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Journal articles on the topic 'Biflavonoids'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Windsor, Peter K., Stephen P. Plassmeyer, Dominic S. Mattock, Jonathan C. Bradfield, Erika Y. Choi, Bill R. Miller, and Byung Hee Han. "Biflavonoid-Induced Disruption of Hydrogen Bonds Leads to Amyloid-β Disaggregation." International Journal of Molecular Sciences 22, no. 6 (March 12, 2021): 2888. http://dx.doi.org/10.3390/ijms22062888.

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Deposition of amyloid β (Aβ) fibrils in the brain is a key pathologic hallmark of Alzheimer’s disease. A class of polyphenolic biflavonoids is known to have anti-amyloidogenic effects by inhibiting aggregation of Aβ and promoting disaggregation of Aβ fibrils. In the present study, we further sought to investigate the structural basis of the Aβ disaggregating activity of biflavonoids and their interactions at the atomic level. A thioflavin T (ThT) fluorescence assay revealed that amentoflavone-type biflavonoids promote disaggregation of Aβ fibrils with varying potency due to specific structural differences. The computational analysis herein provides the first atomistic details for the mechanism of Aβ disaggregation by biflavonoids. Molecular docking analysis showed that biflavonoids preferentially bind to the aromatic-rich, partially ordered N-termini of Aβ fibril via the π–π interactions. Moreover, docking scores correlate well with the ThT EC50 values. Molecular dynamic simulations revealed that biflavonoids decrease the content of β-sheet in Aβ fibril in a structure-dependent manner. Hydrogen bond analysis further supported that the substitution of hydroxyl groups capable of hydrogen bond formation at two positions on the biflavonoid scaffold leads to significantly disaggregation of Aβ fibrils. Taken together, our data indicate that biflavonoids promote disaggregation of Aβ fibrils due to their ability to disrupt the fibril structure, suggesting biflavonoids as a lead class of compounds to develop a therapeutic agent for Alzheimer’s disease.

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2

Girardi, Leury G. J., Michele Morsch, Ana E. Oliveira, Valdir Cechinel-Filho, and Clóvis Antonio Rodrigues. "Separation of Bioactive Biflavonoids from Rheedia gardneriana Using Chitosan Modified with Benzaldehyde." Zeitschrift für Naturforschung C 60, no. 5-6 (June 1, 2005): 408–10. http://dx.doi.org/10.1515/znc-2005-5-607.

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This paper shows the influence of benzenic groups on the chitosan surface for the separation of bioactive biflavonoids from Rheedia gardneriana leaves. The yield of the biflavonoids using chitin modified with benzaldehyde (CH-Bz) as adsorbent in column chromatography was higher than that achieved with silica gel and chitosan. The presence of benzenic groups decreases the polarity of chitosan and consequently the interaction of hydrogen bonding between phenolic hydroxyl (OH) of biflavonoids and amine groups of the adsorbent. Therefore, the separation of these compounds appears to be the result of hydrophobicity and π-π interaction among electrons from the aromatic ring in sorbent and biflavonoid molecules.

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3

Al-Shagdari, Ahmed, Adonis Bello Alarcón, Osmany Cuesta-Rubio, Anna Lisa Piccinelli, and Luca Rastrelli. "Biflavonoids, Main Constituents from Garcinia Bakeriana Leaves." Natural Product Communications 8, no. 9 (September 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800913.

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The genus Garcinia is a source of a large variety of organic compounds including biflavonoids, acylphloroglucinols and xanthones mainly, but few data are available about the chemical composition of Cuban species. The aim of this investigation was to identify the main constituents of G. bakeriana Urb., a rare Cuban endemic plant. A new biflavonoid, 4″’- O-methyl-I3,II8-biapigenin (1), together with 9 known compounds, namely, the biflavonoids amentoflavone (2), 4″’- O-methylamentoflavone (3), 4′- O-methylcupressuflavone (4), GB-2a (5), volkensiflavone (6), 6″-(2-hydroxy-3-methyl-3-butenyl)-amentoflavone (7), I3,II8-biapigenin (8), and GB-1a (9), and the xanthone norathyriol (10), were isolated from the leaves of this species. All the structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, as well as ESIMS analysis. These results showed that the isolated biflavonoids possess a C-C interflavonoid linkage between the apigenin units or its derivatives.

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4

Li, Li, Xia, Tian, Zhang, Rui, Dong, and Xiao. "Anticancer Effects of Five Biflavonoids from Ginkgo Biloba L. Male Flowers In Vitro." Molecules 24, no. 8 (April 16, 2019): 1496. http://dx.doi.org/10.3390/molecules24081496.

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Ginkgo biloba L., an ancient dioecious gymnosperm, is now cultivated worldwide for landscaping and medical purposes. A novel biflavonoid—amentoflavone 7''-O-β-D-glucopyranoside (1)—and four known biflavonoids were isolated and identified from the male flowers of Ginkgo. The anti-proliferative activities of five biflavonoids were evaluated on different cancer lines. Bilobetin (3) and isoginkgetin (4) exhibited better anti-proliferative activities on different cancer lines. Their effects were found to be cell-specific and in a dose and time dependent manner for the most sensitive HeLa cells. The significant morphological changes validated their anticancer effects in a dose-dependent manner. They were capable of arresting the G2/M phase of the cell cycle, inducing the apoptosis of HeLa cells dose-dependently and activating the proapoptotic protein Bax and the executor caspase-3. Bilobetin (3) could also inhibit the antiapoptotic protein Bcl-2. These might be the mechanism underlying their anti-proliferation. In short, bilobetin (3) and isoginkgetin (4) might be the early lead compounds for new anticancer agents.

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5

Skopp, Gisela, and Gerhard Schwenker. "Biflavonoide aus Schinus terebinthifolius Raddi (Anacardiaceae)/ Biflavonoids from Schinus terebinthifolius Raddi (Anacardiaceae)." Zeitschrift für Naturforschung B 41, no. 11 (November 1, 1986): 1479–82. http://dx.doi.org/10.1515/znb-1986-1125.

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6

Cao, Shu-Geng, Keng-Yeow Sim, and Swee-Hock Goh. "Biflavonoids ofCalophyllum venulosum." Journal of Natural Products 60, no. 12 (December 1997): 1245–50. http://dx.doi.org/10.1021/np970303f.

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7

Tih, Anastasie Ewola, Raphael Tih Ghogomu, Beibam Lucas Sondengam, Christelle Caux, and Bernard Bodo. "Minor Biflavonoids fromLophiraalataLeaves." Journal of Natural Products 69, no. 8 (August 2006): 1206–8. http://dx.doi.org/10.1021/np050169w.

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8

Recalde-Gil, Angelica Maria, Luiz Klein-Júnior, Juliana Salton, Sérgio Bordignon, Valdir Cechinel-Filho, Cristiane Matté, and Amélia Henriques. "Aromatase (CYP19) inhibition by biflavonoids obtained from the branches of Garcinia gardneriana (Clusiaceae)." Zeitschrift für Naturforschung C 74, no. 9-10 (September 25, 2019): 279–82. http://dx.doi.org/10.1515/znc-2019-0036.

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Abstract Overexpression of aromatase in breast cancer cells may substantially influence its progression and maintenance. In this sense, the inhibition of aromatase is a key target for the treatment of breast cancer in postmenopausal women. Although several flavonoids had already demonstrated the capacity of inhibiting aromatase activity, the role of biflavonoids as aromatase inhibitors is poorly studied. In this work, the biflavonoids isolated from Garcinia gardneriana, morelloflavone (1), Gb-2a (2) and Gb-2a-7-O-glucose (3) were submitted to in vitro assay to evaluate the aromatase modulatory effect. As results, it was demonstrated that all biflavonoids were able to inhibit the enzyme, with IC50 values ranging from 1.35 to 7.67 μM. This demonstrates that biflavonoids are an important source of scaffolds for the development of new aromatase inhibitors, focusing on the development of new anticancer agents.

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9

Yokosuka, Akihito, Misaki Honda, Hitoshi Kondo, and Yoshihiro Mimaki. "Chemical Constituents of the Whole Plant of Verbena hastata and Their Inhibitory Activity Against the Production of AGEs." Natural Product Communications 16, no. 4 (April 2021): 1934578X2110097. http://dx.doi.org/10.1177/1934578x211009727.

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Two iridoid glycosides (1 and 2), 3 phenolic glycosides (3–5), 1 flavone glycoside (6), 3 biflavonoids (7–9), 1 flavone (10), 2 triterpenes (11 and 12), 1 sterol (13), and 1 naphthoquinone derivative (14) were isolated from the whole plant of Verbena hastata (Verbenaceae). Compounds 3-13 were isolated from V. hastata for the first time. Compound 14 is undescribed in the literature. Incubation of glyceraldehyde and collagen either with phenolic glycosides (3), (4), or (5) or with biflavonoid (8) inhibited the production of advanced glycation end products, with IC50 values of 6.3, 6.4, 6.2, and 6.8 mM, respectively. Aminoguanidine, which was used as a positive control, had an IC50 value of 10.2 mM.

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10

Zhang, Xiaoli, Guocai Wang, Weihuan Huang, Wencai Ye, and Yaolan Li. "Biflavonoids from the Roots of Wikstroemia indica." Natural Product Communications 6, no. 8 (August 2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600815.

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Two new biflavonoids, 4′-methoxydaphnodorin D1 and 4′-methoxydaphnodorin D2, along with six known biflavonoids, were isolated from the roots of Wikstroemia indica. The structures of the new compounds were determined by extensive NMR and HRESIMS spectroscopic analyses in combination with CD measurements.

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11

Geiger, Hans, Wolfgang Stein, Rüdiger Mues, and H. Dietmar Zinsmeister. "Bryoflavone and Heterobryoflavone, Two New Isoflavone-flavone Dimers from Bryum capillare." Zeitschrift für Naturforschung C 42, no. 7-8 (August 1, 1987): 863–67. http://dx.doi.org/10.1515/znc-1987-7-822.

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From the moss Bryum capillare (Bryaceae) two new biflavonoids-bryoflavone and hetero bryoflavone - have been isolated. They are the first examples of a new class of biflavonoids formed by oxidative coupling of a flavone and an isoflavone moiety. The structures of both compounds are proved spectroscopically.

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12

Kang, Fenghua, Sha Zhang, Dekun Chen, Jianbing Tan, Min Kuang, Jinlin Zhang, Guangyuan Zeng, Kangping Xu, Zhenxing Zou, and Guishan Tan. "Biflavonoids from Selaginella doederleinii as Potential Antitumor Agents for Intervention of Non-Small Cell Lung Cancer." Molecules 26, no. 17 (September 5, 2021): 5401. http://dx.doi.org/10.3390/molecules26175401.

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Four new biflavonoids (1–4) were isolated from Selaginella doederleinii together with a known biflavonoid derivative (5). Their structures contained a rare linker of individual flavones to each other by direct C-3-O-C-4′′′ bonds, and were elucidated by extensive spectroscopic data, including HRESIMS, NMR and ECD data. All isolates significantly inhibited the proliferation of NSCLC cells (IC50 = 2.3–8.4 μM) with low toxicity to non-cancer MRC-5 cells, superior to the clinically used drug DDP. Furthermore, the most active compound 3 suppressed XIAP and survivin expression, promoted upregulation of caspase-3/cleaved-caspase-3, as well as induced cell apoptosis and cycle arrest in A549 cells. Together, our findings suggest that 3 may be worth studying further for intervention of NSCLC.

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13

Kumar, Neeraj, Bikram Singh, Pamita Bhandari, Ajai P. Gupta, Sanjay K. Uniyal, and Vijay K. Kaul. "Biflavonoids from Lonicera japonica." Phytochemistry 66, no. 23 (December 2005): 2740–44. http://dx.doi.org/10.1016/j.phytochem.2005.10.002.

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14

Reddy, Bandi A. K., Nimmanapalli P. Reddy, Duvvuru Gunasekar, Alain Blond, and Bernard Bodo. "Biflavonoids from Ochna lanceolata." Phytochemistry Letters 1, no. 1 (April 2008): 27–30. http://dx.doi.org/10.1016/j.phytol.2007.12.005.

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15

D'arc Felicio, Joana, Maria Helena Rossi, Hui Ran Park, Edlayne Gonçalez, Maria Maia Braggio, Jorge M. David, and Ines Cordeiro. "Biflavonoids from Ouratea multiflora." Fitoterapia 72, no. 4 (May 2001): 453–55. http://dx.doi.org/10.1016/s0367-326x(00)00286-0.

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16

SUAREZ, A. "Biflavonoids from Podocalyx loranthoides." Fitoterapia 74, no. 5 (July 2003): 473–75. http://dx.doi.org/10.1016/s0367-326x(03)00065-0.

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17

Pegnyemb, Dieudonné Emmanuel, Raphael Ghogomu Tih, Beibam Lucas Sondengam, Alain Blond, and Bernard Bodo. "Biflavonoids from Ochna afzelii." Phytochemistry 57, no. 4 (June 2001): 579–82. http://dx.doi.org/10.1016/s0031-9422(01)00101-7.

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18

Messanga, Blaise, Raphael Ghogomu Tih, Beibam-Lucas Sondengam, Marie-Thérèse Martin, and Bernard Bodo. "Biflavonoids from Ochna calodendron." Phytochemistry 35, no. 3 (February 1994): 791–94. http://dx.doi.org/10.1016/s0031-9422(00)90607-1.

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19

Feng, Baomin, Yuehu Pei, Huiming Hua, Tao Wang, and Yi Zhang. "Biflavonoids from Stellera chamaejasme." Pharmaceutical Biology 41, no. 1 (January 2003): 59–61. http://dx.doi.org/10.1076/phbi.41.1.59.14701.

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20

Wannan, Bruce S., and Christopher J. Quinn. "Biflavonoids in the julianiaceae." Phytochemistry 27, no. 10 (January 1988): 3161–62. http://dx.doi.org/10.1016/0031-9422(88)80019-0.

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21

Lin, Yuh-Meei, Michael T. Flavin, Ralph Schure, Fa-Ching Chen, Robert Sidwell, Dale I. Barnard, John H. Huffmann, and Earl R. Kern. "Antiviral Activities of Biflavonoids." Planta Medica 65, no. 2 (March 1999): 120–25. http://dx.doi.org/10.1055/s-1999-13971.

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22

Das, Biswanath, Gurram Mahender, Yerra Koteswara Rao, Anabathula Prabhakar, and Bharatam Jagadeesh. "Biflavonoids from Cycas beddomei." CHEMICAL & PHARMACEUTICAL BULLETIN 53, no. 1 (2005): 135–36. http://dx.doi.org/10.1248/cpb.53.135.

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23

Lin, Lie-Chwen, Yuh-Chi Kuo, and Cheng-Jen Chou. "Cytotoxic Biflavonoids fromSelaginella delicatula." Journal of Natural Products 63, no. 5 (May 2000): 627–30. http://dx.doi.org/10.1021/np990538m.

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24

Baba, Kimiye, Michi Yoshikawa, Masahiko Taniguchi, and Mitsugi Kozawa. "Biflavonoids from Daphne odora." Phytochemistry 38, no. 4 (March 1995): 1021–26. http://dx.doi.org/10.1016/0031-9422(94)00676-k.

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25

Nadirov, R. K., K. S. Nadirov, A. M. Esimova, and Zh K. Nadirova. "Electrochemical synthesis of biflavonoids." Chemistry of Natural Compounds 49, no. 1 (March 2013): 108–9. http://dx.doi.org/10.1007/s10600-013-0521-4.

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26

Yang, Ai Mei, Hai Tao Yu, Jie Li Liu, Xiao Long Shi, Yun Men, Rui Wu, and Wei Jie Guo. "Biflavonoids from Euphorbia altotibetica." Chemistry of Natural Compounds 51, no. 6 (November 2015): 1162–63. http://dx.doi.org/10.1007/s10600-015-1518-y.

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27

Rodrigues, Clóvis A., Ana E. Oliveira, Ana F. Schürmann da Silva, Valdir Cechinel Filho, Claudio L. Guimarães, Rosendo A. Yunes, and Franco Delle Monache. "A Comparative Study of Stationary Phase for Separation of Biflavonoids from Rheedia gardneriana Using Column Chromatography." Zeitschrift für Naturforschung C 55, no. 7-8 (August 1, 2000): 524–27. http://dx.doi.org/10.1515/znc-2000-7-808.

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Abstract This paper describes a comparative study by using different chromatographic supports (silica gel, chitin and chitosan) to separate biflavonoids from Rheedia gardneriana by column chromatography. The results indicated that chitin can be used as alternative method, but the yield of the compounds is lower than when silica gel is employed. In contrast, chitosan is not a good chromatographic support for the separation of the biflavonoids under the same experimental conditions.

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28

Lin, Yuh-Meei, Michael T. Flavin, Constance S. Cassidy, Aye Mar, and Fa-Ching Chen. "Biflavonoids as novel antituberculosis agents." Bioorganic & Medicinal Chemistry Letters 11, no. 16 (August 2001): 2101–4. http://dx.doi.org/10.1016/s0960-894x(01)00382-1.

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29

Ngo Mbing, Josephine, Cécile Enguehard-Gueiffier, Alex de Théodore Atchadé, Hassan Allouchi, Joseph Gangoué-Piéboji, Joseph Tanyi Mbafor, Raphael Ghogomu Tih, Jacques Pothier, Dieudonné Emmanuel Pegnyemb, and Alain Gueiffier. "Two biflavonoids from Ouratea nigroviolacea." Phytochemistry 67, no. 24 (December 2006): 2666–70. http://dx.doi.org/10.1016/j.phytochem.2006.07.027.

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30

Malafronte, Nicola, Antonio Vassallo, Fabrizio Dal Piaz, Ammar Bader, Alessandra Braca, and Nunziatina De Tommasi. "Biflavonoids from Daphne linearifolia Hart." Phytochemistry Letters 5, no. 3 (September 2012): 621–25. http://dx.doi.org/10.1016/j.phytol.2012.06.008.

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31

Sum, Tze Jing, Tze Han Sum, Warren R. J. D. Galloway, David G. Twigg, Joe J. Ciardiello, and David R. Spring. "Synthesis of structurally diverse biflavonoids." Tetrahedron 74, no. 38 (September 2018): 5089–101. http://dx.doi.org/10.1016/j.tet.2018.05.003.

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32

Pegnyemb, D. E., R. Ghogomu-Tih, B. L. Sondengam, M. T. Martin, and B. Bodo. "Minor Biflavonoids of Lophira lanceolata." Journal of Natural Products 57, no. 9 (September 1994): 1275–78. http://dx.doi.org/10.1021/np50111a015.

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33

Rao, K. V., K. Sreeramulu, C. Venkata Rao, D. Gunasekar, M. T. Martin, and B. Bodo. "Two New Biflavonoids fromOchna obtusata." Journal of Natural Products 60, no. 6 (June 1997): 632–34. http://dx.doi.org/10.1021/np9604590.

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34

Baba, Kimlye, Masahiko Taniguchi, and Mitsugi Kozawa. "Three biflavonoids from Wikstroemia sikokiana." Phytochemistry 37, no. 3 (November 1994): 879–83. http://dx.doi.org/10.1016/s0031-9422(00)90376-5.

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35

Taniguchi, Masahiko, Akiko Fujiwara, Kimiye Baba, and Nian-He Wang. "Two biflavonoids from Daphne acutiloba." Phytochemistry 49, no. 3 (October 1998): 863–67. http://dx.doi.org/10.1016/s0031-9422(98)00181-2.

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36

Chen, Jih-Jung, Chang-Yih Duh, and Jinn-Fen Chen. "New Cytotoxic Biflavonoids fromSelaginella delicatula." Planta Medica 71, no. 7 (July 2005): 659–65. http://dx.doi.org/10.1055/s-2005-871273.

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37

Acuña, Ulyana Muñoz, Mario Figueroa, Adam Kavalier, Nikola Jancovski, Margaret J. Basile, and Edward J. Kennelly. "Benzophenones and Biflavonoids fromRheedia edulis." Journal of Natural Products 73, no. 11 (November 29, 2010): 1775–79. http://dx.doi.org/10.1021/np100322d.

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38

Yang, Hui, Mario Figueroa, Satoshi To, Scott Baggett, Bei Jiang, Margaret J. Basile, I. Bernard Weinstein, and Edward J. Kennelly. "Benzophenones and Biflavonoids fromGarcinia livingstoneiFruits." Journal of Agricultural and Food Chemistry 58, no. 8 (April 28, 2010): 4749–55. http://dx.doi.org/10.1021/jf9046094.

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39

GEIGER, H. "ChemInform Abstract: Biflavonoids and Triflavonoids." ChemInform 26, no. 1 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199501291.

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40

Ariyasena, Jyamani, Seung-Hwa Baek, Nigel B. Perry, and Rex T. Weavers. "Ether-Linked Biflavonoids fromQuintinia acutifolia." Journal of Natural Products 67, no. 4 (April 2004): 693–96. http://dx.doi.org/10.1021/np0340394.

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41

Silva, Gloria L., Heebyung Chai, Mahabir P. Gupta, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto, Christopher W. W. Beecher, and A. Douglas Kinghorn. "Cytotoxic biflavonoids from Selaginella willdenowii." Phytochemistry 40, no. 1 (September 1995): 129–34. http://dx.doi.org/10.1016/0031-9422(95)00212-p.

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42

Rampendahl, Christoph, Tassilo Seeger, Hans Geiger, and Hans Dietmar Zinsmeister. "The biflavonoids of Plagiomnium undulatum." Phytochemistry 41, no. 6 (April 1996): 1621–24. http://dx.doi.org/10.1016/0031-9422(95)00804-7.

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43

Taniguchi, Masahiko, and Kimiye Baba. "Three biflavonoids from Daphne odora." Phytochemistry 42, no. 5 (July 1996): 1447–53. http://dx.doi.org/10.1016/0031-9422(96)00136-7.

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44

Yang, Bao-Hua, Wei-Dong Zhang, Run-Hui Liu, Chang-Heng Tan, Ting-Zhao Li, Chuan Zhang, Xi-Ke Xu, and Juan Su. "Spiro-biflavonoids fromLarix olgensisHenry var.koreanaNakai." Helvetica Chimica Acta 88, no. 11 (November 2005): 2892–96. http://dx.doi.org/10.1002/hlca.200590232.

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45

Recalde-Gil, Maria Angélica, Luiz Carlos Klein-Júnior, Carolina dos Santos Passos, Juliana Salton, Sérgio Augusto de Loreto Bordignon, Franco Delle Monace, Valdir Cechinel Filho, and Amélia Teresinha Henriques. "Monoamine Oxidase Inhibitory Activity of Biflavonoids from Branches of Garcinia gardneriana (Clusiaceae)." Natural Product Communications 12, no. 4 (April 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200411.

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Garcinia gardneriana is chemically characterized by the presence of biflavonoids. Taking into account that flavonoids are able to inhibit monoamine oxidase (MAO) activity, in the present study, the chemical composition of the branches’ extract of the plant is described for the first time and the MAO inhibitory activity of the isolated biflavonoids was evaluated. Based on spectroscopic and spectrometric data, it was possible to identify volkesiflavone, morelloflavone (1), Gb-2a (2) and Gb-2a-7- O-glucoside (3) in the ethyl acetate fraction from ethanol extract of the branches. Compounds 1-3 were evaluated in vitro and demonstrated the capacity to inhibit MAO-A activity with an IC50 ranging from 5.05 to 10.7 μM, and from 20.7 to 66.2 μM for MAO-B. These inhibitions corroborate with previous IC50 obtained for monomeric flavonoids, with a higher selectivity for MAO-A isoform. The obtained results indicate that biflavonoids might be promising structures for the identification of new MAO inhibitory compounds.

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46

Xu, Kangping, Can Yang, Yuanyuan Xu, Dan Li, Shumin Bao, Zhenxing Zou, Fenghua Kang, Guishan Tan, Shu-Ming Li, and Xia Yu. "Selective geranylation of biflavonoids by Aspergillus terreus aromatic prenyltransferase (AtaPT)." Organic & Biomolecular Chemistry 18, no. 1 (2020): 28–31. http://dx.doi.org/10.1039/c9ob02296a.

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47

Aravind, Aravindakshanpillai P. Anu, Renu Pandey, Brijesh Kumar, Kumarapillai R. T. Asha, and Koranappallil B. Rameshkumar. "Phytochemical Screening of Garcinia travancorica by HPLC-ESI-QTOF Mass Spectrometry and Cytotoxicity Studies of the Major Biflavonoid Fukugiside." Natural Product Communications 11, no. 12 (December 2016): 1934578X1601101. http://dx.doi.org/10.1177/1934578x1601101216.

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Qualitative screening of multiclass secondary metabolites present in the fruits, leaves and stem bark extracts of Garcinia travancorica was carried out using HPLC-QTOF-MS analysis. Twenty-three compounds were identified in the fruits, leaves and stem bark, including two acids (hydroxycitric acid and hydroxycitric acid lactone), eight biflavonoids (morelloflavone, GB-1, GB-1a, GB-2, GB-2a, fukugiside, xanthochymusside and GB-1a glucoside), nine xanthones (α-mangostin, γ-mangostin, 1,5-dihydroxy-3-methoxyxanthone, garciniaxanthone E, 4-(1,1-dimethylprop-2-enyl)-1,3,5,8-tetrahydroxy-xanthone, garcinone A, garcinone B, garcinone C and polyanxanthone C) and four polyisoprenylated benzophenones (gambogenone, aristophenone A, garcinol and garciyunnanin A). Cytotoxicity studies of the major biflavonoid fukugiside reported from G. travancorica leaves revealed a dose-dependent cancer cell growth inhibition in A431 and HeLa cells. The antiproliferative effect appears to be due to the ability of fukugiside to induce S-phase arrest and apoptotic cell death. In HeLa cells, fukugiside reduced the expression of MAPKp38 by 26.1% compared with untreated control.

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48

Bekker, Riaan, E. Vincent Brandt, and Daneel Ferreira. "Biflavonoids. Part 4. Structure and stereochemistry of novel flavanone- and the first isoflavanone-benzofuranone biflavonoids." Tetrahedron 55, no. 33 (August 1999): 10005–12. http://dx.doi.org/10.1016/s0040-4020(99)00559-1.

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49

Guan, Jing, and Shun-Xing Guo. "Three New Biflavonoids from Chinese Dragon's Blood, Dracaena cochinchinensis." Natural Product Communications 7, no. 5 (May 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700510.

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Three new biflavonoids, named (2 Rγ S)-3′-methoxy-8-methylsocotrin-4′-ol (1), (2 Sγ R)-3′-methoxy-8-methylsocotrin-4′-ol (2), and (2 Rγ R)-8-methylsocotrin-4′-ol (3), were isolated from Chinese Dragon's blood [Dracaena cochinchinensis (Lour.) S. C. Chen], together with two known ones. The structures of these new biflavonoids were elucidated by a combination of HR-ESI-MS, 1H NMR, 13C NMR, HMQC, and HMBC spectra. The absolute configurations of compounds 1-4 were determined by quantum chemical calculation of the circular dichroism spectrum and comparison with the experimental CD spectrum.

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50

López-Sáez, José Antonio, María José Pérez-Alonso, and Arturo Velasco-Negueruela. "Notes: The Biflavonoid Pattern of the Moss Bartramia mossmanniana (Bartramiaceae, Musci)." Zeitschrift für Naturforschung C 50, no. 11-12 (December 1, 1995): 895–97. http://dx.doi.org/10.1515/znc-1995-11-1222.

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