Cucurbitane
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Cucurbitane
Cucurbitane is a class of chemical compounds with formula ( CAS number 65441-59-0). It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of a methyl group (carbon number 19) from the 10 to the 9β position in the standard steroid numbering scheme.Satish Kumar and Raj Kumar (1991), ''Dictionary of Biochemistry''. Anmol Publications, India The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon atom (number 5 in the standard steroid numbering scheme). File:5alpha-cucurbitane.svg, 5α-Cucurbitane File:5beta-cucurbitane.svg, 5β-Cucurbitane Derivatives Natural compounds Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals. Natural cucurbitane-related compounds include: Named * Balsaminapenta ...
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Cucurbitacin
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as triterpenes, formally derived from cucurbitane, a triterpene hydrocarbon – specifically, from the unsaturated variant cucurbit-5-ene, or 19(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycosides. They and their derivatives have been found in many plant families (including Brassicaceae, Cucurbitaceae, Scrophulariaceae, Begoniaceae, Elaeocarpaceae, Datiscaceae, Desfontainiaceae, Polemoniaceae, Primulaceae, Rubiaceae, Sterculiaceae, Rosaceae, and Thymelaeaceae), in some mushrooms (including Russula and Hebeloma) and even in some marine mollusks. Cucurbitacins may be a taste deterrent in plants foraged by some animals and in some edible plants preferred by humans, like cucumbers and zucchinis. In laboratory research, cucurbi ...
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Karavilagenin E
Karavilagenin E is a chemical compound found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin. Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in ''n''-hexane. See also * Balsaminapentaol Balsaminapentaol or cucurbita-5,25-diene-3β,7β,23(R),24(R),29-pentaol, is a chemical compound with formula , found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by ... * Balsaminol A * Balsaminol B * Cucurbalsaminol A * Cucurbalsaminol B References Triterpenes Diols {{organic-compound-stub ...
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Balsaminapentaol
Balsaminapentaol or cucurbita-5,25-diene-3β,7β,23(R),24(R),29-pentaol, is a chemical compound with formula , found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009. Balsaminepentaol is an amorphous powder soluble in methanol and ethyl acetate but insoluble in ''n''-hexane. It is cytotoxic at about 50 μM. See also * Balsaminol A * Balsaminol B * Cucurbalsaminol A * Cucurbalsaminol B * Karavilagenin E Karavilagenin E is a chemical compound found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin. Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in ''n''-he ... References {{reflist Triterpenes Polyols ...
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Charantoside
Charantoside is any of several related cucurbitane triterpenoid glycosides found in the fruits bitter melon vine (''Momordica charantia''). They include: * charantoside I, (19R,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23,25-trien-3β-ol 3-O-β-D-glucopyranoside: amorphous solid. * charantoside II, (19R,23R)-5β,19-Epoxy-19,23-dimethoxycucurbita-6,24-dien-3β-ol 3-O-β-D-allopyranoside: amorphous solid. * charantoside III, (23E)-5β,19-Epoxycucurbita-6,23,25-trien-3β-ol 3-O-β-D-glucopyranoside: amorphous solid. * charantoside IV, (23E)-5β,19-Epoxycucurbita-6,23,25-trien-3β-ol 3-O-β-D-allopyranoside: colorless needles, melting at 256–260 °C. * charantoside V, (23R)-5β,19-Epoxy-23-methoxycucurbita-6,24-dien-3β-ol 3-O-β-D-glucopyranoside: colorless needles, melting at 235–240 °C. * charantoside VI, (23S)-5β,19-Epoxy-23-methoxycucurbita-6,24-dien-3β-ol 3-O-β-D-allopyranoside: amorphous solid. * charantoside VII, (23E)-3β-Hydroxycucurbita-6,23,25-trien-5β ...
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Lepidolide
Lepidolide is a chemical compound with formula — specifically, a terpenoid with the cucurbitane Cucurbitane is a class of chemical compounds with formula ( CAS number 65441-59-0). It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by ... skeleton — isolated from the fruiting bodies of the mushroom '' Russula lepida'' (23 mg/7 kg). It is a pale yellow oil, soluble in chloroform. References {{Reflist Triterpenes Dicarboxylic acids Lactones ...
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Hemslecin
Hemslecin is any of several compounds obtained from plants of the genus '' Hemsleya'', which are used in Asian folk medicine. They are triterpene derivatives, specifically with the cucurbitane skeleton, related to cucurbitacin F.Jian-Chao Chen, Gao-Hong Zhang, Zhong-Quan Zhang, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Kai-Bei Yu (2008), "Octanorcucurbitane and Cucurbitane Triterpenoids from the Tubers of ''Hemsleya endecaphylla'' with HIV-1 Inhibitory Activity". ''J. Nat. Prod.'' volume 71, pages 153–155 Jian Chao Chen, Ming Hua Chiu, Rui Lin Nie, Geoffrey A. Cordell and Samuel X. Qiu (2005), "Cucurbitacins and cucurbitane glycosides: structures and biological activities" ''Natural Product Reports'', volume 22, pages 386-399 The hemslecins include: * Hemslecin A, 25-acetoxy-23,24-dihydrocucurbitacin F, from ''Hemsleya endecaphylla'' and from '' Helmseya amabilis'' * Hemslecin B, 23,24-dihydrocucurbitacin F, from ''Hemsleya endecaphylla'' * Hemslecin C, synthesized from h ...
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Balsaminol B
Balsaminol B or 7β-methoxycucurbita-5,24-diene-3β,23(R),29-triol, is a chemical compound with formula , found in the balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009. Balsaminol B is an amorphous powder soluble in methanol and ethyl acetate, but insoluble in ''n''-hexane. It is cytotoxic at about 50 μM. See also * Balsaminapentaol * Balsaminol A * Cucurbalsaminol A * Cucurbalsaminol B * Karavilagenin E Karavilagenin E is a chemical compound found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin. Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in ''n''-he ... References {{reflist Triterpenes Triols ...
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Endecaphyllacin
Endecaphyllacin is either of two similar compounds found in certain plants, such as ''Hemsleya endecaphylla''.Jian-Chao Chen, Gao-Hong Zhang, Zhong-Quan Zhang, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Kai-Bei Yu (2008), "Octanorcucurbitane and Cucurbitane Triterpenoids from the Tubers of ''Hemsleya endecaphylla'' with HIV-1 Inhibitory Activity". ''J. Nat. Prod.'' volume 71, pages 153–155 * Endecaphyllacin A, 2β-hydroxy-20,21,22,23,24,25,26,27-octanorcucurbita-5-ene-3,11,16-trione, . Crystallizes with 1 molecule of methanol as colorless prisms, mp 207-209 °C; * Endecaphyllacin B, 2-hydroxy-20,21,22,23,24,25,26,27-octanorcucurbita-1,5-dien-3,11,16-trione, . It is the aglycon of khekadaengoside L from ''Trichosanthes tricuspidata''. Crystallizes from methanol as colorless prisms, mp 229-231 °C Endecaphyllacins A and B can be extracted from the dried tubers of ''Hemsleya endecaphylla ''Hemsleya'' is a genus of flowering plants belonging to the family Cucurbitaceae. ...
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Balsaminol A
Balsaminol A or cucurbita-5,24-diene-3β,7β,23(R),29-tetraol, is a chemical compound with formula , found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009. Balsaminol A is an amorphous powder soluble in methanol and ethyl acetate but insoluble in ''n''-hexane. It is cytotoxic at about 50 μM. See also * Balsaminapentaol * Balsaminol B * Cucurbalsaminol A * Cucurbalsaminol B * Karavilagenin E Karavilagenin E is a chemical compound found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin. Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in ''n''-he ... References {{reflist Triterpenes Tetrols ...
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Cucurbalsaminol B
Cucurbalsaminol B or 7β-methoxycucurbita-5,23(E)-diene-3β,12β,25-triol, is a chemical compound with formula , found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009. Cucurbalsaminol B is an amorphous powder soluble in methanol and ethyl acetate but insoluble in ''n''-hexane. It is cytotoxic at about 50 μM. See also * Balsaminapentaol * Balsaminol A * Balsaminol B * Cucurbalsaminol A * Karavilagenin E Karavilagenin E is a chemical compound found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin. Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in ''n''-he ... References {{reflist Triterpenes Polyols ...
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Cucurbalsaminol A
Cucurbalsaminol A or cucurbita-5,23(E)-diene-3β,12β,25-triol, is a chemical compound with formula , found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009. Cucurbalsaminol A is an amorphous powder soluble in methanol and ethyl acetate but insoluble in ''n''-hexane. Unlike Cucurbalsaminol B, it is not cytotoxic. See also * Balsaminapentaol * Balsaminol A * Balsaminol B * Cucurbalsaminol B * Karavilagenin E Karavilagenin E is a chemical compound found in the Balsam apple vine (''Momordica balsamina''). It is a cucurbitane-type triterpenoid, related to cucurbitacin. Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in ''n''-he ... References {{reflist Triterpenes Polyols ...
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Datiscoside
Datiscoside is any one of several chemical compounds isolated from certain plants, notably '' Datisca glomerata''. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane (), more specifically from cucurbitacin F Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ....Jian Chao Chen, Ming Hua Chiu, Rui Lin Nie, Geoffrey A. Cordell and Samuel X. Qiu (2005), "Cucurbitacins and cucurbitane glycosides: structures and biological activities" ''Natural Product Reports'', volume 22, pages 386-399 They include: * Datiscoside B, from ''D. glomerata'' * Datiscoside D, from ''D. glomerata'' * Datiscoside H, from ''D. glomerata'' References Triterpene glycosides {{organic-compound-stub ...
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