Sesquiterpene hydrocarbons from the oil of cubeb α-cubebene and β-cubebene

Ohta, Yoshimoto; Sakai, Tsutomu; Hirose, Toshio

doi:10.1016/s0040-4039(00)70179-1

Cited by 30 publications

(19 citation statements)

References 4 publications

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“…The final structure corroborates the gross structure of Ohta, Sakai & Hirose (1966) and confirms the stereochemistry which had been inferred from spectral data (Tanaka, Tanaka, Uda & Yoshikoshi, 1972). The absolute configuration indicated is correct, since it has been shown (Ohta, Sakai & Hirose, 1966)that treatment of ct-cubebene with dry HC1 in ether yields (-)-cadinene hydrochloride, the absolute configuration of which is known.…”

Section: Description Of the Structuresupporting

confidence: 86%

“…1), respectively, by Ohta, Sakai & Hirose (1966). The chemical evidence adduced by these workers did not establish the stereochemistry at the centers indicated by wavy lines in Fig.…”

Section: Introductionmentioning

confidence: 83%

“…The absolute configuration indicated is correct, since it has been shown (Ohta, Sakai & Hirose, 1966)that treatment of ct-cubebene with dry HC1 in ether yields (-)-cadinene hydrochloride, the absolute configuration of which is known. The conjugation in the cyclopropyl ketone moiety inferred from spectral observations is strikingly verified in the geometry of the molecule (Figs.…”

Section: Description Of the Structurementioning

confidence: 90%

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The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C₁₄H₂₂O

Thiessen¹

1977

Acta Crystallogr Sect B

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Section: Description Of the Structuresupporting

confidence: 86%

“…1), respectively, by Ohta, Sakai & Hirose (1966). The chemical evidence adduced by these workers did not establish the stereochemistry at the centers indicated by wavy lines in Fig.…”

Section: Introductionmentioning

confidence: 83%

Section: Description Of the Structurementioning

confidence: 90%

See 1 more Smart Citation

The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C₁₄H₂₂O

Thiessen¹

1977

Acta Crystallogr Sect B

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“…The odor of E. meliifolia leaves is similar to that of apples fruits, this is completely different from that of other Rutaceae plants in Japan. In fact, hexanal and 2-hexenal, detected in E. meliifolia but not in the other 12 species (only detected from R. graveolens other than E. meliifolia), are detected from apples (Ohta et al, 1966). Thus, these substances might be also associated with the oviposition behavior of the Papilio species.…”

Section: Discussionmentioning

confidence: 91%

Inventory of leaf and flower odorants in plants associated with the life cycle of Japanese Papilio butterflies

Inoue¹,

Otani

Niihara

et al. 2021

Preprint

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The odorants of eight Japanese mainland native species (Citrus x deliciosa, Zanthoxylum ailanthoides Siebold & Zucc, Z. schinifolium Sieb. et Zucc., Z. piperitum L., Phellodendron amurense Ruprecht, Orixa japonica Thunb., Skimmia japonica Thunb., and Boenninghausenia albiflora (Hook.) Rchb. ex Meisn.), one tropical species (Euodia meliifolia (Hance) Benth.), and one invasive species (Ruta graveolens) of the Rutaceae family and three Japanese mainland native species (Angelica keiskei (Miq.) Koidz., Heracleum lanatum W. Bartram, Anthriscus sylvestris (Blume) DC), and one invasive species (Foeniculum vulgare Mill.) of the Apiaceae family were analyzed using gas chromatography–mass spectrometry with dynamic–headspace and thermal–desorption methods. These plants are hostplants to Japanese Papilio butterflies. Herein, these 14 plants were classified into six major groups based on the odorant volatiles, which did not correspond to the current phylogenetic classification. Similarly, floral odorant analysis of the six plant species (Clerodendrum trichotomum Thunb., Cayratia japonica (Thunb.) Gagnep., Robinia pseudoacacia L., Lonicera japonica Thunb., C. deliciosa, Z. ailanthoides) visited by Papilio butterflies for nectaring, revealed the presence of linalool in all the flowers. Floral volatiles in C. deliciosa and Z. ailanthoides exhibited moderate resemblance to their respective leaf volatiles. Interestingly, our results in C. trichotomum was not in complete agreement with previous reports, emphasizing the need for newer methods of extraction and analysis.

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“…On the basis of spectral data, chemical degradation and correlation with known cadinane derivatives, Hirose et al (1)(2)(3) have proposed that 1 and 2 correctly represent the structure and absolute stereochemistry of a-cubebene2 and 0-cubebene, respectively, two sesquiterpenes isolated from the commercial oil of cubeb (Piper cubeba L.). Structurally, these two natural products contain the bicyclo[3.l.O]hexane moiety and thus represent a novel and interesting variant of the more normal structures found within the cadinane class of sesquiterpenoids.…”

mentioning

confidence: 99%

Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

Piers¹,

Britton²,

Waal³

1971

Can. J. Chem.

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An efficient total synthesis of the racemic forms of the novel tricyclic sesquiterpenes a-cubebene (1) and 8-cubebene (2) is described. The key step of this synthesis involved the cupric sulfate catalyzed intramolecular cyclization of the olefinic diazoketone 3, which produced, in high yield, (+)-8-cubebene norketone (24) and (f )-l,6-epi-p-cubebene norketone (25), in a ratio of approximately 3:5, respectively.

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Sesquiterpene hydrocarbons from the oil of cubeb α-cubebene and β-cubebene

Cited by 30 publications

References 4 publications

The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C₁₄H₂₂O

The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C₁₄H₂₂O

Inventory of leaf and flower odorants in plants associated with the life cycle of Japanese Papilio butterflies

Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

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Sesquiterpene hydrocarbons from the oil of cubeb α-cubebene and β-cubebene

Cited by 30 publications

References 4 publications

The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C14H22O

The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C14H22O

Inventory of leaf and flower odorants in plants associated with the life cycle of Japanese Papilio butterflies

Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

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Product

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The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C₁₄H₂₂O

The structure and stereochemistry of α- and β-cubebene from the crystal structure of norcubebanone, C₁₄H₂₂O