Clerodane and aromatic seco-clerodane diterpenoids from salvia rhyacophua.

Fernández, María del Carmen; Esquivel, Baldomero; Cárdenas, Jorge; Sánchez, Ana Adela; Toscano, Rubén A.; Rodríguez‐Hahn, Lydia

doi:10.1016/s0040-4020(01)89722-2

Cited by 32 publications

(7 citation statements)

References 7 publications

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“…144 Both rhyacophiline ( 1140 ) and salvireptanolide ( 1141 ) from S. rhyacophila and S. reptans , respectively, have novel skeletons characterized by cleavage of the C-5/C-6 bond and aromatization of the A-ring. 252,398 Compound 1140 's structure was fully established by spectroscopic and X-ray diffraction analyses. 398 Jamesoniellide J ( 1142 ) from J. autumnalis is a seco -clerodane diterpenoid cleaved between C-8 and C-9.…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

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Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

“…252,398 Compound 1140 's structure was fully established by spectroscopic and X-ray diffraction analyses. 398 Jamesoniellide J ( 1142 ) from J. autumnalis is a seco -clerodane diterpenoid cleaved between C-8 and C-9. 187,393 …”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…Splendidin ( 484 ) and splenolide B ( 486 ) were isolated from S. splendens . , Salviarin ( 485 ) was isolated from three Salvia species: S. divinorum , S. greggii , and S. rhyacophila. Investigation of the plant of S. splendens gave three new clerodane-17,12:18,19-diolides: salvisplendins A ( 489 ) and B ( 495 ) and splenolide C ( 497 ). , Polystachynes D ( 499 ) and E ( 500 ) and 501 , isolated from S. polystachya and S. reptans , have an epoxy ring between C-1 and C-2. , The structures were established by spectroscopic methods, including the X-ray analysis of 499 . 502 , 503 , and 504 have a 1,10-epoxy, 2,3-epoxy, and 6,7-epoxy ring, respectively. − …”

Section: Chemical Constituentsmentioning

confidence: 99%

“…Salvianduline C ( 527 ) and salvireptanolide ( 528 ) were two examples in this subgroup that were isolated from S. lavanduloides and S. reptans , respectively. Rhyacophiline ( 529 ) and 7,8-didehydrorhyacophiline ( 531 ) were two other 5,6-seco-clerodanes, with a 7,12:12,20:15,16-triepoxy structural moiety, that were isolated from S. rhyacophila and S. reflexa , respectively. , …”

Section: Chemical Constituentsmentioning

confidence: 99%

“…19,198 Salviarin (485) was isolated from three Salvia species: S. divinorum, 19 S. greggii, 186 and S. rhyacophila. 199 Investigation of the plant of S. splendens gave three new clerodane-17,12:18,19-diolides: salvisplendins A (489) and B (495) and splenolide C (497). 189,200 Polystachynes D (499) and E (500) and 501, isolated from S. polystachya and S. reptans, have an epoxy ring between C-1 and C-2.…”

Section: Diterpenoidsmentioning

confidence: 99%

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Constituents from Salvia Species and Their Biological Activities

et al. 2012

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24 (1R,5R)-1,5-epoxysalvial-4( 14)ene S. sclarea 49 2 salviadienol A S. chinensis 42 25 (2R,5E)-2,12-epoxycaryophyll-5ene S. sclarea 49 3 3β,6β,8a-triacetoxy-4β,5α-epoxy-1-oxogermacr-10(14)-ene S. roborowskii 43 26 (2R,5E)-caryophyll-5-en-12-al S. sclarea 49 4 3β,6β,8a-triacetoxy-4β,5α-epoxygermacr-1(10)E-ene S. roborowskii 43 27 (2S,5E)-caryophyll-5-en-12-al S. sclarea 49 5 3β,6β,8a-triacetoxy-4β,5α:1α,10β-diepoxygermacrane S. roborowskii 43 28 caryophyllene oxide S. sclarea 51, 47 6 salviadienol B S. chinensis 42 S. palaefolia 50 7 trijugin A S. trijuga 45 29 4,10-epoxy-6α-hydroxyguaiane (= buchariol) S. bucharica 343 8 trijugin B S. trijuga 45 30 isospathulenol S. sclarea 49 9 trijugin C S. trijuga 45 31 (1β,3β,4α,5α,6α,8α)-guai-10(14)ene-3,4,6,8-tetrol 3,6,8-triacetate S. roborowskii 48 10 trijugin D S. trijuga 45 32 spathulenol S. eupatorium 361 11 trijugin E S. trijuga 45 S. sclarea 51 12 trijugin F S. trijuga 45 33 nubiol S. nubicola 23 13 trijugin G S. trijuga 45 34 nubenolide S. nubicola 52 14 trijugin H S. trijuga 45 35 nubenolideacetate S. nubicola 52 15 trijugin I S. trijuga 45 36 bisnubidiol S. nubicola 23 16 (1aS*,6R*,6aS*,7aR*,9aR*)-1a,2,6,6a,7a,8,9,9a-octahydro-1a,5,7atrimethylbisoxireno[4,5:8,9]cyclodeca[1,2-b]furan-6-yl acetate (= castanin B) S. castanea 44 37 bisnubenolide S. nubicola 52 6-acetoxyglechomafuran S. roborowskii 43 38 1α,9β-dibenzoyloxy-2β,3β,4βtrihydroxydihydro-β-agarofuran S. palaefolia 50 17 glechomafuran S. palaefolia 47 39 lα-acetoxy-11-hydroxy-2,8-dioxoeudesman-3-en-12-oic acid methyl ester S. palaefolia 53 18 castanin C S. castanea 46 40 11-hydroxy-3,8-dioxo-eudesman-1,4-dien-12-oic acid methyl ester S. palaefolia 53 19 castanin D S. castanea 46 41 β-eudesmol S. microphylla 55 20 castanin E S. castanea 46 42 8α-hydroxy-β-eudesmol S. microphylla 55 21 castanin F S. castanea 46 43 1α-acetoxy-2-oxoeudesman-3,7(11)-dien-8β,12-olide S. palaefolia 53 22 (4R*,5R*,5aS*,8S*,8aR*,8bR*)-8-formyl-4,5,5a,6,7,8,8a,8b-octahydro-5,8b-dihydroxy-3,5a,8-trimethyl-2-oxo-2H-indeno[4,5-b]furan-4-yl acetate (= castanin A) S. castanea 44 44 1α-hydroxy-2-oxoeudesman-3,7(11)-dien-8β,12-olide S. palaefolia 53 23 (3β,4α,6α,8β,9β,10α)-8-(acetyloxy)-3,4:9,10-diepoxygermacr-7(11)-eno-12,6-lactone S. roborowskii 48 45 1α,8α-dihydroxy-2-oxoeudesman-3,7(11)-dien-8β,12-olide S. palaefolia 53, 54 46 1α-acetoxy-8α-hydroxy-2oxoeudesman-3,7(11)-dien-8,12olide S. palaefolia 54

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Effect of Clerodane-Type Diterpenoids Isolated fromSalviaspp. on the Feeding Behaviour ofSpodoptera littoralis

et al. 1996

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Twenty-nine clerodane-type diterpenoids isolated from species of Saluia growing in Mexico, or analogues of them, were tested for antifeedant activity against Spodoptera littoralis larvae using behavioural and electrophysiological bioassays. Eight of the compounds showed potent antifeedant activity in choice and no-choice bioassays and these compounds also stimulated dose-dependent responses from neurones in the lateral styloconic sensilla of S. littoralis.

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Clerodane and aromatic seco-clerodane diterpenoids from salvia rhyacophua.

Cited by 32 publications

References 7 publications

Clerodane diterpenes: sources, structures, and biological activities

Clerodane diterpenes: sources, structures, and biological activities

Constituents from Salvia Species and Their Biological Activities

Effect of Clerodane-Type Diterpenoids Isolated fromSalviaspp. on the Feeding Behaviour ofSpodoptera littoralis

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