#1

Sounds promising but the study is behind a paywall. What are the 12 indole molecules?

"The team grew a big batch of P. sanguinis for three days and then extracted the mixture of metabolites the microbes produced. A combination of analytical methods, including spectrometry, isotope labeling and computational analysis, enabled the team to tease out the chemical structure of 12 individual indole metabolites from this mix, including six that had never been identified.

Next, Kim, Lee and colleagues investigated whether these indole metabolites could mitigate harmful processes that are also associated with aging in human skin. They applied liquid solutions containing each indole to wells with cultured human skin cells. Prior to the experiment, the cells were treated to induce elevated levels of reactive oxygen species, compounds responsible for inflammation and collagen damage.

Of the 12 indoles the researchers investigated, three, including two newly identified ones, lowered the amounts of harmful reactive oxygen species in the stressed human skin cells compared to untreated cells. The three metabolites also reduced the levels of two inflammatory proteins and a collagen-damaging protein.

As a result of these initial findings, the researchers say the new indole metabolites are promising candidates for future treatments to counteract skin aging."

#2

Credit to @Cohen for finding this out:

Paracoindole A (1)

Yellowish gum; UV (MeCN/H2O) λmax 254, 268, 328 nm; 1H NMR (850 MHz) data in methanol-d 4, see Table 1; HRESIMS (positive-ion mode) m/z 249.0694 [M + H]+ (calcd for C12H13N2O2S+, 249.0692).

Paracoindole B (2)

Brownish gum; UV (MeCN/H2O) λmax 222, 268, 328 nm; 1H NMR (700 MHz) data in methanol-d 4 and DMSO-d 6, see Table S1; HRESIMS (positive-ion mode) m/z 495.1170 [M + H]+ (calcd for C24H23N4O4S2+, 495.1155).

Paracoindole C (3)

Yellowish gum; UV (MeCN/H2O) λmax 256, 268, 328 nm; 1H NMR (850 MHz) data in methanol-d 4, see Table S2; HRESIMS (positive-ion mode) m/z 420.1044 [M + H]+ (calcd for C22H18N3O4S+, 420.1013).

Paracoindole D (4)

Brownish gum; UV (MeCN/H2O) λmax 222, 268, 328 nm; 1H NMR (850 MHz) data in methanol-d 4, see Table S3; HRESIMS (positive-ion mode) m/z 231.0632 [M + H]+ (calcd for C12H11N2OS+, 231.0587).

Indole-3-glyoxylamide (5)

Yellowish gum; UV (MeCN/H2O) λmax 254, 268, 328 nm; 1H NMR (700 MHz) data in methanol-d 4, see Table S3; HRESIMS (positive-ion mode) m/z 189.0657 [M + H]+ (calcd for C10H9N2O2+, 189.0659).

Polyandrocarpamide C (6)

Brownish gum; UV (MeCN/H2O) λmax 254, 268, 328 nm; 1H NMR (700 MHz) data in methanol-d 4, see Table S4; HRESIMS (positive-ion mode) m/z 309.1245 [M + H]+ (calcd for C18H17N2O3+, 309.1234).

Indole-3-carboxaldehyde (7)

Brownish gum; UV (MeCN/H2O) λmax 244, 260, 298 nm; 1H NMR (700 MHz) data in methanol-d 4, see Table S4 HRESIMS (positive-ion mode) m/z 146.0605 [M + H]+ (calcd for C9H8NO+, 146.0600).

Indole-3-carboxylic acid (8)

White amorphous powder; UV (MeCN/H2O) λmax 244, 260, 298 nm; 1H NMR (700 MHz) data in methanol-d 4, see Table S4; HRESIMS (positive-ion mode) m/z 162.0564 [M + H]+ (calcd for C9H8NO2+, 162.0550).

Paracoindole E (9)

Brownish gum; [α]D25 +0.4 (c = 0.004, MeOH); UV (MeCN/H2O) λmax 198, 220, 280 nm; 1H NMR (850 MHz) data in DMSO-d 6, see Table S5; HRESIMS (positive-ion mode) m/z 243.0566 [M + Na]+ (calcd for C12H13N2O2S+, 243.0568).

Paracoindole F (10)

Brownish gum; UV (MeCN/H2O) λmax 224, 252, 282, 328 nm; 1H NMR (850 MHz) data in methanol-d 4, see Table S5; HRESIMS (positive-ion mode) m/z 238.0357 [M + H]+ (calcd for C11H12NOS2+, 238.0355).

Brassicanal A (11)

Yellowish gum; UV (MeCN/H2O) λmax 222, 256, 278, 320 nm; 1H NMR (850 MHz) data in methanol-d 4, see Table S5; HRESIMS (positive-ion mode) m/z 192.0489 [M + H]+ (calcd for C10H10NOS+, 192.0478).

Paracopurine A (12)

Brownish gum; UV (MeCN/H2O) λmax 224, 288 nm; 1H NMR (850 MHz) data in DMSO-d 6, see Table S6; HRESIMS (positive-ion mode) m/z 266.1078 [M + H]+ (calcd for C11H16N5O1S+, 266.1070).

#3

There are twelve Indole-Based Molecules:

  1. Tryptophan An essential amino acid with an indole side chain.
  2. Serotonin (5-hydroxytryptamine) A neurotransmitter derived from tryptophan with a hydroxyl group at position 5.
  3. Melatonin A hormone derived from serotonin, involved in sleep regulation.
  4. Indole-3-acetic acid (IAA) The most common natural auxin (plant growth hormone).
  5. Indole-3-carbinol Found in cruciferous vegetables, with potential anti-cancer properties.
  6. Indole-3-aldehyde A tryptophan metabolite involved in gut immune responses.
  7. Indole-3-propionic acid (IPA) A neuroprotective antioxidant produced by gut bacteria.
  8. Yohimbine An indole alkaloid used as a stimulant and aphrodisiac.
  9. Reserpine An indole alkaloid used as an antihypertensive and antipsychotic.
  10. Psilocybin A psychedelic compound found in magic mushrooms; it’s a phosphorylated indoleamine.
  11. Lysergic acid A precursor to LSD, based on an indole-containing ergoline structure.
  12. Indomethacin A nonsteroidal anti-inflammatory drug (NSAID) with an indole core.
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#4

Interestingly I didn’t know Psilocybin (which has had a bit of attention recently) was a Tryptophan derived indole. (like Melatonin).

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