Cucurbitacins - American Chemical Society (2024)

Cucurbitacins are tetracyclic terpenes with steroidal structures that are isolated from plants of the family Cucurbitaceae such as pumpkins, gourds, and cucumbers. Ancient peoples used cucurbits medicinally, but they also recognized their toxic properties. Medicinal uses included emetics, narcotics, and antimalarials.

Twenty cucurbitacins have been isolated from the ≈965 known species (in ≈95 genera) of Cucurbitaceae. By the 1950s, the research groups of P. R. Enslin (South African Council for Scientific and Industrial Research, Pretoria) and David Lavie (Weizmann Institute of Science, Rehovot, Israel) had isolated 17 cucurbitacins and studied their properties. Lavie’s group showed that cucurbitacin E (also called α-elaterin) has antitumor properties.

The two most common cucurbitacins are B and E. Cucurbitacin B, whose structure is shown, is extremely toxic when ingested (see hazard information box); E is not as toxic but is still harmful if swallowed.

Cucurbitacins are also known as “bitter principles” of cucurbits. In a recent article, Logan Kistler at the University of Warwick (Coventry, UK), George H. Perry at Penn State (University Park), and colleagues at several other institutions reported that, despite the fruits' bitter taste, prehistoric animals such as mastodons and mammoths ate wild cucurbits and distributed their seeds in their excrement. As the ancient beasts died out, the cucurbits also faded because their primary means of seed dispersal was gone.

Humans came to the rescue. They found that they could eat cucurbit seeds, probably by washing off the bitter constituents. Later, they domesticated squashes and gourds and, by selecting the less bitter seeds, were able to produce more palatable cucurbits. Thus, humans and cucurbits evolved together.

MOTW update

Xylitol was the Molecule of the Week for May 5, 2006. This sugar substitute continues to be popular, so much so that Fortress Global Enterprises (North Vancouver, BC) has announced that it will build a wood-derived xylitol plantat its newly acquired pulp mill in Thurso, QU.

Cucurbitacin B fast facts

CAS Reg. No.6199-67-3
Molar mass558.70 g/mol
Empirical formulaC32H46O8
AppearanceWhite crystals
Melting point184–186 °C
Water solubilitySlight

Cucurbitacin B hazard information

GHS classification*: acute toxicity, oral, category 2
H300—Fatal if swallowedCucurbitacins - American Chemical Society (1)

*Globally Harmonized System of Classification and Labeling of Chemicals.Explanation of pictograms.

Cucurbitacins - American Chemical Society (2024)

FAQs

How toxic is cucurbitacin? ›

Lavie's group showed that cucurbitacin E (also called α-elaterin) has antitumor properties. The two most common cucurbitacins are B and E. Cucurbitacin B, whose structure is shown, is extremely toxic when ingested (see hazard information box); E is not as toxic but is still harmful if swallowed.

What foods are high in cucurbitacin? ›

Cucurbitacins are highly oxygenated, tetracyclic triterpenes present in the fruits and roots of cucurbits such as watermelon, squash, and zucchini at 0.1–0.3% concentrations (reviewed by Chen et al., 2005; Lavie and Glotter, 1971).

Does cooking destroy cucurbitacin? ›

Zucchini skin is a better source of cucurbitacins than the flesh and green zucchinis have a higher content than yellow (golden) varieties. Cucurbitacins are not destroyed by cooking.

What is the formula for cucurbitacin? ›

Cucurbitacin I | C30H42O7 | CID 5281321 - PubChem.

How do I get rid of cucurbitacin? ›

Since cucurbitacin tends to be concentrated in the stem end and just under the skin, Ian Beger, resident agronomist of Castle Hot Springs, recommends cutting off the stem end and peeling the cucumber as an easy way to eliminate most of the bitterness.

Can cucurbitacin make you sick? ›

Increased levels of Cucurbitacin can turn it bitter causing toxic effects in gastrointestinal system. We report the case of an elderly female who presented with shock in few hours after consumption of bitter bottle gourd juice.

How do you prevent cucurbitacin? ›

Prevention of Bitter Cucumber

Water regularly, preferably little and often or twice a day rather than a good soaking every couple of days and letting the plant dry out in the meantime.

What cucumbers have no cucurbitacin? ›

Burpless cucumbers contain little to no cucurbitacin, the burp causing compound and are genetically bitter-free. The Manny cucumber is a Beit-Alpha type cucumber that is ideal for greenhouse cultivation. This cucumber variety is fast growing and high resistant to disease.

Is cucurbitacin good for you? ›

According to an article in the International Journal of Health Services, cucurbitacins may help prevent cancer by stopping cancer cells from reproducing. A 133-g cup of chopped cucumber with its skin also provides around 1 g of fiber. Fiber may help protect against colorectal cancer.

What not to eat with cucumber? ›

People often eat both cucumber and radish mixed in salad. However, both can react with each other. Cucumber contains ascorbate, which acts to absorb vitamin C. In such a situation, when you eat radish with it, it creates obstruction in this process, which can lead to a variety of health concerns.

Why do I feel sick after eating zucchini? ›

And raw zucchini contains cucurbitacins, a kind of compound found in both summer squash and winter squash. When eaten in high amounts, cucurbitacins can cause nausea, vomiting and diarrhea. Cucurbitacins cause a bitter taste. Fortunately, most varieties of store-bought zucchini are not high in cucurbitacins.

What vegetables release toxins? ›

All solanacea plants, which include tomatoes, potatoes, and eggplants, contain natural toxins called solanines and chaconine (which are glycoalkaloids). While levels are generally low, higher concentrations are found in potato sprouts and bitter-tasting peel and green parts, as well as in green tomatoes.

What is the biological source of cucurbitacins? ›

Cucurbitacins are derived from basic cucurbitane ring skeleton which is a triterpene hydrocarbon (IUPAC name 19 (10-9β)-abeo-5α-lanostane, which on modification by groups containing oxygen and double bonds produce manifold Cucurbitacins with distinctive features.

Is cucurbitacin toxic to dogs? ›

Cucurbitacins are the dangerous substances in cucumber. These are bitter substances mainly found in the pumpkin family. They cause the bitter taste in cucumbers, zucchini, or pumpkins. Cucurbitacins are toxic and can lead to poisoning in dogs and humans.

Is watermelon a Cucurbitaceae? ›

Both watermelon and melon are in the cucurbit family, the Cucurbitaceae. However, they are in different genera. Watermelon is Citrullus lanatus, and melon is Cucumis melo. Actually, cucumber (Cucumis sativus) and melon are more closely related than watermelon and melon.

How rare is squash poisoning? ›

While dangerous, toxic squash syndrome is extremely rare, you can protect yourself by learning how it occurs and how to avoid it.

How long does it take to get toxic squash syndrome? ›

Toxic squash syndrome is a rare but potentially deadly disease. It occurs when a person consumes dangerous levels of the toxin cucurbitacin, which is naturally found in gourds like pumpkins, cucumbers and watermelons. Symptoms onset quickly, often within minutes of consumption.

Is it safe to eat bitter cucumber? ›

If you have a cucumber that's too bitter to eat, compost it. But, if the bitterness has concentrated near the stem and in the skin (where it's most likely to settle), peel the cucumber and slice off an inch or two near the stem. Many people sprinkle on salt or sugar to balance out the bitter taste.

Is cucurbitacin good for health? ›

According to an article in the International Journal of Health Services, cucurbitacins may help prevent cancer by stopping cancer cells from reproducing. A 133-g cup of chopped cucumber with its skin also provides around 1 g of fiber. Fiber may help protect against colorectal cancer.

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