Cucurbitane

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title: "Cucurbitane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["lanostanes", "triterpenes"] topic_path: "general/lanostanes" source: "https://en.wikipedia.org/wiki/Cucurbitane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 421516894 | ImageFile = Cucurbitane.svg | ImageAlt = | IUPACName = 19-Nor-5ξ,9β,10α-lanostane | SystematicName = (1R,3aS,3bR,5aΞ,9aR,9bS,11aR)-3a,6,6,9b,11a-Pentamethyl-1-[(2R)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene | OtherNames = |Section1={{Chembox Identifiers | CASNo = 65441-59-0 | CASNo_Comment = (5α/β) | CASNo_Ref = | UNII_Ref = | UNII = VQU8QE865A | PubChem = 71306377 | ChEBI_Ref = | ChEBI = 73245 | SMILES1 = CC@H[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C | SMILES1_Comment = (5α) | ChemSpiderID1_Ref = | ChemSpiderID1 = 25936933 | ChemSpiderID1_Comment = (5α) | InChI1 = 1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 | InChI1_Comment = (5α) | InChIKey1 = ZYZJWAJOTPNVPI-AUAIAXQGBW | StdInChI_Ref = | StdInChI = 1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 | StdInChI_Comment = (5α) | StdInChIKey_Ref = | StdInChIKey = ZYZJWAJOTPNVPI-AUAIAXQGSA-N | SMILES2 = CC@H[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C | SMILES2_Comment = (5β) | ChemSpiderID2_Ref = | ChemSpiderID2 = 28639243 | ChemSpiderID2_Comment = (5β) | InChI2 = 1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1 | InChI2_Comment = (5β) | InChIKey2 = ZYZJWAJOTPNVPI-QJMYWHNVBB | InChI3 = 1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1 | InChI3_Comment = (5β) | InChIKey3 = ZYZJWAJOTPNVPI-QJMYWHNVSA-N |Section2={{Chembox Properties | C=30 | H=54 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}

Cucurbitane is a tetracyclic chemical compound with formula . 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.

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

Cucurbitane is the core chemical structure of a class of derivatives known as cucurbitane-type triterpenoids or simply as cucurbitanes.

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

Unnamed

References

References

  1. (1969). "The Nomenclature of Steroids — Revised Tentative Rules". European Journal of Biochemistry.
  2. Satish Kumar and Raj Kumar (1991), ''Dictionary of Biochemistry''. Anmol Publications, India
  3. Jun Ma, Paul Whittaker, Amy C. Keller, Eugene P. Mazzola, Rahul S. Pawar, Kevin D. White, John H. Callahan, Edward J. Kennelly, Alexander J. Krynitsky, Jeanne I. Rader. (2010). "Cucurbitane-Type Triterpenoids from Momordica charantia". Planta Med.
  4. (2005). "Cucurbitacins and cucurbitane glycosides: Structures and biological activities". Natural Product Reports.
  5. (2009). "Cucurbitane-Type Triterpenoids from the African PlantMomordica balsamina". Journal of Natural Products.
  6. (1962). "Note on a Hypoglycaemic Principle Isolated from the fruits of ''Momordica charantia''". Journal of the University of Bombay.
  7. (2007). "Cucurbitane-Type Triterpenoids from the Fruits of ''Momordica charantia'' and Their Cancer Chemopreventive Effects". Journal of Natural Products.
  8. (2007). "Cucurbitane and hexanorcucurbitane glycosides from the fruits of ''Cucurbita pepo'' cv ''dayangua''". Journal of Asian Natural Products Research.
  9. (2008). "Octanorcucurbitane and Cucurbitane Triterpenoids from the Tubers ofHemsleya endecaphyllawith HIV-1 Inhibitory Activity". Journal of Natural Products.
  10. Jian-Wen Tan, Ze-Jun Dong, Zhi-Hui Ding and Ji-Kai Liu (2002), [http://www.znaturforsch.com/ac/v57c/s57c0963.pdf "Lepidolide, a Novel Seco-ring-A Cucurbitane Triterpenoid from ''Russula lepida'' (Basidiomycetes)"]. ''Zeitschrift für Naturforschung'' Series C, volume 57C issue 11/12, pages 963-965.
  11. (2009). "Kuguacins F–S, cucurbitane triterpenoids from Momordica charantia". Phytochemistry.
  12. (2008). "Trinorcucurbitane and cucurbitane triterpenoids from the roots of ''Momordica charantia''". Phytochemistry.
  13. (2008). "Eight New Cucurbitane Glycosides, Kuguaglycosides A – H, from the Root ofMomordica charantia L". Helvetica Chimica Acta.
  14. (2003). "Anticarcinogenic activity of natural sweeteners, cucurbitane glycosides, from ''Momordica grosvenori''". Cancer Letters.
  15. (1997). "Triterpenes, A Sterol and a Monocyclic Alcohol From ''Momordica Charantia''". Phytochemistry.
  16. (1990). "New cucurbitane trirterpenoids from ''Momordica charantia''". Journal of Natural Products.
  17. Daniel Bisrat Mekuria, Takehiro Kashiwagi, Shin-ichi Tebayashi, and Chul-Sa Kim (2006)"Cucurbitane Glucosides from ''Momordica charantia'' Leaves as Oviposition Deterrents to the Leafminer, ''Liriomyza trifolii''". ''Z. Naturforsch.'', volume 61c, pages 81–86
  18. (2009). "New Cucurbitane Triterpenoids and Steroidal Glycoside from Momordica charantia". Molecules.
  19. (2006). "Momordica charantia Constituents and Antidiabetic Screening of the Isolated Major Compounds". Chemical & Pharmaceutical Bulletin.
  20. (2010). "One new cucurbitane triterpenoid from the fruits of Momordica charantia". European Journal of Chemistry.
  21. link. (2011-10-07 Journal of Integrative Plant Biology, volume 38, issue 6, pages, 489–494)
  22. (1997). "Cucurbitane triterpenoids from the leaves of Momordica foetida". Phytochemistry.
  23. (2010). "Evaluation of Cucurbitane-type Triterpenoids from ''Momordica balsamina'' on P-Glycoprotein (ABCB1) by Flow Cytometry and Real-time Fluorometry". Anticancer Research.
  24. (2010). "Cucurbitane Triterpenoids from Momordica charantia and Their Cytoprotective Activity in tert-Butyl Hydroperoxide-Induced Hepatotoxicity of HepG2 Cells". Chemical & Pharmaceutical Bulletin.

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