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A clerodane diterpene (or clerodane diterpenoid) is a compound terpene derivative, more precisely a bicyclic diterpenoid. It is rather a rare form of diterpenoid and is structurally related to the bicyclic diterpenoids labdane and ginkgolide. Its biosynthesis in plants (mostly present in the families Lamiaceae and Asteraceae) takes place in the chloroplasts. Some forms can be useful intermediates in organic synthesis.^[1] Some clerodanes like clerodin (3-desoxy-caryoptinol) from the leaves of Clerodendrum infortunatum (Verbenaceae) have anthelminthic properties, others like ajugarins are repellent to herbivore predators (mostly insects and their larvae) or have a very bitter taste, such as gymnocolin.

Some examples for clerodanes are ajugarins I to V extracted from bugleweeds like Ajuga remota, Ajuga ciliata, Ajuga decumbens, common skullcap (Scutellaria galericulata), and germanders (Teucrium sp.), cascarillin from Croton eleuteria, columbins from Jateorhiza columba, Jateorhiza palmata and guduchi (Tinospora cordifolia), gymnocolin from Gymnocolea inflata, hardwickiic acid from Hardwickia species (Fabaceae). Neo-clerodane diterpenes can have hallucinogenic properties such as salvinorin A, a trans-neoclerodane diterpenoid from Salvia divinorum.^[2]

References

^ Arns S, Barriault L (2007). "Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis". Chem. Commun. (Camb.) (22): 2211–21. doi:10.1039/b700054p. PMID 17534496.
^ Shirota O, Nagamatsu K, Sekita S (2006). "Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum". J. Nat. Prod. 69 (12): 1782–6. doi:10.1021/np060456f. PMID 17190459.

External links

Clerodane diterpenes at the US National Library of Medicine Medical Subject Headings (MeSH)

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1. LSDおよび他の一般的な幻覚剤による中毒 intoxication from lsd and other common hallucinogens

English Journal

Assessment of the chemopreventive effect of casearin B, a clerodane diterpene extracted from Casearia sylvestris (Salicaceae).

Prieto AM, dos Santos AG, Oliveira AP, Cavalheiro AJ, Silva DH, Bolzani VS, Varanda EA, Soares CP.SourceUNESP-Univ. Estadual Paulista, Araraquara, School of Pharmaceutical Sciences, Department of Clinical Analysis, Rua Expedicionários do Brasil 1621, Araraquara, SP, Brazil.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2013 Mar;53:153-9. doi: 10.1016/j.fct.2012.11.029. Epub 2012 Nov 28.
Studies have shown that Casearia sylvestris compounds protect DNA from damage both in vitro and in vivo. Complementarily, the aim of the present study was to assess the chemopreventive effect of casearin B (CASB) against DNA damage using the Ames test, the comet assay and the DCFDA antioxidant assay
PMID 23200890

Chemical composition and efficacy of dichloromethane extract of Croton sphaerogynus Baill. (Euphorbiaceae) against the cattle tick Rhipicephalus microplus (Acari: Ixodidae).

Righi AA, Motta LB, Klafke GM, Pohl PC, Furlan CM, Santos DY, Salatino ML, Negri G, Labruna MB, Salatino A.SourceBotany Department, Institute of Biosciences, University of São Paulo, Brazil. adnerighi@gmail.com
Veterinary parasitology.Vet Parasitol.2013 Feb 18;192(1-3):292-5. doi: 10.1016/j.vetpar.2012.11.005. Epub 2012 Nov 14.
The cattle tick Rhipicephalus microplus is widely distributed in tropical and subtropical regions, causing high economic impact on cattle production. The control of tick infestations is regarded worldwide as critical and has been based on the use of organophosphates, synthetic pyretroids, amitraz an
PMID 23200750

Japanese Journal

Parvitexins A-E, Clerodane-Type Diterpenes Isolated from the in Vitro-Cultured Liverwort, Scapania parvitexta

KATAYAMA Kinya,SHIMAZAKI Kazuko,TAZAKI Hiroyuki,HASA Yasuhiro,MIYOSHI Masako,KOSHINO Hiroyuki,FURUKI Tatsuo,NABETA Kensuke
Bioscience, biotechnology, and biochemistry 71(11), 2751-2758, 2007-11-23
… New clerodane-type diterpenes, designated as parvitexins A (1)–E (5), were isolated from the in vitro-cultured liverwort, Scapania parvitexta. … These compounds were determined to be monoacetylated clerodane-type diterpenes based on spectroscopic evidence. …
NAID 10027521153

Clerodane Diterpenoids and Flavonoids with NGF-Potentiating Activity from the Aerial Parts of Baccharis gaudichaudiana

GUO Yuanqiang,LI Yushan,XU Jing,LI Ning,YAMAKUNI Tohru,OHIZUMI Yasushi
Chemical & pharmaceutical bulletin 55(10), 1532-1534, 2007-10-01
… A new clerodane diterpene, 15-hydroxy-16-acetoxy-ent-clerod-3-en-18-oic acid (1), together with three known clerodane diterpenes (2-4) and three known flavones (5-7), were isolated from the aerial parts of Baccharis gaudichaudiana. …
NAID 110006404706