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Journal articles on the topic 'Halogenated monoterpene'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Shilling, Andrew J., Jacqueline L. von Salm, Anthony R. Sanchez, et al. "Anverenes B–E, New Polyhalogenated Monoterpenes from the Antarctic Red Alga Plocamium cartilagineum." Marine Drugs 17, no. 4 (2019): 230. http://dx.doi.org/10.3390/md17040230.

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The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic halogenated monoterpenes (2–5) as well as undescribed compounds of the same class, anverenes B–D (6–8). Examination of another chemogroup yielded an undescribed cyclic halogenated monoterpene anverene E (9) as its major secondary metabolite. Elucidation of structures was achieved through one-dimensional (1

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2

Hellén, H., H. Hakola, K. H. Pystynen, J. Rinne, and S. Haapanala. "C<sub>2</sub>-C<sub>10</sub> hydrocarbon emissions from a boreal wetland and forest floor." Biogeosciences Discussions 2, no. 6 (2005): 1795–814. http://dx.doi.org/10.5194/bgd-2-1795-2005.

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Abstract. Emissions of various C2-C10 hydrocarbons and halogenated hydrocarbons from a boreal wetland and Scots pine forest floor were measured by static chamber technique in south-western Finland. Isoprene was the main non-methane hydrocarbon emitted by the wetland but also small emissions of ethene, propane, propene, 1-butene, 2-methylpropene, butane, pentane and hexane were detected. The isoprene emission from the wetland was observed to follow the commonly used isoprene emission algorithm. The mean emission potential of isoprene was 224 μg m−2 h−1 for the whole season. This is lower than t

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3

Hellén, H., H. Hakola, K. H. Pystynen, J. Rinne, and S. Haapanala. "C<sub>2</sub>-C<sub>10</sub> hydrocarbon emissions from a boreal wetland and forest floor." Biogeosciences 3, no. 2 (2006): 167–74. http://dx.doi.org/10.5194/bg-3-167-2006.

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Abstract. Emissions of various C2-C10 hydrocarbons (VOCs) and halogenated hydrocarbons (VHOCs) from a boreal wetland and a Scots pine forest floor in south-western Finland were measured by the static chamber technique. Isoprene was the main non-methane hydrocarbon emitted by the wetland, but small emissions of ethene, propane, propene, 1-butene, 2-methylpropene, butane, pentane and hexane were also detected. The isoprene emission from the wetland was observed to follow the commonly-used isoprene emission algorithm. The mean emission potential of isoprene was 224 µg m-2 h-1 for the whole season

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4

Cikoš, Ana-Marija, Mladenka Jurin, Rozelindra Čož-Rakovac, Stela Jokić, and Igor Jerković. "Update on Monoterpenes from Red Macroalgae: Isolation, Analysis, and Bioactivity." Marine Drugs 17, no. 9 (2019): 537. http://dx.doi.org/10.3390/md17090537.

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Macroalgae produce a wide range of monoterpenes as secondary metabolites of mevalonate (MVA) and/or methylerythritol phosphate (MEP) pathway (often including haloperoxidase action). Great biodiversity of macroalgal monoterpenes was reported including acyclic, monocyclic, and bicyclic structures. Halogenated monoterpenes exhibited significant biological activity (e.g., anticancer, antiplasmodial, and insecticidal) that is influenced by the number of present halogens (higher halogen content is preferable, especially bromine) and their position within the monoterpene skeleton. In distinction from

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5

Bracegirdle, Joe, Zaineb Sohail, Michael J. Fairhurst, et al. "Costatone C—A New Halogenated Monoterpene from the New Zealand Red Alga Plocamium angustum." Marine Drugs 17, no. 7 (2019): 418. http://dx.doi.org/10.3390/md17070418.

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Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the planar structure of 7 was achieved through conventional NMR and (−)-HR-APCI-MS techniques, and the absolute configuration by comparison of experimental and DFT-calculated ECD spectra. The absolute configuration of 8 was determined using Mosher’s method. Compound 7 showed mild antibac

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6

Jung, Michael E., Derin C. D'Amico, and Willard Lew. "Efficient total synthesis of the cytotoxic halogenated monoterpene aplysiapyranoid A." Tetrahedron Letters 34, no. 6 (1993): 923–26. http://dx.doi.org/10.1016/s0040-4039(00)77455-7.

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7

Mann, Maryssa G. A., Henry B. Mkwananzi, Edith M. Antunes, et al. "Halogenated Monoterpene Aldehydes from the South African Marine AlgaPlocamium corallorhiza." Journal of Natural Products 70, no. 4 (2007): 596–99. http://dx.doi.org/10.1021/np060547c.

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8

Jung, Michael E., and Willard Lew. "Efficient total synthesis of the cytotoxic halogenated monoterpene aplysiapyranoid D." Journal of Organic Chemistry 56, no. 4 (1991): 1347–49. http://dx.doi.org/10.1021/jo00004a001.

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9

Maliakal, Sanjiv, Donald P. Cheney, and Gregory L. Rorrer. "HALOGENATED MONOTERPENE PRODUCTION IN REGENERATED PLANTLET CULTURES OFOCHTODES SECUNDIRAMEA(RHODOPHYTA, CRYPTONEMIALES)." Journal of Phycology 37, no. 6 (2001): 1010–19. http://dx.doi.org/10.1046/j.1529-8817.2001.00120.x.

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10

Rocha, Djenisa, Ana Seca, and Diana Pinto. "Seaweed Secondary Metabolites In Vitro and In Vivo Anticancer Activity." Marine Drugs 16, no. 11 (2018): 410. http://dx.doi.org/10.3390/md16110410.

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Isolation, finding or discovery of novel anticancer agents is very important for cancer treatment, and seaweeds are one of the largest producers of chemically active metabolites with valuable cytotoxic properties, and therefore can be used as new chemotherapeutic agents or source of inspiration to develop new ones. Identification of the more potent and selective anticancer components isolated from brown, green and red seaweeds, as well as studies of their mode of action is very attractive and constitute a small but relevant progress for pharmacological applications. Several researchers have ca

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11

Williard, Paul G., and Stephen E. De Laszlo. "Total synthesis of halogenated monoterpene marine natural products via the Diels-Alder reaction." Journal of Organic Chemistry 50, no. 20 (1985): 3738–49. http://dx.doi.org/10.1021/jo00220a013.

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12

JUNG, M. E., and W. LEW. "ChemInform Abstract: Efficient Total Synthesis of the Cytotoxic Halogenated Monoterpene Aplysiapyranoid D (I)." ChemInform 22, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199128208.

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13

San-Martin, A., and J. Rovirosa. "Variations in the halogenated monoterpene metabolites of plocamium cartilagineum of the chilean coast." Biochemical Systematics and Ecology 14, no. 5 (1986): 459–61. http://dx.doi.org/10.1016/0305-1978(86)90002-5.

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14

Shiyanga, Aina N., Michael Knott, and Petrina Kapewangolo. "In vitro Anti-HIV and Antimicrobial Activities of a Halogenated Monoterpene from a Namibian Plocamium Species of Marine Algae." Current Bioactive Compounds 16, no. 3 (2020): 363–67. http://dx.doi.org/10.2174/1573407215666190111153845.

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Background: The marine red alga Plocamium naturally produces halogenated monoterpenes with varied biological activities. In our continuing efforts to discover new lead compounds for the treatment of HIV/AIDS as well as novel antibacterial compounds, various Namibian Plocamium species have been investigated. Methods: A rare but known compound namely 1E,3R,4S,5E,7Z-1-bromo-3,4,8-trichloro-7- (dichloromethyl)-3-methylocta-1,5,7-triene (1) was isolated from a Namibian Plocamium red alga. The anti-HIV activity of compound 1 was investigated against three HIV enzymes namely, HIV protease, reverse tr

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15

Shapumba, Christ W., Michael Knott, and Petrina Kapewangolo. "Antioxidant activity of a halogenated monoterpene isolated from a Namibian marine algal Plocamium species." Journal of Food Science and Technology 54, no. 10 (2017): 3370–73. http://dx.doi.org/10.1007/s13197-017-2784-4.

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16

Egorin, Merrill J., D. Marc Rosen, Sara E. Benjamin, Patrick S. Callery, Dorothy L. Sentz, and Julie L. Eiseman. "In vitro metabolism by mouse and human liver preparations of halomon, an antitumor halogenated monoterpene." Cancer Chemotherapy and Pharmacology 41, no. 1 (1997): 9–14. http://dx.doi.org/10.1007/s002800050701.

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17

Polzin, Jason J., Gregory L. Rorrer, and Donald P. Cheney. "Metabolic flux analysis of halogenated monoterpene biosynthesis in microplantlets of the macrophytic red alga Ochtodes secundiramea." Biomolecular Engineering 20, no. 4-6 (2003): 205–15. http://dx.doi.org/10.1016/s1389-0344(03)00054-6.

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18

Vetter, Walter, Natalie Rosenfelder, Stefan Kraan, and Josef Hiebl. "Structure and origin of the natural halogenated monoterpene MHC-1 and its concentrations in marine mammals and fish." Chemosphere 73, no. 1 (2008): 7–13. http://dx.doi.org/10.1016/j.chemosphere.2008.06.020.

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19

Polzin, Jason P., and Gregory L. Rorrer. "Halogenated monoterpene production by microplantlets of the marine red algaOchtodes secundiramea within an airlift photobioreactor under nutrient medium perfusion." Biotechnology and Bioengineering 82, no. 4 (2003): 415–28. http://dx.doi.org/10.1002/bit.10588.

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20

Pereira, RC, and MA Vasconcelos. "Chemical defense in the red seaweed Plocamium brasiliense: spatial variability and differential action on herbivores." Brazilian Journal of Biology 74, no. 3 (2014): 545–52. http://dx.doi.org/10.1590/bjb.2014.0080.

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Species of Plocamium are known as prolific sources of halogenated secondary metabolites exhibiting few explored ecological roles. In this study the crude extracts from specimens of P. brasiliensecollected in two distinct places, Enseada do Forno and Praia Rasa, Búzios, Estado do Rio de Janeiro, were evaluated as defense against the sea urchin Lytechinus variegatus and the crab Acanthonyx scutiformis. These specimens produce a similar amount of crude extract and also halogenated monoterpene compound-types, but individuals of P. brasiliense from Praia Rasa exhibit a major compound representing a

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21

Rosenfelder, Natalie, та Walter Vetter. "Stable carbon isotope composition (δ13C values) of the halogenated monoterpene MHC-1 as found in fish and seaweed from different marine regions". Journal of Environmental Monitoring 14, № 3 (2012): 845. http://dx.doi.org/10.1039/c2em10838k.

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22

Polzin, J. J., and G. L. Rorrer. "136 Metabolic Flux Analysis of Halogenated Monoterpene Biosynthesis in Microplantlet Suspension Cultures of the Marine Red Macroalgae Ochtodes Secundiramea and Portieria Hornemannii." Journal of Phycology 39, s1 (2003): 47–48. http://dx.doi.org/10.1111/j.0022-3646.2003.03906001_136.x.

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23

Gao, Donqhui, Roy Okuda, and Viorica Lopez-Avila. "Supercritical Fluid Extraction of Halogenated Monoterpenes from the Red Alga Plocamium cartilagineum." Journal of AOAC INTERNATIONAL 84, no. 5 (2001): 1313–31. http://dx.doi.org/10.1093/jaoac/84.5.1313.

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Abstract Supercritical fluid extraction (SFE) of the marine red alga Plocamium cartilagineum, which is known to contain complex mixtures of halogenated monoterpenes, was investigated. P. cartilagineum samples were extracted by SFE with carbon dioxide and modified carbon dioxide containing up to 10% methanol at different pressure and temperature conditions to establish the optimum conditions for extraction. These conditions were then used in the extraction of halogenated monoterpenes from 2 different samples of P. cartilagineum: one from Davenport, CA, and the other from Casa Beach (San Diego,

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24

Egorin, M. J., Dorothy L. Sentz, D. Marc Rosen, et al. "Plasma pharmacokinetics, bioavailability, and tissue distribution in CD 2 F 1 mice of halomon, an antitumor halogenated monoterpene isolated from the red algae Portieria hornemannii." Cancer Chemotherapy and Pharmacology 39, no. 1-2 (1996): 51–60. http://dx.doi.org/10.1007/s002800050537.

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25

Coll, JC, and AD Wright. "Tropical Marine Algae. I. New Halogenated Monoterpenes From Chondrococcus hornemannii (Rhodophyta, Gigartinales, Rhizophyllidaceae)." Australian Journal of Chemistry 40, no. 11 (1987): 1893. http://dx.doi.org/10.1071/ch9871893.

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Four linear halogenated monoterpenes: (2Z,6E)-1,8-dichloro-3-chloromethyl-7-methylocta- 2,6-diene (1), (E)-1,2-dibromo-3-chloromethylene-7-methyloct-6-ene (2), (Z)-1-chloro-3-chloromethyl-7-methylocta-2,6-diene (3) and (Z)-1,6-dichloro-3-chloromethyl-7-methylocta-2,7- diene (4), and two epimeric bicyclic monoterpenes (2R*,3(8) E,4S*,6R*)-6-bromo-2-chloro-1,4- oxido-3(8)- ochtodene (5) and (2S*,3(8)E,4S*,6R*)-6-bromo-2-chloro-1,4-oxido-3(8)- ochtodene (6) have been isolated from the red alga Chondrococcus hornernannii collected on the Great Barrier Reef, Australia. The structures were assigned

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26

Argandoña, Victor H., Juana Rovirosa, Aurelio San-Martín, et al. "Antifeedant Effects of Marine Halogenated Monoterpenes." Journal of Agricultural and Food Chemistry 50, no. 24 (2002): 7029–33. http://dx.doi.org/10.1021/jf025857p.

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27

Sabry, Omar M. M., Douglas E. Goeger, Frederick A. Valeriote, and William H. Gerwick. "Cytotoxic halogenated monoterpenes from Plocamium cartilagineum." Natural Product Research 31, no. 3 (2016): 261–67. http://dx.doi.org/10.1080/14786419.2016.1230115.

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28

König, Gabriele M., Anthony D. Wright, and Rocky de Nys. "Halogenated Monoterpenes fromPlocamiumcostatumand Their Biological Activity1." Journal of Natural Products 62, no. 2 (1999): 383–85. http://dx.doi.org/10.1021/np980408y.

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29

Ferreira, Wilton José, Rodrigo Amaro, Diana Negrão Cavalcanti, et al. "Anti-Herpetic Activities of Chemical Components from the Brazilian Red Alga Plocamium Brasiliense." Natural Product Communications 5, no. 8 (2010): 1934578X1000500. http://dx.doi.org/10.1177/1934578x1000500802.

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The CH2Cl2 crude extract and a fraction enriched with halogenated monoterpenes of the Brazilian red alga Plocamium brasiliense were evaluated for cytotoxicity and against the virus HSV-1. The extract showed low cytotoxicity compared with the fraction containing monoterpenes. The crude extract showed, in vitro, a high reduction of infectivity of the virus HSV-1.

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30

Tarhouni-Jabberi, Safa, Ons Zakraoui, Efstathia Ioannou та ін. "Mertensene, a Halogenated Monoterpene, Induces G2/M Cell Cycle Arrest and Caspase Dependent Apoptosis of Human Colon Adenocarcinoma HT29 Cell Line through the Modulation of ERK-1/-2, AKT and NF-κB Signaling". Marine Drugs 15, № 7 (2017): 221. http://dx.doi.org/10.3390/md15070221.

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31

Barrow, Kevin D., and Catherine A. Temple. "Biosynthesis of halogenated monoterpenes in Plocamium cartilagineum." Phytochemistry 24, no. 8 (1985): 1697–704. http://dx.doi.org/10.1016/s0031-9422(00)82537-6.

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32

Coll, JC, BW Skelton, AH White, and AD Wright. "Tropical Marine Algae. II. The Structure Determination of New Halogenated Monoterpenes From Plocamium hamatum (Rhodophyta, Gigartinales, Plocamiaceae)." Australian Journal of Chemistry 41, no. 11 (1988): 1743. http://dx.doi.org/10.1071/ch9881743.

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The structure determinations of new halogenated monoterpenes, isolated from collections of Plocamium hamatum J. Agardh , are reported. One collection of P. hamatum afforded (1R*,2R*,4S*,5R*,1′E)-1,2,4- trichloro-5-(2′-chloroethenyl)-1,5-dimethylcyclohexane (1) whose relative stereochemistry was determined by X-ray crystallography. Extensive use of two-dimensional carbon-hydrogen correlation experiments enabled unambiguous assignments of proton and carbon resonances to be made for this new compound. Complete carbon assignments for the related metabolite mertensene (2) are reported. A second col

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33

Rivera, Patricio, Luis Astudillo, Juana Rovirosa, and Aurelio San-Martín. "Halogenated monoterpenes of the red alga Shottera nicaensis." Biochemical Systematics and Ecology 15, no. 1 (1987): 3–4. http://dx.doi.org/10.1016/0305-1978(87)90072-x.

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34

Inés, Concepcián de, Victor H. Argandoña, Juana Rovirosa, et al. "Cytotoxic Activity of Halogenated Monoterpenes from Plocamium cartilagineum." Zeitschrift für Naturforschung C 59, no. 5-6 (2004): 339–44. http://dx.doi.org/10.1515/znc-2004-5-609.

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Nine halogenated monoterpenes isolated from the red alga Plocamium cartilagineum have been evaluated for their cytotoxic effects on the tumor cell lines CT26 (murine colon adenocarcinoma), SW480 (human colon adenocarcinoma), HeLa (human cervical adenocarcinoma) and SkMel28 (human malignant melanoma) with several multidrug resistance mechanisms and the mammalian non-tumor cell line CHO (Chinese hamster ovary cells). The activities of these compounds were compared with those of the insecticide γ-hexachlorocyclohexane (lindane) due to chemical structure similarities. Compounds 1, 2, 3, and 5 exhi

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35

Dı́az-Marrero, Ana R., Mercedes Cueto, Enrique Dorta, Juana Rovirosa, Aurelio San-Martı́n, and José Darias. "New halogenated monoterpenes from the red alga Plocamium cartilagineum." Tetrahedron 58, no. 42 (2002): 8539–42. http://dx.doi.org/10.1016/s0040-4020(02)01019-0.

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36

quiñoa, Emilio, Luis Castedo, and Ricardo Riguera. "The halogenated monoterpenes of Aplysia punctata. A comparative study." Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 92, no. 1 (1989): 99–101. http://dx.doi.org/10.1016/0305-0491(89)90319-2.

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37

Louw, Stefan, Lineekela Kandjengo, and Michael G. Knott. "Gas Chromatography-Mass Spectrometry (GC-MS) Combined with Retention Index Prediction for the Rapid Identification of Halogenated monoterpenes from a Namibian Plocamium species." Natural Product Communications 12, no. 2 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200217.

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Plocamium species collected from the Namibian coast display morphological features similar to those of both P. rigidum and P. suhrii which makes identification of these species a difficult task. It has been reported that the major secondary metabolites found in various Plocamium species are unique to each species [1]. In this study GC-MS combined with a retention index (RI) prediction strategy was used for the rapid identification of halogenated monoterpenes characteristic of a particular Namibian Plocamium species. The RIs of the metabolites were matched with the predicted RIs of halogenated

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38

Afolayan, Anthonia F., Maryssa G. A. Mann, Carmen A. Lategan, Peter J. Smith, John J. Bolton, and Denzil R. Beukes. "Antiplasmodial halogenated monoterpenes from the marine red alga Plocamium cornutum." Phytochemistry 70, no. 5 (2009): 597–600. http://dx.doi.org/10.1016/j.phytochem.2009.02.010.

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39

Kusumi, Takenori, Hideaki Uchida, Yoshinobu Inouye, Midori Ishitsuka, Hiroshi Yamamoto, and Hiroshi Kakisawa. "Novel cytotoxic monoterpenes having a halogenated tetrahydropyran from Aplysia kurodai." Journal of Organic Chemistry 52, no. 20 (1987): 4597–600. http://dx.doi.org/10.1021/jo00229a029.

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40

Kuniyoshi, Masayuki, Naomasa Oshiro, Takayuki Miono, and Tatsuo Higa. "Halogenated Monoterpenes Having a Cyclohexadienone from the Red AlgaPortieria Hornemanni." Journal of the Chinese Chemical Society 50, no. 1 (2003): 167–70. http://dx.doi.org/10.1002/jccs.200300023.

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41

Palma, Rodrigo, Mario Edding, Juana Rovirosa, Aurelio San-Martín, and Victor H. Argandoña. "Effect of Photon Flux Density and Temperature on the Production of Halogenated Monoterpenes by Plocamium cartilagineum (Plocamiaceae, Rhodophyta)." Zeitschrift für Naturforschung C 59, no. 9-10 (2004): 679–83. http://dx.doi.org/10.1515/znc-2004-9-1012.

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Abstract The effect of different photon flux densities (PFD) and temperatures on the relative growth rate (RGR) and the concentration of three halogenated monoterpenes in samples of Plocamium cartilagineum L.( Dixon), a marine alga (Rhodophyceae), were studied. The highest RGR (22.8 ± 0.04 d-1) was obtained at 15 °C and 41 μmol m-2 s-1 of PFD and the lowest (18.0 ± 0.2 d-1) was obtained at 18 °C and 120 μmol m-2 s-1. The different temperatures and light used in assays did not affect significantly the production of organic compounds. The production of mertensene and violacene was not affected s

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42

Louw, Stefan, Lineekela Kandjengo, Jonathan Ortmann, and Michael Knott. "Halogenated monoterpenes from Namibian Plocamium rigidum: Accurate quantification and chemotaxonomic relevance." South African Journal of Botany 133 (September 2020): 5–9. http://dx.doi.org/10.1016/j.sajb.2020.06.026.

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43

Andrianasolo, Eric H., Dennis France, Susan Cornell-Kennon, and William H. Gerwick. "DNA Methyl Transferase Inhibiting Halogenated Monoterpenes from the Madagascar Red Marine AlgaPortieriahornemannii." Journal of Natural Products 69, no. 4 (2006): 576–79. http://dx.doi.org/10.1021/np0503956.

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44

Barahona, Luis F., and Gregory L. Rorrer. "Isolation of Halogenated Monoterpenes from Bioreactor-Cultured Microplantlets of the Macrophytic Red AlgaeOchtodessecundirameaandPortieriahornemannii." Journal of Natural Products 66, no. 6 (2003): 743–51. http://dx.doi.org/10.1021/np0206007.

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45

Motti, Cherie A., Peter Thomas-Hall, Kehau A. Hagiwara, Charles J. Simmons, Rick Willis, and Anthony D. Wright. "Accelerated Identification of Halogenated Monoterpenes from Australian Specimens of the Red AlgaePlocamium hamatumandPlocamium costatum." Journal of Natural Products 77, no. 5 (2014): 1193–200. http://dx.doi.org/10.1021/np500059h.

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46

Knott, Michael G., Jo-Anne de la Mare, Adrienne L. Edkins, et al. "Plaxenone A and B: Cytotoxic halogenated monoterpenes from the South African red seaweed Plocamium maxillosum." Phytochemistry Letters 29 (February 2019): 182–85. http://dx.doi.org/10.1016/j.phytol.2018.12.009.

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47

Song, Yin-Ping, Feng-Ping Miao, Sheng-Tao Fang, Xiu-Li Yin, and Nai-Yun Ji. "Halogenated and Nonhalogenated Metabolites from the Marine-Alga-Endophytic Fungus Trichoderma asperellum cf44-2." Marine Drugs 16, no. 8 (2018): 266. http://dx.doi.org/10.3390/md16080266.

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One new bisabolane sesquiterpene, bisabolan-1,10,11-triol (1), one new norbisabolane sesquiterpene, 12-nor-11-acetoxybisabolen-3,6,7-triol (2), two new naturally occurring monoterpenes, (7S)- and (7R)-1-hydroxy-3-p-menthen-9-oic acids (3 and 4), one new naturally occurring trichodenone, dechlorotrichodenone C (5), one new chlorine-containing trichodenone, 3-hydroxytrichodenone C (6), one new diketopiperazine, methylcordysinin A (7), and one new naturally occurring oxazole derivative, 4-oxazolepropanoic acid (8), were isolated from the culture of a marine brown alga-endophytic strain (cf44-2) o

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Sardina, F. Javier, Emilio Quiñoá, Luis Castedo, and Ricardo Riguera. "STRUCTURAL ELUCIDATION OF MARINE HALOGENATED MONOTERPENES BY 2D-NMR AND NOE DIFFERENCE SPECTROSCOPY. A STEREOCHEMICAL CORRECTION." Chemistry Letters 14, no. 6 (1985): 697–700. http://dx.doi.org/10.1246/cl.1985.697.

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de la Mare, Jo-Anne, Jessica C. Lawson, Maynard T. Chiwakata, Denzil R. Beukes, Adrienne L. Edkins, and Gregory L. Blatch. "Quinones and halogenated monoterpenes of algal origin show anti-proliferative effects against breast cancer cells in vitro." Investigational New Drugs 30, no. 6 (2012): 2187–200. http://dx.doi.org/10.1007/s10637-011-9788-0.

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Shilling, AJ, JL Salm, RM Young, et al. "Isolation and characterization of halogenated monoterpenes in the investigation of the ecological relationship between Antarctic Plocamium cartilagineum and Paradexamine fissicauda." Planta Medica 81, S 01 (2016): S1—S381. http://dx.doi.org/10.1055/s-0036-1596673.

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