New sesquiterpene lactones from Artemisia herba alba

Segal, Ruth; Sokoloff, S.; Haran, Batyah; Zaitschek, D.V.; Lichtenberg, Dov

doi:10.1016/s0031-9422(00)94365-6

Cited by 34 publications

(14 citation statements)

References 11 publications

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“…The plant material collected from both North African locations contained similar sesquiterpene lactones. In addition to herbolide A [1] (11), its deacetyl derivative [2] (11), herbolide B [3] (11), herbolide D [5] (12), the eudesmanolide [10} (8), balchanolide (13), 8ot-acetoxytaurin (14), 11 ß, 13-dihydroanhydroverlotorin (15), shonachalin A (15), spathulenol (16), the coumarin, herniarin, and/>-hydroxy acetophenone, we isolated the new products 4 (deacetylherbolide D) 6, 7,8, and 9• In addition, the material from Morocco furnished the davanone-like derivatives 11-16 (7,17), with compound 12 being novel. Lactone 4, C15H2204, displayed it absorption bands at 3400 and 1760 cm"1, which indicated the presence of hydroxyl and lactone functions.…”

Section: And Discussionmentioning

confidence: 99%

New Germacranolides and Eudesmanolides from North African Artemisia herba-alba

Marco¹,

Sanz‐Cervera²,

Ocete³

et al. 1994

J. Nat. Prod.

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A8smm.Specirnens of Artemisia berba-alba collected in two North African locations afforded four new germacranolides, a new eudesmanolide, and a new C,,-acid related to davanone. Their structures were established through a combination of spectroscopic techniques and chemical correlations. Furthermore, a corrected structure is proposed for the elemanolide, shonachalin D.Artemisia berba-alba Asso (Asteraceae), a medicinal plant that occurs around the Mediterranean basin, has been the object of several previous chemical studies. Segal and co-workers investigated chemotypes of A. berba-alba collected in various locations in Egypt and Israel and isolated several new germacranolides and eudesmanolides, named herbolides A-J (1). Spanish subspecies ofA. berba-alba were studied by our group. In the course of these studies, we obtained a number of sesquiterpene lactones with the germacrane and eudesmane framework, many of which are novel (2-6). A striking difference between our compounds and those isolated by Segal et al. was the presence of oxygen functions at C-9 (germacrane and eudesmane numbering) in lactones from the African specimens. Another group did not find lactones of this type in plant material collected in the Sinai desert (7). Nevertheless, a recent investigation on an Egyptian specimen afforded some new sesquiterpene lactones, with two of them bearing oxygen functions at C-9 (8). Intrigued by these differences in the chemical composition, which could perhaps reflect taxonomic differences at the subspecies or even species level, we investigated A. berba-alba collected in Morocco and Tunisia (9,lO). The results of this study are described in this communication.

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Section: And Discussionmentioning

confidence: 99%

New Germacranolides and Eudesmanolides from North African Artemisia herba-alba

Marco¹,

Sanz‐Cervera²,

Ocete³

et al. 1994

J. Nat. Prod.

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“…We have already reported the structure of herbolide B (Hull & Kennard, 1978). The crystal structure determination of (I) was undertaken (a) to confirm the structure earlier deduced from chemical and spectroscopic results (Segal et al, 1977), in particular the position of the two double bonds; and (b) to allow calculation of the sign of the circular-dichroism couplet from exciton theory.…”

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“…The title compound (I; trivial name herbolide A) is one of three sesquiterpene lactones isolated from the composite plant Artemisia herba alba (Segal, Sokoloff, Haran, Zaitschek & Lichtenberg, 1977). We have already reported the structure of herbolide B (Hull & Kennard, 1978).…”

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(9S,11S)-9-Acetoxydihydrocostunolide (herbolide A)

Jones¹,

Kennard²

1979

Acta Crystallogr Sect B

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“…A. herba alba has been used by local populations in their native countries in folk medicine, in particular, as an anthelmintic (3,4). It is known by the Arabic name "Shih" (3,4).…”

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“…herba alba has been used by local populations in their native countries in folk medicine, in particular, as an anthelmintic (3,4). It is known by the Arabic name "Shih" (3,4). The essential oils of some varieties of A. herba alba have been known for over seventy-five years (5), but more extensive phytochemical investigations of this species have only been recently reported.…”

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confidence: 99%