Clerodane diterpenes from Haplopappus deserticola (original) (raw)

A new antibacterial clerodane diterpenoid from the resinous exudate of Haplopappus uncinatus

Journal of Ethnopharmacology, 2006

The antibacterial activity of Haplopappus uncinatus is attributed to a new clerodane diterpenoid, 18-acetoxy-cis-cleroda-3-en-15-oic acid (10␤H, 16 19␤, 17␤, 20␣ form) (1), isolated as a major component from the resinous exudates of its twigs and leaves, together with the inactive 3,5-dihydroxy-6,7,3 ,4 -tetramethoxyflavone, n-alkanes and a few sesquiterpenoids.

Diterpenes Derived from Clerodane Skeleton from Some Compo sitae Plants

Zenodo (CERN European Organization for Nuclear Research), 1998

The structures of the clerodane derivatives solidagonal acid, a diterpene with new carbon skeleton, a hydroperoxyclerodane (3Phydroperoxy-4,18-dehydro-3,4-dihydrokolavenic acid), 2-oxo-kolavenic acid lactone, 2a-acetoxyhardwickiic acid, 10-epi-nidoresedic acid, 16-oxo-15,168-hardwickiic acid, 15-methoxy-16-oxo-15,16H-hardwickiic acid, 15-methoxy-16-oxo-nidoresedic acid, nor-hardwickiic acid, 15-methoxy-16-oxo-15,16H-strictic acid, 110r-strictic acid, 15-desmethoxy-16-oxo-15,16H-strictic acid, 15-oxo-14,168-strictic acid, 16-oxo-14,15-epoxystrictic acid alongwith several known diterpenes, isolated from the Indian Compositae plants Solidago altissima, Grangea maderaspatana and Pulicaria angustifolia, have been deduced mainly from high field 1 H nmr, high resolution mass spectrometry and noe difference spectroscopy.

Neo-clerodane diterpenoids from Clerodendrum inerme

Phytochemistry, 2005

Three neo-clerodane diterpenoids, inermes A, B and 14,15-dihydro-15b-methoxy-3-epicaryoptin, have been isolated from the hexane extract of the leaves of Clerodendrum inerme in addition to an epimeric mixture of 14,15-dihydro-15-hydroxy-3-epicaryoptin. Structures of these compounds have been elucidated on the basis of spectral studies.

Diterpenes from Haplopappus chrysanthemifolius

Phytochemistry, 1999

Three new diterpenes were isolated from the aerial part of Haplopappus chrysanthemifolius and assigned the structures 6ahydroxy-ent-labd-8(17)-en-15-oic acid, 3b-acetoxy-ent-labd-8(17)-en-15-oic acid and 18a-acetoxylabd-8(17)-en-15-oic acid. The structures were elucidated by high ®eld NMR spectroscopy. #

ANALYSIS OF MASS SPECTRAL DATA OF DITERPENES ISOLATED FROM CLERODENDRON INFORTUNATUM

Terpenes are the largest group of phytochemicals that exhibit beneficial interactions in organisms. Diterpenes of plant are dominated in research area due to their novel chemical structure and medicinal values. The majority of diterpenes exhibited cytotoxic, antitumor and antimicrobial activities in vitro. Several diterpenes are reported in Clerodendron infortunatum. The objectives of present study was the isolation, purification and structural investigation of isolated diterpens by compairing 1 H and 13 C of Mass spectral data and previously known standard structures.

Neo-clerodane diterpenes from Ajuga turkestanica

Phytochemistry letters, 2008

The ethyl acetate extract of the aerial parts of Ajuga turkestanica afforded 6 neo-clerodane diterpenes, including two novel compounds, 14, 15-dihydroajugachin B (1) and 14-hydro-15-methoxyajugachin B (2), in addition to the known diterpenoids chamaepitin (3), ajugachin B (4), ajugapitin (5) and lupulin A (6). Structures were established through exhaustive NMR spectroscopic analysis and chemical transformation in the case of 1. The full 1H and 13C NMR assignment of the C-15 R and S configurations of 14-hydro-15-methoxyajugachin B and chamaepitin were elucidated.

neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity

Phytochemistry Reviews, 2007

The presence of several types of allelochemicals has been reported from Ajuga, a Labiatae genus comprising more than 40 species of wide distribution in extratropical regions of both hemispheres. The genus is of great medicinal and economic importance and among the biological properties of the secondary metabolites, the antifeedant activity against pest insects appears to be related to the presence of neo-clerodane type diterpenes. This review focuses on the isolation and structural elucidation of this type of compounds from Ajuga species and the hemisynthetic compounds of closely related structure obtained. The reported biological activity of crude extracts and isolated diterpenes will be briefly commented.

New Labdane-Type Diterpenoids from Leonurus heterophyllus SW

Chemical and Pharmaceutical Bulletin, 2005

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 Discussion The 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) was isolated as an amorphous powder, [a] D 25 ϩ8.4°(cϭ1.19, CHCl 3). Its molecular formula was determined to be C 20 H 28 O 3 by positive-ion high-resolution (HR)-FAB-MS (m/z 315.1923, [MϩNa] ϩ). The IR spectrum indicated the presence of g-lactone (1747 cm Ϫ1) and conju-938