data and chemical correlation. Bisnicalaterine A showed moderate cytotoxicity against various human cancer cell lines.
    Matched MeSH terms: Indole Alkaloids/isolation & purification*; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry
  17. Bisleuconothine A Induces Autophagosome Formation by Interfering with AKT-mTOR Signaling Pathway
    Wong CP, Seki A, Horiguchi K, Shoji T, Arai T, Nugroho AE, et al.
    J Nat Prod, 2015 Jul 24;78(7):1656-62.
    PMID: 26176165 DOI: 10.1021/acs.jnatprod.5b00258
    We have previously reported that bisleuconothine A (Bis-A), a novel bisindole alkaloid isolated from Leuconotis griffithii, showed cytostatic activity in several cell lines. In this report, the mechanism of Bis-A-induced cytostatic activity was investigated in detail using A549 cells. Bis-A did not cause apoptosis, as indicated by analysis of annexin V and propidium iodide staining. Expression of all tested apoptosis-related proteins was also unaffected by Bis-A treatment. Bis-A was found to increase LC3 lipidation in MCF7 cells as well as A549 cells, suggesting that Bis-A cytostatic activity may be due to induction of autophagy. Subsequent investigation via Western blotting and immunofluorescence staining indicated that Bis-A induced formation but prevented degradation of autophagosomes. Mechanistic studies showed that Bis-A down-regulated phosphorylation of protein kinase B (AKT) and its downstream kinase, PRAS40, which is an mTOR repressor. Moreover, phosphorylation of p70S6K, an mTOR-dependent kinase, was also down-regulated. Down-regulation of these kinases suggests that the increase in LC3 lipidation may be due to mTOR deactivation. Thus, the cytostatic activity shown by Bis-A may be attributed to its induction of autophagosome formation. The Bis-A-induced autophagosome formation was suggested to be caused by its interference with the AKT-mTOR signaling pathway.
    Matched MeSH terms: Indole Alkaloids/isolation & purification; Indole Alkaloids/pharmacology*; Indole Alkaloids/chemistry
  18. Bisleuconothines B-D, Modified Eburnane-Aspidosperma Bisindole Alkaloids from Leuconotis griffithii
    Nugroho AE, Zhang W, Hirasawa Y, Tang Y, Wong CP, Kaneda T, et al.
    J Nat Prod, 2018 11 26;81(11):2600-2604.
    PMID: 30362746 DOI: 10.1021/acs.jnatprod.8b00749
    Three new bisindole alkaloids, bisleuconothines B-D (1-3), were isolated from the bark of Leuconotis griffithii. Their structures were elucidated by 1D and 2D NMR spectroscopy and DFT calculations. Bisleuconothine B (1) is the first monoterpene indole alkaloid dimer featuring bridges between both C-16-C-10' and C-2-O-C-9'. All compounds were deemed noncytotoxic (IC50 > 10 μM) when tested against A549 human lung adenocarcinoma cells.
    Matched MeSH terms: Indole Alkaloids/isolation & purification*; Indole Alkaloids/chemistry
  19. Leucophyllinines A and B, bisindole alkaloids from Leuconotis eugeniifolia
    Tang Y, Nugroho AE, Hirasawa Y, Tougan T, Horii T, Hadi AHA, et al.
    J Nat Med, 2019 Jun;73(3):533-540.
    PMID: 30911994 DOI: 10.1007/s11418-019-01297-5
    Two new bisindole alkaloids, leucophyllinines A (1) and B (2) consisting of eburnane and quebrachamine-type skeletons were isolated from the bark of Leuconotis eugeniifolia, and their structures were elucidated on the basis of spectroscopic data. Leucophyllinines A and B showed antiplasmodial activities against Plasmodium falciparum 3D7.
    Matched MeSH terms: Indole Alkaloids/isolation & purification*; Indole Alkaloids/chemistry*
  20. Bisnicalaterines B and C, atropisomeric bisindole alkaloids from Hunteria zeylanica, showing vasorelaxant activity
    Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, et al.
    J Org Chem, 2010 Jun 18;75(12):4218-23.
    PMID: 20469917 DOI: 10.1021/jo1006762
    Two new bisindole alkaloids, bisnicalaterines B and C (1 and 2) consisting of an eburnane and a corynanthe type of skeletons, were isolated from the bark of Hunteria zeylanica. Their absolute structures were determined by combination of NMR, CD, and computational methods, and each of them was shown to be in an atropisomeric relationship. Bisnicalaterines B and C (1 and 2) showed potent vasorelaxant activity on isolated rat aorta.
    Matched MeSH terms: Indole Alkaloids/isolation & purification; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry*
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