Higher isoprenoids—VIII: Diterpenoids from the oleoresin of hardwickia pinnata part 1: hardwickiic acid

  title={Higher isoprenoids—VIII: Diterpenoids from the oleoresin of hardwickia pinnata part 1: hardwickiic acid},
  author={R. Misra and R. C. Pandey and S. Dev},
Abstract The oleoresin from Hardwickia pinnata Roxb. is shown to be a complex blend of sesquiterpenes and diterpenes. (−)-Copaene, (−)-caryophyllene and humulene account for over 90% of the sesquiterpenes present. The diterpenes, which constitute some 60% of the oleoresin, have been found to consist of a series of closely related new diterpenoids of ent -clerodane type. Evidence leading to the elucidation of the absolute stereostructure of the main diterpenoid-hardwickiic acid—is presented. 
Clerodane diterpenoids from Pulicaria wightiana.
Five clerodane diterpenoids have been isolated from the aerial parts of Pulicaria wightiana along with 3'5,6-trihydroxy-3,4',7-trimethoxyflavone and 2-methyl-5-Hydroxy-chroman-4-one, which were not reported earlier from this plant. Expand
Further syphonosides from the sea hare Syphonota geographica and the sea-grass Halophila stipulacea
Abstract The unusual structural features of syphonoside ( 1 ), recently reported from the marine mollusc Syphonota geographica and its prey Halophila stipulacea , stimulated further investigations onExpand
12-Hydroxyhardwickic acid and sonderianial, neo-clerodanes from Croton sonderianus
Abstract Two new neo -clerodane diterpenes, 12-hydroxyhardwickic acid and sonderianial have been characterized from the hexane extract of the roots of Croton sonderianus . Their structures wereExpand
Ent-clerodane diterpenoids from the liverwort Jungermannia paroica
The liverwort Jungermannia paroica furnished four ent-clerodanes, kolavelool (ent-cleroda-3,14-dien-13ξ-ol), ent-(Z)-3β,4β-epoxyclerod-13(14)-en-15-al, ent-(E)-3β,4β-epoxyclerod-13(14)-en-15-al, andExpand
Antibacterial compounds from Salvia adenophora Fernald (Lamiaceae).
Results confirm that clerodanes and, particularly, prostaglandin-like compounds can be considered as interesting antimicrobial agents deserving further study. Expand
Clerodane and 5 10-Seco-Clerodane-type diterpenoids from Salvia involucrata
Abstract From the leaves of Salvia involucrata Cav., eight clerodane diterpenoids were isolated, of which 1−3 have not been previously described. Their structures were established by spectroscopicExpand
Bacterial terpene cyclases.
This review summarises the accumulated knowledge about characterised bacterial terpene cyclases and the special cases of the geosmin and 2-methylisoborneol synthases that are both particularly widespread in bacteria. Expand
Absolute configuration of labdanes and ent-clerodanes from Chromolaena pulchella by vibrational circular dichroism.
The aerial parts of Chromolaena pulchella biosynthesize two groups of diterpenes belonging to opposite enantiomeric series, specifically, the furanoid ent-clerodanes and labdanes, which support a biogenetic proposal to diter penes found in the studied botanical species. Expand
The chemistry of Salvia divinorum
Salvia divinorum is a hallucinogenic sage used to treat illness by the Mazatec Indians of Mexico. Salvinorin A (1a), a neoclerodane diterpenoid isolated from the plant, is a potent, selective agonistExpand
Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus*
GcoA is the first known caryolan-1-ol synthase, isolated from microorganisms from plants and fungi and synthesized by a proton attack on the C-8/C-9 double bond of (+)-β-caryophyllene. Expand


Studies in sesquiterpenes—XLVI : Sesquiterpenes from the oleoresin of Dipterocarpus pilosus: Humulene epoxide—III, caryophyllenol—I and caryophyllenol—II☆☆☆★
Abstract Oleoresin from Dipterocarpus pilosus has been shown to be a complex blend of sesquiterpenes (∼18%) and triterpenoid—both tetracyclic and pentacyclic. A complete analysis of the sesquiterpeneExpand
11-dehydro (-)-hardwickic acid from Croton oblongifolius
Abstract Of the two closely related furanoid diterpenes isolated from the stem-bark of Croton oblongifolius, one is a new acid whose constitution has been established asExpand
Structure elucidation of some ent-clerodane diterpenes from Dodonaea boroniaefolia and Cyanostegia augustifolia
Two diterpene alcohols (1) and (2) and a hydroxy acid isolated as the ester (7) have been obtained from D. boroniaefolia. Their structures have been established by correlation with the acid (10) byExpand
Constituents of Solidago Species. Part III. The Constitution of Diterpenoids from Solidago juncea Ait.
The constitution and stereochemistry of five new diterpenoids from Solidago juncea Ait., junceic acid (3a), the related epoxide (6a), junceanol W(4a), junceanol X (4b), and junceanol Y (5a), haveExpand
Volatile constituents of black-rotted sweet potato and related substances
Abstract From the volatile component of sweet potatoes infected by Ceratostomella fimbriata (“black rotted” disease), four β-substituted furans, viz. ipomeamarone (1), batatic acid (45), ipomeanineExpand
Studies in sesquiterpenes—XLII : Isolongifolene (part 3): Systematic degradation
Isolongifolene has been systematically degraded to a bisnor-keto acid, the spectral characteristics of which are in full accord with the structure (II) assigned earlier to isolongifolene.
Über Caryophyllen, V. Die Betulenole
α- und β-Betulenol, aus dem Blattknospenol von Betula lenta L., konnten durch Reduktion zum α- und β-Tetrahydrobetulenol und zum Caryophyllan (Tetrahydrocaryophyllen), durch weitere Umsetzungen undExpand
Studies in sesquiterpenes—XXXVIII: Structure of humulene epoxide-I and humulene epoxide-II
Abstract Evidence leading to the assignment of absolute stereostructures I and II to (−)-humulene epoxide-I and (−)-humulene epoxide-II respectively is presented. Partial synthesis of (±)-humuleneExpand
Stereochemistry of clerodanes. X-Ray structure of a key diterpenoid from Solidago arguta Ait
X-Ray structural studies of the diterpenoid (1) from Solidago arguta have confirmed the relative stereo-chemistries assigned to (1) and a large group of related compounds including marrubiaside (3),Expand
Identification d'un acide diterpenique du bourgeon de cassis
The acidic fraction of benzenic extract of Blackberry bud (Ribes nigrumL.) show a diterpene acid identified as hardwickiic acid by IR., UV., RMN. and SM.