Keikipukalides, Furanocembrane Diterpenes from the Antarctic Deep Sea Octocoral Plumarella delicatissima
During a 2013 cruise in the Southern Ocean we collected specimens of the octocoral Plumarella delicatissima between 800 and 950 m depth. Five new furanocembranoid diterpenes, keikipukalides A–E (1–5), the known diterpene pukalide aldehyde (6), and the known norditerpenoid ineleganolide (7) were isol...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2018-01, Vol.81 (1), p.117-123 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Thomas, Santana A. L von Salm, Jacqueline L Clark, Shane Ferlita, Steve Nemani, Prasanth Azhari, Ala Rice, Christopher A Wilson, Nerida G Kyle, Dennis E Baker, Bill J |
| description | During a 2013 cruise in the Southern Ocean we collected specimens of the octocoral Plumarella delicatissima between 800 and 950 m depth. Five new furanocembranoid diterpenes, keikipukalides A–E (1–5), the known diterpene pukalide aldehyde (6), and the known norditerpenoid ineleganolide (7) were isolated from the coral. These Plumarella terpenes lack mammalian cytotoxicity, while 2–7 display activity against Leishmania donovani between 1.9 and 12 μM. Structure elucidation was facilitated by one- and two-dimensional NMR spectroscopy and mass spectrometry, and keikipukalides A and E were confirmed by X-ray crystallography. |
| doi_str_mv | 10.1021/acs.jnatprod.7b00732 |
| format | Article |
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L ; von Salm, Jacqueline L ; Clark, Shane ; Ferlita, Steve ; Nemani, Prasanth ; Azhari, Ala ; Rice, Christopher A ; Wilson, Nerida G ; Kyle, Dennis E ; Baker, Bill J</creator><creatorcontrib>Thomas, Santana A. L ; von Salm, Jacqueline L ; Clark, Shane ; Ferlita, Steve ; Nemani, Prasanth ; Azhari, Ala ; Rice, Christopher A ; Wilson, Nerida G ; Kyle, Dennis E ; Baker, Bill J</creatorcontrib><description>During a 2013 cruise in the Southern Ocean we collected specimens of the octocoral Plumarella delicatissima between 800 and 950 m depth. Five new furanocembranoid diterpenes, keikipukalides A–E (1–5), the known diterpene pukalide aldehyde (6), and the known norditerpenoid ineleganolide (7) were isolated from the coral. These Plumarella terpenes lack mammalian cytotoxicity, while 2–7 display activity against Leishmania donovani between 1.9 and 12 μM. 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These Plumarella terpenes lack mammalian cytotoxicity, while 2–7 display activity against Leishmania donovani between 1.9 and 12 μM. Structure elucidation was facilitated by one- and two-dimensional NMR spectroscopy and mass spectrometry, and keikipukalides A and E were confirmed by X-ray crystallography.</description><subject>Animals</subject><subject>Antarctic Regions</subject><subject>Anthozoa - chemistry</subject><subject>Crystallography, X-Ray - methods</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>Leishmania donovani - drug effects</subject><subject>Macrocyclic Compounds - chemistry</subject><subject>Macrocyclic Compounds - isolation & purification</subject><subject>Macrocyclic Compounds - pharmacology</subject><subject>Mass Spectrometry - methods</subject><subject>Nuclear Magnetic Resonance, Biomolecular - methods</subject><issn>0163-3864</issn><issn>1520-6025</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUFv1DAQhS0EokvhHyDkI4dmGdtxEl-QqpZCRaUiAWfLsSes2yQOtoPUf4_Lbiu4cJqD33t-Mx8hrxlsGXD2zti0vZlNXmJw27YHaAV_QjZMcqga4PIp2QBrRCW6pj4iL1K6AQABSj4nR1zxBqRsN2T3Gf2tX9ZbM3qH6YRerNHMweLUl4n03GeMC86Y6BDDRPMO6emcTbTZW3qOuNCvaOi1zcGGaEb6ZVwnE3EcDXU4emuyT8lP5iV5Npgx4avDPCbfLz58O_tUXV1_vDw7vapMXatcCdk42XSyV13jFLa2q9GKVjpUjbGiHgbZcckcsxLqHtTAO-UEd0ox1w1Qi2Pyfp-7rP2EzuKcSy29xNIh3ulgvP73ZfY7_SP80rJVDOquBLw9BMTwc8WU9eSTvV9oxrAmzVQRlltzVqT1XmpjSCni8PgNA30PSRdI-gGSPkAqtjd_V3w0PVApAtgL_tjDGudysf9n_gZbKKQu</recordid><startdate>20180126</startdate><enddate>20180126</enddate><creator>Thomas, Santana A. 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| ispartof | Journal of natural products (Washington, D.C.), 2018-01, Vol.81 (1), p.117-123 |
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| subjects | Animals Antarctic Regions Anthozoa - chemistry Crystallography, X-Ray - methods Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Leishmania donovani - drug effects Macrocyclic Compounds - chemistry Macrocyclic Compounds - isolation & purification Macrocyclic Compounds - pharmacology Mass Spectrometry - methods Nuclear Magnetic Resonance, Biomolecular - methods |
| title | Keikipukalides, Furanocembrane Diterpenes from the Antarctic Deep Sea Octocoral Plumarella delicatissima |
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