Prehispanolone, a labdane diterpene from Leonurus heterophyllus

Hon, Po‐Ming; Lee, Chi-Ming; Shang, Hong-Sheng; Cui, Yuxin; Wong, H. N. C.; CHANG, Hson-Mou

doi:10.1016/0031-9422(91)84154-k

Cited by 39 publications

(23 citation statements)

References 9 publications

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“…Several metabolites have been isolated from L. japonicus that substantiate the recorded activities. For instance, the iridoid glucoside leonurid, isoquercetin, two phenolic glycosides (Sugaya et al, 1998), melatonin (Chen et al, 2003), b-sitostenone (Hotta et al, 2003) and several diterpenes exclusively of the labdane type have been characterized from its aerial parts (Savona et al, 1982;Hohn et al, 1991Hohn et al, , 1993Satoh et al, 2003;Boalino et al, 2004;Giang et al, 2005a,b). The occurrence of the labdane compounds, and the fast and dense growth of L. japonicus makes this plant a renewable source of useful medicinal materials.…”

Section: Introductionmentioning

confidence: 96%

Labdane diterpenes from Leonurus japonicus leaves

et al. 2006

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Section: Introductionmentioning

confidence: 96%

Labdane diterpenes from Leonurus japonicus leaves

et al. 2006

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“…Some of the chemical constituents such as: flavanoids, iridoids, phenylpropanoid glycosides, proteins, sterols and fatty acids, as well as clerodane-and/or labdanetype diterpenoids from various species of the genus Leonurus show antiplatelet aggregation activity (Hon et al, 1991;1993).…”

Section: Introductionmentioning

confidence: 99%

Ursolic acid: a potent Inhibitor of superoxides produced in the cellular system

Ali

Ibrahim

Jalil

et al. 2007

Phytotherapy Research

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Triterpenoids of ursane class: ursolic acid, ilelatifol D, corosolic acid and euscaphic acid were isolated for the first time from Leonurus cardiaca, a member of the family Lamiaceae. The isolated compounds were tested for their cell-based antiinflammatory potential by suppressing respiratory burst activity and superoxide scavenging property by using xanthine/xanthine oxidase system to produce superoxides in the cell-free system. Ursolic acid was found to be an excellent inhibitor for the superoxides produced in the cellular system, while the same was inactive in the superoxide scavenging activity in cell-free system.

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“…The relative stereochemistry of 8 was determined as follows. Table 2) spectroscopic data of 9 were reminiscent of those of hispanolone (3), 2) which was also isolated from the same extract, in the Decalin ring and of 6 in the C-9 side chain. .…”

mentioning

confidence: 84%

New Labdane-Type Diterpenoids from Leonurus heterophyllus SW.

Giang

Sơn²,

Matsunami

et al. 2005

Chem. Pharm. Bull.

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In Vietnamese traditional medicine, the plant Leonurus heterophyllus SW. is known as Ich mau thao, Sung uy, or Choi den. The dried aerial parts of L. heterophyllus (Herba Leonuri) are applicable in the treatment of menstrual pain and child birth, as well as high blood pressure, blood stasis, heart disorders, and dysentery. The dried ripe fruits (Fructus Leonuri) are used to treat edema and as a diuretic.1) Several prefuranic and furanic labdane-type diterpenoids were isolated in previous studies on L. heterophyllus collected in Guangdong province, China.2,3) It is well known that the chemical composition of plants is geographically varied, and the reason for that may be related to the ability of each species to cope with its habitat environment. Therefore we carried out systematic extraction and isolation of the L. heterophyllus species grown in Vietnam, which led to the structure determination of nine labdane-type diterpenoids, including five new compounds, designated leoheteronins A-E (5-9), two phytosterols as a mixture of b-sitosterol and stigmasterol, and the flavone genkwanin (10). The structures of the known diterpenoids hispanone (1), leoheterin (2), hispanolone (3), and galeopsin (4), and 10 were determined by comparing their physical ([a] D ) and spectroscopic data with the literature values.3-6) Compounds 2-4 were among the previous isolates from L. heterophyllus, 1 was isolated from Ballota species (Lamiaceae) 4) but for the first time from a Leonurus species, and 10 is considered to be a chemotaxonomic marker of the genus Leonurus.7) This paper deals with the structure elucidation of the five new labdane-type diterpenoids 5-9. Results and DiscussionThe extraction of the dried aerial parts of L. heterophyllus with MeOH and sequential fractionation using solvents of increasing polarity gave n-hexane-, ethyl acetate-, and 1-BuOHsoluble fractions. Separation of the n-hexane-soluble fraction with silica (Si) gel open-column chromatography, octadecyl Si (ODS) gel open-column chromatography, and repeated preparative ODS HPLC led to the isolation of compounds 1-10 together with a mixture of b-sitosterol and stigmasterol.Leoheteronin A (5) C-16)], six methylene and one methine groups, and two quaternary carbons. Analysis of the data suggested the structure of 5 to be 15,16-epoxylabda-8,13-diene-7,15-dione, which was confirmed on comparison of the NMR data with those of the related compound leopersin G. (Table 1) and 13 C-NMR (Table 2) (Table 1) and 13 C-NMR (Table 2) spectroscopic data showed that 7 was closely related to 5, and the presence of an additional hydroxyl group was deduced from the mass unit of 7. Five new natural labdane-type diterpenoids (5-9), designated leoheteronins A-E, together with four known diterpenoids (1-4), two phytosterols as a mixture of b b-sitosterol and stigmasterol, and the flavone genkwanin (10) were isolated from the aerial parts of Leonurus heterophyllus SW. (Lamiaceae) collected in northern Vietnam. Compound 1 was isolated for the first time from a Leonurus species, an...

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Prehispanolone, a labdane diterpene from Leonurus heterophyllus

Cited by 39 publications

References 9 publications

Labdane diterpenes from Leonurus japonicus leaves

Labdane diterpenes from Leonurus japonicus leaves

Ursolic acid: a potent Inhibitor of superoxides produced in the cellular system

New Labdane-Type Diterpenoids from Leonurus heterophyllus SW.

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