Clerodane derivatives from Polyalthia viridis

Kijjoa, Anake; Pinto, Madalena; Pinho, Paulo; Tantisewie, Bumrung; Herz, Werner

doi:10.1016/0031-9422(90)85137-5

Cited by 52 publications

(48 citation statements)

References 6 publications

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“…Additionally, eight known compounds were identified by comparison of their measured spectroscopic data with literature values. The known compounds comprised three substances that were previously reported to occur in the genus Callicarpa [calliterpenone, 15,16 euscaphic acid, 17,18 and salvigenin 19,20 ], and five new to the taxon [genkwanin, 21 3β,16ξ-dihydroxycleroda-4(18), 13-dien-15,16-olide, 22 16ξ-hydroxycleroda-3,13-dien-15,16-olide, 23 5-hydroxy-7,4′-dimethoxyflavone, 24 and 2-formyl-16ξ-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide 25,26 ].…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida^,1

Jones

Lobo-Echeverri

et al. 2007

J. Nat. Prod.

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Bioassay-guided fractionation of the combined fruits, leaves, and twigs (fruiting branches) of Callicarpa americana, collected from a plot in a forested area in southern Florida, led to the isolation of six new clerodane diterpenes (1-6) and eight known compounds. The structures of 1-6 [12(S), 16ξ-dihydroxycleroda-3,13-dien-15,16-olide (1), 12(S)-hydroxy-16ξ-methoxycleroda-3,13-dien-15,16-olide (2), 12(S)-hydroxycleroda-3,13-dien-15,16-olide (3), 16 ξ-hydroxycleroda-3,11 (E),13-trien-15,16-olide (4), 3β,12(S)-dihydroxycleroda-4(18),13-dien-15,16-olide (5), and 12(S)-hydroxycleroda-3,13-dien-16,15-olide (6)] were elucidated by interpretation of spectroscopic data and chemical methods. The absolute configuration at C-12 in 1 and 3 was ascertained using the Mosher ester technique. The cytotoxicity of all isolates was tested against a panel of human cancer cell lines, and compounds 1, 4, and 6, and the known compounds genkwanin, 16ξ-hydroxycleroda-3,13-dien-15,16-olide, and2-formyl-16ξ-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide were active (ED 50 <5 μg/mL). However, 1 was found to be inactive against human cancer cells implanted in mice using a hollow-fiber tumor model. Callicarpa americana L. is a shrub native to the southeastern United States. 2 Although the genus has been considered traditionally as a member of the plant family Verbenaceae, molecular and micro-morphological observations have prompted contemporary taxonomic authorities to reclassify Callicarpa as a member of the family Lamiaceae. 3-5 Preparations of the bark of C. americana have been used to treat fever, 6 the leaves to treat dropsy, 7 and the roots to alleviate colic, 8 dysentery, 9 and skin cancer. 10 The roots and branches have been used in preparations intended to relieve malaria, rheumatism, and fever. 8 The leaf essential oils of C. americana have antialgal and mosquito-deterrent properties, and numerous essential oil components have been identified from the leaves of C. americana. [11][12] As part of an ongoing effort to discover novel anticancer agents from plants, 13 a chloroformsoluble extract of the combined fruits, leaves, and twigs of C. americana was investigated, using cytotoxicity against hormone-dependent prostate cancer cells (LNCaP) to guide the isolation of active constituents. This plant material was obtained from a forest plot in southern Florida using a plot-based collection method (briefly reviewed in ref. 13 ).⊥ Dedicated to the late Dr. Kenneth L. Rinehart of the University of Illinois at Urbana-Champaign for his pioneering work on bioactive natural products.*Author to whom correspondence should be addressed. Tel: (614) Results and DiscussionThe dried fruits, leaves, and twigs of Callicarpa americana L. were extracted with methanol and partitioned following a previously described protocol. 14 Based on the cytotoxic activity of the chloroform-soluble portion, bioassay-guided fractionation using a number of chromatographic techniques was carried out, guided by activity against LNCaP cells. This investigation re...

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida^,1

Jones

Lobo-Echeverri

et al. 2007

J. Nat. Prod.

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“…as well as unrelated plants. (Iwamura et al, 1978a(Iwamura et al, , 1978b(Iwamura et al, , 1978cIwamura, 1979;Toong et al, 1988;Kijjoa et al, 1990;Versini et al, 1994). However, JH acid, an intermediate in some Lepidopteran insect species, was not incorporated into JH III.…”

Section: Discussionmentioning

confidence: 99%

Biosynthetic Pathway of Insect Juvenile Hormone III in Cell Suspension Cultures of the Sedge Cyperus iria

et al. 2001

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In most insect species, juvenile hormones regulate critical physiological processes such as metamorphosis and reproduction. In insects, these sesquiterpenoids are synthesized by retrocerebral endocrine organs, the corpora allata, via the classical mevalonate (MVA) pathway. One of these compounds, juvenile hormone III (JH III), has also been identified in the sedge Cyperus iria. In higher plants, biosynthesis of the sesquiterpenoid backbone may proceed through two distinct pathways: the MVA pathway or the 2C-methyl erythritol 4-phosphate pathway or through a combination of both pathways. Cell suspension cultures of C. iria were used to elucidate the biosynthetic pathway of JH III in the plant. Enzyme inhibition and labeling studies conclusively demonstrated that the biosynthesis of the sesquiterpenoid backbone of JH III proceeds via the MVA pathway. Inhibitor and precursor feeding studies also suggest that later steps of JH III biosynthesis in C. iria are similar to the insect pathway and that the final enzymatic reaction in JH III biosynthesis is catalyzed by a cytochrome P 450 monooxygenase.Juvenile hormones are a group of structurally related sesquiterpenoids that regulate critical physiological processes including metamorphosis and reproduction in most insect species (Gilbert et al., 1996). Juvenile hormone III (JH III), methyl-10R,11-epoxy-3,7,11-trimethyl-2E,6E-dodecadienoate, has also been identified in the sedge Cyperus iria (Toong et al., 1988).The presence of an insect hormone and its high levels in C. iria throughout development suggest that this compound may play a role in protection of the plant against insect herbivory (Toong et al., 1988; Bede et al., 1999a). However, there is no evidence that JH III functions as a feeding deterrent. Therefore, any antiherbivory activity would arise from its ability to interfere with insect development. In two laboratory studies, contact of insects with C. iria effectively disrupted development (Toong et al., 1988;Schwartz et al., 1998). These effects were attributed to the JH III content of the plant. However, conclusive evidence that this hormone protects C. iria against insect herbivory has not yet been demonstrated. We have proposed alternatively that JH III may function as an allelopathic agent in C. iria (Bede and Tobe, 2000). This plant species is an extremely invasive weed, responsible for economic losses in many important crops such as rice (Oryza sativa; Holm et al., 1977; Catling, 1992). Treatment of seeds with JH III delays lettuce (Lactuca sativa) seed germination and inhibits shoot growth of rice seedlings (Bede and Tobe, 2000). Therefore, it is possible that this compound confers an ecological advantage to C. iria by leaching from the roots, in which the highest levels are localized, into the immediate environment and affecting the germination and growth of neighboring competing plant species.Temporal and spatial changes in JH III levels are observed in C. iria throughout development (Bede et al., 1999a). JH III levels increased in the immature se...

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“…pentandra, 20) Polyalthia longifolia, [21][22][23] Solidago altissima, 24,25) and Clausena dunniana. 26) It should be noted that this is the first isolation of clerodane with rearranged ring-A from Vitex species.…”

Section: Resultsmentioning

confidence: 99%

A Novel Clerodane Diterpene from <i>Vitex cofassus</i>

et al. 2017

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Clerodane derivatives from Polyalthia viridis

Cited by 52 publications

References 6 publications

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida^,1

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida^,1

Biosynthetic Pathway of Insect Juvenile Hormone III in Cell Suspension Cultures of the Sedge Cyperus iria

A Novel Clerodane Diterpene from <i>Vitex cofassus</i>

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Clerodane derivatives from Polyalthia viridis

Cited by 52 publications

References 6 publications

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida,1

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida,1

Biosynthetic Pathway of Insect Juvenile Hormone III in Cell Suspension Cultures of the Sedge Cyperus iria

A Novel Clerodane Diterpene from <i>Vitex cofassus</i>

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Product

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Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida^,1

Cytotoxic Constituents from the Fruiting Branches of Callicarpa americana Collected in Southern Florida^,1